Pharmacognosy 2

Download as pdf or txt
Download as pdf or txt
You are on page 1of 340

1.

SEPARATION AND ISOLATION OF PLANT CONSTITUENTS (BSM)

COLUMN CHROMATOGRAPHY

– Chromatography is the term used to describe a separation technique in


which a mobile phase carrying a mixture is caused to move in contact
with a selectively absorbent stationary phase.
– There are a number of different kinds of chromatography, which differ in
the mobile and the stationary phase used.
– Column Chromatography was developed by the American chemist D.T
Day in 1900, M.S. Tswett, the Polish botanist, in 1906 used adsorption
columns in his investigations of
plant pigments.

1
1.SEPARATION AND ISOLATION OF PLANT CONSTITUENTS (BSM)

– Column chromatography is one of the most useful methods for the


separation and purification of both solids and liquids.
– This is a solid - liquid technique in which the stationary phase is a solid &
mobile phase is a liquid.
PRINCIPLE
– Adsorption
– Mixture of components dissolved in the M.P is introduced in to the
column. Components moves depending upon their relative affinities.
– Adsorption column chromatography, the adsorbent, packed in a glass
column, and a solvent, the mobile phase, that moves slowly through the
packed column. A solvent used as a mobile phase is called an eluent.

2
1.SEPARATION AND ISOLATION OF PLANT CONSTITUENTS (BSM)

3
1.SEPARATION AND ISOLATION OF PLANT CONSTITUENTS (BSM)

– A compound attracted more strongly by the mobile phase will move


rapidly through the column, and elute from, or come off, the column
dissolved in the eluent.
– In contrast, a compound more strongly attracted to the stationary phase
will move slowly through the column.

– Experimental aspects of column chromatography:


– Adsorbents: The usual adsorbents employed in column chromatography
are silica, alumina, calcium carbonate, calcium phosphate, magnesia,
starch, etc.,
– Alumina is generally suitable for chromatography of less polar
compounds. Silica gel gives good results with compounds containing
polar functional groups.

4
1.SEPARATION AND ISOLATION OF PLANT CONSTITUENTS (BSM)

– Adsorbent in C.C should meet following criteria


◘ Particles should be spherical in shape & uniform in size
◘ Mechanical stability must be high
◘ They shouldn’t react chemically
◘ It should be useful for separating for wide variety of compounds
◘ It should be freely available & inexpensive

(The particle size of the commercially available grade is in the range 50 –


200 µm.)

Selection of Stationary Phase


– Success of chromatography depends upon proper selection of S.P, it
depends on the following:
1. Removal of impurities
2. No. of components to be separated
3. Length of the column used
4. Affinity differences b/w components
5. Quantity of adsorbent used

5
1.SEPARATION AND ISOLATION OF PLANT CONSTITUENTS (BSM)

Mobile Phase
– They act as solvent, developer & eluent. The function of a mobile phase
are:
– As developing agent
– To introduce the mixture into the column – as solvent
– To developing agent
– To remove pure components out of the column – as eluent
– The choice of the solvent is depend on the solubility characteristics of the
mixture. The solvents should also have sufficiently low boiling points to
permit ready recovery of eluted material.
– However, polarity as seen the most important factor in adsorption
chromatography.
– Different mobile phases used: ( in increasing order of polarity)
– Petroleum ether, carbon tetrachloride, cyclohexane, ether, acetone,
benzene, toluene, esters, water, etc
– It can b e used in either pure form or as mixture of solvents

COLUMN CHARACTERISTICS:
– The main function of all the columns is to support the stationary phase.
– The material of the column is mostly good quality neutral glass since it
shouldn’t be affected by solvents. An ordinary burette can also be used as
column for separation.
– Column dimensions - length & diameter ratio (10:1,30:1 or 100:1)
– Various accessories are attached to the top and bottom of the column for
maintenance of the elution process.

– The length of the column depends upon:


– Number of compounds to be separated
– Type of adsorbent used
– Quantity of the sample

6
1.SEPARATION AND ISOLATION OF PLANT CONSTITUENTS (BSM)

– Affinity of compounds towards the adsorbent used


– Better separation will be obtained with a long narrow column than short
thick column because number of plates will be more.
Packing techniques in C.C
– There are two types of preparing the column, they are:
– i. Dry packing / dry filling
– Ii. Wet packing / wet filling
– The column should be free from impurity, before using column, it should
be washed properly and dry it.
– Before filling column with stationary phase, cotton/glass wool is kept
– It should be uniformly filled
Dry Packing Technique
 Adsorbent is packed in the column in dry form
 Fill the solvent, till equilibrium is reached
DEMERIT: Air bubbles are entrapped b/w M.P & S.P→ cracks appear in the
adsorbent layer.
– After filling tapping can be done to remove void spaces.

7
1.SEPARATION AND ISOLATION OF PLANT CONSTITUENTS (BSM)

Wet Packing Technique


» ideal & common technique
The material is slurried with solvent and generally added to the column in
portions.
◊ S.P settles uniformly & no crack in the column of adsorbent.
» solid settle down while the solvent remain upward.
» this solvent is removed then again cotton plug is placed.

Introduction of the Sample


– The sample which is usually a mixture of components is dissolved in
minimum quantity of the mobile phase.

8
1.SEPARATION AND ISOLATION OF PLANT CONSTITUENTS (BSM)

– The entire sample is introduced into the column at once and get adsorbed
on the top portion of the column.
– From this zone, individual sample can be separated by a process of
elution.

9
1.SEPARATION AND ISOLATION OF PLANT CONSTITUENTS (BSM)

– Development technique ( Elution)


– By elution technique, the individual components are separated out from
the column. The two techniques are:
– (i) Isocratic elution technique : in this elution technique , same solvent
composition or solvent of same polarity is used throughout the process of
separation.
– Example: chloroform only

(ii) Gradient elution techniques:


( gradient – gradually)
 Solvents of gradually ↑ polarity or ↑ elution strength are used during the
process of separation.

10
1.SEPARATION AND ISOLATION OF PLANT CONSTITUENTS (BSM)

 E.g. initially benzene, then chloroform, then ethyl acetate then


chloroform.
 DETECTION OF COMPONENTS
 If the compounds separated in a column chromatography procedure are
colored, the progress of the separation can simply be monitored visually.
 If the compounds to be isolated from column chromatography are
colorless. In this case, small fractions of the eluent are collected
sequentially in labelled tubes and the composition of each fraction is
analyzed by TLC.
 Eluting the sample: Components a, b, and c separate as column
progresses.
 Fractions can be collected in test tubes, vials, beakers, or Erlenmeyer
flasks.

Analyzing the fractions:


– Analyze the fractions by thin-layer chromatography

11
1.SEPARATION AND ISOLATION OF PLANT CONSTITUENTS (BSM)

– FACTORS AFFECTING COLUMN EFFICIENCY


1. Dimension of the column: column efficiency has been improved by
increasing length/width ratio of the column.
2. Particle size of column packing: separation to be improved by decreasing
the particle size of the adsorbent.
3. Activity of the adsorbent
4. Temperature of the column: The speed of the elution increases at higher
temperatures.
5. Packing of the column
6. Quality of solvents: solvents having low viscosities is giving better
results.
APPLICATIONS
►Separation of mixture of compounds
►Purification process
►Isolation of active constituents
►Estimation of drugs in formulation
►Isolation of active constituents
►Determination of primary and secondary glycosides in
digitalis leaf.
► separation of diastereomers
– Advantages of C.C
» Any type of mixture can be separated
» Any quantity of mixture can be separated
» Wider choice of Mobile Phase
» Automation is possible
– Disadvantages of C.C
» Time consuming
» more amount of Mobile Phase are required
» Automation makes the techniques more complicated & expensive.
12
2.CARBOHYDRATES NOTES BY BILAL MALIK

Carbohydrates
The Germans first and foremost introduced the word ‘kohlenhydrates’ which
was later on coined to carbohydrates. The name obviously suggests that these
compounds are essentially the hydrates of carbon
• Carbohydrates, were defined as a group of compounds composed of
carbon, hydrogen and oxygen in which the latter two elements are in
the same proportion as in water and were expressed by a formula
(CH2O)n, that is, hydrates of carbon.
• All organic compounds containing hydrogen and oxygen in the
proportion found in water are not carbohydrates.
• For example, formaldehyde HCHO for the present purpose can be written
as C(H2O); acetic acid CH3COOH written as C3(H2O)2; and lactic acid
CH3CHOHCOOH written as C3(H2O)3 are not carbohydrates.
• Also, a large number of carbohydrates such as rhamnose (C6H12O5),
cymarose (C7H14O4), digitoxose (C6H12O4), etc., are known which do
not contain the usual proportions of hydrogen to oxygen.
• From the discussion, it can be concluded that the definitions described is
not correct; however, carbohydrates are now defined chemically as
Polyhydroxy aldehyde or Polyhydroxy ketones or compound that on
hydrolyses produce either of the above.
• Carbohydrates are among the first products that are form as a result of
photosynthesis.
• They constitute a large proportion of the plant biomass and are
responsible, as cellulose, for the rigid cellular framework and, as starch,
for providing an important food reserve.
• Of special pharmacognostic importance is the fact that sugars unites with
a wide variety of other compounds to form glycosides and secondary
metabolites.
• Mucilage act as water-retaining vehicles, where as gums and mucilage,
which are similar in composition and properties, are formed in the plant
by injury or stress and usually appear as solidified exudates; both are
typically composed of uronic acid and sugar units.
• Low molecular weight carbohydrates are crystalline, soluble in water and
sweet in taste, for example, glucose, fructose, sucrose, etc.

13
2.CARBOHYDRATES NOTES BY BILAL MALIK

• The high molecular weight carbohydrates (polymers) are amorphous,


tasteless and relatively less soluble in water, for example, starch,
cellulose, inulin, etc

CLASSIFICATION

Monosaccharides
• The term ‘monosaccharides’ is employed for such sugars that on
hydrolysis yield no further, lower sugars.
• The monosaccharides are subdivided as bioses, trioses, tetroses, pentoses,
hexoses, heptoses, depending upon the number of carbon atoms they
possess.
Bioses
• They contain two carbon atoms. They do not occur free in nature.
Trioses
• They contain three carbon atoms ,for example, glyceraldehydes.
Tetroses
• They contain four carbon atoms, for example, erythrose, threose, etc.

14
2.CARBOHYDRATES NOTES BY BILAL MALIK

Pentoses
• They are very common in plants and are the products of hydrolysis of
polysaccharides like hamicelluloses, mucilages and gums, for example,
ribose, arabinose and xylose.

Hexoses
• They are monosaccharides containing six carbon atoms and are
abundantly available carbohydrates of plant kingdom. They are further
divided into two types: aldoses and ketoses. They may be obtained by
hydrolysis of
• Aldoses : Glucose, galactose
• Ketoses : Fructose and sorbose

15
2.CARBOHYDRATES NOTES BY BILAL MALIK

• Heptoses
They contain seven carbon atoms, vitally important in the photosynthesis
of plant and glucose metabolism of animals and are rarely found accumulated in
plants, for example, glucoheptose and manoheptose.

Disaccharides:
• Carbohydrates, which upon hydrolysis yield two molecules of
monosaccharides, are called as disaccharides.
• Sucrose Hydrolysis Glucose + fructose (sugarcane), Maltose Hydrolysis
Glucose + Glucose (malt sugar), Lactose Hydrolysis Glucose + Galactose
(cow’s milk).

Trisaccharides:
• These liberate three molecules of monosaccharides on hydrolysis.
• Raffinose Hydrolysis Glucose + fructose + galactose (in beet)
(sugarcane),
Gentianose Hydrolysis Glucose + Glucose + fructose (gentian roots).

Tetra-saccharides
• Stachyose, a tetrasaccharide, yields on hydrolysis, four molecules of
monosaccharide, found in manna.

16
2.CARBOHYDRATES NOTES BY BILAL MALIK

Polysaccharides:
• On hydrolysis they give an indefinite number of monosaccharides.
• By condensation, with the elimination of water, polysaccharides are
produced from monosaccharides.
• Depending upon the type of product of hydrolysis these are further
classified as Pentosans and Hexosans.
• Xylan is pentosan, whereas starch, insulin and cellulose are the examples
of hexosans.
• Cellulose is composed of glucose units joined by β-1, 4 linkages, whereas
starch contains glucose units connected with α- 1, 4 and α- 1, 6 units.
• Polyuronides, gums and mucilages are the other pharmaceutically
important polysaccharide derivatives.

SUCROSE:
 It is called table sugar.
 It is formed by combination of 2 units of monosaccharide Fructose &
Glucose.

17
2.CARBOHYDRATES NOTES BY BILAL MALIK

SUGAR CANE:
 Common names:
Sugar cane, noble cane (English), sarkara (Sanskrit), paunda (Hindi).
 Botanical name:
Saccharum officinarum L.
 Family:
Poaceae (grass family)
 Part used:
 Thick, joined fibrous stalks.
 Habitat
Hot humid tropics, in moist soils.
Brazil is the largest producer of Sugar cane in world. It is also cultivated in
Pakistan, India, China, Thailand & Mexico.

DESCRIPTION:
 Tropical, perennial grass, that form lateral shoots.
 Sweet in taste , outer surface is greenish brown, while inner surface is
yellowish white.

18
2.CARBOHYDRATES NOTES BY BILAL MALIK

 Typically it is 3 to 4m in length & 5cm in diameter.

CULTIVATION:
 It is cultivated in Tropic & Sub tropic areas with plentiful supply of water
& Sun light for continuous period of more then 6 month each year.
 It grows on highly fertile soil.
 It is harvested by hand or mechanically.
 In hand harvesting, the field is first set on fire,
 Fire burns dry leaves & kills the insects etc leaving stalks & roots harm
less & then they are Cut just above the ground level.
 In mechanical harvesting, Sugar cane harvester is used.
PROCESSING:
Two stages
1. Milling, 2. Refining.
1. MILLING:
In this stage, the cane juice is extracted by different techniques.
2.REFINING
 The juice is centrifuged to remove impurities.
 After this the sugar solution is clarified by adding phosphoric acid and
Ca. hydroxide.
 After filtering the syrup is decolorized by activated carbon.

19
2.CARBOHYDRATES NOTES BY BILAL MALIK

 The purified syrup is then concentrated and crystallized in vacuum to


produce refined sugar.
 To produce granules, sugar must be dried by heating in rotary dryer and
then by blowing cool air through it.
CHEMICAL CONSTITUENTS :
 11-16 % fibers
 12-16 % soluble sugars (sucrose)
 2-3 % non sugar
 63-73 % water

Uses:
 Used as table sugar.
 Used as sweetening agent in syrups.
 Used as demulcent.
 Used as bacteriostatic and preservative.
 Used to mask disagreeable tastes in troches and tablets.
 Used to relive low B.P.
 Used to treat diarrhea.
 It is also used as taste enhancer and preservative in food industry.

SUGAR BEET:
Synonyms-
Spinach Beet. Sea Beet. Garden Beet. White Beet.
BOTANICAL NAME :
Beta vulgaris (Linn.)
FAMILY :
Chenopodiaceae.

20
2.CARBOHYDRATES NOTES BY BILAL MALIK

Parts Used---Leaves, root.


Habitat :
IT is grown in temperate zone.
Russia is the largest producer of sugar beet, it is also cultivated in U.S,
Germany, Ukraine, Turkey.

https://www.youtube.com/watch?v=ZVxPkv0r7JY

DESCRIPTION :

• It has conical , white fleshy root.


21
2.CARBOHYDRATES NOTES BY BILAL MALIK

• Sugar is formed through process of Photosynthesis in leaves and stored


In root.
• Its weight is mostly o.5 – 1 kg.
• It is green or purple In color.
• It has broad leaves with crown which is usually leveled with or just
above ground surface.
PROCESS :
 After harvesting the beet roots are washed , sliced into thin strips and
passed through machines to extract sugar content.
 The juice is mixed with hot milk of lime (Ca. hydroxide in water) , the
thin juice is concentrated via evaporation to make thick juice ,
 The crystals are then formed which are further dried and granulated to
form sugar.
Chemical constituents:
 It contains certain amount of sucrose,
 The HCl-isolated pectin contained 81.8% galact-uronic acid.
 Also contain folic acid and other minerals such as sodium , Mg , Ca , Fe
,vitamin A , vitamin C.
Uses:
 1.It have zero saturated fat , contain increased carbohydrates and is great
instant source of energy.
 2.It also contain minerals such as sodium , magnesium , calcium , iron ,
vitamin A , vitamin C etc.
 3.Contain folic acid for production & maintenance Of new cell.
 4.It guard against cancers especially colon cancer [Pectin extracted from
sugar beet, used as an anticancer].
 5. It cleanse the blood , cleanse colon & strengthen gall bladder & liver.
 6. It also treats & cure boils and acne.
 7.also used in beverages.

22
2.CARBOHYDRATES NOTES BY BILAL MALIK

Dextrose:
D-glucose
D(+)-glucopyranose
 Naturally present in grapes and other fruits.
Preparation
 Usually obtained by hydrolysis of starch.
 Heating at 45 lb presure for 35 min.
 Dextrose is then crystalized,washed and dried.
 99-100% pure.
Uses:
 NUTRIENT ( mouth, enema, injection)
 Dextrose and NaCl inj
 Present in anticoagulant citrate phosphate dextrose soln (storage of
blood).
 Food industry

Liquid Glucose:
 Obtained by incomplete hydrolysis of starch
 Composed of Dextrose, also contains Dextrin, Maltose and Water.
Preparation
 Corn starch is mixed with dil HCl at 30 lb pressure for 22 min
 Centrifuged and filtered
 Evaporated to syrupy liquid.
Description:
 Thick colourless or yellowish liquid
 Odourless and sweet in taste.

23
2.CARBOHYDRATES NOTES BY BILAL MALIK

Uses:
 Sweetning agent in pharma industry
 Substitute of sucrose in syrup
 Tablet binder and coating agent.

Fructose:
 D-fructose,
 Levulose ,
 D(-) fructopyranose,
 Fruit sugar.

 A Ketone sugar occurs naturally in fruits and honey.


 Also obtained from sucrose and inulin on hydrolysis.

Description:
 Colourless crystals or white crystalline powder
 Odourless and sweet in taste
 Soluble in water
Uses:
 Food for diabetic people
 Diabetic acidosis
 Infant feeding formulas
 Ingredient in electrolyte replinsher, given parentrally.

24
2.CARBOHYDRATES NOTES BY BILAL MALIK

HONEY:
Synonyms
Madhu, Madh, Mel, Purified Honey.
Biological Source
Honey is a viscid and sweet secretion stored in the honey comb by various
species of bees, such as Apis mellifera, Apis dorsata, Apis florea, Apis indica
belonging to family Apideae.
Geographical Source
Honey is available in abundance in Africa, India, Jamaica, Australia,
California, Chili, Great Britain and New Zealand.

Collection and Preparation of Honey:


 The nectar of the flowers is a watery solution containing 25% sucrose
and 75% water. The worker bee sucks this nectar through its hollow tube
of mouth (proboscis) and deposits in honey-sac located in abdomen.
 The enzyme invertase present in saliva of the bee converts nectar into
invert sugar, which is partially utilized by the bee and the remaining is
deposited into honey comb.
 Honey comb is smoked to remove the bees and honey is obtained by
applying the pressure to it or allowing it to drain naturally.
 The honey of commerce is heated to 80°C and allowed to stand. The
impurities which float over the surface are skimmed off and the liquid is
diluted with water to produce honey of 1.35 density.

 Honey is liable to fermentation, unless it is suitably processed. Honey is


heated to 80°C and cooled rapidly before it is sent to the market, so as to
avoid fermentation.
 If honey is not prepared by centrifugation method, is required to be
filtered through wet cloth or funnel.

HONEY
Morphology:

25
2.CARBOHYDRATES NOTES BY BILAL MALIK

 Pale yellow to reddish brown viscid fluid


 Pleasant and Characteristic odour
 Sweet, slightly acrid Taste
 The taste and odour of honey depends upon the availability of
surrounding flowers from which nectar is collected.
 On prolonged storage it usually turns opaque and granular due to
crystallization of dextrose and is termed as ‘Granulated honey’.
History:
 The honey was first known historically as a flavoured sweetening
agent and was once the official honey of the National Formulary.
 Its use dates back to ancient times, with Egyptian medical texts
(between 2600 and 2200 B.C.) mentioning honey in at least 900
remedies.

 During war time it was used on wounds as an antiseptic by the ancient
Egyptians, Greeks, Romans, Chinese, and even by the Germans as late as
World War I.
 Almost all early cultures universally hailed honey for its sweetening and
nutritional qualities, as well as its topical healing properties for sores,
wounds and skin ulcers.
 It has consistently appeared in modern use for the same purposes by the
laity and medical profession.
 Today, bees are commonly kept in Europe, the Americas, Africa and
Asia; at least 300,000 tons of honey is produced annually.
Chemical Constituents:
Moisture 14–24%,
Dextrose 23–36%,
Levulose (Fructose) 30–47%,
Sucrose 0.4–6%,
Dextrin and Gums 0–7% and
Ash 0.1–0.8%.

26
2.CARBOHYDRATES NOTES BY BILAL MALIK

 Besides, it is found to contain small amounts of essential oil, beeswax,


pollen grains, formic acid, acetic acid, succinic acid, maltose, dextrin,
colouring pigments, vitamins and an admixture of enzymes, diastase,
invertase and inulase.
 The sugar contents in honey varies widely from one country to another as
it is exclusively governed by the source of the nectar and also the
enzymatic activity controlling the conversion into honey.

Uses:
 Honey shows mild laxative, bactericidal, sedative, antiseptic and
alkaline characters.
 It is used for cold, cough, fever, sore eye and throat, tongue and duodenal
ulcers, liver disorders, kidney and other urinary disorders, pulmonary
tuberculosis, marasmus, rickets, scurvy and insomnia.
 It is applied as a remedy on open wounds after surgery.
 It is also useful in healing of carbuncles other and skin inflammation.
 Honey, mixed with onion juice, is a good remedy for arteriosclerosis in
brain.
 Diet rich in honey is recommended for infants, convalescents, diabetic
patients and invalids.
 Honey is an important ingredient of certain lotions, cosmetics, soaps and
creams.
 Honey is used as an ingredient in various cough preparations.
 It is also used to treat asthma.
Adulterant and Substitutes:
Due to the relatively high price of pure honey, it is invariably adulterated
ether with artificial invert sugar or simply with cane-sugar syrup.
These adulterants or cheaper substituents not only alter the optical
property of honey but also its natural aroma and fragrance.

27
2.CARBOHYDRATES NOTES BY BILAL MALIK

STARCH:
Synonyms
Amylum.
Biological Source
Starch consists of polysaccharide granules obtained from the grains of
Maize (Zea mays Linn.);
Rice (Oryza sativa Linn.)
Wheat (Triticum aestivum Linn.); belonging to family Gramineae .
Potato (Solanum tuberosum Linn.), family Solanaceae.

Geographical Source
Most of tropical, as well as, sub-tropical countries prepare starch
commercially.

Preparation of Starch
Potato Starch:
 The potatoes are washed to remove the earthy matter.
 They are crushed or cut and converted into slurry.
 Slurry is filtered to remove the cellular matter.
 After filtration, the milky slurry containing starch is purified by
centrifugation and washing.
 Then, it is dried and sent to the market.

28
2.CARBOHYDRATES NOTES BY BILAL MALIK

Rice Starch :
 The broken pieces of rice resulted during the polishing are used for
processing.
 The pieces of rice are soaked in water with dilute sodium hydroxide
solution (0.5%), which causes softening and dissolution of the gluten
(general name for wheat or rice protein).
 The soaked rice pieces are crushed and starch prepared as preceeded in
potato.

Corn starch:
 Maize grains are washed thoroughly with water to remove the adhered
organic matter.
 They are softened by keeping in warm water for 2–3 days.
 Sufficient sulphur dioxide is passed to the medium to prevent
fermentation.( Fermentation is a metabolic process that converts sugar
to acids, gases, or alcohol. Endosperm is a tissue produced inside the
seeds of most of the flowering plants following fertilization. It surrounds
the embryo and provides nutrition in the form of starch, though it can
also contain oils and protein)
 The swollen kernels are passed through attrition mill to break the grains,
so as to separate the endosperm and outermost coating.
 The starchy material contains gluten; most of this is removed by simple
sieving and then by washing several times with cold water.
 Then centrifuged or filter-pressed and finally, dried in flash dryers on a
moving belt dryer to get starch.

Wheat Starch:
 The wheat flour is converted into dough(Dough= Flour mixed with
water) and kept for a while.
 The gluten in the dough swells and the masses are taken to grooved
rollers, wherein water is added with constant shaking.

29
2.CARBOHYDRATES NOTES BY BILAL MALIK

 The starchy liquid coming out of the rollers is processed conveniently to


take out the starch, which is then dried and packed suitably.
Description:
 Colour:
Rice and maize starch are white, while wheat is cream coloured and
potato is slightly yellowish.
 Odour
Odourless
 Taste
Mucilaginous (Mucilaginous polysaccharide substance extracted as
a viscous or gelatinous solution from plant roots, seeds, etc., and used in
medicines and adhesives.)
 Shape
Starch occurs as fine powder or irregular or angular.

Microscopic Characters:
Rice Starch:
The granules are simple or compound.
Simple granules are polyhedral while compound granules are ovoid.

Rice starch
30
2.CARBOHYDRATES NOTES BY BILAL MALIK

Wheat Starch:

 Simple lenticular granules which are circular or oval in shape.

 Granules contain hilum at the centre and concentric faintly marked


striations.
 Rarely, compound granules with two to four components are also
observed.

Wheat starch

Maize Starch:
Granules are polyhedral or rounded, with distinct cavity in the centre or
two to five rays cleft.

31
2.CARBOHYDRATES NOTES BY BILAL MALIK

Potato Starch:
 Generally, found in the form of simple granules, which are sub-
spherical, somewhat flattened irregularly ovoid in shape.
 Hilum is present near the narrower end with well-marked.

Chemical Constituents:
 Chemically starch contains two different polysaccharides,
Amylose (β-amylose) and
Amylopectin (α-amylose).
 Amylose is water soluble and amylopectin is water insoluble, but swells
in water and is responsible for the gelatinizing (Starch gelatinization is a
process of breaking down the intermolecular bonds of starch molecules
in the presence of water and heat ) property of the starch.
 Amylose gives blue colour with iodine, while amylopectin yields bluish
black colouration.

32
2.CARBOHYDRATES NOTES BY BILAL MALIK

Identification Tests:
 1. 1 g of starch is boiled with 15 ml of water and cool. The translucent
viscous jelly is produced.
 2. The jelly turns deep blue by the addition of solution of iodine.

Blue colour disappears on warming and reappears on cooling.

Uses:
 As a nutritive, demulcent, protective and as an absorbent.
 In the preparation of dusting talcum powder for application over the
skin.
 As antidote in iodine poisoning.
 As a disintegrating agent in tablets
 As diluent in dry extracts of crude drug and is a diagnostic aid in the
identification of crude drugs.
 As a starting material for the commercial manufacture of liquid glucose,
dextrose and dextrin(Dextrins are a group of low-molecular-weight
carbohydrates produced by the hydrolysis of starch or glycogen).

Cellulose:
 Cellulose (C6H10O5)n is a long-chain polysaccharide carbohydrate, of beta-
glucose.
 It forms the primary structural component of plants and is not digestible
by humans

Structure of Cellulose
33
2.CARBOHYDRATES NOTES BY BILAL MALIK

History:
 Being found as the principal component of cell walls in higher plants
where it provides the main structural feature. Therefore,
 Cellulose is considered as the most abundant naturally occurring organic
substance on earth.
 It was first noted as such in 1838 by Anselm Payen.
 It occurs in almost pure form in cotton fibre at 98% in combination with
lignin and hemicellulose.
 Cellulose is the most abundant form of living terrestrial biomass.

Applications:
 Cellulose is processed to make cellophane and rayon.
 Cellophane has several applications in pharmaceutical packaging due to
its suitable characteristics such as good compatibility, durability,
transparency and elasticity.
 Cellulose is also used within the laboratory as a solid-state substrate for
thin layer chromatography.
 Cellulose is a major constituent of paper.
Derivatives:
 The hydroxyl groups of cellulose can be partially or fully reacted with
various chemicals to provide derivatives with useful properties.
 They have the general formula

Cellulose-O-R
 Cellulose esters and cellulose ethers are the most important commercial
materials.
 Among the esters are cellulose acetate and triacetate, which are used in
cosmetics.

34
2.CARBOHYDRATES NOTES BY BILAL MALIK

Uses of Cellulose:
 Anticake agents
 Emulsifier
 Stabiliser
 Dispersing agent
 Thickener
 Gelling agent
Microcrystalline cellulose (MCC) is the most known cellulose which
extensively used in pharmaceutical industries. MCC grades are
multifunctional pharmaceutical excipients which can be used as
 compressibility enhancer,
 binder in wet and dry granulation processes,
 thickener and viscosity builder in liquid dosage forms
 and free-flowing agents in solid dosage forms.
 Application in bioadhesive and mucoadhesive drug delivery systems.
 Bioadhesives are considered as novel drug delivery systems. These
dosage forms are formulated to use on the skin and mucus membranes
of gastrointestinal, ear, nose, eye, rectum and vagina.
 The main excipients of these formulations are adhesive and film-former
polymer(s).

Cellulose based products:


 Cellulose is the major constituent of Cotton (98%)and Wood(40-
50%).Cotton and wool are the major reservoirs for all cellulose products
such as paper, textiles and construction materials.
 The Paper production industry is of great economic significance to the
world.
 The Textile industry is of great economic significance and relies heavily
on cellulose both for natural and synthetic fibres.

35
2.CARBOHYDRATES NOTES BY BILAL MALIK

 The construction industry also utilizes cellulose in products i.e. Carbon


fibre reinforced polymers (CFRP’s) and cellulose nitrate. This was the
first successful plastic. It is used in making toilet pieces and other
industrial items.

Cellulose based Products:


Cellulose acetate (CA),
The polymers like cellulose acetate (CA), cellulose
acetate phthalate (CAP) and cellulose acetate butyrate (CAB) do not form gel
in presence of water and they are widely used for preparing pH sensitive and
semi-permeable microporous membranes.
 These membranes are employed for wide variety of controlled release
coating of pharmaceuticals especially in enteric or osmotic drug delivery
devices.
 Used in making packaging materials, toys, tools etc.

Ethyl cellulose
 Aqueous dispersions of ethyl cellulose or its organic solutions can be
used for coating of extended release formulations. After ingestion of
these formulations, an insoluble viscose gel is forming around the tablet
which doesn’t allow to drug to freely release from dosage form.
 Because of water insolubility of EC, it is often used in conjunction with
water soluble polymers such as MC
 It is the lightest and most expensive of the cellulosics.

Methyl cellulose
 It is used in the food, cosmetic, and pharmaceutical industries.
 Is non toxic, non-allargic and is a weak adhesive.
 Methylcellulose is used as
 a tablet and capsule disintegrant,

36
2.CARBOHYDRATES NOTES BY BILAL MALIK

 a tablet binder, and


 as a viscosity-increasing agent.
 It exists as a free-flowing white powder and dissolves in cold water to
yield a clear gel.

 Methylcellulose (Citrucel) is also a bulk-forming laxative that works by


absorbing water and swelling in the intestines.
 In its pure state it is used for cleaning the spines of books.
 It works as an excellent solvent of hide glue.

37
3.ALKALOIDS BY BILAL MALIK

Alkaloids:
1. Primary metabolites
2. Secondary metabolites
Alkaloids are very important group of chemical compounds; approximately
12,000 in number, having application in different areas of the economy,
industry, trade, and services.
 A precise definition of the term 'alkaloid' (alkali-like) is somewhat
difficult because there is no clear-cut boundary between alkaloids and
naturally occurring complex amines.

Definition: the term “alkaloid” (alkali-like) is commonly used to designate


basic heterocyclic nitrogenous compounds of plant origin that are
physiologically active.
Typical alkaloids are
 Derived from plant sources,
 Basic,
 Contain one or more nitrogen atoms (usually in a heterocyclic ring)
and
 Usually have a marked physiological action on man or other animals.

Deviation from Definition :


 Basicity: Some alkaloids are not basic e.g. Colchicine, Piperine,
Quaternary alkaloids.
 Nitrogen: The nitrogen in some alkaloids is not in a heterocyclic ring e.g.
Ephedrine, Colchicine, Mescaline.
 Plant Origin: Some alkaloids are derived from Bacteria, Fungi, Insects,
Frogs, Animals.

Types of Alkaloids:

39
3.ALKALOIDS BY BILAL MALIK

TRUE
PROTOALKALOIDS PSEUDOALKALOIDS
ALKALOIDS

Derived from NOT derived from amino acids


amino acids
Derived from simple amines

Basic in Basic in Nature Very weak basicity


Nature

N atom in N atom not in heterocyclic N atom in heterocyclic ring or not


heterocyclic ring
ring

e.g. Atropine, e.g. Mescaline, Ephedrine e.g. Caffeine


Morphine

False alkaloids are non alkaloids give false positive reaction with alkaloidal reagents.

New Definition:
Alkaloids are cyclic organic compounds containing nitrogen in a negative state
of oxidation with limited distribution among living organisms.

40
3.ALKALOIDS BY BILAL MALIK

Distribution and occurrence:


Rare in lower plants.
 Dicots are more rich in alkaloids than Monocots.
 Families rich in Alkaloids: Apocynaceae, Rubiaceae, Solanaceae and
Papaveracea.
 Families free from Alkaloids: Rosaceae, Labiatae
Distribution in Plant:
 All Parts e.g. Datura
 Barks e.g. Cinchona
 Seeds e.g. Nux vomica
 Roots e.g. Aconite
 Fruits e.g. Black pepper
 Leaves e.g. Tobacco
 Latex e.g. Opium
Forms of Alkaloids:
 Free bases

41
3.ALKALOIDS BY BILAL MALIK

 Salts with Organic acids e.g. Oxalic, acetic acids


 Salts with inorganic acids e.g. HCl, H2SO4.
 Salts with special acids:
 e.g. Meconic acid in Opium
 Quinic acid in Cinchona
 Glycosidal form e.g. Solanine in Solanum.

Functions of alkaloids in plants:


 There are several speculations about the advantages of their presence
in plants, including:
1. Poisonous agents :
They may act as protective against insects and herbivores due to their
bitterness and toxicity.
2. End products of detoxification reactions:
They are, in certain cases, the final products of detoxification (waste
products).
3. Regulatory growth factors:
They, sometimes, act as growth regulators in certain metabolic systems.
4. Reserve substances capable of supplying nitrogen or other elements
necessary to the plant’s economy.
5. Source of energy : They may be utilized as a source of energy in case of
carbon dioxide deficiency
6. Source of nitrogen in case of nitrogen deficiency

Nomenclature:
 The name of all alkaloids should end with the suffix ‘-ine’.
 The names of the alkaloids are obtained in various ways:
1. From the generic name of the plant yielding them, e.g. atropine.
2 From the specific name of the plant yielding them, e.g. cocaine.

42
3.ALKALOIDS BY BILAL MALIK

3 From the common name of the drug yielding them, e.g. ergotamine.
4 From their physiologic activity, e.g. emetine. that acts as emetic.
5 From the discoverer, e.g. pelletierine.
6 A prominent physical character, such as Hygrine that is hygroscopic.

Physical Properties:
I- Condition:
 Most alkaloids are crystalline solids.
 Few alkaloids are amorphous solids e.g. emetine.
 Some are oxygen-free and are liquids that are either:
Volatile e.g. nicotine and coniine, or
Non-volatile e.g. pilocarpine and hyoscine.
II- Color:
The majority of alkaloids are colorless but some are colored e.g.
 Colchicine and berberine are yellow.
 Canadine is orange.
III- Solubility:
 Both alkaloidal bases and their salts are soluble in alcohol.
 Generally, the bases are soluble in organic solvents and insoluble in
water
Exceptions:
 Bases soluble in water: caffeine, ephedrine, codeine, colchicine,
pilocarpine and quaternary ammonium bases.
 Bases insoluble or sparingly soluble in certain organic solvents:
morphine in ether, theobromine and theophylline in benzene.
 Salts are usually soluble in water and, insoluble or sparingly soluble in
organic solvents.
Exceptions:
 Salts insoluble in water: quinine monosulphate.
43
3.ALKALOIDS BY BILAL MALIK

 Salts soluble in organic solvents: apoatropine hydrochlorides are soluble


in chloroform.
 Colour Reagents:
1- Froehd’s Reagent: Phosphomolybdic acid
2- Marqui’s Reagent: Formaldehyde/ Conc. H2SO4
3- Mandalin’s Reagent: Sulphovanidic acid
4- Erdmann’s Reagent: Conc. HNO3/Conc. H2SO4
5- Mecke's Reagent: Selenious acid / conc. H2SO4
6- Shaer's Reagent: Hydrogen peroxide / conc. H2SO4
7- Rosenthaler's Reagent: Potassium arsenate / conc. H2SO4
8- Conc. HNO3

Physico-chemical properties:
 Most alkaloids are well-defined crystalline substances which unite with
acids to form salts.
 In the plant they may exist in the free state, as salts or as N-oxides.
 In addition to the elements carbon, hydrogen and nitrogen, most alkaloids
contain oxygen.
 Coniine and nicotine are oxygen-free and are liquids
 Although colored alkaloids are rare, berberine, for example, is yellow
and the salts of sanguinarine are copper-red.
 As a general rule, alkaloids as bases are not soluble or are sparingly
soluble in water, soluble in apolar or only slightly polar organic solvents.

Alkaloids test:
 2 ml of each extract/fraction in 1% HCl solution and
 added few drops of dragendorff reagent
 which give orange colour precipitate indicates the presence of alkaloids.
Alkaloidal precipitating reagents

44
3.ALKALOIDS BY BILAL MALIK

1. Mayer’s reagent (potassiomercuric iodide solution)


2. Wagner’s reagent (solution of iodine in potassium iodide)
3. Dragendorff’s reagent (potassium bismuth iodide)

Detection of alkaloid:-
-Wagner's test: (I2/kI):Reddish brown precipitate .
-Mayer’s: (HgCl2 Creamy precipitate with True alkaloid.
-Hagger's test: (Picric acid) Yellow precipitate with True alkaloid.
-Dragendroff: (Potassium Bismuth Iodide) Reddish Brown precipitate .

-Tannic acid solution: different alkaloid colored


precipitate .

Classification of Alkaloids:

Generally, there are two broad divisions:


1. Heterocyclic or typical alkaloids, divided into 14 groups according to
their ring structure.
2. Nonheterocyclic or atypical alkaloids, sometimes called ‘protoalkaloids’.
3. Alkaloids are usually classified according to the nature of the
basic chemical structures from which they derive.

45
3.ALKALOIDS BY BILAL MALIK

Me
N

N N N
H H N

Piperidine Pyridine Pyrrolidine Tropane Quinoline

NH N NH
N NH N
H N N N
Isoquinoline Tetrahydro- Indole Imidazole Purine
isoquinoline

46
3.ALKALOIDS BY BILAL MALIK

47
3.ALKALOIDS BY BILAL MALIK

Biosynthetic origin:
 Alkaloids are formed from amino acids some but other precursors like
terpenes or steroids, are often also built into the final alkaloidal skeleton.
 The amino acids that most often serve as alkaloidal precursors include:
phenylalanine, tyrosine, tryptophan, histidine, anthranilic acid, lysine and
ornithine.

Extraction:
-The extraction is fractional extraction (From less Polar to more Polar).
-Defeating by non polar solvent (Petroleum Ether, benzene, alkane,….)
To get red of Chlorophyll, Wax, Volatile oil, Fixed oil.
-Filtration, For marc use methanol or ethanol 95%
Evaporate by rotary evaporator (to Concentrate)
-Add Tartaric acid 2% and Ethyl acetate will separate into two layer:
-Organic layer (For week or neutral alkaloid )

48
3.ALKALOIDS BY BILAL MALIK

-Aqueous layer (acidic layer, Tartaric acid) which have alkaloidal salt. To
break the salt add NH3 or Sodium bicarbonate. then add ethyl acetate
again so will it separate into two layer again:
Aqueous layer (Quaternary alkaloids 4º )
Organic layer (For basic alkaloid 10,2º,3º)

EXTRACTION OF ALKALOIDS:
Any method which possessed following characteristics will be
considered as a good technique; if it will accelerate:
1. Wetting of the surface of the herb particles.
2. Permeability of cell walls.
3. Rate of dissolution of cell contents in the solvent.
4. Outward diffusion of the solution.
IDEAL PROPERTY OF SOLVENT:
1. It should be non-toxic and selective.
2. It should not cause the extract to complex or dissociate.
3. It should be preservative in action.
4. It should promote rapid physiologic absorption of the extract.
5. It should be easily evaporated at low heat.
NOTE:- Alcohol (Ethanol) will meet all above criteria.
SELECTION OF ALKALI:
1. use of strong alkali not recommended in case of fatty drug e.g. seeds
to avoid saponification, which results in strong emulsion during
extraction.
2. Salts of strong base with mineral acid need the use of stronger alkali.
3.Ammonia is a alkali of choice as it is sufficiently basic to liberate most
of alkaloid , as well as ,volatile and easily evaporate after extraction.
Solvents:

49
3.ALKALOIDS BY BILAL MALIK

1.Organic water-immiscible solvent:-Chloroform, Benzene , ether,


ethylene chloride.

2.Organic water-miscible solvent:--Ethyl and Methyl alcohol.


.
3.Aqeous acid:--Cheap but not used because it also extract impurities like
sugar, mucilage, tannins, coloring matter

STAS-OTTO METHOD:
The technique involve the distribution of alkaloidal bases between acid or
aqueous solution and immiscible organic solvent.

Method I:
A). stage1:--Powdered material is moistened with water and mixed with
alkali like sodium & potassium carbonate , ammonia, lime. Make a paste
with water ,dry ,and then re-powder.
Lime(calcium hydroxide),combines with acid , tannins, and other
phenolic substances and sets free alkaloids.
B).Stage2:-- Extract the free alkaloids by hot continous percolation with
chloroform or any other organic solvents.
The free alkaloids dissolve together with other substances soluble in
solvent.
C).Stage3:--Agitate the chloroform soln. with successive portion of
dil.sulphuric acid separating the aqueous layer before adding the next
portion of acid.
D).Stage4:--Make the mixed aqueous liquid alkaline with ammonia,
collect the precipitate that forms, wash with water and dry.
Ammonia decomposes the alkaloidal sulphates forming ammonium
sulphates ,soluble in water ,and the free alkaloid which being practically
insoluble in water is precipitated.

50
3.ALKALOIDS BY BILAL MALIK

Method II:
The powder is extracted with water soluble organic solvents such as
MeOH or EtOH which are good solvents for both salts and free bases.
And the resultant extract is submitted to same process as that of method1.
ADVANTAGE :-- This method requires no alkali, gives good
penetration of drug, therefore only 4 extraction may be needed , whereas
method1 requires 10-12 extraction, i.e. Economical.

Pharmacological activity and uses:


CNS
 depressants (morphine) or
 stimulants (caffeine)
Autonomic nervous system
 Sympathomimetics (ephedrine)
 Sympatholytics (yohimbine)
parasympathomimetic (pilocarpine)
 Anticholinergics (atropine)
 Ganglioplegics (nicotine).

51
3.ALKALOIDS BY BILAL MALIK

 local anesthetics (cocaine),


 agents to treat fibrillation (quinidine),
 antitumor agents (vinblastine),
 Antimalarials (quinine),
 antibacterials (berberine), and
 amebicide (emetine).

52
3.ALKALOIDS BY BILAL MALIK

A)Pyridine --- piperidine Alkaloids:

Areca:
 Synonyms: Areca nut or Betel Nut (Local: Paan Supari )
 Botanical name: Areca catechu
 Family : Palmae
 Part used: Dried, ripe seeds.
 Geo Location: Tropical Pacific, Asia, and parts of east Africa.

53
3.ALKALOIDS BY BILAL MALIK

Description:
 Areca- a Spanish and Portuguese term for betel nut
 Catechu- East Indian name for an astringent extract or juice.
 The seeds are cut into narrow pieces and rolled inside Betel leaf, rubbed
over with lime and chewed by the natives. They stain the lips and teeth
red and also the excrement, they are hot and acrid when chewed.
 It is a medium-sized tree, growing straight to 20 m tall, with a trunk 10–
15 cm in diameter.
 The leaves are 1.5–2 m long, pinnate, with numerous, crowded leaflets.

54
3.ALKALOIDS BY BILAL MALIK

 The areca nut is not a true nut, but rather a drupe. It is commercially
available in dried, cured and fresh forms.
 While fresh, the husk is green and the nut inside is soft while in the ripe
fruit, the husk becomes yellow and nut becomes hard.
 Areca mixed with lime, the leaves of Piper betle and occasionally
gambir is known as “PUNSUPARI”. This mixture is used as a stimulant
masticatory (chewing).
 It Consists of 0.45% alkaloids, 15% tannins, lipids, volatile oils and gum.
 Display of the items usually included in a chewing session: The betel
leaves are folded in different ways according to the country and most
have a little calcium hydroxide daubed inside. Slices of the dry areca nut
are on the upper left hand and slices of the tender areca nut on the upper
right. The pouch on the lower right contains tobacco, a relatively recent
introduction

Constituents:

55
3.ALKALOIDS BY BILAL MALIK

 The medicinal components are primarily associated with the nut and
betel quid.
 The nuts contain at least 9 structurally related pyridine alkaloids,
including arecoline, arecaidine, arecaine, arecolidine, guvacine,
isoguvacine, guvacoline, and coniin.
 The most common is the parasympathetic stimulant alkaloid arecoline
(causes neurotoxicity through enhancement of oxidative stress and
suppression of the antioxidant protective system). It also responsible
for addiction.
 The total alkaloid content can reach 0.45%.
TRADITIONAL USES:
 In Ayurvedic medicine, betel nut is used as a diuretic, digestive,
anthelmintic, astringent, and cardiotonic.
 The nuts are used in Traditional Chinese Medicine to treat diarrhoea, low
blood pressure, slow heart rate, and other intestinal troubles.
 They use the root for liver disease and the fruit along with opium for the
treatment of intestinal troubles.
 The betel nut can cause black stained teeth and gums to those who chew
it regularly, although it is excellent for maintaining a healthy digestive
tract, especially in disease-ridden areas.
 However, it has been proposed that betel nut is a carcinogen. Though this
may be due to the common modern addition of tobacco products. Betel
nut can also cause bronchoconstriction, and so should be avoided by
asthmatics.

LOBELIA:
 Synonyms: Indian tobacco, Puke-weed, Asthma-Weed
 Bot: name: Lobelia inflata
 Family : Lobeliaceae
 Part used: The dried flowering herb, and seeds.
 Geo Location: Dry places in the northern United States, Canada and in
English gardens.

56
3.ALKALOIDS BY BILAL MALIK

Description:
 The herb is named after the botanist Matthias de Lobel, a native of Lille,
who died in London in 1616.
 It is an erect annual or biennial herb, 1 to 2 feet high; flower are stalked
and pale violet-blue in colour.
 Commercially, it is usually prepared in compressed, oblong packages,
the colour is a yellowish green, the odour irritating, the taste, after
chewing, very like that of tobacco, burning and acrid, causing a flow of
saliva.
Constituents:
 Extracts of Lobelia contain 14 alkaloids which LOBELINE is the major
and most important. It has a pungent volatile oil, resin, lipids, and gum.
Lobeline or alpha lobeline

57
3.ALKALOIDS BY BILAL MALIK

This occurs as colorless crystals which are slightly soluble in water but
readily soluble in hot alcohol.
Pharmacological effects:
 Similar but weaker pharmacological effects than nicotine on the
peripheral circulation, neuromuscular junctions, and CNS.
 Lobeline improves acute lung injury in animal study.
 It has antidepressant-like properties in mice.
 Lobeline (10, 20 and 30 mg/kg, i.p.) significantly delayed and
antagonized the onset of Pentylenetetrazol -induced seizures.
 Anti-smoking preparations
 Lobeline sulfate incorporated in tablets or lozenges are smoking
deterrents.
 Lobeline diminishes the behavioral and neurochemical effects of nicotine
and amphetamines, and is considered a potential pharmacotherapy for
drug abuse and addiction.
 Lobeline had placebo effect on decreasing the physical craving for
cigarettes.
Traditional uses :
 Traditionally used by the Native Americans for asthma
 Chronic bronchitis
 Injection of lobeline hydrochloride is used in the re-suscitation of
newborn infants.

58
3.ALKALOIDS BY BILAL MALIK

B) Tropane Alkaloids:

Introduction:
 These are ester alkaloids resulted from the coupling of organic acids with
amino alcohol (Base).
 The parent base is the “Tropane” base.

H
N
1
7 2
NH
6 5
4
3

 Tropane Alkaloids are classified into:


1- Solanaceous Tropane Alkaloids.
2- Erythroxylon (Coca) Alkaloids.

1.Solanaceous Tropane Alkaloids:


 Occurrence:
Atropa, Datura, Hyoscyamus
 Main Alkaloids are:
1- Atropine.
2- Hyoscyamine.
3. Hyoscine (Scopolamine).

1)Atropa belladonna:
The deadly nightshade

59
3.ALKALOIDS BY BILAL MALIK

Synonyms: Deadly Nightshade, Devil’s Herb, Apples of Sodom


Bot name: Atropa belladonna
Family: Solanaceae
Geo Location:
Native to Eurasia, Naturalized in many parts of the world,
Cultivated/harvested in US.
 Atropa
 From the Greek godess Atropos
 Belladonna
 “Beautiful Lady” in Italian
 The name Atropa is derived from that of the Greek goddess
Atropos, one of the three Greek fates or destinies who would
determine the course of a man's life by the weaving of threads that
symbolized his birth, the events in his life, and finally his death,
with Atropos cutting these threads to mark the last of these.
 The name "belladonna" comes from the Italian language, meaning
"beautiful lady"; originating either from its usage as cosmetic for the face
or, more probably, from its usage to increase the pupil size in women.

60
3.ALKALOIDS BY BILAL MALIK

Morphology:

 Low growing perennial herb that grows 2-6 ft tall


 Not hardy
 Thick root
 Leaves
 Simple, alternate
 Flowers
 Solitary bell-shaped
 5-lobe
 Dull red-purple or greenish purple
 Fruit
 Glossy, purple-black berries
 Green berries turn purplish-black as plant matures

61
3.ALKALOIDS BY BILAL MALIK

Active Compounds:

History of Uses:
 Romans used plant as a “weapon”
 Contaminated enemies food storage
 Used to poison the troops of Marcus Antonius during the Parthian
Wars.

62
3.ALKALOIDS BY BILAL MALIK

 Scottish troops used it during a truce to subdue the invading Danes.


 Scottish troops put belladonna into enemies’ liquor [hard alcohol
is an alcoholic beverage] supply
 Waited for enemies to fall asleep and then kill them.
 “Truth serum” in the old days
 Used in many legal battles and court cases
 Cosmetics:
 Spanish and Italian Women
 Extracts used as eye drops to dilate pupils, giving pupils a
more intense, hypnotic, and attractive appeal
 Because pupil dilate when people are aroused; therefore,
making eye contact more intense.
 Pain reducer
- Scopolamine added to morphine to cause “twilight sleep”
 Lessened the pain and mortality of childbirth.
 Life saver:
 In 1943 (WWII), the Germans had developed a nerve gas in which
atropine was the only antidote.

Uses in Medicine:
 Slows action of smooth muscle system
 Parkinson’s symptoms
 Irregularities in heart rate
 Dilates pupils
 Reduces salivation
 Stomach and bladder cramps
 Helps to relax pre-surgery patients
 Combats infection and decreases pain when combined with methylene
blue, phenyl salicylate, and benzoic acid.

63
3.ALKALOIDS BY BILAL MALIK

 Prevents nausea and vomiting caused by motion sickness


 Counteracts the effects of nerve gas.
 Atropine sulphate is used as a mydriatic and
cycloplegic(Cycloplegic drugs are generally muscarinic receptor
blockers. These include atropine, cyclopentolate, homatropine,
scopolamine and tropicamide. They are indicated for use
in cycloplegic refraction (to paralyze the ciliary muscle in order to
determine the true refractive error of the eye) and the treatment of
uveitis.) for eye examinations.
 Hyoscyamine is used as the sulphate or hydrobromide for GI problems
and Parkinson's disease.

Effects on Humans/side effcts:


 Increased/rapid heart rate
 Fits of laughter
 Inability to urinate
 Dilated pupils
 Dryness of mouth
 Nausea, vomiting
 Muscle failure

2) Hyoscyamus niger :
Common Henbane

64
3.ALKALOIDS BY BILAL MALIK

Syn: Common Henbane Hog's-bean.


Bot name: Hyoscyamus niger
Family: Solanaceae
Parts Used: Fresh leaves, flowering tops,branches and seeds
Geo Location: Throughout Central and Southern Europe and in Western Asia,
extending to India and Siberia.

History:
• Its botanical name Hyoscyamus is derived from the Greek words hyos
and cyamos, signifying 'the bean of the hog,' which animal is supposed to
eat it with impunity.
• An old AngloSaxon name for it was 'Belene,' probably from the bell-
shaped flowers; then it became known as 'Hen-bell,'
• and from the time that its poisonous properties were recognized this name
was changed to 'Henbane.
• It is also inclined that the name Henbane is derived from the Spanish
hinna (a mule), e.g. 'henna bell,' referring to the similarity of its seed-
vessel to the bell hung upon the neck of the mules.
• The medicinal uses of Henbane date from remote ages; it was well known
to the Ancients, being particularly commended by Dioscorides (first
century A.D.), who used it to procure sleep and allay pains.
• The annual and biennial form of henbane exist and both are used for
medicine but biennial is considered official

Morphology :

65
3.ALKALOIDS BY BILAL MALIK

The plant growing during summer to a height from 1 to 2 feet.


• The leaves are greyish-green colour and spread out on all sides from
the root, they are oblong with acute points.
• The flowers often yellow, without any purple markings
• The seed-capsule opens transversely by a convex lid and contains
numerous small seeds.
• The whole plant has a powerful, oppressive, nauseous odour.
Constituents:
• The chief constituent of Henbane leaves is the alkaloid
• Hyoscyamine,
• together with smaller quantities of Atropine and
• Hyoscine.
• The chief constituent of the seeds is about 0.5 to 0.6 per cent of alkaloid,
consisting of
• Hyoscyamine,
• with a small proportion of Hyoscine.
• The seeds also contain about 20 per cent of fixed oil
Medicinal Uses:
 Antispasmodic, hypnotic, mild diuretic. The leaves have long been
employed as a narcotic medicine.
 It is similar in action to belladonna and stramonium, though milder in its
effects.
 The drug combines the therapeutic actions of its two alkaloids,
Hyoscyamine and Hyoscine.

66
3.ALKALOIDS BY BILAL MALIK

3.DATURA
Jimson Weed

Syn : Jimson weed, Thorn Apple, Mad Apple

Bot Name : Datura stramonium


Family : Solanaceae
Parts Used : Leaves, seeds.
Habitat : Throughout the world, except the colder or Arctic regions.

History :
 The name “Jimson” comes from the word “Jamestown.” Early colonists
were known to have found the weed growing in abundance in Jamestown.
 Dating and analysis of remains show 4000 years of use.
 Was used as an aphrodisiac in the Middle Ages.
 Very toxic and can cause hallucinations

67
3.ALKALOIDS BY BILAL MALIK

Description:
 Grows to about 1.5m tall.
 Annual shrub that grows mainly in the summer months (July – October).
 Requires sunlight to grow.
 Prefers neutral or basic, dry soils.
 Large, white, funnel shaped flowers grow to about 5-10cm long.
 Its fruits are large, thorny pods filled with seeds.

.
Traditional Uses:
 Aphrodisiac
 Wound and burn healer
 Treating colds and asthma
 Recent uses include treatments of epilepsy, acute mania
 Over-the-counter powders and cigarettes were sold for asthma treatment.
Banned in 1968 as an over-the-counter drug.
Preparations:
 Leaves are rolled into cigarettes for asthma treatment
 Seeds can be crushed and used in drinks or teas
 Flowers can be boiled
 Leaf extracts or seeds can be made into pill form.

68
3.ALKALOIDS BY BILAL MALIK

Constituents:
 Atropine
 Scopolamine (main cause of hallucinations)
 Hyoscyamine
 Other tropanes.

Scopolamine:
 Central nervous system depressant
 Antimuscarinic effects similar to atropine
 Commonly used to prevent motion sickness
 Blocks short-term memory
 Also used as a gastrointestinal and urinary antispasmodic
Hyoscyamine:
 Has similar, but more potent, antimuscarinic effects as atropine and
scopolamine
 Used as an adjunct in treatments of peptic ulcer disease and Zollinger-
Ellison syndrome

69
3.ALKALOIDS BY BILAL MALIK

 Antidote to cholerinesterase inhibitors


Contraindications:
 Due to the dangerous effects of datura, its use is not recommended, but is
still used in many areas.
 The accumulation of acetylcholine leads to persistent stimulation of
nicotinic receptors, possibly altering fetal development.
 Adverse Effects
 All parts of Datura are toxic
 Overdosing on Jimson weed will lead to:
 Visual hallucinations
 Disorientation
 Speech incomprehension
 Dilated pupils
 Can be fatal
 Many cases of severe acute anticholinergic toxidrome
 Delirium, agitation and seizures
 Scopolamine is known to be the main cause of hallucinations

70
3.ALKALOIDS BY BILAL MALIK

C) Quinoline alkaloids

 Quinoline alkaloids
 Cinchona Alkaloids
 It diverting to 4 main compounds
 Quinine.
 Cinchonine.
 Cinchonidine.
 Quindine.

Cinchona
Peruvian Bark

71
3.ALKALOIDS BY BILAL MALIK

 Synonyms
Red Bark Cinchona Bark Peruvian Bark
Quina , Fever tree
 Bot Name;
Cinchona officinalis

Family Rubiaceae
 Part Used : Dried Bark from stem and branches.
72
3.ALKALOIDS BY BILAL MALIK

 Habitat ; South America, but cultivated in India, Java, Ceylon, etc.


History:
 The name of the genus is from Chinchón, the wife of a viceroy of Peru in
1638.
In the Viceroyalty of Peru, the court physician was summoned and urged
to save the countess from the waves of fever and chill threatening her life,
but every effort failed to relieve her.

 At last, the physician administered some medicine he had obtained from


the local Indians, who had been using it for similar syndromes. The
countess survived the malarial attack and reportedly brought the cinchona
bark back with her when she returned to Europe in the 1640s.
 The Cinchona plants are large shrubs or small trees with evergreen
foliage, growing 16–49 ft in height.
 The leaves are opposite, rounded to lanceolate and 10–40 cm long.
 The flowers are white, pink or red, produced in terminal panicles.
 The fruit is a small capsule containing numerous seeds.

Constituents:
Alkaloids
 Quinine,

73
3.ALKALOIDS BY BILAL MALIK

 Cinchonidine,
 Cinchonine,
 Quinidine,
 Quinamine,
 Hydroquinine, and
Quinic acid

Quinidine

74
3.ALKALOIDS BY BILAL MALIK

Cinchonidine Cinchonine

Medicinal Uses:
 Quinine has been used for the treatment of malaria and associated
febrile states
 Febrifuge, tonic and astringent; valuable for influenza, neuralgia and
debility.
 The liquid extract is useful as a cure for drunkenness. The powdered
bark is often used in tooth-powders, owing to its astringency
 Cinchona in decoction is a useful gargle and a good throat astringent.

75
3.ALKALOIDS BY BILAL MALIK

D) Isoquinoline Alkaloids

Opium:

 Synonyms- Poppy, Mawseed


 Bot Name Papaver somniferum
 Family: Papaveraceae
 Parts Used- Capsules, flowers.

76
3.ALKALOIDS BY BILAL MALIK

 Habitat-
The Opium Poppy is indigenous to Asia, and is cultivated largely in
European and Turkey, Persia, India and China for the production of Opium.
 The term opium is from the Greek opion meaning poppy juice,
 Papaver is the Latin name for the poppy
 somniferum is Latin and means to produce sleep.
Description:
 The plant is an erect, herbaceous annual, varying much in the colour of its
flowers, as well as in the shape of the fruit and colour of the seeds.
 All parts of the plant, but particularly the walls of the capsules contain a
system of laticiferous vessels, filled with a white latex.
 The flowers vary in colour from pure white to reddish purple.

 The capsules vary in shape and size. They are usually hemispherical, but
depressed at the top, where the many-rayed stigma occupies the centre
 The small kidney-shaped seeds, minute and very numerous, are attached
to lateral projections from the inner walls of the capsule and vary in
colour from whitish to slate.
 Opium is extracted from the poppy heads before they have ripened.

77
3.ALKALOIDS BY BILAL MALIK

 When the petals have fallen from the flowers, incisions are made in the
wall of the unripe capsules.
 Care being taken not to penetrate to the interior.
 The exuded juice, partially dried, is collected by scraping.
 The scrapings being formed eventually into cakes, which are wrapped in
poppy leaves or paper and further dried in the sun.
 The white milky juice darkening during the drying.

Raw opium

Collection:

78
3.ALKALOIDS BY BILAL MALIK

79
3.ALKALOIDS BY BILAL MALIK

History:
 The drug was known in very remote times and the Greeks and Romans
collected it.
 It is probable that the physicians of the Arabian school introduced the
drug into India, as well as into Europe.
 It was originally used only as a medicine, the practice of opium eating
having first arisen, probably in Persia.
Chemical constituents:
More than 30 alkaloids
 Morphine (4 to 21%)
 Codeine (0.8 to 2.5%) less active but more safer
 Noscapine (4 to 8%) [noscapine is not sedative and has been used as
antitussive drug in various countries]
 Papaverine (0.5 to 2.5%) [is an opium alkaloid antispasmodic drug,
used primarily in the treatment of visceral spasm, vasospasm (especially
those involving the heart and the brain, vasodilating agent and
occasionally in the treatment of erectile dysfunction]
 Thebaine (0.5 to 2%). Thebaine is not used therapeutically, but as the
main alkaloid extracted it can be converted industrially into a variety of
compounds including oxycodone, oxymorphone,, naloxone.
 Other include narceine, protopine, laudanine, codamine, cryptopine,
lanthopine and meconidine.

80
3.ALKALOIDS BY BILAL MALIK

Medicinal uses:
 Acts on central nervous system. First stimulates and then depresses the
nerve response.
 Relieve pain, diarrhea, dysentery and cough.
 As antispasmodic
 Antisecretory
 Astringent

81
3.ALKALOIDS BY BILAL MALIK

E) Indole Alkaloids

 1)Rauwolfia
 2)Physostigma
 3)Nux vomica

1) Rauvolfia serpentine:

82
3.ALKALOIDS BY BILAL MALIK

Common Names:-
Chota-Chand (Hindi)
Serpent wood (English)
Snake root (Hindi).
Bot name: Rauvolfia serpentina
Family:- Apocynaceae
Medicinally Important parts:- Roots and leaves.
Geo Location: It is mostly found in the decidous forest of Nepal, India,
Pakistan and Srilanka.

Description:

83
3.ALKALOIDS BY BILAL MALIK

 Evergreen, glabrous, errect and grows up to a height of 60 cm.


 It consist of long irregularly yellowish root.
Botanical description:-
 Leaves:- Simple and opposite
 Fruits:- Round, dark, purple or blackish when ripe.
 Flower:- Glabrous, white or pinkish, with deep red peduncle.

Chemical Constituents:-
The major chemical constituents are:-
 Serpentine
 Reserpine
 Ajmaline
 Ajmalicine
 Ricinn-amine

84
3.ALKALOIDS BY BILAL MALIK

Ajmalicine:-

Molecular structure of Reserpine:-

Therapeutic Uses:
 Fever
 Constipation

85
3.ALKALOIDS BY BILAL MALIK

 Joint pain
 Hypnotic
 As anti-hypertensives
 As sedatives properties
Pharmacological action:
 Reserpine is used to treat mild to moderate hypertension.
 These are normally involved in controlling heart rate, force of contraction
and peripheral resistance.
 The effects of reserpine include respiratory inhibition, stimulation of
peristalsis and influence on the temperature regulating centre.
Ethnomedical uses:
 As the antidote against the bites of venomous reptiles, insect and
animal bites.
 Used in the anxiety states.
 Traditionally being used in the intestinal disorder.

2) Physostigma:

86
3.ALKALOIDS BY BILAL MALIK

• Synonyms:
Ordeal Bean, Calabar Bean
• Bot Name: Physostigma venenosum
• Family: Leguminosae (bean)
• Part Used: Seeds
• Habitat:
West Africa. Has been introduced into India and Brazil.
Description:
 The plant came into notice in 1846 and was planted in the Edinburgh
Botanical Gardens, where it grew into a strong perennial creeper.
 It is a great twining climber, pinnately trifoliate leaves, purplish bean-
like flowers; seeds are two or three together in dark brown pods.

 The natives of Africa employ the bean as an ordeal owing to its very
poisonous qualities. They call it esere, and it is given to an accused
person to eat.
87
3.ALKALOIDS BY BILAL MALIK

 If the prisoner vomits within half an hour he is accounted innocent,


otherwise, considered as guilty.
 A draught of the pounded seeds infused in water is said to have been
fatal to a man within an hour.
Constituents:
The chief constituent is the alkaloid
 Physostigmine (a reversible cholinesterase inhibitor; LD50= 3 mg/kg in
mice.).
 Calabarines,
 Eseridine, and
 Eseramine.
Medicinal Uses:
 Chiefly used for diseases of the eye; it causes rapid contraction of the
pupil and disturbed vision.
 Also used as a stimulant to the unstriped (Unstriped = Muscle tissue that
contracts without conscious control) muscles of the intestines in chronic
constipation.
 It has been shown to improve long term memory (animal studies). No
significant effects in clinical trial for Alzheimer's disease.
 Its action on the circulation is to raise blood-pressure.

 It depresses the central nervous system, causing muscular weakness.


 It has been employed internally for its depressant action in epilepsy,
cholera, and given hypodermically in acute tetanus.

3)Nux Vomica
Synonyms:
Poison Nut, Dog Button, Quaker Button
88
3.ALKALOIDS BY BILAL MALIK

Bot Name: Strychnos nux-vomica


Family: Loganiaceae

Part Used: Dried ripe seeds.


Habitat: India and South East Asia.

 It is a major source of the highly poisonous intensely bitter alkaloids


Strychnine and Brucine, derived from the seeds inside the tree's round,
green to orange fruit.
 The seeds contain approximately 1.5% strychnine, and the dried flowers
contain 1.0%.
 The tree's bark also contains brucine and other poisonous compounds.
Description:
 S. nux-vomica is a medium-sized tree with a short thick trunk.
 The leaves are about 4 inches long and 3 inches wide.
 The flowers are small with a pale green colour with a funnel shape.

89
3.ALKALOIDS BY BILAL MALIK

 The fruit are about the size of a large apple with a smooth and hard shell
which when ripened is a mild shade orange colour.
 The flesh of the fruit is soft and white with a jelly-like pulp containing
five seeds covered with a soft woolly substance.
 The seeds are removed from the fruit when ripe.
 They are then cleaned, dried and sorted.
 The seeds have the shape of a flattened disk completely covered with
hairs.
 The seeds are hard.
Constituents:
 Nux Vomica contains the alkaloids Strychnine , Brucine and traces of
strychnicine.
 The glucoside Loganin, about 3 % fatty matter, caffeotannic acid and a
trace of copper.
 The pulp of the fruit contains about 5 % of loganin together with the
alkaloid strychnicine.

Medical uses:
 There are no uses in modern medicine, although it was widely used in
medicine before World War II.
 The use of strychnine is highly regulated in many countries, and is mostly
used in baits to kill feral mammals including wild dogs, foxes, and
rodents.
 Strychnine is a deadly poison with a lethal dose to humans of about 30 to
120 mg. LD50 = 16 mg/kg in humans, 1–2 mg/kg orally in rats.

https://www.youtube.com/watch?v=OLdCLJ_UqPM

90
3.ALKALOIDS BY BILAL MALIK

 The properties of Nux Vomica are those of the alkaloid


strychnine. Strychnine is eliminated with a half-life of about 12
hours.
 The most direct symptom caused by strychnine is violent
convulsions due to a simultaneous stimulation of the motor or
sensory ganglia of the spinal cord. During the convulsions, there
is a rise in blood pressure.

 Brucine closely resembles strychnine in its action, but is slightly


less poisonous as it only causes paralysis of the peripheral motor
nerves.
 Cytotoxic and Antitumer effects in animal studies

91
3.ALKALOIDS BY BILAL MALIK

F)Imidazole Alkaloids

Pilocarpus:
• Synonyms:
Arrudabrava, Jamguarandi, Juarandi.
• Bot Name: Pilocarpus jaborandi
• Family: Rutaceae
• Part Used: Dried Leaves and roots.
• Habitat: South America.

92
3.ALKALOIDS BY BILAL MALIK

History:
• In sixteenth centaury it was first recorded that the Guarani Indians of
Brazil were using jaborandi to treat mouth ulcers, colds and flu, a remedy
against gonorrhea and kidney stones
• It was often used as an antidote to various poisons or toxins due to its
ability to promote sweating, urination and salivation.
Traditional uses:
In folk medicine systems in the tropics where it grows jaborandi has been used
as a natural remedy for epilepsy, convulsions, gonorrhea, fever, influenza,
pneumonia,
gastrointestinal inflammations, kidney disease, psoriasis, neurosis, and as an
agent to promote sweating.
• The introduction of jaborandi leaves to western medicine was in 1873,
when Symphronio Coutinho, a Brazilian doctor, went to Paris for a
European doctoral degree, taking with him samples of the leaves.
• The studies of a French Physician showed that jaborandi leaves
"increases enormously the perspiration and saliva, and, in a much less
degree, the secretion from the mucous membranes of the nose, the
bronchial tubes, and the stomach and intestines.
Description:
• The shrub grows from 4 to 5 feet high.
• The bark is smooth and greyish.
• The flowers are thick, small, and reddish-purple in colour.
Constituents:
• The principal constituents are the three alkaloids,
• Pilocarpine ,
• Isopilocarpine and
• Pilocarpidine.
• Pilocarpine, only in the proportion of 0.5% is found as a soft, viscous
mass yielding crystalline salts.

93
3.ALKALOIDS BY BILAL MALIK

• Hydrochlorate of Pilocarpine is official in the United States, and in some


European Pharmacopoeias.
Medicinal Uses:
 The crude drug is rarely used, its actions being due to the alkaloid,
Pilocarpine.
 It is antagonistic to atropine.
 Its principal use is as a powerful and rapid diaphoretic. It induces
salivation and excites most gland secretions, some regarding it as a
galactagogue.
 Jaborine, of which there is a small quantity in the leaves, resembles
atropine, and is antagonistic to pilocarpine, so that an impure pilocarpine
may vary largely in effect.
It is useful in
 psoriasis,
 baldness,
 chronic catarrh,
 tonsillitis, and
 particularly in edema .

94
3.ALKALOIDS BY BILAL MALIK

G)Steroidal Alkaloids
 The steroidal alkaloids represent a close structural relationship to sterols
i.e., they contain cyclopentanophenanthrene nucleus.
 The steroidal alkaloids may be broadly classified into two major groups,
namely:
 (a) Solanum Alkaloids
 (b) Veratrum Alkaloids
Cyclo-pentano-phenanthrene nucleus:

Veratrum:
 Synonyms: Hellebore
 Bot. Name: Veratrum album
Family: Lilaceae
Parts Used: Rhizome, root.
Habitat: Europe, Does not occur in the British Isles.

95
3.ALKALOIDS BY BILAL MALIK

Description:
 Veratrum album is distinguished by its yellowish-white flower.
 The fresh rhizome has an alliaceous odour, but when dried it has no
marked smell.
 Its taste is first sweet, then bitter and acrid, leaving the tongue tingling
and numb.
 It is stated to have been one of the principal poisons used in Europe for
arrows, daggers, etc.
Constituents:
It contains
 Jervine,
 Pseudo-jervine,
 Rubijervine,
 Veratralbine and
 Veratrine.
Recent: Jervine, veratramine, and their analogues as prostate cancer migration
and proliferation inhibitors
Medicinal Uses:
 A violent, irritant poison. When snuffed up the nose it occasions profuse
running of the nose; when swallowed, severe vomiting and profuse
diarrhoea.

96
3.ALKALOIDS BY BILAL MALIK

 It was formerly used in cerebral affections, such as mania, epilepsy, etc.,


and for gout, as a substitute for colchicum.
 It is occasionally used in the form of an ointment or decoction in skin
diseases such as scabies, or to kill lice, but even this use is not free from
danger.
 The principal use of the plant is in veterinary medicine.

97
3.ALKALOIDS BY BILAL MALIK

(h) Alkaloidal amines


1)Colchicum.
2)Ephedra,

1) Colchicum:
Common names: Meadow Saffron, Meadow Saffran, Autumn Crocus, Naked
Ladies, Upstart.
Biologcal source:
 Colchicum autumnale Linn.
 The dried ripe seeds, collected in early summer, as well as the (corm)
tubers (dried) are the medicinal parts of the plant.
 The genus name is from Colchis on the black sea, where the plant
flourishes; autumnale refers to the season when the plant blooms.
Distribution:
 Colchicum autumnale is primarily a central European plant found in
Northern Ireland, England, northern Germany, southern Poland, the
Ukraine, Bulgaria, Turkey, Albania and northern Spain. It also grows in
central Asia.
History:
 Dioscorides mentions a colchicum
 the Arabs recommended the use of the corm for gout in medieval times,
 but the drug was abandoned because of its toxicity.
 It again came into use in Europe about the middle of seventeenth century.

98
3.ALKALOIDS BY BILAL MALIK

Morphology:
 Colchicum can grow to 40 cm in height.
 The 3 to 4 broadly lanceolate leaves are tulip-like leaves appear together
with the fruit in spring.
 They are 8 to 25 cm long, 2 to 4 cm wide and overlap at the base to form
a tube.
 Characteristics: All parts of the plant are very poisonous and have a
disgustingly bitter and scratchy taste.
Collection:
99
3.ALKALOIDS BY BILAL MALIK

 Colchicum seeds are the dried seeds of Colchicum autumnale harvested


in the wild in June or July and air dried.
 Colchicum bulbs are the cut and dried tubers of the plant harvested in
early summer.
 After the surrounding leaves have been removed, the tubers are cut into
slices and dried at temperatures of 60°C or lower.
 Colchicum flowers are collected from the wild in late summer and
autumn and then air-dried.
Chemical constituents:
 colchicum contains
 Tropolone alkaloids: colchicine, colchicoside and N-deacetyl- N-formyl-
colchicine; companion alkaloids include demecolcine.

100
3.ALKALOIDS BY BILAL MALIK

101
3.ALKALOIDS BY BILAL MALIK

102
3.ALKALOIDS BY BILAL MALIK

Medicinal uses:
 • Gout
 • Mediterranean fever(amilial Mediterranean fever (FMF), also known
as Armenian disease, is a hereditary inflammatory disorder).
The drug was previously used for skin tumors, psoriasis, necrotic
vasculitis(Necrotizing vasculitis is a rare condition that involves inflammation
of the blood vessel walls.), tendovaginitis(Tendovaginitis=an acute or chronic
inflammation of the tendon sheath, occurring in the region of the hand, the
wrist joint, the forearm (radial and ulnar tenobursitis), the foot, the ankle joint,
and the Achilles tendon (achillobursitis).), and inflammation of the
gastrointestinal tract, liver cirrhosis, acute and chronic leukemia; also for lice,

103
3.ALKALOIDS BY BILAL MALIK

asthma, dropsy(dropsy= old-fashioned or less technical term for oedema;) and


rheumatism.

104
3.ALKALOIDS BY BILAL MALIK

(i) Purine Bases:

Tea:
• Synonyms:
Thea sinensis, Thea Veridis, Thea bohea, Thea stricta Jassamica, Camellia
theifera.
• Bot Name: Camellia sinensis
Family: Camelliaceae
• Part Used: Dried leaf
• Habitat:
Assam; cultivated in Ceylon, Japan, Java, and elsewhere where climate
allows.

Description:
• A small evergreen shrub cultivated to a height of 7 to 8 feet. Bark is
rough and grey. Leaves are dark green, lanceolate margins shortly serrate,
young leaves hairy, older leaves are glabrous.
• Flowers solitary or two or three together on short branchlets.
• Fruit is a smooth, flattened, rounded, a size of a small nut.

105
3.ALKALOIDS BY BILAL MALIK

Production:
• Tea leaves are the fermented and/or dried leaves of Camellia sinensis.
• Green Tea is produced by steaming the fresh-cut leaf. Black Tea is
produced by allowing the leaves to oxidize. During oxidation, enzymes
present in the tea convert many of the polyphenolic therapeutic
substances to less active compounds.
• Oxidation does not occur with Green Tea because steaming process
inactivates enzymes responsible for oxidation.
• The anti-oxidant activity of Green Tea is six times greater than that of
Black Tea
• Constituents:
• Caffeine, tannin (10 to 20 per cent gallotannic acid), boheic acid,
volatile oil, aqueous extract, protein wax, resin, ash and theophylline.
• https://www.youtube.com/watch?v=YrjTQ9M0FFY
Medicinal Uses:
 Black tea is used for improving mental alertness
 Improve learning, memory and information processing skills
 It is also used for treating headache and low blood pressure
 Preventing heart disease, including “hardening of the arteries”
(atherosclerosis) and heart attack
 Preventing Parkinson's Disease; and
 reducing the risk of stomach and colon cancer, lung cancer, ovarian
cancer, and breast cancer
 It is also used for type 2 diabetes, stomach disorders, vomiting, diarrhea,
and as a diuretic to increase urine flow.
 Some people use black tea for preventing tooth decay and kidney stones
 In combination with various other products, black tea is used for weight
loss
Taken moderately by healthy individuals it is harmless, but in excessive
quantities it will produce unpleasant nervous and dyspeptic symptoms, the
green variety being decidedly the more injurious.

106
4)GLYCOSIDES BY BILAL MALIK

Glycosides
 A glycoside is any molecule in which a sugar group is bonded through its
anomeric carbon to another group via glycosidic bond.

 A glycosidic bond is a certain type of chemical bond that joins a sugar


molecule to another molecule.
 A substance containing a glycosidic bond is a glycoside.
 The sugar group is known as the glycone and the nonsugar group as the
aglycone or genin part of the glycoside.
 The glycone can consist of a single sugar group (monosaccharide) or
several sugar groups (oligosaccharide).
 The sugars found in glycosides may be glucose and rhamnose
(monosaccharides)
 or,
 more rarely, deoxysugars such as the cymarose found in cardiac
glycosides.

107
4)GLYCOSIDES BY BILAL MALIK

 In plants glycosides are both synthesized and hydrolysed under the


influence of more or less specific enzymes.
 They are crystalline or amorphous substances that are soluble in water or
alcohols and insoluble in organic solvents like benzene and ether.
 Chemically glycosides are considered as sugar-ether. In pure state
glycosides is mostly levorotatory, colourless, bitter.

CLASSIFICATION:
 On the basis of glycone,
 by the type of glycosidal linkage, and
 by the aglycone

CLASSIFICATION On the Basis of Glycone:


 If the glycone group of a glycoside is glucose, then the molecule is a
glucoside;
 if it is fructose, then the molecule is a fructoside;
 if it is glucuronic acid, then the molecule is a glucuronide, etc.

CLASSIFICATION On the Basis of Glycosidic Linkage :


 1. O-glycosides:
Sugar molecule is combined with phenol or –OH group of aglycon, for
example, cardiac glycosides, anthraxquinone glycosides like sennosides etc
 2. N-glycosides:
Sugar molecule is combined with N of the –NH (amino group) of aglycon,
for example, nucleosides
 3. S-glycosides:
Sugar molecule is combined with the S or SH (thiol group) of aglycon, for
example, Sinigrin.
 4. C-glycosides:

108
4)GLYCOSIDES BY BILAL MALIK

Sugar molecule is directly attached wit C—atom of aglycon, for example,


Anthraquinone glycosides like Aloin, and Flavan glycosides, etc.
CLASSIFICATION On the Basis of Aglycone:

Functions of glycosides:
 Converting toxic materials to non or less toxic.
 Source of energy (sugar reservoir).
 Storing harmful products such as phenol.
 Some glycosides have antibacterial activity, so they protect the plants
from bacteria and diseases.
 Regulation for certain functions(growth).
 Some have beautiful colours (pollenation process).
 Like alkaloids, many plant glycosides possess physiological activity, e.g.
the cardiac glycosides are used medicinally.
Extraction and Isolation:

109
4)GLYCOSIDES BY BILAL MALIK

 Because of the wide range of physical and chemical properties of


glycosides and other constituents associated with them, no common
general method for their isolation is recommended.
 Water, methanol, water-ethanol and ethanol are the most common
solvents for extraction of glycosides.

Precautions before Extraction


Deactivation of enzymes:

 Drying for 15-30 min at 100 0C followed by slow drying at a low


temperature.
 Dipping the fresh material into boiling water or boiling alcohol for 10-
20 min.
 Boiling the fresh plant material with acetone.
 Freeze-drying of the plant material before extraction (lyophilization).

Extraction of glycosides:
 The plant material is macerated with water and then treated with lead
acetate to precipitate proteins and tannins.
 It is then filtered and lead is removed as lead sulphide by a current of
hydrogen sulphide.
 The solution is then shaken with ethanol or water in a Soxhlet extractor.
 In the extract so obtained the enzyme is destroyed by heating it to a
temperature of about 65°C.
 Then, the extract is concentrated to get the glycoside which is then
purified by employing usual methods.

(a) Cardioactive glycosides: Digitalis, Strophanthus and white squill.


(b) Anthraquinone glycosides: Cascara, Aloe, Rhubarb, Cochineal and Senna.
(c) Saponin glycosides: Glycyrrhiza, Sarsaparilla.
(d) Cyanophore glycosides: Wild cherry.

110
4)GLYCOSIDES BY BILAL MALIK

(e) Isothiocyanate glycosides: Black mustard.


(f) Lactone glycosides: Cantharide.
(g) Aldehyde glycosides: Vanilla.
(h) Miscellaneous glycosides: Gentian, Quassia, Dioscorea.

A)Cardioactive glycosides:
Steroid Glycosides
From a therapeutic perspective, this particular group of compounds may be
regarded as one of the most important of all naturally occurring plant products.
Cardio-active Glycosides:
Mechanism:
Increase the force of systolic contraction
Shorten length of systole
As a result
Heart have more time to rest between contraction.
Therapeutic activity depends upon;
1. Chemical nature of aglycone
2. Number of sugars
What are they used for?
 Cardiac glycosides are cardiotonic drugs
 Used in the treatment of congestive heart failure and cardiac arrhythmia
 Aglycone is steroidal.
 Aglycone may be;
 Cardenolide (5-membered lactone at place of R)
 Bufadinolide (6-membered lactone at place of R)

111
4)GLYCOSIDES BY BILAL MALIK

 According to the type of lactone ring Cardiac Glycosides are classified


into:
 Cardinolides:
They are C-23 containing 5-membered unsaturated lactone ring
e.g. Digitalis & Strophanthus
 Bufadienolides:
They are C-24 containing 6-membered unsaturated lactone ring
e.g. Squill
O
O

17

17

112
4)GLYCOSIDES BY BILAL MALIK

The Sugar Part:


 The glycosides usually contain 3 to 4 sugars attached at C-3 OH.
 Beside Glucose and Rhamnose they usually contain deoxysugars.

1 ) Digitalis:

Botanical Origin:
Digitalis purpurea
Digitalis lanata
Family:
Plantigenaceae
Part used:
Dried leaves
Collection:
Leaves collected from 2nd year growth of plant in June before opening of
flower.
Drying is done by applying artificial heat (temperature not more than 65°C).
 Geographical Sources
 It is mainly found in England, Germany, France, North America, India,
Iraq, Japan, Kurdistan, Mexico, Nepal, Spain, Turkey.
113
4)GLYCOSIDES BY BILAL MALIK

 Chemistry:
 Four aglycons in Digitalis
 Digitoxigenin
 Gitoxigenin
 Gitatoxigenin
 Digoxigenin (only in Digitalis lanata)

114
4)GLYCOSIDES BY BILAL MALIK

115
4)GLYCOSIDES BY BILAL MALIK

Derivatives D. purpurea D. lanata

Digitoxigenin Digitoxin Acetyl digitoxin


Glucodigitoxin Lanatoside A
(Digitoxin + 1 (Acetyl digitoxin + 1
glucose) glucose)

Gitoxigenin Gitoxin Lanatoside B


Glucogitoxin (Acetyl gitoxin + 1
glucose)
(Gitoxin + 1
glucose)

Gitatoxigenin Gitatoxin Lanatoside E


(Acetyl Gitatoxin + 1
glucose)

Digoxigenin Digoxin
Acetyl digoxin
Lanatoside C
(Acetyl digoxin + 1
glucose)
Deslanoside
(Digoxin + 1 glucose)

116
4)GLYCOSIDES BY BILAL MALIK

2 ) Strophanthus:
Botanical Origin:
Strophanthus kombe
Strophanthus hispidus
Family:
Apocynaceae
Part used:
Dried ripe seeds
Collection:
Fruits are collected when fully ripen i.e. in June and July

 Geographical Source
 It is mainly found in East Africa near lakes of Nyasaland and
Tanganyika, Portuguese, Cameroon. The tribal are using this seeds as
arrow poison.
 Chemistry:
 Active constituent is Strophanthin.
 Upon hydrolysis it yields;

117
4)GLYCOSIDES BY BILAL MALIK

 Strophanthidin
 Sugars (alpha D-glucose + beta D-glucose + beta D-cymarose)
 Apart from Strophanthin, there are;
 30% fixed oils
 Resin / Mucilage
 Nitrogenous bases ( Trigonellin, Choline )

Uses:
Cardiac stimulant
Diuretic

3) White squill:
Botanical Origin:
Urginea maritima
Family:

118
4)GLYCOSIDES BY BILAL MALIK

Liliaceae
Part used:
Dried fleshy scales of bulb
Collection:
Bulbs are collected in August. Outer scale is removed and inner scale is divided
into pieces and dried in sunlight.

Geographical Source:
 It is found to be indigenous to those countries located near the
Mediterranean region, such as: France, Malta, Italy, Greece, Spain,
Algeria and Morocco.
 Chemical Constituents
 Squill has the following glycosides, namely:
 Glucoscillaren A = Scillarenin + Rhamnose + Glucose + Glucose;
 Scillaren A = Scillarenin + Rhamnose + Glucose;
 Proscillaridin A = Scillarenin + Rhamnose.

119
4)GLYCOSIDES BY BILAL MALIK

Uses:
 Emetic
 Expectorant
 Cardiac tonic
 Diuretic

Physical and Chemical properties of cardiac glycosides:


 Solubility:
 Glycosides are soluble in water and alcohols.
 Increase number of sugars increase water solubility.
 Aglycones soluble in CHCl3 and EtOH.

120
4)GLYCOSIDES BY BILAL MALIK

B) Anthraquinone Glycosides:
Anthracene Glycosides
 Anthracene glycosides represent a major class of glycosides.
 They are abundantly found in various dicot plant families, such as:
Ericaceae, Euphorbiaceae, Leguminoseae, Lythreaceae, Polygonaceae,
Rhamnaceae, Rubiaceae and Verbenaceae to name a few.

 Interestingly, some monocots belonging to the family Liliaceae also


exhibits the presence of anthracene glycosides.
 Besides, they are also present in certain varieties of fungi and lichens.

1)Aloe:
 Synonym: Aloe
 Biological Source:
Aloe is the dried latex of leaves of various species of Aloes, namely:
 Aloe barbadensis Miller (Curacao Aloe);
 Aloe ferox Miller (Cape Aloe);
 Aloe perryi Baker ( Socotrine Aloe);
 Aloe africana Miller and

121
4)GLYCOSIDES BY BILAL MALIK

 Aloe spicata Baker ( Cape Aloe).


 All these species belong to the family Liliaceae.

Geographical Source:
 Curacao, Barbados, Aruba :
 West Indian Islands, Cape Town (South Africa) :
 Cape Aloes in Socotra and Zanzibar Islands
 It is also cultivated in Europe and the North West Himmalayan region in
India.
Preparation:
General Method
 The leaves are transversely cut at the base and the incised ends placed
downwards in a ‘V’ shaped trough(Trough= a long, narrow open
container) having a hole at its bottom.
 The latex drains down the trough and is collected in individual containers
placed beneath.
 The latex is evaporated in a kettle made of copper till it attains such a
consistency that it may be poured into metallic blocks where it gets
solidified.

122
4)GLYCOSIDES BY BILAL MALIK

 When the latex is concentrated gradually and then cooled slowly, it gives
rise to an opaque product. The aloe thus obtained is termed as ‘hepatic’ or
‘livery’ aloe.
 If the latex is concentrated rapidly, followed by sudden cooling the
resulting product appears to be transparent and relatively brittle in nature.
The broken surface has a vitreous or glassy surface. Such a product is
commonly known as ‘vitreous’, ‘lucid’ or ‘glassy’ aloe.
Chemical Constituents:
 Aloe-emodin occurs in the free state and as a glycosides in various
species of Aloe. Its concentration various in different species.
[Antidiabetic, protect the jejunum in rats with sepsis, antibacterial, radio-
protectant against radiation-induced intestinal injury, antiinflammtory
through multiple mechanism, skin disorders,
 Aloin (barbaloin), antiinflammtory, anticancer, antibacterial and
cytotoxic,
 Isobarbaloin (Curacao aloes), β-barbaloin (Cape aloes) .
 Also contain Resin. The principal resin present in the aloes is known
as aloesin [aloesin, or aloe-gel exerts anti-inflammatory activity in a rat
colitis model; in vitro radical scavenging activity of different]
Uses:
 Though, aloes is an official drug, that is mostly used as a purgative by
exerting its action mainly on colon.
 Aloes find its usefulness as an external aid to painful inflammatory
manifestations.
 It constitutes an important ingredient in the ‘Compound Tincture of
Benzoin’ ( Friar’s Balsam).
 Aloe gel made from the mucilaginous latex of A. vera is frequently
employed in the treatment and cure of radiation burns to get immediate
relief from itching and pains.

123
4)GLYCOSIDES BY BILAL MALIK

2) Rhubarb:
 Synonyms:
Rheum; Radix rhei; Rhubarb rhizome.
 Biological Source:
Rhubarb is the rhizome and roots of
 Rheum officinale Bail.,
 R. palmatum L.,
 Rheum emodi Wall ;
 R. webbianum Royle
 Family Polygonaceae.

 The rhizome and roots are mostly collected from 6-7 year old plants just
prior to the flowering season.
 They are commercially available either with intact cortex or partially
decorticated.
Geographical Source
 It is obtained largely from cultivated as well as wild species of Rhubarb
grown in regions extending from Tibet to South East China.
 It is also found in Germany and several European countries.

124
4)GLYCOSIDES BY BILAL MALIK

 In India it is grown extensively in Kashmir, Kullu, Sikkim, Uttar Pradesh,


Punjab.
 It is also found in Nepal.
 It is cultivated in Southern Siberia and North America.
Preparation
 The rhizomes are collected either in spring or in autumn from 6 to 10 year
old plants. Grown at an altitude of more than 3, 000 meters.
 These are duly cleaned, decorticated and dried.
 The relatively larger rhizomes are cut into small pieces either
longitudinally or transversely.
 The cut fragments are threaded and dried in the shade.
 They are also dried artificially in an atmosphere of hot wooden boxes and
exported for commercial consumption.
Chemical Constituents:
 Rhubarb essentially contains mainly the anthraquinone glycosides range
between 2 to 4.5% and the astringent components.
 The anthraquinone glycosides are broadly classified into four categories
as:
 Anthraquinones with —COOH moiety—e.g., Rhein; Gluco-rhein;
 [antiinflammtory in chronic joint diseases in in vivo and in vitro studies

125
4)GLYCOSIDES BY BILAL MALIK

 anthraquinones without —COOH moiety—e.g., Emodin; Aloe-


Emodin; Chrysophanol; Physcion;

 Anthrones and Dianthrones of Emodin—as shown below:

 Heterodianthrones—e.g. Palmidin A, B, and C, which are produced


from two different anthrone molecules, as stated under:
 Palmidin A : Aloe-emodin anthrone + Emodin anthone
 Palmidin B : Aloe-emodin anthrone + Chrysophanol anthrone
 Palmidin C : Emodin anthrone + Chrysophanol anthrone

126
4)GLYCOSIDES BY BILAL MALIK

Uses
 It is used mainly in the form of an ointment in the treatment and cure of
chronic eczema, psoriasis and trichophytosis—as a potent keratolytic
agent. [https://www.youtube.com/watch?v=OMCU26CGkQg]
 It is employed in the treatment of diarrhoea.
 It is also used as a purgative.
Cascara Sagrada
 Interestingly, the very name ‘cascara sagrada’ is Spanish for the sacred
bark;
 Rhamnus is the ancient classical name for buckthorn, and Purshianus was
attributed as a mark of honour and respect to the great German botanist
Friedrich Pursch.
 Synonyms Sacred bark; Chitten bark; Chittin bark; Purshiana bark;
Persian bark; Bearberry bark; Bearwood; Cascara bark; Cortex Rhamni
purshianae.
 Biological Source Cascara sagrada is the dried bark of Rhamanus
purshiana DC., belonging to family Rhamnaceae, from which a naturally
occurring cathartic is extracted.
 It is usually collected at least one year prior to its use.
 Geograhical Source
 It is invariably obtained from cultivated as well as wild shrubs and small
trees grown in Northern Idaho, West to Northern California, North
Carolina, Oregon, in Kenya and Western Canada.
 Preparation
 The bark is collected, during the dry season (April to August) from the 8
to 9 years old trees that have gained a height of 16-18 meters with their
stems having a diameter of 8 to 10 cm, by inflicting longitudinal incisions
on the fully developed stems.
 The bark is carefully stripped off from the branches and the stems.
 They are subsequently allowed to dry in shade by putting their inner-
surface facing the ground so as to permit the completion in the enzymatic
conversion of the anthranol derivative i.e., glycosides (an emetic

127
4)GLYCOSIDES BY BILAL MALIK

principle) to its anthraquinone derivative usually present in the fresh


drug, thereby exerting a milder cathartic activity.
 During this span of one year the drug must be duly protected from rain or
humid environment so as to check the growth of mould.
 Chemical Constituents
 The cascara sagrada bark is found to contain two major types of
anthracene compounds, namely:
 (a) Normal O-Glycosides These are based on emodin like structures and
constitute about 10 to 20% of the total glycosides, and Aloin-like C-
Glycosides These comprise of about 80 to 90% of the total glycosides.
 The two C-glycosides are known as barbaloin and deoxybarbaloin (or
chrysaloin) as given below:

 The main active constituents are four glycosides usually designed as


Cascarosides A, B, C and D.
 it has been established that the cascarosides A and B are solely based on
optical isomers of barbaloin ; whereas cascarosides C and D on optical
isomers of deoxybarbaloin.
 However, from a close inspection of all the four basically primary
glycosides of barbaloin and deoxybarbaloin it may be revealed that they
possess the characteristic features of O-glycosides as well as C-
glycosides.
 Use
 As cathartic
128
4)GLYCOSIDES BY BILAL MALIK

C)Saponin Glycosides
- "Sapo" is Latin name for soap (soap-like)
-Group of organic compounds that form persistent froth when shaken with
water even in dilute solution.
Properties:
• - Soluble in water, alcohol and mixture of them.
• Form persistent froth with water.
• - Used as detergent (surfactant) and emulsifying agent
• - Cause haemolysis of RBC’s if reach the blood (injection).
• - Only small part absorbed when taken orally.
• - Enhance the absorption of other drugs.
• - Form precipitate with Ba(OH)2-

Classification of Saponins:
• According to the nature of the aglycone, saponins are classified into
Steroidal and Triterpenoidal saponins.
• According to sugar: monodesmoside (one sugar chain), Bidesmoside
(two sugar chains)
29 30

21 22 sugars 19 20

12 18 E
18 20
24 26 11 17
17 13
11 25 26
19 1 D 28
D 25 14
sugars 1 C sugars
14 27 8
10 A B
A B 3 27 sugars
3 7
7 HO 5
HO 5
23 24

Steroidal Sapogenin Triterpenoidal Sapogenin

Triterpenoidal Saponins:
- Very common in Dicot plants

129
4)GLYCOSIDES BY BILAL MALIK

- Contain 30 carbon atoms


- Horse chestnut seed: aescin
- Liquorice root: glycyrrhizin
- Senega: senegins

1) Liquorice
• Synonyms :
Glycyrrhiza; Liquorice root; Glycyrrhizae radix.

Biological Sources:
• Liquorice consists of subterranean peeled and unpeeled stolons, roots and
subterranean stems of Glycyrrhiza glabra Linn, and other species of
Glycyrrhiza, belonging to family Leguminosae.

130
4)GLYCOSIDES BY BILAL MALIK

• The word Glycyrrhiza has been derived from the Greek origin that means
sweet root; and glabra means smooth and usually refers to the smooth,
pod-like fruit of this particular specie.
Geographical Sources:
• It is mainly found in China, Europe, India, Iraq, Japan,Kurdistan, Spain,
Turkey, and the United States.
Preparation:
 The roots are usually harvested after 3 to 4 years from its plantation when
they mostly display enough growth.

 The rhizomes and roots are normally harvested in the month of October,
particularly from all such plants that have not yet borne the fruits, thereby
ascertaining maximum sweetness of the sap.
 The rootlets and buds are removed manually and the drug is washed with
running water.
 The drug is first dried under the sun and subsequently under the shade till
it loses almost 50% of its initial weight.
 The large thick roots of the Russian Liquorice are usually peeled before
drying.

131
4)GLYCOSIDES BY BILAL MALIK

 It is an usual practice in Turkey, Spain and Israel to extract a substantial


quantity of the drug with water.
 The resulting liquid is filtered and evaporated in vacuo and the
concentrated extract is molded either into sticks or other suitable forms.
Chemical Constituents:
• Glycyrrhiza comprises of a saponin like glycoside known as
glycyrrhizin.
• Glycyrrhizin is found to be 50 times as sweet as sugar.
• Glycyrrhizin upon hydrolysis loses its sweet taste
• and gives rise to the aglycone glycyrrhetic acid together with two
molecules of glucuronic acid.

COO-
30

12
O
11

K+, Ca++

2 glucuronic acid O
Glycyrrhetic acid

 A host of other chemical constituents essentially include are namely:


• Coumarin derivatives e.g., umbelliferone and herniarin;
• Flavonoid glycoside e.g., liquiritoside; isoliquiritoside, liquiritin;
isoliquiritin, rhanoliquiritin, and rhamnoisoliquiritin;
• Also include asparagine, dihyrostigmasterol, glucose, mannitol and about
20% of starch.
Uses of liquorice:
1) Flavoring agent, sweetener in Pharmaceutical preparation.

132
4)GLYCOSIDES BY BILAL MALIK

2) Demulcent and expectorant.


3) Treatment of peptic ulcer, and gastritis
4) Treatment of Rheumatoid arthritis and Inflammatory conditions even
hemorrhoids.
5) Treatment of liver diseases and hepatoprotective, antiviral.

Side effects:
Salt and water retention, elevation of blood pressure in susceptible persons.

2)Sarsaparilla:

Botanical source
• Smilax aristolochiaefolia
• Smilax regelii
• Smilax febrifuga
• The plants produce numerous roots 3 m or so long which are attached to a
short rhizome.

133
4)GLYCOSIDES BY BILAL MALIK

• The roots are cut sufficient.


However remaining in the ground for the plant to resume its growth.
• Sometimes the rhizome as well as the roots are collected
• After drying in the sun the drug is made into bundles and the bundles into
bales.

Morphology:
• These consist of long roots with or without pieces of rhizome and an
aerial stem.
• The commercial varieties differ from one another in colour, ridges and
furrows.
• The drug is nearly odourless but has somewhat sweetish and acrid taste.
Constituents:
• The main constituent is a saponin glycoside, sarsaponin which on
hydrolysis yields sarsasapogenin and dextrose.
• It also contains a small proportion of starch, sarsapic acid, and fatty acids,
palmitic, stearic, behenic, oleic and linolic.

Uses:
• In the treatment of syphilis, rheumatism and certain skin diseases
• Sarsaparilla is widely used as vehicle, and large quantities are employed
in the manufacture of non alcoholic drinks.
• The genins are used in the partial synthesis of cortisone and other
steroids.
134
4)GLYCOSIDES BY BILAL MALIK

D)Cyanogenic Glycosides
Cyanophore glycosides
• The cyanogenic glycosides are named so because they yield either
hydrocyanic acid upon hydrolysis or they essentially possess a
hydrocyanic acid in the aglycone moiety.
• They are also designated as ‘cyanophore glycosides ’ [blue coloration].
• Rosaceae being the most prominent one amongst them.
• cyanogenic glycoside containing drug substances, as such do not exert
any specific therapeutic activity, but they are invariably employed as
viable pharmaceutical aids, such as: flavouring agents.
• A large number of cyanogenic glycosides were isolated and identified
from various plant sources, namely:
• Linamarin [impaired motor coordination in rats, neurotoxin, ]
• Linustatin
• Lotaustralin and
• Lucumin
• A few important examples of naturally occurring drug substances
containing cyanogenic glycosides are;
• Bitter almond,
• Wild cherry bark and
• Linseed.

1) Wild Cherry Bark:


• Synonyms
Verginian Prune Bark; Wild Black Cherry
• Biological Source
• It is the dried bark of Prunus serotina Ehrk, and Prunus macrophylla
Sieb, belonging to family Rosaceae.

135
4)GLYCOSIDES BY BILAL MALIK

Geographical Source:
• Wild Cherry bark is found to be indigenous to the Eastern States of
USA and certain parts of Canada.
• However, in the United States it is found abundantly in Dakota, Florida,
Missisipi, North Carolina and Virginia.
Preparation:
 It has been established that the wild cherry bark possesses the highest
potency only during the autumn.
 As the inner layer of the bark contains a substantial amount of Hydrogen
cyanide(Hydrogen cyanide poisonous and flammable liquid that boils
136
4)GLYCOSIDES BY BILAL MALIK

slightly above room temperature, at 25.6 °C (78.1 °F).), hence soon after
collection, it is necessary to get rid of the inner layer.
 Consequently, after the removal of cork as well as a portion of the cortex,
give rise to an uniform dark brown coloured product, which is
commercially known as Rossed Bark.
 The resulting Rossed bark is dried in the shade and stored carefully in a
dry place for onward transmission to several countries as a valued export
material.
Chemical Constituents:
• Wild cherry bark essentially contains a cyanogenic glycoside termed as
prunasin
(mandelonitrile glucoside)

• Besides, the drug also contains p-coumaric acid, scopoletin i.e., b-


methylesculetin, benzoic acid and trimethyl gallic acid.

137
4)GLYCOSIDES BY BILAL MALIK

Uses:
 The syrup of wild cherry is mostly employed as a flavoured vehicle in
cough syrup.
 Wild cherry is used for colds, whooping cough, bronchitis and
other lung problems; diarrhea; gout; digestive disorders; pain; and cancer
 It is also used in cough syrups because of its sedative, expectorant,
drying, and cough-suppressing effects.

E) Thioglycosides
• This specific group of glycosides is also referred to as ‘Thiocynate
Glycosides’ or ‘Sulphurated Glycosides’ or Isothiocyanate
Glycosides’ in various literatures.
• The aglycone portion of such glycoside essentially contains isothiocynate
residue having sulphur plus nitrogen atoms.

• In general, the thioglycosides are specifically abundant in several


families, such as:
• Cruciferae,
• Capparidaceae and
• Rosaceae.

138
4)GLYCOSIDES BY BILAL MALIK

1) Black Mustard:
Biological Sources :
These are dried ripe seeds of Brassica nigra Linn., or Brassica juncea Linn,
belonging to family Cruciferae.

Brassica nigra Brassica juncea

Brassica Juncea Seeds

139
4)GLYCOSIDES BY BILAL MALIK

Geographical Sources:
• B. nigra is extensively cultivated in various parts of Europe and United
States.
• B. juncea is widely grown in different parts of India, Russia
Preparation:
• The thioglycoside sinigrin is obtained from the defatted black- mustard
seed by employing standard methods.
• It is usually present in the seeds to the extent of 4%.
• Black mustard seeds are powdered and defatted with petroleum ether.
• The defatted meal is boiled with ethanol to destroy the enzyme.
• The resulting marc is squeezed while hot, dried at 100°C and macerated
in cold water for 3-4 hours with constant stirring, since Sinigrin is fairly
soluble in cold water.
• The liquid content is decanted and maceration is repeated a number of
times to ensure complete extraction of the thioglycoside.
• The combined aqueous extract is collected and treated with mild alkalies,
such as : Barium carbonate, so as to neutralize any free acidity.
• The liquid is now concentrated under vaccum to a syrupy consistency.
• The resulting syrup is boiled with ethanol (95% w/v) for about 2-3 hours
to allow sinigrin to dissolve and at the same time to precipitate the
mucilage- components.
• The alcholoic extracts are filtered and allowed to cool slowly when
sinigrin crystallizes out (approximately 4%).
Chemical Constituents:
• The black mustard seed contains a thioglycoside i.e., sinigrin. It is also
known as myronate potassium or allyl glucosinolate

140
4)GLYCOSIDES BY BILAL MALIK

• The allyl isothiocyanate i.e. the volatile oil component of mustard is


responsible for the characteristics pungent odour of mustard oils.
• Besides it contains fixed oil (30%), proteins (20%) and volatile oil (0.7-
1.3%).
Sinigrin:
• Studies conducted on the pharmacological activities of sinigrin have
revealed
• anti-cancer,
• antibacterial,
• antifungal,
• antioxidant,
• anti-inflammatory,
• wound healing properties and biofumigation.

Uses:
• A paste of black mustard seed is mostly in form of plaster or poultice as
rubefacient and counter irritant.
• In higher doses when administered internally it acts as an emetic.
• Black mustard seeds are invariably used as a widely accepted condiment
in the preparation of pickles, curries and vegetables.
• The fixed oil is widely employed as a popular edible oil.

141
4)GLYCOSIDES BY BILAL MALIK

F) Aldehyde Glycosides
Vanilla:
• Synonyms
Vanilla beans, Vanilla pods.
• Biological Sources
Vanilla consists of the cured fully grown but unripe fruits of Vanilla
fragrans (Salis.), belonging to family Orchidaceae.

Geographical Sources:
• The plant is indigenous to the Eastern coast of Mexico.
• Presently, it is widely cultivated in West Indies, Java, Madagascar,
Ceylon, France, Indonesia, Uganda, Hawaii and India.
Preparation:
• The full grown and unripe fruits are hand picked at that particular stage
when their color changes from green to yellow.

• These fruits are allowed to undergo fermentation (Fermentation is a


metabolic process that converts sugar to acids, gases, or
alcohol.)whereby a characteristic flavour and aroma develops gradually.
142
4)GLYCOSIDES BY BILAL MALIK

• The very important and critical process of fermentation essentially


consists of slow drying in shades at a controlled temperature.
• Fermentation helps in the conversion of vanilloside to vanillin and
glucose respectively.
Chemical Constituents:
 The fruits of vanilla pod contains between 2 to 2.75% vanillin, which is
essentially present in the form of glucovanillin.
 Vanillin in the dose of 200 mg/kg demonstrated aphrodisiac properties in
male wistar rats
 It also contains another glycoside known as glucovanilline alcohol,
which upon hydrolysis yields vanillic alcohol and glucose.
 The vanillic alcohol on oxidation gives vanillin.

Uses:
1. It is mostly used as a pharmaceutical aid for flavouring various liquid
preparations.
2. Vanillin enhances the chocolate flavor of cocoa based malted milk foods.

143
4)GLYCOSIDES BY BILAL MALIK

• G)Lactone glycosides

Cantharidin
is an odorless, colorless
Biological Sources:
Cantharidin, a type of is a chemical compound secreted by many
species of blister beetle, and most notably by the Spanish fly, Lytta vesicatoria
belonging to the family Meloidae
• . It has been found that the soft parts of the insect are the chief seat of
cantharidin. Besides, cantharidincontain 0.5 to 0.95 of cantharidis.

Isolation:
• The various steps involved in the isolation of cantharidin are:
1. The dried insects are collected and powdered. Then treated with an acid
whereby the cantharidin gets liberated in the form of its corresponding
salts.
2. The resulting product is subjected to extraction, of both cantharidin and
fat, by the help of ethyl acetate in a Soxhlet apparatus.

144
4)GLYCOSIDES BY BILAL MALIK

3. The solvent is removed carefully under reduced pressure and the crude
cantharidin crystallizes out.
4. The fat may be removed with the help of petroleum ether, in which
cantharidin is only negligibly soluble.
5. Ultimately, the crude defatted cantharidin is dissolved in a minimum
quantity of hot ethanol and allowed to cool when cantharidin crystallizes
out in its purest form.
Characteristic Features:

145
4)GLYCOSIDES BY BILAL MALIK

1. Cantharidin is obtained as orthorhombic plates or as scales having mp


218°C.
2. It sublimes at 110 °C (12 mm Hg, 3-5 mm distances).
3. It is practically insoluble in cold water and somewhat soluble in hot
water. 1g dissolves in 40 ml acetone; 65 ml chloroform; 560 ml ether;
150 ml ethyl acetate; and soluble in oils.
Uses:
1. It is mostly used as a vesicant(Vesicant=chemical agent that causes
burns and destruction of tissue both internally and externally).
2. It is also employed as a
rubefacient and counterirritant in veterinary practice.
Cantharidin, a promising anti-cancer medication, is limitedly prescribed due to
the risk of hepatic toxicity.

146
5)PLANT STEROIDS BY BILAL MALIK

PLANTS STEROIDS:
Contents:
• What are steroids?
• Sources
• Nomenclature
• Biosynthesis
• Plant steroids and their uses
 Plant sterols
 Cardiac glycosides
 Steroidal sapogenins
 Ecdysones
 Withanolides
• Animal steroids and their uses
 Steroid hormones (Sex hormones and adrenocortical
hormones)
 Bile acids
 Ecdysones

INTRODUCTION:
• Steroids comprise a natural product class of compounds widely
distributed throughout nature.
• A steroid is an organic compound with four rings arranged in a specific
configuration.
• Steroids have two principal biological functions: certain steroids (such as
cholesterol) are important components of cell membranes which alter
membrane fluidity, and many steroids are signaling molecules which
activate steroid hormone receptors.

147
5)PLANT STEROIDS BY BILAL MALIK

• Hundreds of steroids are found in plants, animals and fungi. All steroids
are manufactured in cells from the sterols:
• lanosterol (animals and fungi) or
• cycloartenol (plants).
• Plant steroids (aka Phytosteroids) are naturally occuring steroids that are
found in plants.
• Examples include digoxin, digitoxin, diosgenin, and guggulsterone, as
well as phytosterols like β-sitosterol and other phytoestrogens like
isoflavones.
• Guggulsterone-E and guggulsterone-Z, are the potent hypolipidemic and
hypocholesterolemic bioactive molecules present in the gum resin of
Commiphora wightii.
• In plants, cholesterol is widely distributed but often present in minute
quantities; other steroids not found in animals (the Phytosterols) tend to
predominate.
NOMENCLATURE:
• A steroid is any compound that contains a cyclo-penta-noper-hydro-
phenanthrene nucleus.
• Each parent tetracyclic hydrocarbon bears a specific stem name. Steroids
are numbered and rings are lettered as indicated in the structural formula
for cholesterol.
• When the rings of a steroid are denoted as projections onto the plane of
the paper, an atom or group attached to a ring is termed α if it lies below
the plane and β if it lies above the plane.
• The use of a stem name implies that atoms or groups attached at the ring
junction positions 8,9,10,13 & 14 are oriented as shown (8α ,9α , 10β,
13β, 14α) and a carbon chain attached to position 17 is assumed to be β
oriented.
• The configuration of hydrogen or a subsyituent at the ring-junction
position 5 is always designated by adding α or β after the numeral 5. This
numeral and letter are placed immediately before the stem name.
• For example, the chemical name of cholic acid is 3α, 7α, 12α-
trihydroxy-5β-cholan-24-oic acid.

148
5)PLANT STEROIDS BY BILAL MALIK

Some naturally occuring steroids..

149
5)PLANT STEROIDS BY BILAL MALIK

BIOSYNTHESIS:
• The hundreds of steroids found in animals, fungi, and plants are made
from lanosterol (in animals and fungi) or cycloartenol (in plants).
• Lanosterol and cycloartenol derive from cyclization of the triterpenoid
squalene.
• In animals the biosynthesis of steroids follows the mevalonate pathway,
which uses acetyl-CoA as building blocks for dimethylallyl
pyrophosphate (DMAPP) and isopentenyl pyrophosphate (IPP). In
subsequent steps DMAPP and IPP join to form geranyl pyrophosphate
(GPP), which synthesizes the steroid lanosterol.
• In plants, the non-mevalonate pathway uses pyruvate and glyceraldehyde
3-phosphate as substrates.
• Squalene  Squalene oxide   Protosteryl cation  
Cycloartenol   Sitosterol  Stigmasterol
• Steroids are formed biosynthetically from isopentenyl pyrophosphate
(active isoprene).
• Steroid biosynthesis in plants proceeds via mevalonate and FPP in the
cytosol but differs from the pathway in mammals and fungi because of
the intermediary of the unusual cyclopropane ring-containing sterol
cycloartenol. A series of intricately co-ordinated Wagner-Meerwein
rearrangements accompanies the cascade of cyclization events which
produce the cycloartenol skeleton.
• Formation of cholesterol may be considered as a general mechanism of
steroid biosynthesis:

150
5)PLANT STEROIDS BY BILAL MALIK

• Acetate –>–> mevalonate–>–> isopentenyl –>–> pyrophosphate –>–>


squalene –>–> cholesterol

151
5)PLANT STEROIDS BY BILAL MALIK

Pyruvate +
Acetyl-CoA
Glyceraldehyde
phosphate

Acetoacetyl-CoA
Deoxy xylose phosphate

HMG-CoA
2-C-methyl-D-erthritol
4-phosphate
Mevalonate
Various erythitol
phosphate
Mevalonate intermediates
pyrophosphate

2-methylbutane-1,4-diol
IsoPentenyl
diphosphate
pyrophosphate (IPP)
+ Dimethylallyl
pyrophosphate Isopentenyl
pyrophosphate+
Dimethylallyl
Squalene pyrophosphate

Lanosterol Squalene

Cholesterol Cycloartenol

Steroid hormones Campesterol


Bile Acids Sitosterol

1) PLANT STEROLS:
• The first steroid isolated from nature were a series of C27-C29 alcohols
that were found in the lipid fractions of many tissues. These compounds
were solids and therefore named sterols from the greek stereos- meaning
solid.
• The most widely occuring sterol is cholesterol. It has been identified in
animals, algae, fungi, actinomycetes, bacteria, ferns and higher plants.

152
5)PLANT STEROIDS BY BILAL MALIK

• The plant sterols are similar to cholesterol and vary only in carbon side
chains and/or presence or absence of a double bond. More than 200
sterols and related compounds have been identified.
• The most common sterol in plants is β-sitosterol, a C29 compound.
• Closely related to β-sitosterol is stigmasterol, first isolated from calabar
beans but is also found in soybean oil.
• Stanols are saturated sterols, having no double bonds in the sterol ring
structure.
• Free phytosterols extracted from oils are insoluble in water, relatively
insoluble in oil, and soluble in alcohols.
• The richest naturally occurring sources of phytosterols are vegetable oils
and products made from them.
• Phytosterols are currently approved by the U.S FDA for use as a food
additive; however, there is some concern that they may block absorption
not only of cholesterol (thus helping to reduce cholesterol), but of other
important nutrients as well.
• At present, the American Heart Association has recommended that
supplemental plant sterols be taken only by those diagnosed with elevated
cholesterol, and has particularly recommended that they not be taken by
pregnant women or nursing mothers.

Sitosterols:
• Composition: The drug sitosterols is a mixture of β-sitosterols and
certain saturated sterols.
• It contains no less than 95% of total sterols and not less than 85% of
unsaturated sterols.
• Characteristics: It is a white, odourless, tasteless powder that is
practically insoluble in water.
• Source: They are widely distributed throughout the plant kingdom and
may be obtained from wheat germ oil, rye germ oil, cottonseed oil, corn
oil and other seed oils.

153
5)PLANT STEROIDS BY BILAL MALIK

• Uses: Sitosterols is a hypocholesterolemic agent used in the treatment of


atherosclerosis. The sitosterols are poorly absorbed and compete with
cholesterol for absorption sites in the intestine.
• Dose: 3g, 3 times a day before meals.
• Cytellin® a sitosterols suspensions is hydroalcoholic suspension of β-
sitosterol and a small amount of dihydro- β -sitosterol.

2) STEROIDAL SAPOGENINS:
• Sapogenins are the aglycones, or non-saccharide, portions of the family
of natural products known as saponins. Steroidal sapogenins contain
steroid framework as their key organic feature. Some steroidal sapogenins
can serve as a practical starting point for the semisynthesis of particular
steroid hormones.
• Occurrence:
• They are found in many monocotyledonous families. particularly the
Dioscoreacea (e.g. Dioscorea spp.) Agavaceae (e.g. Agave and Yucca
spp.) and Smilacacea (smilax spp.).
• In the dicotyledons the occurrence of diosgenin in Fenugreek
(Leguminosae) and of steroidal alkaloids in Solanum (Solanaceae) is of
potential importance. Some species of Strophanthus and Digitalis contain
both steroidal saponins and cardiac glycosides.

Saponin (not steroidal)

154
5)PLANT STEROIDS BY BILAL MALIK

Some steroidal sapogenins and their sources:

Uses:
• Steroidal saponins are of great pharmaceutical importance because of
their relationship to compounds such as the sex hormones, cortisone,
diuretic steroids, vitamin D and the cardiac glycosides.
• Some plant saponins can weakly mimic the human hormones that they
resemble. For example, yam (Dioscorea spp.) contains variable amounts
of a saponin called diosgenin, which can be converted into hormones
such as progesterone and estrogen. In fact, Mexican yam (D. composita)
has been used to make oral contraceptives
• Hecogenin (steroid isolated from Agave sisalana) with C-ring
substitution provides a practical starting material for the synthesis of
corticosteroids.
• Solanum species are noted for the production of C27 steroidal alkaloids.
Some of these alkaloids are the nitrogen analogues of Solasodine &
diosgenin etc. They are employed in the partial synthesis of steroidal
drugs.

155
5)PLANT STEROIDS BY BILAL MALIK

• Diosgenin, obtained from fenugreek (Trigonella foenum graecum), has


been found to exert anti-carcinogenic properties (cancer
chemopreventive), such as inhibiting proliferation and inducing apoptosis
in a variety of tumor cells.

3) CARDIAC GLYCOSIDES:
• Occurrence:
• These glycosides are found in the plant genera Digitalis, Scilla, and
Strophanthus. They are used in the treatment of heart diseases, e.g.,
congestive heart failure and arrhythmia.
• A considerable number of plants throughout the plant kingdom contain
steroidal glycosides which exert on the failing heart a slowing and
strengthening effect. These steroids occur as glycosides with sugars
attached at the 3-position of the steroid nucleus.
• Structure of glycosides
• Two types of genin may be distinguished: cardenolides (C23 steroids)
and bufanolides (C24 steroids).
• The sugar moieties, attached to the aglycone by a C-3, B-linkage are
composed of upto four sugar units.
• Bufalin, ouabain and digoxin are a few toxic cardiac glycosides. Digoxin
from the foxglove plant is used clinically, whereas bufalin and ouabain
are used only experimentally due to their extremely high potency.

Genins of some cardiac glycosides and their sources:


• CARDENOLIDES
• Digitoxigenin (Digitalis purpurae) (Digitalis lanata)
• Gitoxigenin (Digitalis purpurae) (Digitalis lanata)
• Gitaloxigenin (Digitalis purpurae) (Digitalis lanata)
• Digoxigenin (Digitalis lanata)
• Diginatigenin (Digitalis lanata)
• Strophanthidin (Strophanthus combes)
• Oubagenin (Strophanthus gratus)

156
5)PLANT STEROIDS BY BILAL MALIK

• Sarmentogenin (Strophanthus sarmentosus)


• Oleaderigenin (Nerium oleader)
• BUFADIENOLIDES
• Scillarenin (Urignea maritima)
• Scilliphaeosidin (Squill)
• Hellebrigenin (Helleborus niger)

4) STEROID HORMONES:
• The steroid hormones can be divided into two classes:
• The sex hormones and the adrenocortical hormones.
• Sex hormones are produced in the gonads and fall into 3 chemically and
physiologically distinct categories:
• The estrogens & progestins (regulates various functions of female
reproductive tract) and androgens (stimulates development of the male
reproductive organs)
• The adrenocortical hormones are produced by the outer cortical portion of
the adrenal glands and they are divided into 2 classes, depending on their
biologic activity:
• Mineralocorticoids (affects the excretion of fluid and electrolytes) and
glucocorticoids (affects intermediary metabolism)
Commercial Production of Steroids:
• At the present time, the principal source of the steroid chemical nucleus
used in the drug industry is the plant kingdom.
• Initially, the source of steroid hormones was from gonads and adrenal
glands of animals but the amount of hormones present in these glands
was extremely small and large quantities of glands were required to
isolate mg quantities of hormones.
• A vast amount of research has resulted in extension and improvement of
the basic procedure of isolation.

157
5)PLANT STEROIDS BY BILAL MALIK

• Inexpensive starting materials like stigmasterol from soybeans, hecoenin


from the sisal industry or diosgenin from dioscorea species are now
employed to produce compounds of potential therapeutic importance.
Examples:
• Stigmasterol may be converted chemically to progesterone, which in
turn, incubated in large fermentors with suitable conditions to yield 11-a-
hydroxyprogesterone, which may then be converted chemically to
cortisone.
• Diosgenin is used to prepare cortexolone and is then converted by
streptomyces fradiae to corticol (hydrocortisone)
• Cortisone or cortisol is dehydrogenated by Corynebacterium simplex to
yield prednisolone.
Therapeutic uses:
• Sex steroids are used to treat low levels of these hormones in the body,
for diseases that destroy muscles, anemia, delayed puberty, hormone
sensitive cancers (breast, prostate cancer) etc.
• Testosterone -> Breast cancer that has spread to other parts of the body.
• Dehydroepiandrosterone (DHEA)/ Prosterone -> in post-menopausal
women for pain.
• Estrogens -> Oral contraceptives, Hormone replacement therapy in
hypogonadal, transgender or menopausal women.
• Non-medicinal use of anabolic steroids: in Body building as
‘performance enhancing drug’
• Glucocorticoids may be used in low doses in adrenal insufficiency.
• In much higher doses, oral or inhaled glucocorticoids are used to suppress
various allergic, inflammatory, and autoimmune disorders. Inhaled
glucocorticoids are the second-line treatment for asthma.
• They are also administered as post-transplantory immunosuppressants
to prevent the acute transplant rejection and the graft-versus-host disease.
• Glucocorticoids are potent anti-inflammatories.

5) BILE ACIDS:
158
5)PLANT STEROIDS BY BILAL MALIK

• In the liver of man and other animals the side chain of cholesterol is
degraded to C24 steroids, which possess a C-24 carboxyl. These steroids
are collected as the bile, therefore they are referred to as bile acids.
• Primary bile acids formed in the liver of man are: Cholic acid and
chenodesoxycholic acid.
• Des-oxycholic acid and lithocholic acid are produced in the intestinal
tract by the action of microorganisms.
• Generally, bile acids are conjugated to glycine or taurine through a
peptide bond. The conjugated bile aids are discharged into the duodenum
to where they act as emulsifying agents to aid in the absorption of fats.
Functions of Bile Acids:
• Eliminates cholesterol from the body,
• Drives the flow of bile to eliminate certain catabolites (including
bilirubin)
• Emulsifies fat-soluble vitamins to enable their absorption,
• Aids in motility and the reduction of the bacteria flora found in the small
intestine and biliary tract.
• Bile acids also act as steroid hormones having various direct metabolic
actions in the body through the nuclear receptor Farnesoid X receptor
(FXR)
Ox bile extract:
• Bile salts are the sodium salts of the conjugated acids and are the
principal constituent of ox bile extract.
• Preparation:
1. Partial evaporation of fresh ox bile
2. Precipitation of the mucus and albuminous matter with alcohol
3. Filteration
4. Washing
5. Evaporating the combined filtrates to dryness at a temperature not
exceeding 80 C.

159
5)PLANT STEROIDS BY BILAL MALIK

• It contains an amount of the sodium salts of glycocholic acid and


taurocholic acid equivalent to not less than 45% of cholic acid.
• Use:
• Choleretic (substances that increase the volume of secretion of bile from
the liver as well as the amount of solids secreted).
• Helps in digestion of food
• People, who have had their gallbladder removed, use ox bile to
supplement their bile production with meals.
• Dose: 300 mg
• Non-prescription product: Bilron Pulvules®

6) WITHANOLIDES:
• Withanolides are a group of at least 300 naturally occurring steroids built
on an ergostane skeleton
• In 1968, the structure of a constituent lactone (withaferin A) of Withania
somnifera was determined, since then many more compounds have been
characterized.
• Other genera of the family in which they occur include: Aenistus, Datura,
Hyoscyamus, Iochroma, Jaborosa, Lycium, Nicandra, Physalis and
Solandra.
• The first report of a withanolide from the Labiatae concerns the
characterization of a new compound, ajugin, from ajuga parviflora whole
plants.
Examples and Uses:
• They have potential pharmacological value as sedatives, hypnotics,
antiseptics and anti-mitotics.
• Some withanolides are cell differentiation inducers- compounds of a new
type of anti tumour agent.
• Withaferin A acts as an anti angiogenic compound by inhibiting
Transcription Factors Sp1 and NF-κB. Withaferin A also inhibits
angiogenesis on chick chorioallantoic membrane. Withanalides inhibit
COX-2 and exhibit anti-inflammatory activity.

160
5)PLANT STEROIDS BY BILAL MALIK

• Salpichrolides A, B and G (isolated from Salpichroa origanifolia)


exhibit an inhibitory effect on the growth of larva of the Mediterranean
Fruit Fly
• The nicandrenones of Nicandra physalodes are another group of
withanolides with insecticidal effects.

7) ECDYSONES:
• The ecdysis of insects relates to the moults which larvae undergo during
their transformation into an adult, a process controlled by complex
hormonal mechanisms.
• Ecdysones, insect-moulding hormones, are substances which stimulates
these changes and one example is ecdysone itself, first isolated from silk-
worm pupae.
• Ecdysone is a steroidal prohormone of the major insect molting hormone
20-hydroxyecdysone, which is secreted from the prothoracic glands
• In plants they occur in much greater variety and abundance, where they
appear mostly as protective agents against herbivorous insects.
• Insects do not themselves biosynthesize steroids de novo and rely on
plant materials for suitable precursors.
• Ecdysterone is also an example of one which has been obtained from
both plant and insect sources.
• In the plant, cholesterol is a precursor of insect-moulding hormones and
in one morphological group of helleborus, it has been shown that they are
formed together with bufadienolides and saponins.

161
5)PLANT STEROIDS BY BILAL MALIK

• Ecdysterone (20-Hydroxyecdysone) is also an example of one which


has been obtained from both plant and insect sources.
• In the plant, cholesterol is a precursor of insect-moulding hormones and
in one morphological group of helleborus, it has been shown that they are
formed together with bufadienolides and saponins.
• In arthropods, it acts through the ecdysone receptor. Although mammals
lack this receptor, it may affect mammalian (including human) biological
systems in vitro, but there is uncertainty whether any in vivo or
physiological effects occur.
• 20-Hydroxyecdysone is an ingredient of some supplements that aim to
enhance physical performance and increase muscle mass, but there is no
clinical evidence for this effect.

162
6. LIPIDS NOTES BY BILAL MALIK

LIPIDS:
• Lipids (fixed oils, fats, and waxes) are esters of long-chain fatty acids
and alcohols, or of closely related derivatives.
• The chief difference between these substances is the type of alcohol;
• In fixed oils and fats, glycerol combines with the fatty acids;
• In waxes, the alcohol has a higher molecular weight, e.g.,
cetyl alcohol[CH3(CH2)15OH].
Fats and oils are made from two kinds of molecules:
• glycerol (a type of alcohol with a hydroxyl group on each of its three
carbons) and
• three fatty acids joined by dehydration synthesis. Since there are three
fatty acids attached, these are known as triglycerides.
Triglyceride:
O
H2C O C R
O
HC O C R'
O
H2C O C R''
• where R, R', and R" are long alkyl chains; the three fatty acids RCOOH,
R'COOH and R"COOH can be all different, all the same, or only two the
same.
• Fats, which are mostly from animal sources, have all single bonds
between the carbons in their fatty acid tails, thus all the carbons are also
bonded to the maximum number of hydrogens possible.
• Since the fatty acids in these triglycerides contain the maximum possible
amount of hydrogens, therefore are called saturated fats.
• The hydrocarbon chains in these fatty acids are, thus, fairly straight and
can pack closely together, making these fats solid at room temperature.

163
6. LIPIDS NOTES BY BILAL MALIK

• Oils, mostly from plant sources, have some double bonds between some
of the carbons in the hydrocarbon tail, causing bends in the shape of the
molecules.
• Because some of the carbons share double bonds, they’re not bonded to
as many hydrogens as they could if they weren’t double bonded to each
other. Therefore these oils are called unsaturated fats.
• Because of the kinks in the hydrocarbon tails, unsaturated fats (or oils)
can’t pack as closely together, making them liquid at room temperature.
Production of fixed oils and fats:
Fixed oils and fats of vegetable origin are obtained by:
1. Extraction by expression
Fixed oils are obtained by expression in hydraulic presses. If the
expression is carried out in the cold, the oil is known as a "cold-pressed oil." In
contrast, if the expression is carried out in heat, the oil is known as a "hot-
pressed oil."
2. Extraction by solvents
Sometimes organic solvents are used for the extraction of oils.
• Animal fats are separated from other tissues by rendering with steam,
with or without pressure. The heat melts the fat, which rises to the top and
may be separated by decantation.
Biosynthesis of lipids:
• The biosynthesis of saturated and unsaturated fatty acids is from
combinations of acetate units (acetate pathway).
Applications of fixed oils and fats:
1. Soap manufacture
2. Suppositories, tablet coating
3. Dietary supplements
4. Emulsifying agents
5. Manufacture of paints, varnishes and lubricants
6. Therapeutic uses (castor oil).

164
6. LIPIDS NOTES BY BILAL MALIK

 Examples
 Castor oil
 Olive oil
 Peanut oil
 Soybean oil
 Sesame oil
 Almond oil
 Cottonseed oil
 Corn oil

Waxes:
• Like fats, waxes are esters of fatty acids. The alcohol, however, is not
glycerol but usually a long-chain, high-molecular weight alcohol.
• In plants, waxes are generally found covering the external parts, like the
epidermis of leaves and fruits, where their main function is to prevent the
loss of water.
• Wax is also produced by insects, e.g. the honeycombs of bees and wasps.
USES OF WAX
1. Wax is used in pharmacy to make soft ointments harder and to prepare
lips-salves, [lips balm].
2. The technical uses of waxes are substantial, e.g. in shoe polishes and car
waxes.
Examples:
• Jojoba wax (Simmondsia chinensis)
• Beeswax (Apis mellifera)
• Carnauba wax (Copernicia cerifera)

165
6. LIPIDS NOTES BY BILAL MALIK

FIXED OILS:

PHYSICAL PROPERTIES:
 Cannot be distilled (unless decomposed). This distinguishes fixed oils
from volatile oils.
 Leaves a permanent, translucent stain on filter paper.
 Specific gravity < 1.
 All insoluble in water. Soluble in organic solvents.
 Most develop a rancid odour when exposed to air, moisture & light for
prolonged periods of time (hydrolysis of esters & liberation of fatty acids)
 All have characteristic odours.
 Varying viscosities.
BEFORE EXTRACTION:
Plant material to be pressed undergoes strict quality control.
- absence of foreign matter & deterioration
GENERAL PRELIMINARY PROCEDURES:
- Cleaning & drying
SPECIFIC PRELIMINARY PROCEDURES (depends on the seeds’
botanical structure)

166
6. LIPIDS NOTES BY BILAL MALIK

- Olives: washed
- Cotton: Delintering
- Castor seeds & ground nuts: decorticating.
- Peanuts, soybeans, sunflower seeds: Shelled.
METHODS OF EXTRACTION:
i. Extraction by Expression
- Cold Expression
- Hot Expression
ii. Extraction by Solvents
1. EXTRACTION BY EXPRESSION:

 Screw presses are normally used to express oils from plant material
because they give a better yield than older hydraulic presses.
 They also operate at higher pressure and continuously (not in batches).
 Before undergoing expression, seeds rich in proteins are cooked at 90ºC
 frees the oil by bursting the cell structures & coagulates the proteins.
A fast drying step normally follows.
a. COLD EXPRESSION:
 Oils for medicinal uses are extracted at room temperature. Only a portion
of the oil is obtained.
 Oil is normally less viscous with less odour than with hot expression
(better quality).

167
6. LIPIDS NOTES BY BILAL MALIK

 The remaining pressed material may then be ground, heated and pressed
to express any remaining oil.

b. HOT EXPRESSION:
 The residue left after cold expression is broken down and treated with
steam. This causes the remaining oil cells to rupture.
 Even after hot expression, 10 % of the oil remains in the plant material.
ii. EXTRACTION BY SOLVENTS:
This type of method is used only for technical oils (not medicinal oils).
Seeds used: Intact or partially extracted by expression.
Solvent: Normally hexane (BP: 65 ºC)
Method: Solvent is added to the cleaned, hulled & roughly milled seeds.
The organic phase is recovered. (Organic phase: solution containing the
oil in the solvent (called miscella) , and also solvent soaked defatted
meal).
Oil recovery: 95 – 99%

QUANTITATIVE CHEMICAL TESTS:


i. Physical Constants
ii. Chemical Constants

168
6. LIPIDS NOTES BY BILAL MALIK

i)PHYSICAL CONSTANTS:
a. Specific Gravity
b. Melting / Congealing Point
c. Refractive Index
d. Viscosity
e. Optical Rotation

ii)CHEMICAL CONSTANTS:
a. Acid Values
b. Saponification Value
c. Ester Value
d. Iodine Value
e. Unsaponifiable Matter
f. Acetyl value.

169
6. LIPIDS NOTES BY BILAL MALIK

CLASSIFICATION:
On the basis of their ability to absorb
oxygen from air;
• a)Drying oil
• b)Non-drying oil
• c)Semi-drying oil

a) Drying oil:
When exposed to air, undergo oxidation and form tough and hard film. These
are usually used in paints and varnishes.
For example;
Linseed oil
b) Non-Drying oil:
These oils neither undergo oxidation nor form tough and hard film.
For example;
Olive oil
c) Semi-Drying oil:
When exposed to air, undergo little bit oxidation and form tough and thin film.
For example;
Cottonseed oil

Oleic acid [unsaturated]:


The American Heart Association (AHA), also recommends for the general
population to consume fish, especially oily fish, at least twice a week.
Beneficial effects including
 Reduce coronary heart disease risk
 Effective in cancer,
 Autoimmune diseases
170
6. LIPIDS NOTES BY BILAL MALIK

 Inflammatory diseases
 Facilitate wound healing
 Skin repair based on this fatty acid mainly found in the Mediterranean
diet.

Linoleic acid [unsaturated]:


Conjugated linoleic acids (CLA) are a family of at least 28 isomers of linoleic
acid found mostly in the meat and dairy products
• Anti -carcinogenic
• Anti -atherogenic
• Anti -diabetogenic
• Decreases body fat Decreases body fat
• Increases lean body mass Increases lean body mass
• Improves immune response Improves immune response
• a number of dairy companies have used food technology to substitute
milk fat with PUFA, oleic acid, or combinations of both to produce
“healthier” milks

Palmitic acid [C16H32O2]:


Excess carbohydrates in the body are converted to palmitic acid. Palmitic acid is
the first fatty acid produced during fatty acid synthesis and the precursor to
longer fatty acids.
Rats fed a diet of 20% palmitic acid and 80% carbohydrate for extended periods
showed alterations in central nervous system control of insulin secretion, and
suppression of the body's natural appetite-suppressing signals from leptin and
insulin (the key hormones involved in weight regulation).
• Palmitic acid strongly boosts metastasis in mouse models of human
oral cancer cells. Among all fatty acids, it has the strongest effect in
boosting the metastatic potential

171
6. LIPIDS NOTES BY BILAL MALIK

Stearic acid [C18H36O2]:


• In general, the applications of stearic acid exploit its bifunctional
character, with a polar head group that can be attached to metal cations
and a nonpolar chain that confers solubility in organic solvents.
• A common misperception is that all SFAs are alike in terms of their
cardiovascular disease risk. However, research demonstrates that
individual SFAs differ in their effects on blood cholesterol levels.
• Studies in humans also indicate that stearic acid is uniquely different
from other long-chain SFAs and that it does not raise blood total and
LDL cholesterol levels.
• stearic acid has been shown to have a neutral effect on blood total and
low density lipoprotein (LDL) cholesterol levels.
• With respect to inflammation, one study in adult male volunteers found
that high levels of stearic acid (11% of total calories) increased plasma
fibrinogen levels (a marker of inflammation), whereas markers of
inflammation were not affected when stearic acid was consumed at a
level of 7% of total calories, which is above the current intake of 3% of
total calories.
172
6. LIPIDS NOTES BY BILAL MALIK

• Diets containing stearic acid at levels of 8% to 13% of calories appear to


have no effect on blood pressure.
• In short, there is no evidence that intakes of stearic acid equal to or
slightly higher than amounts typically consumed have any adverse effects
on these cardiovascular disease risk factors.

OLIVE OIL:

Olive oil is the oil expressed from the ripe fruits of Olea europea (Oleaceae
Family).
The latifolia variety bears larger fruit, but the longifolia variety yields the best
oil.
Common Names: Salad oil, sweet oil
Geographical Sources: Mediterranean, California, Spain, France, Greece &
Tunisia.
OLIVE OIL: CHARACTERISTICS:
Olive oil: Pale yellow liquid, sometimes with a green tint.
Oil has a slight odour & bland taste.
OLIVE OIL: CONSTITUENTS:
Oils from different sources differ slightly in their constituents (composition).
This may result due to the different varieties of olive used, or to climate
differences.

173
6. LIPIDS NOTES BY BILAL MALIK

2 types of oil are distinguished


i. That produced in Italy, Spain, Asia
(contains more olein & less linolein)
ii. Produced in Tunisia

OLIVE OIL: USES & ACTIONS:


Used in the preparations of soaps, plasters etc.
May protect against colonic cancer (due to its action on prostaglandins).
Olive oil is a nutrient widely used in cooking.
It has also been used as a vehicle for oily suspensions for injections and
topically as a demulcent and emollient. Historically, it has been used as a
laxative.
Olive oil is an element of the Mediterranean diet and is promoted as a
beneficial source of dietary fat to improve the lipid profile and reduce
cardiovascular morbidity
{Oleic acid may be responsible for the hypotensive (blood pressure reducing) effects of olive
oil.[25] Adverse effects also have been documented, however, since both oleic
and monounsaturated fatty acid levels in the membranes of red blood cells have been
associated with increased risk of breast cancer,[26] although the consumption of oleate in
olive oil has been associated with a decreased risk of breast cancer}

174
6. LIPIDS NOTES BY BILAL MALIK

CASTOR OIL:

175
6. LIPIDS NOTES BY BILAL MALIK

Definition: Castor oil is a fixed oil obtained from the seeds of ricinus
communis (Euphorbiaceae).
Geographical Sources: Native to India. Produced in Brazil, India, China,
Russia & Thailand.
BOTANICAL CHARACTERISTICS:
o Seeds show considerable difference in colour & size.
o They are oval, slightly compressed
o Colour: uniform grey, brown or black, mottled with brown or black.
o If grown in good conditions, they have very little odour & the taste is
slightly acrid.
o If the testa are broken, rancidity will develop.
CASTOR OIL: PREPARATION:
90% of the world’s castor oil is prepared in India & Brazil. Small amounts of
raw seeds are now exported.
Method of preparation: Seeds are removed from the testa. Kernels are cold-
pressed with a hydraulic press. Oil is then refined by steaming, filtration &
bleaching.
Cold-expression yields 33% of medicinal oil. Further amounts of lower quality
oil may be obtained by other methods
CASTOR OIL: CHARACTERISTICS:
Medicinal castor oil is a colourless or pale yellow liquid, with a slight odour &
faintly acrid taste.
Acid value: increases with age. If initially high – indicates the use of damaged
sees or careless extraction or storage.
Viscosity: Extremely high
CASTOR OIL: CONSTITUENTS:
Castor seeds contain 46-53 % fixed oil.
These fixed oils consist of the glycosides of
- Ricinoleic
- Isoricinoleic

176
6. LIPIDS NOTES BY BILAL MALIK

- Steric
- Dihydroxystearic acids
The cake, after expression, contains extremely poisonous toxins (ricins)
CASTOR OIL: USES & ACTIONS:
Castor oil is used to treat constipation. It may also be used to clean out
the intestines before a bowel examination/surgery.
Castor oil is known as a stimulant laxative. It works by increasing the
movement of the intestines, helping the stool to come out.
Because of the ricin, the seeds have a much more violent action than
the oil and is not used as a purgative in the West.

ALMOND OIL:

177
6. LIPIDS NOTES BY BILAL MALIK

Almond oil is the fixed oil obtained by expression from the seeds of
Prunus amygdalus (Roseceae)
Geographical Sources: Mediterranean countries: North Africa, France, Spain,
Italy.
Sweet and Bitter Almonds:
 The sweet almond is 2–3 cm in length, rounded at one
end, and pointed at the other. The bitter almond is 1.5–2
cm in length but of similar breadth to the sweet almond.
 Bitter almonds are sometimes found in samples of sweet almonds,
especially in those from N. Africa. Their presence may be detected the
sodium picrate test for cyanogenic glycosides.
ALMOND OIL: CONSTITUENTS:
 Both varieties of almond contain 40–55% of fixed oil, about
 20% of proteins, mucilage and emulsin.
 Almond oil consists of a mixture of glycerides of oleic (62–86%), linoleic
(17%), palmitic (5%), myristic (1%), palmitoleic, margaric, stearic,
linolenic, arachidic, gadoleic, behenic and erucic acid. Bitter almond oil
contains benzaldehyde and 2–4% of hydrocyanic acid.,
and vitamins and antioxidants (mostly Vitamin E and Vitamin K).
 Almond oil is a rich source of vitamin E.
 Bitter almonds contain 2.5-4% cyanogenic glycoside, amygdalin.
ALMOND OIL: PRODUCTION & CHARACTERS:
 Almond oils is produced by grinding the seeds & expressing them in a
canvas bag between slightly heated iron plates.
 They are sometimes ground before expression .The oil is then clarified
by filtration.
 Bitter almonds, after maceration on hydrolysis of amygdalin yield a
volatile oil that is used as a flavouring agent.
 Oil is pale yellow liquid with a slight odour & bland, nutty taste.
ALMOND OIL: ACTIONS & USES:
‡ Hydrocyanic acid-free oil is used for flavouring purposes
178
6. LIPIDS NOTES BY BILAL MALIK

‡ Almond oil is great for digestion, and can also prove to be an effective
laxative.
‡ as a vehicle for oily injection.
‡ Expressed almond oil is an emollient and an ingredient in
‡ Cosmetics.
‡ If applied directly, almond oil can often provide relief from muscular
pain[Applied to glandular swellings of the neck].
‡ Ingesting almond oil is also great for boosting the immune system, which
will in turn lessen chances of becoming ill.

ARACHIS OIL (peanut):

Definition: Arachis oil is obtained by expression from the seeds of


arachis hypogaea (Leguminosae).
Common Names: Earth-nut, ground nut, peanut.
Geographicl Sources: Tropical Africa, India, Brazil, USA & Australia.
PREPARATION:

179
6. LIPIDS NOTES BY BILAL MALIK

 During ripening, the fruits bury themselves in the sandy soil in which
the plants grow. Each fruit contains 1-3 red-brown seeds.
 Fruits shelled by machine.
 Kernels contain 40-50% fixed oil.
 Because of the high oil content of the seeds, when crushed, it is
difficult to express. Therefore, after boiling, part of the oil is removed in
a low pressure expeller and the remaining cake is solvent extracted. The 2
oil fractions are then mixed together before undergoing purification.
ARACHIS OIL: CONSTITUENTS:
Glycosides of
- Oleic
- Linoleic
- Palmitic
- Arachidic
- Stearic
- Lignoceric
- And other acids
ARACHIS OIL: ACTIONS & USES:
 Peanut oil is used to lower cholesterol and prevent heart disease.
 It is also used to decrease appetite as an aid to weight loss. Some people
use it to help prevent cancer.
 Peanut oil is sometimes applied directly to the skin for arthritis and joint
pain, dry skin and eczema.
 Rectally, peanut oil is used in ointments and medicinal oils for treating
constipation.
 Pharmaceutical companies use peanut oil in various products they prepare
for internal and external use.

180
6. LIPIDS NOTES BY BILAL MALIK

LINSEED OIL:

Definition: Linseed is the dried ripe seed of Linum usitassimum


(Linaceae).
Common Names: Linseed, flax-seed
Geographical Sources: S. America, India, USA, Canada, England.
LINSEED: CONSTITUENTS:
 30-40 % fixed oils
 Mucilage
 Protein
 Small amounts of cyanogenetic glycosides: Linamarin &
Lotaustralin
 Flavonoids
 Lignan – potential cancer preventative

LINSEED OIL:

181
6. LIPIDS NOTES BY BILAL MALIK

Linseed oil is a yellow-brown oil with a characteristic odour & bland taste.
Extraction of linseed oil is done by hot expression of linseed seeds. The cake
is adjusted to leave in sufficient oil to make it suitable for cattle feed.
LINSEED OIL: CONSTITUENTS:
Linolenic acid
Linoleic acid
Oleic acid
Myristic
Stearic
Palmitic acids

USES & ACTIONS:


 Linseed oil is an edible oil widely used as a nutritional supplement.
 Flaxseed oil contains short-chain omega-3 fatty acids - an essential fatty
acids, which may offer some health benefits for cardiovascular diseases
by lowering serum cholesterol level,
 Reducing inflammation and decreasing platelet aggregation.
 Flaxseed oil supplements were also studied to have health benefits for
patients with diabetes mellitus by decreasing insulin resistance and in
relieving pain.
 Flaxseed being rich in fiber has been traditionally used to treat varieties
of gastrointestinal conditions and offers health benefits for diarrhea,
 constipation, irritable bowel syndrome
 sores and inflammation in the lining of intestines.

OIL OF THEOBROMA Cocoa butter:

Theobroma oil is obtained from the ground kernels of


theobroma cacao (Sterculiaceae) by hot expression.

182
6. LIPIDS NOTES BY BILAL MALIK

The oil is filtered and allowed to set into moulds.


Common Names:
Cocoa butter, Cocoa, Chocolate Tree
Botanical origin:
Theobroma cacao
Family:
Sterculiaceae
Part used:
Seeds
Geographical Sources:
America, Cultivated in Ceylon and Java

 Cocoa butter is yellowish white solid and brittle below 25°C.


 It has pleasant chocolate odour and taste.

183
6. LIPIDS NOTES BY BILAL MALIK

 It is insoluble in water but soluble in chloroform, petroleum ether, ether


and benzene.
 Specific gravity ranges from 0.858 to 0.864,
 melting point between 30°C and 35°C,
 Refractive index varies from 1.4637 to 1.4578,
 saponification value is 188–195, and iodine value 35–40.

THEOBROMA OIL:CONSTITUENTS:
2% Theobromine
40-60% solid fa
Mucilage
Glycerides of
- Stearic 34%
- Palmitic 25%
- Oleic 37%
- Arachidic and other acids
- Glyceride structure is responsible for nongreasiness of product.
It is the most expensive of all the fixed oils, and is commonly adulterated with
waxes, stearin, animal or vegetable tallows.
THEOBROMA OIL:CONSTANTS & USES:
 Boiling point: 31-34 ºC. This makes it ideal for the use in the preparation
of suppositories.
 It reduces the formation of stretch marks during pregnancy by keeping
the skin supple
 It is used as an ingredient in cosmetic ointments and in pharmacy for
coating pills.
 It has excellent emollient properties and is used to soften and protect
chapped hands and lips.
 It is used as an ingredient in lotion bars, lip balms, body butters, soaps,
and belly balms for expectant mothers.
184
6. LIPIDS NOTES BY BILAL MALIK

 Diuretics .

COTTON-SEED OIL:

Botanical origin:
Gossypium herbaceum
Family: Malvaceae
Part used: Seeds
Geo Location:
Native to Asia and Africa. Now it is cultivated in Egypt, China, India, Turkey,
and southern US.
Collection:

185
6. LIPIDS NOTES BY BILAL MALIK

Constituents:
Glycerides of;
• Linoleic acid
• Oleic acid
• Palmitic acid
• Stearic acid
• Arachidic acid
• Myristic acid
Uses:
Food
Emollient
Vehicle for injections
Preparation of hydrogenated vegetable oils
Soap manufacture

CORN OIL:
186
6. LIPIDS NOTES BY BILAL MALIK

Botanical origin:
Zea mays
Family:
Gramineae
Part used:
Embryo
Production
 Almost all corn oil is expeller pressed, then solvent extracted using
hexane. The solvent is evaporated from the corn oil, recovered, and re-
used.
 After extraction, the corn oil is then refined by degumming and/or alkali
treatment, both of which remove phosphatides. Alkali treatment also
neutralizes free fatty acids and removes color (bleaching).
 Final steps in refining include winterization (the removal of waxes), and
deodorization by steam distillation.
Constituents:
Glycerides of;
• Oleic acid
• Linoleic acid
• Stearic acid
• Arachidic acid
• Palmitic acid

187
6. LIPIDS NOTES BY BILAL MALIK

• Myristic acid
• Lignoceric acid
Uses:
Vehicles in pharmaceutical and cosmetic preparation
Solvent for injections
Nutrient

COCONUT OIL:

Botanical origin:
Cocos nucifera
Family:
Palmae
Part used:
Dried solid part of Endosperm.
The tree rises upto height of 30 meters and bears 100 or more fruits
Production:

188
6. LIPIDS NOTES BY BILAL MALIK

• Dry process
• Dry processing requires the meat to be extracted from the shell and dried
using fire, sunlight, or kilns to create copra.
• The copra is pressed or dissolved with solvents, producing the coconut
oil.
• A portion of the oil extracted from copra is lost to the process of
extraction.
Wet process
• The wet process uses raw coconut rather than dried copra, and the protein
in the coconut creates an emulsion of oil and water.
• The more critical step is breaking up the emulsion to recover the oil. This
is made by prolonged boiling, but this produces a discolored oil and is not
economical.
• Modern techniques use centrifuges and pre-treatments including cold,
heat, acids, salts etc or some combination of them
Constituents:
Glycerides of;
• Lauric acid
• Myristic acid
• Capric acid
• Caprylied acid
• Caproic acid
• Oleic acid
• Palmitic acid
• Stearic acid
Uses:
Nutrient
Confectionaries
Cosmetics
Ointment base
189
6. LIPIDS NOTES BY BILAL MALIK

MUSTARD OIL:

Botanical origin:
Brassica juncea
Family:
Cruciferae
Part used:
Seeds
• It is an annual plant with a much-branched stem, and lobed, roughly lyre-
shaped leaves, 16cm (6 in) long.
• Bright yellow flowers are produced in summer, followed by small, erect,
4-angled pods with dark brown seeds.

Extraction
• The seeds are to be dried in sun and then cleaned by shakers to remove
dust and foreign matter. The seeds are initially steamed and then passed
through the expeller and the process is repeated till the maximum oil is
extracted out of the seeds.
190
6. LIPIDS NOTES BY BILAL MALIK

• The filtered oil is filled into containers


Constituents:
Glycerides of;
• Linoleic acid
• Oleic acid
• Erucic acid
Uses:
Nutrient
Rubefacient
In preparation of liniment
Mustard oil has got a typical pungent and sharp flavour that is because of
the presence of a compound called Allyl Isothiocyanate. This oil has
about 60% monounsaturated fatty acids (MUFA), 21% polyunsaturated
fats (PUFA) and about 12% saturated fats. A higher amount of MUFA
and PUFA distinguishes it from other types of fats
Reduces Risk of Cardiovascular Disease
Stimulates Digestion
Good for Skin and Hair

SESAME OIL (Teel oil/Benne oil):

191
6. LIPIDS NOTES BY BILAL MALIK

Botanical origin:
Sesamum indicum
Family: Pedaliaceae
Part used: Seeds
Geo Location:
South Asia, Africa, West Indies, Southern US
• The plant is annual herb attaining a height of 1 meter.
• Seeds are small,flattend ,oval, shiny and whittish,yellowish or reddish.
• Fixed oil is obtained by expression.
• Oil is pale yellow, odourless and has bland taste
Constituents:
Glycerides of;
• Linoleic acid
• Oleic acid

192
6. LIPIDS NOTES BY BILAL MALIK

• Stearic acid
• Palmitic acid
• Arachidic acid
And other components include;
• Sesamin
• sesamolin
Uses:
Solvent for intramuscular injection
Nutritive
Demulcent
Emollient
Laxative

SUNFLOWER OIL:

Botanical origin:
Helianthus annus
Family: Compositae
Part used: Seeds
Geo Location: Native to America. India Russia Argentina Ukraine

193
6. LIPIDS NOTES BY BILAL MALIK

 The name Helianthus, being derived from helios (the sun) and anthos (a
flower), has the same meaning as the English name Sunflower
 it is an annual herb, with a rough, hairy stem, 3 to 12 feet high
 The flower-heads are composed of many small tubular flowers arranged
compactly on a flattish disk
 The oil pressed from the seeds is of a citron yellow colour and a sweet
taste
 EXTRACTION:
 For the extraction of the oil, the seeds are bruised, crushed and ground to
meal in a roller mill, under chilled iron or steel cylinders.
 The mass, after being packed in bags, is placed in hydraulic presses,
under a pressure of 300 atmospheres or more, and allowed to remain
under pressure for about seven minutes. The oil thus obtained is known as
cold pressed oil.
Constituents:
Glycerides of;
• Palmitic acid
• Stearic acid
• Arachidic acid
• Oleic acid
• Linoleic acid
• Behenic acid
Uses:
Nutritive
Preparation of hydrogenated products
Sunflower oil is used for constipation and lowering “bad” LDL
cholesterol.

VOLATILE OILS VS FIXED OILS:

194
6. LIPIDS NOTES BY BILAL MALIK

Volatile oils Fixed oils

Volatilize at room temperature Don't get volatiles at


room temperature

Obtained by distillation Obtained by extraction

Leave no spot after evaporation After evaporation, do


leave spot

Cannot be saponified Can be saponified

Mixtures of oleoptenes and Esters of fatty acid with


stereoptenes glycerol

High refractive index Low refractive index

FATS VS FIXED OILS:


195
6. LIPIDS NOTES BY BILAL MALIK

Fats Fixed oils

Solid at room temperature Liquid at room temperature

Contain saturated glycerides e.g. Contain unsaturated glycerides


glyceryl stearate e.g. glyceryl oleate

WAXES:
“Wax” is sometimes used to describe hard paraffin (HC mixture), but it is best
confined to natural mixtures containing large amounts of esters derived from
higher monohydric alcohols of the methyl alcohol series combined with fatty
acids.
In this series the alcohols change from liquids to solids, become less soluble in
water & have higher melting points & MWs.
WAXES – EXAMPLES:
Vegetable products
(e.g. carnauba wax)
Animal products
e.g. beeswax & wool-fat.
Waxes are abundant in nature (epidermal surfaces) – but only a limited number
have commercial significance.

196
6. LIPIDS NOTES BY BILAL MALIK

FATS VS WAXES:
Fats may be saponified by either aqueous or alcoholic alkali, but waxes are only
saponified by alcoholic alkali.
This is used to determine if fats were added to adulterate waxes.
WAXES – COMPOSITION:
Fats consists almost entirely of esters.
Waxes: esters (palmitate type), free acids, HC’s, free alcohols & sterols.
Acid values of waxes also tend to be higher than those of fats.

WOOL FAT:
DEFINITION: Wool fat (anhydrous lanolin) is a purified fat-like substance
prepared from the wool of the sheep, Ovis aries (Bovidae).
WOOL FAT: PREPARATION:
Raw wool contains considerable quantities of ‘wool grease’ or crude lanolin, the
potassium salts of fatty acids & earthy matter.
Raw lanolin is separated by ‘cracking’ with sulphuric acid & purified to be fit
for medicinal use. Purification may be done by centrifuging with water & by
bleaching.
WOOL FAT: CHARACTERS:
Wool fat is a pale yellow, tenacious substance with a faint but characteristic
odour.
It is insoluble in water.
Melting point: 36-42ºC
Soluble: in ether & chloroform.
Like other waxes, it is not readily saponified by aqueous alkali, but with a
alcoholic solution of alkali.
Saponification value: 90 – 105.
Iodine value: 18 – 32.
Acid value: not more than 1

197
6. LIPIDS NOTES BY BILAL MALIK

WOOL FAT: CONSTITUENTS:


25 % water
Cholesterol & isocholesterol (main active constituents).
Unsaturated alcohols
Fatty acids
(- lanoceric
- lanopalmitic
- & carnaubic fatty acids)
WOOL FAT: USES:
Wool fat is used as an emollient base for creams & ointments.

BEESWAX:
DEFINITION: Beeswax is obtained by melting and purifying the honeycomb
of Apis mellifica and other bees.
Zoological origin:
Apis mellifera
Apis dosarta
Apis cerana
Apis indica
Apis florea
Family:
Apidae
Source:
Bee hives
GEOGRAPHICAL SOURCES: West Indies, California, Chile, Africa,
Madagascar & India.
Separate monographs exist for yellow and white beeswax.

198
6. LIPIDS NOTES BY BILAL MALIK

Production:
Worker bees have eight wax-producing mirror glands. The size of these
wax glands depends on the age of the worker and after daily flights begin
these glands gradually atrophy. The new wax scales are initially glass-
clear and colorless becoming opaque afterwards.
The wax of honeycomb is nearly white, but becomes progressively more
yellow or brown by incorporation of pollen oils and propolis.
BEESWAX: PREPARATION:
Wax is secreted by worker bees in cells on the ventral surface of the last 4
segments of their abdomen. The wax passes out through pores in the chitinous
plates of the sternum & is used, particularly by the young workers, to form the
comb.
Honey bees use the beeswax to build honeycomb cells In which their young are
raised and honey and pollen Are stored.
For the wax-making bees to secrete wax, the
ambient temperature in the hive has to be 33 to 36°C
(91 to 97 °F).
To produce their wax, bees must consume about eight times as much honey by
mass.
When beekeeper extract the honey, they cut off the wax caps from each
honeycomb cell with an
uncapping knife or machine.
The wax may further be clarified by heating in water.
PREPARTION OF
YELLOW BEESWAX:
Yellow beeswax is prepared, after removal of the honey, by melting the comb
under water. This causes solid impurities to sink to the bottom while any
residual honey is dissolved). This is then strained and the wax is allowed to
solidify in suitable moulds.
PREPARATION OF WHITE BEESWAX:
White beeswax is prepared from yellow beeswax which is treated with charcoal,
potassium permangante, chromic acid, or chlorine, by the slow bleaching action

199
6. LIPIDS NOTES BY BILAL MALIK

of light, air & moisture. In this method the melted wax is allowed to fall on a
revolving cylinder which is kept moist. This then slowly becomes bleached.
This is then repeated at least one more time. The wax is finally cast into circular
cakes.

BEESWAX: CHARACTERS:
Beeswax is a yellow-brown or yellow-white solid.
It breaks with a granular fracture & has a characteristic odour.
It is insoluble in water & slightly soluble in cold alcohol, but dissolves in
chloroform and also in warm fixed & volatile oils.
BEESWAX: CONSTITUENTS:
Beeswax is a true wax:
Beeswax is a tough wax formed from a mixture of
several compounds.
Consists of 80% myricin
(myricyl palmitate)
Contains a little myricyl stearate.
Free cerotic acid
Aromatic substances

Its main components are;


Palmitate
Palmitoleate
Hydroxypalmitate
oleate esters of long-chain (30-32 carbons)
Aliphatic alcohols
with the ratio of triacontanyl Palmitate to cerotic acid, the two principal
components, being 6:1.

Applications:
200
6. LIPIDS NOTES BY BILAL MALIK

Making of honeycomb foundation


Beeswax is an ingredient in surgical bone wax
Purified and bleached beeswax is used as:
• Coating for cheese
• Protectant of the food as it ages
• Food additive
• As a component of shoe polish, furniture polish
• As a component of modelling waxes

BEESWAX: ADULTERANTS:
Japan wax: not a true wax, but a fat (may be saponified by means of boiling
aqueous sodium hydroxide – waxes are unaffected by aqueous alkali).
Japan wax is prepared from the fruits of Rhus (Anacardiaceae).
BEESWAX: USES:
Beeswax is used for the preparation of plasters, ointments and polishes.

COOKING OILS:
Do not use fresh, unrefined, mechanically pressed, light & oxygen protected
EFA-rich seed oils for cooking.
Labels: “Cholesterol Free”.
Opened bottles should be kept in the fridge & used with 3-6 weeks. Olive oil
can keep well for up to 2 years.
NB: Cooking method influences the type of oil you use.

201
6. LIPIDS NOTES BY BILAL MALIK

LENOLIN:
Lanolin is also called wool wax or wool grease. It is a yellow waxy substance
secreted by the sebaceous glands of wool bearing animals. Most lanolin used by
humans comes from domestic sheep.

Constituents:
A typical high purity grade of lanolin is
composed predominantly of;
Long chain waxy esters
lanolin alcohols
lanolin acids

202
6. LIPIDS NOTES BY BILAL MALIK

lanolin hydrocarbons
It has been estimated that there may be between 8,000 and 20,000 different
types of lanolin ester present in lanolin .
Production:
o Lanolin is extracted by washing the wool in hot water with a special wool
scouring detergent to remove dirt, wool grease (crude lanolin), suint
(sweat salts), and anything else stuck to the wool.
o The wool grease is continuously removed during this washing process
by centrifugal separators, which concentrate the wool grease into a wax-
like substance melting at approximately 38 °C (100 °F).
Applications:
Lanolin and its many derivatives are used extensively in high value
cosmetics, facial cosmetics, lip products etc
Lanolin is used commercially in many industrial products ranging
from rust-proof coatings to lubricants.
Lanolin is often used as a raw material for producing cholecalciferol
(vitamin D3).
Anhydrous lanolin is also used as a lubricant for brass instrument tuning
slides.
Lanolin can also be restored to woolen garments to make them water and
dirt repellent.

JOJOBA OIL:

203
6. LIPIDS NOTES BY BILAL MALIK

Botanical origin:
Simmondsia chinensis

Family:
Simmondsiaceae
Part used:
seeds
Constituents:
This oil is rare in that it is an extremely long
(C36-C46) straight-chain wax ester
Uses:
In cosmetics as a moisturizer
As a carrier oil for specialty fragrances
Bio-diesel fuel for cars and trucks
Biodegradable lubricant.

SPERMACETI:

Source:
Spermaceti is a wax present in the head cavities of the whale i.e. Physeter
macrocephalus.

204
6. LIPIDS NOTES BY BILAL MALIK

Extraction:
Spermaceti is extracted from oil by
crystallization at 6 °C. When treated by pressure and
a chemical solution of caustic alkali, spermaceti
forms brilliant white crystals that are hard but oily to
the touch, and are devoid of taste or smell.
Uses:
Ingredient in cosmetics
Leather working
Lubricants
Making of candles
Dressing of fabrics
Pharmaceutical excipient (in ointments)

205
6. LIPIDS NOTES BY BILAL MALIK

CARNAUBA WAX:

Botanical origin:
Copernicia cerifera
Copernicia prunifera
Family:
Arecaceae
Part used:
Leaves
Constituents:
Carnauba consists mostly of;
Aliphatic esters
Diesters of 4-hydroxycinnamic acid
ω-hydroxycarboxylic acids
Fatty acid alcohols
Methoxy cinnamic acid

Uses:
Automobile waxes
Shoe polishes
Dental floss
Food products such as sweets,
Floor and furniture waxes and polishes
Use for paper coatings
Emollient

206
7. VOLATILE OILS NOTES BY BILAL MALIK

VOLATILE OILS
 Volatile or essential oils, as their name implies. are volatile in steam
 They differ entirely in both chemical and physical properties from
fixed oils. With the exception of oils such as oil of bitter almonds
which are produced by the hydrolysis of glycosides.
 these oils are contained largely as such in the plant.
 They are secreted in oil cells. In secretion ducts or cavities or in
glandular hairs.
 They are frequently associated with other substances such as gums and
resins and themselves tend to resinify on exposure to air.
 Volatile oils are sweet-smelling liquids, and they emit fragrance to the
food and are also slight bitter in taste. Thus, they help to enhance the
secretion of digestive enzyme in the alimentary tract
 Volatile oils, when fresh, are colourless liquids. A few are crystalline or
amorphous solid.
 On long standing, they become darker in colour, especially when exposed
to air and direct sunlight.
 Volatile oil should, therefore, be stored in tightly closed amber-coloured
bottles in a cool, dry place.
 Volatile oils are slightly soluble in water but are readily soluble in ether,
alcohol and most of organic solvents.

Volatile oil/ essential oil Fixed Oil

Volatile oil can evaporate when Fixed oils do not evaporate at


placed under room temperature room temperature

They can be extracted easily by They require some specific


the distillation process techniques for extraction.

207
7. VOLATILE OILS NOTES BY BILAL MALIK

There is no spot (no permanent Some type of spot (permanent


stain) left after evaporation stain) left after evaporation

They are unable to undergo


Fixed oils can be easily sponified.
saponification

Volatile oils are mixture of


hydrocarbon terpenes,
sesquiterpenes and polyterpenes Esters of higher fatty acids &
and their oxygenated derivatives glycerin are called as fixed oils.
obtained from various parts of the
plants

Posses high refractive index Posses low refractive index

These are optically active. These are optically inactive.

Their primary source is leaves, Their major source is seeds of the


roots, in petals and bark. plant.

CLASSIFICATION:
(a) Hydrocarbon volatile oils: Cubeb and Turpentine oil.
(b) Alcoholic volatile oils: Peppermint, Coriander and Cardamom.
(c) Aldehydic volatile oils: Bitter orange peel, Sweet orange peel, Lemon
Cinnamon and Bitter almond oil
(d) Ketonic volatile oils: Camphor, Spearmint, Caraway, Buchu
(e) Phenolic volatile oils: Clove, Thyme.
(f) Phenolic ether volatile oils: Fennel, Anise, Myristica.
(g) Oxide volatile oils: Eucalyptus, Chenopodium.
(h) Ester volatile oils: Rosemary.
(i) Miscellaneous volatile oils: Allium, Anethum.

208
7. VOLATILE OILS NOTES BY BILAL MALIK

a)HYDROCARBON VOLATILE OILS:


i) CUBEB

DEFINITION: Cubeb is the dried, full-grown, unripe fruit of Piper cubeba


Linn.
Botanical source: Piper cubeba
Family: Piperaceae.
Geographical Sources
Java, Penang, and other parts of East Indies
MACROSCOPICAL FEATURES:
A creeper or climbing perennial plant, with a bunch of dioecious flowers in
spikes.
Odour: aromatic and characteristic-
Taste: strongly aromatic and pungent and somewhat bitter.
Commercial cubebs consist of the dried berries, round in shape and looks like
black pepper, but with stalks attached – the "tails" in "tailed pepper". The dried
pericarp is wrinkled, and its color ranges from grayish-brown to black. The seed
is hard, white and oily
The stalked berries are slightly larger than black peppercorns, have a furrowed
surface and most are hollow. They are sold whole and should be crushed or
ground before use.

209
7. VOLATILE OILS NOTES BY BILAL MALIK

Constituents:
Volatile oil (10 - 18 %)
Resins
Amorphous cubebic acid
Colourless crystalline cubebin.
By extraction with ether yields oleo-resin (22%).

USES OF CUBEB:
 Stimulant, carminative, aphrodisiac much used as a remedy for
gonorrhoea, after the first active inflammatory symptoms have subsided;
also used in leucorrhoea(Leucorrhoea: is a thick, whitish or yellowish vaginal
discharge. There are many causes of Leukorrhea, the usual one being estrogen
imbalance.), cystitis, urethritis, abscesses(An abscess (Latin: abscessus) is a
collection of pus that has built up within the tissue of the body. Signs and
symptoms of abscesses include redness, pain, warmth, and swelling. The
swelling may feel fluid filled when pressed) of the prostate gland, piles and
chronic bronchitis.
 Cubeb was frequently used in the form of cigarettes for asthma, chronic
pharyngitis and hay fever

CUBEB OIL:
About 15% of a volatile oil is obtained by distilling cubebs with water
Monoterpenes:
• Sabinene 50%
• α-thujene
• Carene
Sesquiterpenes

210
7. VOLATILE OILS NOTES BY BILAL MALIK

• Caryophyllene
• Copaene
• α- and β-Cubebene
• δ-Cadinene
• Germacrene
Oxides 1,4- and 1,8-cineole and the alcohol cubebol.
CUBEB OIL – USES:
Cubeb essential oil is pungent, slightly camphorous, with a touch of nutmeg. It
has
 Stimulant,
 Expectorant,
 Carminative,
 Antiseptic, and
 Diuretic properties

ii) TERPENTINE OIL:


• Syn Name: Oil of turpentine, Turpentine tincture, Turpentine spirit.
• B.O: Pinus Longifolia Roxb.
• Pinus roxburghii Sargent.
• Pinus excelsa Wall.
• Family: Pinaceae

COLLECTION:
• Pinus oleoresin is a normal i.e. physiological product of pine. The amount
produced is generally enhanced by injury or by treatment with 50%
H2SO4. It is secreted in plant tissues in specific cavities or resin ducts.
The cavities are themselves formed either in a schizogenous or lysigenous
fashion.

211
7. VOLATILE OILS NOTES BY BILAL MALIK

• These are anastinosing in nature. When one of the passages is open as in


wound from a distance. The acid treatment crumpled the thin walled
parenchyma.
• This permits the duct channel to become larger providing a more rapid
flow of oleoresin and two methods of collection have been used;
• 1. Box method.
• 2. Cup and gutter method
• CHARACTERISTICS:
• Turpentine oil is colourless liquid possessing a characteristic odour and
taste. It is soluble in alcohol and has a specific gravity of 0.854-0.868 at
25C.
• CONSTITUENTS:
• Turpentine consists of Dicyclic monoterpenes such as d & L a-pinene and
camphene. [Camphene induced apoptosis by the intrinsic pathway in
melanoma cells & exerted antitumor activity in vivo]
• It also contains monocyclic monoterpenes such as dipentene and methyl
carbachol and also bormyl acetate etc.
Uses:
 Turpentine oil is now rarely given internally.
 Externally it is used as counter irritant,
 rubifaciant in lotions,
 also as mild antiseptic.
 It is also used as solvent for waxes in the production of
synthetic camphor, shoe polishes and furniture polishes.

b) OXIDE VOLATILE OILS:


a binary compound of an element or a radical with oxygen

i) EUCALYPTUS LEAF:
DEFINTION:

212
7. VOLATILE OILS NOTES BY BILAL MALIK

Eucalyptus leaf consists of the whole or cut dried leaves of the older
branches of Eucalyptus globulus, (Myrtaceae).
GEOGRAPHICAL SOURCES
Portugal, Spain, China, Brazil, Australia, India, Pakistan & Paraguay.
Eucalyptus – DESCRIPTION:
MACROSCOPICAL
• Older dried leaves are grey-brown & have lateral veins.
• Secretory oil cells are visible in leaves held to the light.
MICROSCOPIC
• Epidermal cells have a thick cuticle.
• Mesophyll has schizogenous oil glands
• Calcium oxalate crystals.
EUCALYPTUS OIL:
Eucalyptus oil is the volatile oil obtained by the distillation of the fresh leaves
of Eucalyptus globulus and other species of Eucalyptus,
It is rectified, if necessary. It should contain not less than 65% of cineole.

Only a certain amount of species produce oil suitable for medicinal use – the
main criteria is a high cineole content and low amounts of phellandrene and
aldehydes.
CHARACTERISTICS:
 Colourless or pale yellow liquid.
 Aromatic & camphoraceous in odour.
 Pungent & camphoraceous in taste, which is followed by a sensation of
cold.
 It is soluble in 90% alcohol, fixed oils, fats and in paraffin and insoluble
in water.
CONSTITUENTS:
• At least 70 volatile oils: Chiefly contains cineole, also known as
eucalyptol (about 80%). Cineol (or eucalyptol) is by far the most
213
7. VOLATILE OILS NOTES BY BILAL MALIK

important member of the family and virtually exists in a class of its own.
It is anesthetic, antiseptic, and works as an expectorant.
It also contains:
 Pinene
 Camphene
 Traces of Phellandrene
 Citronellal
 Geranyl acetate
EUCALYPTUS OIL – USES:
 Decreasing the symptoms of
nasopharyngeal infections
 Treating coughs
 Chronic bronchitis
 Decongestant
 Counter-irritant
 Antiseptic
 Expectorant
Official preparations
Mixtures, inhalations, Nasal Drops, lozenges; also applied externally as
ointments and liniments.

ii)CHENOPODIUM OIL:
DEFINTION: Chenopodium oil is a volatile oil obtained by steam distillation
from the fresh flowering and fruiting plants (except roots) of Chenopodium
ambrosioldes; var. anthelminticum Linn., Family: Chenopodiaceae
GEOGRAPHICAL SOURCES
Eastern and Central U.S.A, Caribbean islands, Europe, Maryland, Mexico,
Canada, India and Pakistan
Description:

214
7. VOLATILE OILS NOTES BY BILAL MALIK

• Colour- Colourless to light yellow coloured liquid.


• Odour: Unpleasant and characteristic.
• Taste- - Bitter and burning.
• Solubility- It is soluble in 8 volumes of alcohol (70%) and insoluble in
water.
Chemical Constituents:
• The herb contains 0.5 to 1.0% volatile oil, while fruits contain 1 to 4% of
oil.
• The oil contains chiefly ascaridole which is an unsaturated terpene
peroxide (70 to 80%)
• p-cymene about 20%
• Myrcene
• 1 –limonene
• Camphor.

Uses:
• Use as anthelmintic
• Specifically for round-worms (Ascaris).
• Used to expel hook-worms and dwarf tape-worms.
• It has no action on large tape-worms.
• Used against intestinal amoebae and in veterinary practice.

215
7. VOLATILE OILS NOTES BY BILAL MALIK

• Storage: Chenopodium oil is stored in closed containers, in cool places


away from light.

c) PHENOLIC VOLATILE OILS


Phenols - are responsible for the fragrance of an oil. They are antiseptic, anti-
bacterial, and strongly stimulating but can also be quite caustic to the skin. They
contain high levels of oxygenating molecules and have antioxidant properties.

i)CLOVE:

DEFINITION: Cloves are the dried flower buds of Syzygium aromaticum


(Eugenia caryophyllus), (Myrtaceaea).
Geographical Sources
Indonesia, Pakistan & Brazil, Zanzibar, Pemba.
HISTORY OF CLOVE:
Cloves were used in China as early as 266 BC, and by the 4th century, they were
known in Europe, although very expensive.
Same as with nutmeg, the Dutch also destroyed all trees from surrounding
native islands to secure a monopoly, and cultivated them only in a small group
of islands.
In 1770, the French managed to introduce clove trees to Mauritius, and started
cultivating them there, as well as in Zanzibar, Penang and Sumatra.
COLLECTION & PREPARATION:

216
7. VOLATILE OILS NOTES BY BILAL MALIK

The flower buds are collected when the lower part turns green-crimson. The
cloves are dried in the open air on mats & separated from their peduncles
(forming clove stalks which are also sold commercially).
If left on the tree for too long, the buds open & the petals fall, leaving “brown
cloves”. Later the fruits (“mother cloves”) are produced.
MACROSCOPICAL FEATURES:
Cloves are 10-17.5 mm long.
The head consists of 4 slightly projecting calyx teeth, 4 membranous petals and
numerous incurved stamens around a large style.
Odour: Spicy & Pungent
Taste: Aromatic
MICROSCOPICAL FEATURES:
Heavy cuticularized epidermis
Numerous oil cells (shizolysigenous)
Calcium oxalates (cluster crystals & prisms)
Stomata (epidermis of sepals)
Starch (Fruit – “mother cloves”)
CONSTITUENTS:
14-21% Volatile oils
• Mainly eugenol & isoeugenol
• Sitosterol
• Stigmasterol
• Campesterol
Tannins
Triterpene acids & esters
Glycosides
USES OF CLOVE:
Stimulant aromatic
Spice
217
7. VOLATILE OILS NOTES BY BILAL MALIK

For the preparation of volatile oil


Sesquiterpenes: potential anti-carcinogenic compounds
CLOVE OIL:
Oil distilled in Europe and the US normally does not need purification, while oil
distilled in other areas does.
After purification, the oil is sold with varying eugenol contents.
Oil of cloves is yellow or colourless, is slightly heavier than water.
CLOVE OIL – CONSTITUENTS:
Volatile oils – mainly eugenol & acetyleugenol Sesquiterpenes.
Oil of clove – like other volatile/essential oils – should be stored in a well-fitted,
air-tight container, & should be protected from light & heat.
CLOVE OIL – USES:
 Aromatic
 Stimulant
 Flavouring Agent
antifungal, antiseptic, antiviral, aphrodisiac and stimulating properties.
The oil is used for treating a variety of health disorders including
toothaches, indigestion, cough, asthma, headache, stress and blood
impurities. The most important and common use of clove oil is in dental
care. Several toothpastes, mouth wash and oral care medications contain
clove oil as an important ingredient.

ii) THYME & THYME OIL:


DEFINITION: The whole leaves and flowers of Thymus vulgaris. Or Thymus
zygis
(Family: Labiatae)
GEOGRAPHICAL SOURCES
Indigenous to Central & Southern Europe, Eastern Africa, India, Turkey,
Pakistan & North America.
MACROSCOPICAL FEATURES:

218
7. VOLATILE OILS NOTES BY BILAL MALIK

It is an ancient herb used in medicine by the Greeks, the Egyptians and the
Romans.
Evergreen perennial shrub that grows up to 45 cm (18 inches) high
Woody root system
Much-branched stem
Small elliptical greenish gray aromatic leaves upto 12mm in length and
opposite.
leaves are almost stalkless with margins curved inwards and highly aromatic
Pale purple or white flowers
ACTIVE CONSTITUENTS:
The main chemical components are:
Thymol
Carvacrol
Linalol
Borneol
Camphene
α -thujone
α –pinene
β-pinene
p-cymene
α -terpinene
β-caryophyllene

219
7. VOLATILE OILS NOTES BY BILAL MALIK

Other Constituents:
Flavonoids: Flavonone and Dihydroflavonals
Biphenyls, Rosmarinic acid, Tannins, Resins, Triterpenes

Thyme Oil:
• Thyme oil is extracted by hydro- distillation method
• It has a rather sweet, yet strongly herbal smell and is reddish-brown to
amber
• It is extracted from the fresh or partly dried flowering tops and leaves of
the plant by water or steam distillation and the yield is 0.7 -1.2 %.
ACTIONS & USES:
Culinary uses:
• Flavouring agent
(to flavour meats, soups, Lamb)
Medicinal use:
• The main component of the essential oil of thyme, thymol, is active
against Salmonella and Staphylococcus bacteria. the antiseptic tonic
properties of thyme make it a useful tonic for the immune system in
chronic, especially fungal, infections as well as an effective remedy for
chest infections such as bronchitis, whooping cough, and pleurisy.
Therapeutic properties of thyme oil:
• antirheumatic, antiseptic, antispasmodic, bactericidal, bechic,
carminative, diuretic, expectorant, insecticide, stimulant, tonic and
vermifuge
• Industrial :
• Industrial The essential oil of thyme is used to preserve processed meat
and butter, and in making chewing gum, ice cream, candy, and the liqueur
Benedictine. Thymol is active ingredient in mouthwashes (Listerine)
• COSMETIC :
• COSMETIC it is used for skin problems such as oily skin, sciatica, acne,
dermatitis, eczema and insect bites

220
7. VOLATILE OILS NOTES BY BILAL MALIK

d) ESTER VOLATILE OILS:


i) ROSEMARY & ROSEMARY OIL:

DEFINITION:
Rosemary consists of dried Stems, leaves and flowers of Rosmarinus
officinalis (also known as Rosmarinus coronarium) of the Labiatae
Most sources interpret the Latin name as rosmarinus“ dew of the sea”.
GEOGRAPHICAL SOURCES:
Native to the Mediterranean regions, southern Europe, South Africa, India and
Pakistan
MACROSCOPICAL FEATURES:
Stem
Rosemary is an evergreen, shrubby herb that grows to a height of 1 to 2 m, with
a unique aromatic odour and a camphoraceous undertone. The erect stems are
divided into numerous long, slender branches that have ash-coloured and scaly
bark.
Leaves
The branches bear opposite, leathery thick leaves which are lustrous,
linear, dark green above and grey somewhat wooly below.
Flower
The flowers are small and pale blue to deep blue. Much of the volatile essential
oils reside in their calyces.
Rosmary Constituents:
 Hydroxy-cinnamic acid [antioxidant in various oxidative stress induced
disorders]

221
7. VOLATILE OILS NOTES BY BILAL MALIK

 Rosmanol
 Epi-rosmanol
 Rosmarinic acid
 Carnosic acid
 Carnosol
 α and β amyrin
 Ursolic acid
 Oleanolic acid

Rosemary Oil:
• Rosemary oil is extracted from the fresh flowering tops by steam
distillation. It yields 1.0 - 2.0 %.
Description:
 Rosemary oil is colorless to pale yellow
 It has a powerful aromatic refreshing herbal smell,
 It is clear in color
 and watery in viscosity
Rosemary Oil – CONSTITUENTS:
• It contains 0.8-6 % of Esters and 8-20 % of alcohols. The main chemical
components of rosemary oil are:
• α –pinene [induced apoptosis in cancer cells]
• Borneol [alleviates mechanical hyperalgesia in models of chronic
inflammatory and neuropathic pain in mice]
• β -pinene
• Camphor
• Bornyl acetate
• Camphene [induces intrinsic apoptosis in melanoma cells and displays
antitumor activity in vivo].
• 1,8-cineole [1,8-cineole acts as a P450 inhibitor-like compound,
improving the toxicity of other xenobiotics]

222
7. VOLATILE OILS NOTES BY BILAL MALIK

• limonene.
• https://www.youtube.com/watch?v=uuIxH0bS0Hw
ROSEMARY OIL USES:
COSMETIC
 Rosemary acts on the hair follicles by stimulating growth and acts against
dandruff.
 It is used in preparations for acne and dermatitis.
 Rosemary is also one of the ingredients used in the preparation of eau de
cologne.
 It is added to liniments as a fragrant stimulant.
ROSEMARY OIL USES:
PHARMACEUTICAL AND THERAPEUTIC
 Rosemary oil has a pronounced action on the brain as it clears the mind
and aids the memory. It is an external stimulant and a relaxant for
nervousness, muscle spasms, headaches, migraines, neuralgia, mental
fatigue and nervous exhaustion.
 The antiseptic action of rosemary oil is especially suitable for intestinal
infections and diarrhoea, and it also eases colitis, dyspepsia, flatulence,
hepatic disorders and jaundice.
 On the respiratory system rosemary oil is effective for asthma,
bronchitis and whooping cough. It may ease congestion, puffiness and
swelling and also may improve acne, dermatitis and eczema.
 Diuretic
 Its stimulating action may benefit scalp disorders and encourage hair
growth.
 Rosemary has been used as a folk remedy against rheumatism, and
treating of wounds.
 It has been used in the treatment of cancer and as a tonic to the kidneys.
 FOOD AND FLAVOURING

223
7. VOLATILE OILS NOTES BY BILAL MALIK

 Rosemary is used in food products and non alcoholic beverages. Fresh


and dried rosemary leaves, whole or ground, are used as seasonings for
soups, stews, sausages, meat, fish, and poultry.
 INDUSTRIAL
 It is used as an ingredient in soaps, creams, candles, deodorants, hair
tonics, and shampoos. It is also used in many household cleaners and air
fresheners. It is a major constituent of some organic pesticides. The
antibacterial and antioxidant activity of rosemary is used to extend the
keeping quality of fats and meat.
 OTHER
 Rosemary is used as a groundcover and garden plant. It can be planted as
hedge.
 It is a good source of nectar for bees. The plant is used as an insect
repellent.

e)MISCELLANEOUS VOLATILE OILS:


i)ANETHUM- DILL:

DEFINITION: consist of dried ripe fruits of Anethum graveolens Linn. family


Umbelliferae
GEOGRAPHICAL SOURCES:Anethum is indigenous to South Europe and
cultivated in England Germany Romanv and Mediterranean countries
Cultivation and Collection:

224
7. VOLATILE OILS NOTES BY BILAL MALIK

The cultivation of the drug is done by sowing the fruits. It needs sandy loam
soil, devoid of gravels, with slightly acidic nature.
It is a cold weather crop and is grown during rabi season. Its sowing is done in
October and the crop is harvested in March/April.
The umbels are collected after full maturity, dried thoroughly and shaken to
separate the fruits.
Fruits removed and then packed into the bags are sieved, excess of foreign
organic matter is removed and then packed into the bags.
MACROSCOPICAL FEATURES:
The fruits are yellowish or pale brown with narrow wings.
Odour and Taste: Aromatic and characteristic
Size: The fruits are about 4 mm in length, 2 to 3 mm in width and 1 mm in
thickness.
Shape: Broadly ovate, strongly compressed dorsally. The fruits are found in the
form of mericarps usually separated and free from pedicel.
Each mericarp is yellow in colour, lateral rides of mericarp are extended as
wings.
ANETHUM- DILL OIL:
Extraction
• Dill oil is extracted by steam distillation, mainly from the seeds, or the
whole herb, fresh or partly dried.
Oil properties
• Dill oil has a grass-like smell and colorless or pale yellow liquid with a
watery viscosity.
ACTIVE CONSTITUENTS:
Volatile oil (2.4 – 4.0%):
The chief constituent of the volatile oil is aromatic liquid, known as carvone (43
to 63%).
It also contains:
Dihydrocarvone,
D-limonene,
225
7. VOLATILE OILS NOTES BY BILAL MALIK

Phellandrene and other terpenes.


Fixed oil and proteins.
Uses:
• It is used as an aromatic, a stimulant, carminative and also in gastric
disturbances of infants and children. The oil of dill is used in the
preparation of dill water, gripe water and also as flavouring agent.
Substitutes:
• It is substituted by Indian dill obtained from Anethum sowa . The volatile
oil of Indian dill contains dill-apiole. Indian dill is generally used, in the
veterinary practices, since the dill-apiole, is regarded as a poisonous
substance.

ii) Garlic:
DEFINITION: consist of dried ripe bulb of Allium sativum Linn. Family:
Liliaceae
{The name is of Anglo-Saxon origin, being derived from gar (a spear) and lac
(a plant), in reference to the shape of its leaves}
GEOGRAPHICAL SOURCES
Garlic occurs in central Asia, southern Europe and USA. It is widely cultivated
in India and Pakistan.
Cultivation:
• Divide the bulbs into their component 'cloves' - each bulb will divide into
eight or fifteen cloves and with a dibber put in the cloves separately,
about 2 inches deep and about 6 inches apart, leaving about 1 foot
between the rows.
• When planted early in the spring, in February or March, the bulbs should
be ready for lifting in August, when the leaves will be beginning to witer.
• Should the summer have been wet and cold, they may probably not be
ready till nearly the middle of September.
Morphology:
• Garlic is a bulbous perennial herb, closely related to the onion.

226
7. VOLATILE OILS NOTES BY BILAL MALIK

• It has a tall, erect flowering stem that reaches 2-3 feet in height.
• The plant has pink or purple flowers that bloom in mid to late summer.
• It is a perennial herb having bulbs (the only part eaten) that is of a
compound nature, consisting of numerous (8-15) bulblets, known
technically as 'cloves,' grouped together between the membraneous scales
and enclosed within a whitish skin, which holds them as in a sac.
• Outer surface of each clove is convex while the inner one is concave.

• The flowers are placed at the end of a stalk rising direct from the bulb and
are whitish, grouped together in a globular head, with an enclosing kind
of leaf or spathae, and among them are small bulbils.
• Odour: When crushed gives odour that is because of allicin.
Constituents:
• The potentially active chemical constituents reported are
• Sulfur compounds: aliin, allicin, ajoene, allylpropyl disulfide, diallyl
trisulfide, sallylcysteine, vinyldithiines, S-allylmercaptocystein, and
others
• Enzymes: allinase, peroxidases, myrosinase, and others
227
7. VOLATILE OILS NOTES BY BILAL MALIK

• Amino acids and their glycosides: arginine and others


• Selenium, germanium, tellurium and other trace minerals
Medicinal Uses:
• Traditionally, it has been used to treat chronic bronchitis,
• respiratory catarrh(Catarrh=is a disorder or inflammation of the mucous
membranes in one of the airways or cavities of the body),
• recurrent colds,
• whooping cough,
• bronchitic asthma, influenza and chronic bronchitis.
• Modern use of garlic and garlic preparations is focused on their
• reputed antihypertensive,
• anti-atherogenic,
• antithrombotic,
• antimicrobial,
• fibrinolytic,
• cancer preventive and lipid-lowering effects.

228
8)RESINS NOTES BY BILAL MALIK

Resins:
Introduction:
• Resins are amorphous solid or semisolid substances that are invariably
water insoluble but mostly soluble in alcohol or other organic solvents.
• Physically they are found to be hard, translucent or transparent and
fusible i.e., upon heating they first get softened and ultimately melt.
• Chemically, they are complex mixtures of allied substances, such as:
resin acids, resin alcohols (resinols), resino-tannols, resin esters and
gluco-resins.
• Thus, Resins as amorphous products having an inherent complex
chemical entity.
• Resins are normally produced either in schizogenous ducts or in cavities
and are regarded as the end products of metabolism.
• They are electrically non-conductive and combustible in nature.

Oleoresins:
• Oleoresins are homogenous mixtures of resins and volatile oils.
• These are the vegetative (asexual) secretions obtained as natural products
and composed of resin dissolved in essential oils.
Distribution of Resins in Plants:
• The resins and resinous substances are more or less extensively
distributed throughout the entire plant kingdom, specifically the
Spermatophyta i.e., the seed plants.
• Notably, their presence is almost rare and practically negligible in the
Pteridophyta i.e., the ferns and their allies.
• However, the resins have not been reported in the Thallophyta i.e., the
sea-weeds, fungi etc.
• These findings and observations lead to the fact the resins are the overall
and net result of metabolism in the higher plants,
• since the majority of them belong to the phyllum Angiosperum i.e., seed-
enclosed flowering plants, and Gymnosperm i.e., naked-seed non-
flowering plants.

229
8)RESINS NOTES BY BILAL MALIK

Occurrence of Resins in Plants:


• In the plants resins usually occur in different secretory zones or
structures.
• (i) Resin Cells : Ginger–Zingiber officinale (Family: Zingiberaceae);
• (ii) Schizogenous Ducts : Pine Wood–Pinus polustris (Family:
Pinaceae).
• (iii) Glandular Hairs : Cannabis–Cannabis sativa (Family: Moraceae)
• The formation of resins in the plant is by virtue of its normal
physiological functions. However, its yield may be enhanced in certain
exceptional instances by inflicting injury to the living plant, for instance:
Pinus.
• Many resisnous products are not formed by the plant itself unless and
until purposeful and methodical injuries in the shape of incisions are
made on them and the secretion or plant exudates are tapped carefully,
such as: Balsam of Talu and Benzoin.
• In other words, these resins are of pathological origin.
• One school of thought has categorically termed the secretion exclusively
obtained from the naturally occurring secretory structure as the Primary
Flow.
• Whereas the one collected through man-made-incisions on the plant i.e.,
abnormally formed secretary structures, as the Secondary Flow.

Physical Properties of Resins:


 1. Resins are hard, transparent or translucent brittle materials.
 2. They are invariably heavier than water having the specific gravity
ranging from 0.9-1.25.
 3. Resins are more or less amorphous materials but rarely crystallisable in
nature.
 4. On being heated at a relatively low temperature resins first get softened
and ultimately melt down thereby forming either an adhesive or a sticky
massive fluid, without undergoing any sort of decomposition or
volatilization.

230
8)RESINS NOTES BY BILAL MALIK

 5. On being heated in the air i.e., in the presence of oxygen, resins usually
burn readily with a smoky flame by virtue of the presence of a large
number of C-atoms in their structure.
 6. On being heated in a closed container i.e., in the absence of oxygen,
they undergo decomposition and very often give rise to empyreumatic
products i.e., products chiefly comprising of hydrocarbons.
 7. Resins are bad conductors of electricity, but when rubbed usually
become negatively charged.
 8. They are practically insoluble in water, but frequently soluble in
ethanol, volatile oils, fixed oils, chloral hydrate and non-polar organic
solvents e.g., benzene, n-hexane and petroleum ether.
Chemical Properties of Resins:
 1. Resins, in general, are enriched with carbon, deprived of nitrogen and
contain a few oxygen in their respective molecules.
 2. Majority of them undergo slow atmospheric oxidation.
 3. Resins are found to be a mixture of numerous compounds rather than a
single pure chemical entity.
 4. Their chemical properties are exclusively based upon the functional
groups present in these substances.
 5. Consequently, the resins are broadly divided into resin alcohols, resin
acids, resin esters, glycosidal resins and resenes (i.e., inert neutral
compounds).
 6. It is also believed that resins are nothing but oxidative products of
terpenes.
 7. They may also be regarded as the end-products of destructive
metabolism.
 8. The acidic resins when treated with alkaline solutions they yield soaps
(or resin-soaps).
Preparation of Resins:
 No general method has either been suggested or proposed for the
preparation of resins. In fact, there are two categories of resinous
products, namely:
 (a) Natural Resins

231
8)RESINS NOTES BY BILAL MALIK

 (b) Prepared Resins

a) Natural Resins:
 These resins usually formed as the exudates from various plants obtained
either normally or as a result of pathogenic conditions.
 These are also obtained by causing deep incisions or cuts in the trunk of
the plant.
 They may also be procured by hammering and scorching, such as:
balsam of Peru.
Prepared Resins:
The resins obtained are by different methods:
 (i) The crude drug containing resins is powdered and extracted with
ethanol several times till complete exhaustion takes place.
 The combined alcoholic extract is either, evaporated on a electric water-
bath slowly or poured slowly into cold distilled water.
 The precipitated resin is collected, washed with cold water and dried
carefully under shade or in a vacuum desiccator,
Examples: Podophyllum; Scammony and Jalap.
 (ii) In the case of alco-resins, organic solvents with lower boiling points
are normally employed e.g., solvent ether (bp 37°C), acetone (bp 56.5°C)
for their extraction.
 (iii) In the instance of gum-resins, the resin is extracted with 95% (v/v)
ethanol.
• https://www.youtube.com/watch?v=PXOLSuB79yE
Chemical Composition of Resins:
The constituents of resins may be classified as
(i) Resin Acids
e.g. Colophony and Copaiba.
(ii) Resin Esters and their Decomposition Products
e.g. Asafoetida, Benzoin, Balsam of Peru and Tolu.

232
8)RESINS NOTES BY BILAL MALIK

(iii) Resenes
e.g. Mastic, Myrrh, Olibanum.
Classification of Resins:

C. Classification based on constituents


• According to the major constituents present either in the resin or resin
combinations.
• Examples: Resins; Oleo-resins; Oleo-gum resins; Balsams

233
8)RESINS NOTES BY BILAL MALIK

Colophony:
Synonym: Rosin
Biological Source:
It is the residue left after distilling off the volatile oil from the oleoresin
obtained from Pinus palustris and other species of Pinus belonging to family
Pinaceae.
Generally, it is offered as wood rosin obtained from exudate from incisions
in the living tree , P. palustris and finally from tall oil rosin.
It is chiefly produced in the USA.
https://www.youtube.com/watch?v=Nu-FEad49P8
Characteristic Features:
 Fuses gradually at 100°C and at a higher temperature it burns with a
smoky flame, while leaving not more than 0.1% of ash as a residue.
 The alcoholic solution of colophony turns into milky-white on addition
of water.
 It is a pale yellow to amber, translucent fragments, brittle fracture at
ordinary temperature.
 https://www.youtube.com/watch?v=qTAJNmTV-_E
 It has turpentine-like odour and taste.
 Its acid number is not less than 150.
 It is almost insoluble in water, but freely soluble in ethanol, benzene,
ether, glacial acetic acid and oils.
Chemical Tests
 1. Dissolve 0.1 g of powdered colophony resin in 10 ml of acetic
anhydride, add one drop of sulphuric acid and shake well. The
appearance of a purple colour which rapidly changes to violet colour.
Chemical Constituents:
 1. Colophony contains 90% resin acids known as abietic acid. The
remaining 10% as resene-an inert substance and esters of fatty acids.
 2. It also contains a mixture of dihydroabietic acid and dehydroabietic
acid.

234
8)RESINS NOTES BY BILAL MALIK

 3. On being heated at 300°C, abietic acid undergoes further molecular


rearrangement to produce neo-abietic acid.
Abietic acid (AA), terpenoid:
1. Anti-inflammatory effects
2. Immunomodulatory effects
3. Attenuates allergic airway inflammation in a mouse allergic asthma model
4. The anticonvulsant activity of abietic acid at 30 and 100 mg/kg
5. Abietic and dehydroabietic acid are interesting diterpenes with antibacterial
and antifungal activity.
Uses of Colophony:
 1. Colophony is used in pharmacy for the preparation of zinc oxide
plasters, ointments and other adhesive plasters.
 2. It is widely used in the manufacture of printing inks, rubber, dark
varnishes, sealing wax, and thermoplastic floor tiles.
 3. It also finds its application as varnish and paint dries, cements, soaps,
wood polishes, paper, plastics, fireworks, tree wax, sizes, rosin oil.
 4. It is used for waterproofing cardboard, walls etc.

Podophyllum:
• Synonyms: Podophyllum resin, May apple, Mandrakes Root, Indian
apple, Vegetable calomel.
• Biological Sources:
Podophyllum is the dried rhizomes and roots of Podophyllum peltatum.
• Family: Berberidaceae
Preparation:
• Extract powdered podophyllum (1kg) by means of slow percolation until
it is almost exhausted of its resin content, using ethanol as the
menstruum.
• Carefully concentrate the percolate by evaporation until the residue
attains the consistency of a thin syrup.

235
8)RESINS NOTES BY BILAL MALIK

• Pour the resulting syrupy liquid with constant stirring into 1 L of distilled
water containing 10 ml of concentrated HCl and previously cooled to a
temperature less than 10°C.
• Allow the precipitate to settle down completely, decant the clean
supernatant liquid and wash the precipitate with cold distilled water
slowly, dry the resin and powder it.
Characteristic Features:
• It is a light brown to greenish-yellow powder, or small, yellowish, bulky,
fragile lumps usually becoming darker in shade on exposure to either heat
or light.
• It has a characteristic faint odour and a bitter acrid taste.
• It is freely soluble in ethanol, it is also soluble in dilute alkaline solution.
Chemical Constituents:
• Podophyllum contains 3.5 to 6% of resin. The most important ones
present in the podophyllum resin are podophyllotoxin (20% in American
Podophyllum) and almost up to 40% in Indian Podophyllum.
• Besides, it also contains α-peltatin (10%) and β-peltatin (5%).
• The resin also comprise of the closely related dimethylpodophyllotoxin
and its glycoside; and dehydropodophyllotoxin, as well as quercetin-a
tetra-hydroxy flavonol.
Uses:
• 1. Peltatin has shown antiviral activity
• 2. It is used as a slow-acting purgative.
• 3. Podophyllotoxin possesses anti-tumour properties and may be used in
the treatment of cancer.
• 4. It is invariably prescribed with other purgatives, henbane or belladonna
to prevent griping in infants.

Cannabis:
Synonyms:

236
8)RESINS NOTES BY BILAL MALIK

Indian Hemp, Indian cannabis, Marihuana, Marijuana, Bhang, Ganja,


Charas, Hashish.
Biological Source:
Cannabis consists of the dried flowering tops of cannabis sativa ,
belonging to family Moraceae.
Preparation:
After research carried out on the selective cultivation of Cannabis, two of its
genetic types have been evolved, namely:
• (i) Drug Type, and
• (ii) Hemp Type
Drug type (Cannabis):
 It is the rich (upto 15%) in the psychoactive constituent (–)-Δ9-trans-
tetra-hydrocannabinol.
Strong analgesic, hypothermia, sedative, Causes Inhibition of naloxone-induced
withdrawal in morphine dependent mice.
I.V administration produced a decrease in blood pressure and heart rate
 For the specific drug usages either the resin (hashish) or the flowering
tops of the female plant (marijiana) is employed

 The male plant also generates an equivalent quantity of the active


constituents; however, it is not concentrated into a resin but found
throughout the entire plant.

(–)-Δ9-trans-tetra-hydrocannabinol

237
8)RESINS NOTES BY BILAL MALIK

Hemp Type (Cannabis):


It contains very little active principal. Cannabidiol is the predominant
cannabinoid present in it.

Chemical Constituents:
• Besides, the resin contains several active constituents, such as:
cannabinol, cannin, cannabol, tetrahydrocannabinol, cannabigerol,
cannabichromene and Δ8-tetrahydrocannabinol.
• It also contains choline, volatile oil and trigonelline.
• Indian Hemp seeds contain 20% of fixed oil.
Uses
• It has been used as a sedative in equine [relating to or affecting horses
or other members of the horse family]colic.
Uses of Cannabis
• 1.Used to reduce nausea and vomiting during chemotherapy
• 2. To improve appetite in people with HIV/AIDS, and to treat chronic
pain and muscle spasms.
• 3.Its use for other medical applications, however, is insufficient for
conclusions about safety or efficacy
• Common side effects include dizziness, feeling tired, vomiting, and
hallucinations

Turpentine:
• Synonym: Gum turpentine

238
8)RESINS NOTES BY BILAL MALIK

• Biological Source: Turpentine is the oleoresin obtained from pinus


palustris and from other species of Pinus, belonging to the natural order
Pinaceae.
• Preparation
Turpentine is usually collected from the slash pine i.e., Pinus elliottii
and Pinus palustris, which grow in abundance in the Northern Florida, Georgia,
and North and South Carolina.
• The oleoresin is normally secreted in the ducts that are situated almost
beneath the cambium in the sapwood.
• In spring the bark is neatly cut from the tree with the help of a long-
handled cutting knife known as the “bark-hack”.
• After the removal of the chipped bark, the freshly exposed surface is
quickly sprayed with a solution of 50% (w/w) sulphuric acid. The flowing
oleoresin is guided by galvanized metal gutters right into the various
containers tied close to the tree-trunk.
• The thick liquid thus collected is removed as turpentine by pot-still
distillation periodically.
Characteristic Features:
• The gum turpentine is an yellowish, opaque, sticky mass having a
characteristic odour and taste.
• It is almost insoluble in water, but soluble in ether, ethanol, chloroform
and glacial acetic acid.
Chemical Constituents:
• The gum-turpentine when subjected to steam-distillation yields 15 to 30%
of a volatile oil known in the trade as “turpentine oil”.
• It contains mainly the terpenes, such as: dextro- and laevo-α-pinene, β-
pinene and camphene.
Uses:
• 1. It is employed externally as a counterirritant.
• 2. It is also used as a rubefacient.
• 3. It is used as a constituent of stimulating ointments.
• 4. It is employed industrially as an insecticide.

239
8)RESINS NOTES BY BILAL MALIK

• 5. It is used as a solvent for waxes.


• 6. It is utilized extensively in the production of synthetic camphor.
• 7. It is used in making various types of polishes

Myrrh:
• Synonyms:
Gum Myrrh, Myrrha.
• Biological Source:
Myrrh is an oleo-gum-resin obtained from the stem and branches of
Commiphora obyssinica or from other species of Commiphora
belonging to family Burseraceae.
https://www.youtube.com/watch?v=u9fQdXOnB7Y
https://www.youtube.com/watch?v=EFFUNRSxjVw
Preparation:
• The plants usually exude yellow coloured resin after proper incisions are
made in the bark of a tree.
It gradually hardens and becomes dark or reddish-brown in appearance.
The mass is collected by the native tribals of Somalia for trading.
Characteristic Features:
• Myrrh normally occurs either in the form of isolated irregular, rounded
tears of 2.5 cm in diameter or as masses duly formed by the
agglomeration of these tears.
• The tears are dull, rough and reddish-brown in appearance.
• It has a strong aromatic odour and possesses an acrid, bitter taste.
Chemical Constituents:
Myrrh contains volatile oil (7-17%), resin (20-25%), gum (57-61%), and
bitter principle (3 to 4%).
The resin is found to consist of a mixture of α-, β-, and γ-commiphoric acids
(resin acids).

240
8)RESINS NOTES BY BILAL MALIK

The oleo-gum-resin yields alcohol-soluble extract not less than 30%.


It also contains phenolic compound such as: pyrocatechin and protocatechuic
acid.

Uses:
• 1. It is used chiefly in perfumes and incense.
• 2. It is frequently employed as an antiseptic and stimulant.
• 3. Myrrh acts as an astringent to the mucous membrane and hence it find
its application in oral hygiene formulations, such as: gargles, mouth-
washes.
• 4. It is also used as a carminative.
• Chemopreventive effects of myrrh (Commiphora molmol) in
hepatocarcinogenic rats.
• In vitro cytotoxic and anti-inflammatory effects of myrrh oil
• It inhibit Oxidative stress and immunotoxic effects of lead.
• Resin is widely used in Asia as a cholesterol-lowering agent based on
Indian Ayurvedic medicine

Asafoetida:
• Synonyms
Asafetida; Asant; Devil's dung; Food of the Gods; Gum Asafoetida.
• Biological Sources
Asafoetida the oleo-gum-resin is obtained as an exudation of the
decapitated rhizome on roots of Ferula assafoetida ; Ferula foetida and some
other species of Ferula, belonging to the nature order Umbelliferae.
Preparation:
241
8)RESINS NOTES BY BILAL MALIK

• Asafoetida is generally present as a milky liquid in the large


schizogenous ducts and lysigenous cavities.
• These ducts and cavities are located more intensively in the cortex region
of the stem and root. The drug is obtaining chiefly from the stem.
• The fully grown plants are usually cut down to the crown region during
the spring. The exposed surface is protected by a covering made up of
twigs and leaves. After about a month, the hardened resinous substance is
collected by scrapping.
Characteristic Features:
• The drug occurs normally as soft mass or irregular lumps or ‘tears’ or
agglomeration of tears. The tears are brittle and tough.
• Asafoetida has a strong, persistent garlic-like odour and having a bitter
acrid taste. This oleo-gum-resin when triturated with water it gives a
milky emulsion.
Chemical Constituents:
• Asafoetida contains volatile oil (8-16°C) gum (25%) and resin (40-60%).
• The volatile oil essentially consists of some organic sulphides
responsible for attributing the characteristic garlic-like odour.
• The resin consists of notannol, resinotannol i.e., the resin alcohols, which
are present partially in the free state and partially in the combined form
with ferulic acid.
• It also contains umbellic acid and umbelliferone; the latter is found
combined with ferulic acid, but it gets generated on being treated with
dilute HCl.
Uses:
• 1. It is abundantly used in India and Iran as a common condiment and
flavouring agent in food products.
• 2. It is also an important ingredient in Worcestershire Sauce.
• 3. It is used as a repellant [2% (w/v) suspension] against dogs, cats, deer,
rabbits etc.
• 4. It is used seldomly as an antispasmodic, carminative, expectorant and
laxative.

242
8)RESINS NOTES BY BILAL MALIK

• 5. It is still employed in veterinary externally to prevent bandage chewing


by dogs.
• 6. It is also used as a powerful nerving stimulant especially in nervous
disorders related to hysteria.

Balsams:
• Balsams are the resinous mixtures that essentially contain large quantum
of benzoic acid, cinnamic acid or both, or esters of these organic aromatic
acids.
• Naturally occurring balsams
Storax
Peruvain Balsam
Tolu Balsam
Benzoin
https://www.youtube.com/watch?v=ZeZkE3337CM

Storax:
Synonyms
Styrax; Sweet oriental gum; Levant Storax
Biological Source
Storax is the balsam obtained from the trunk of Liquid amber orientalis
belonging to the natural order Hamamelidaceae.
Preparation
The storax is a pathological product formed as a result of injury
caused to the plant. It generally, exudes into the natural cavities between the
bark and the wood. The crude storax, thus collected from these cavities in

243
8)RESINS NOTES BY BILAL MALIK

suitable containers, is further purified by dissolving in ethanol, filtration and


subsequent evaporation of the solvent to obtain the pure storax.
Characteristic Features:
• The balsam storax is a semiliquid grayish, sticky and opaque mass.
• Storax is transparent in thin layers, possesses a characteristic agreeable
balsamic taste and odour.
• It is denser than water.
• It is almost insoluble in water, but completely soluble in warm ethanol,
ether and acetone.
Chemical Constituents:
Storax contains the following chemical compounds:
• α-and β- storesin and its cinnamic ester (30-50%),
• Styracin (5-10%)
• phenylpropyl cinnamate (10%)
• free-cinnamic acid (5-15%)
• Levorotatory oil (0.4%)
• Small amounts of ethyl cinnamate, benzyl cinnamate and
• traces of vanillin and styrene (C6H5CH=CH2).
Uses:
1. It is used in fumigating powders.
2. It finds its application in perfumery.
3. It is employed as an imbedding material in microscopy.
4. It is used as an expectorant, antiseptic and stimulant.
5. It is employed as a preservative for fatty substances e.g., lard and tallow.
6. It is also used as a flavouring agent for tobacco.
7. It is a vital ingredient of “Compound Benzoin Tincture”.

244
8)RESINS NOTES BY BILAL MALIK

Peruvian Balsam:
Synonyms: Balsam Peru; Black balsam; China oil;
Biological Source:
Balsam Peru is obtained from Toluifer pereiare belonging to family
Leguminosae.
Preparation:
Peruvian Balsam is a pathological product and is obtained usually by
inflicting injury to the trees. * It is prepared by beating the stems of the trees
with mallet.
*After a week the injured areas of the stem are scorched so as to separate the
bark from the stem and after a similar duration the bark is peeled off
completely.
* The desired balsam starts exuding freely from all the exposed surfaces, which
are then covered carefully with cloth to absorb the exuding balsam.
* The cloth that are completely soaked with the balsam is then removed and
boiled with water in a large vessel slowly.
* The balsam gets separated and settles at the bottom of the vessel. The
supernatant layer of water is removed by decantation and the residual balsam is
dried and packed in the containers.
Characteristic Features:
• It is a dark brown, viscid liquid having a pleasant aromatic odour.
• It has a peculiar warm bitter taste and persistent aftertaste which
resembles like vanilla.
• The Balsam Peru is transparent in thin films. It does not harden on being
exposed to atmosphere. It is brittle when cold.
• It is almost insoluble in water and petroleum ether but soluble in ethanol,
chloroform and glacial acetic acid.
Chemical Constituents:
Peruvian balsam contains
• Free benzoic and cinnamic acids (12-15%)
• Benzyl (40%)

245
8)RESINS NOTES BY BILAL MALIK

• Esters of these acids (5.2-13.4% cinnamein)


• Volatile oil (1.5-3%).
• Resins esters (30-38%) composed of peru-resinotannol cinnamate and
benzoate
• Vanillin and peruviol (nerolidol).

Uses:
1. It is a local protectant and rubefacient.
2. It also serves as a parasiticide in certain skin disorder.
3. It is used as an antiseptic and is applied externally either as ointment alone or
in alcoholic solution.
4. It acts as an astringent to treat hemorrhoids.
1. Peru Balsam is used as miticide, to aid in healing of indolent wounds, as
scabicide and parasiticide, in skin catarrh, diarrhoea, ulcer therapy, as local
protectant, and rubefacient.
2. It is an antiseptic and vulnerary and as a stimulating expectorant.
It is also employed in perfumery and some
chocolate flavourings, also in making of odours.
Peruvian Balsam is topically used as an antiseptic to
treat burns, frostbites, cracks, erythema, pruritus, ulcers,
246
8)RESINS NOTES BY BILAL MALIK

and wounds. Its suppositories are used to cure pain, pruritus, piles, and other
anal disorders. It is an ingredient in
cosmetic and hygiene products (soups, creams, lotions,
detergents) and in fixative. It can cause contact dermatitis
in some people

Tolu Balsam:
Synonyms
Thomas balsam; Opobalsam; Resin Tolu.
Biological Source
Tolu Balsam is a balsam obtained from toluifera balsamum belonging to
family Leguminosae.
It is also obtained from myroxylon balsamum
Family: Fabaceae.
Preparation:
• Tolu Balsam is considered to be a pathological product produced in the
new wood formed as a result of inflicted injury. For its preparation, it is
an usual practice to make ‘V’ shaped incisions deep into the body of the
main trunk.
• The exudate thus produced is collected in cups held strategically just at
the base of each incisions. Balsam of Tolu is collected from these cups,
mixed and packed in air-tight sealed tins.
Characteristic Features:
• It is a yellowish-brown or brown semifluid or nearly solid resinous mass.
• It has a characteristic aromatic vanilla-like odour and slightly pungent
taste.
• It is usually brittle when cold.
• It is found to be transparent in thin layers, and shows numerous crystals
of cinnamic acid.

247
8)RESINS NOTES BY BILAL MALIK

• It is almost insoluble in water and petroleum ether, but freely soluble in


ethanol, benzene chloroform, ether, glacial acetic acid and partially in
Carbon disulfide or NaOH solution.
Chemical Constituents:
• The drug contains resin esters (75-80%), tolu-resinotannol cinnamate
along with a small proportion of the benzoate;
• volatile oil (7-8%)-containing chiefly benzyl benzoate [ insect repellant,
treat scabies and lice]
• Free cinnamic acid (12-15%), free benzoic acid (2-8%), vanillin and other
constituents in small quantities.
• It also contains cinnamein (5-13%).
Uses:
1. It is used extensively in perfumery, confectionery and chewing gums.
2. It is used widely as an expectorant in cough mixture.
3. It also finds its application as an antiseptic in the form of its tincture.

Benzoin:
Synonyms: Bitter almond-oil camphor.
Biological Source:
Benzoin in the balsamic resin obtained from styrax benzoin and styrax
paralleloneurus , generally known in trade as Sumatra Benzoin belong to the
family Styraceae
Preparation:
• Benzoin is also a pathological product that is obtained by incising a deep-
cut in the bark. It has been observed that after a span of about eight
weeks, the exudating balsamic resin tends to become less sticky in nature
and firm enough to collect. The entire exudate is usually collected in two
stages:
• Stage 1: First tapping-yields almond tears, and
• Stage 2: Second tapping-yields a more fluid material.
Characteristic Features:
248
8)RESINS NOTES BY BILAL MALIK

• It occurs as blocks or irregular masses of tears having variable sizes


usually imbedded either in an opaque or translucent matrix.
• It is brittle, and from within the tears are milky white in appearance.
• It generally becomes soft when warmed and gritty when chewed.
• The matrix is grayish brown to reddish in colour.
• Its taste is quite agreeable, balsamic and resembles to that of storax. It has
a resinous and aromatic taste.
Chemical Constituents:
The chemical constituents Sumatra Benzoin are :
• It contains free balsamic acids, largely cinnamic acid (10%), benzoic
acid (6%)-along with their corresponding ester derivatives.
• Teriterpene acids, namely: 19-hydroxyloleanolic and 6-hydroxyoleanolic
acids, cinnamyl cinnamate, phenyl propyl cinnamate, phenylethylene and
lastly the traces of vanillin.
• It yields not less than 75% of alccohol-soluble extractives.
Uses:
1. Compound benzoin tincture is frequently employed as a topical
protectant.
2. It is valuable as an expectorant when vapourized.
3. It finds its usage as a cosmetic lotion usually prepared from a simple
tincture.

249
9)TANNINS NOTES BY BILAL MALIK

Tannins
• The name ‘tannin’ is derived from the French ‘tanin’ (tanning substance)
and is used for a range of natural polyphenols. Tannins are complex
organic, non-nitrogenous plant products, which generally have astringent
properties.
• The term ‘tannin’ was first used in 1796 to denote substances which
have the ability to combine with animal hides to convert them into
leather which is known as tanning of the hide.
• According to this, tannins are substances which are detected by a tanning
test due to its absorption on standard hide powder. The test is known as
Goldbeater’s skin test.
• The conversion of raw animal hides into leather has traditionally been
carried out with plant-derived tannins.
• Many different cultures have developed the process of tanning. The
compounds that bind to the plant proteins are called (by definition)
tannins.
How tanning works
• Animal skins are made up of protein called collagen (among other
things). This protein is readily degraded by bacteria and fungi.
• When tannins bond to the collagen, the cross-linked fibers are no longer
susceptible to attack.
• The tannin must effectively crosslink the protein, but must also have
desirable color properties and meet many other requirements.
CHARACTERISTICS OF TANNINS:
• 1. Tannins are colloidal solutions with water.
• 2. Non crystalline substance.
• 3. Soluble in water (exception of some high molecular weight
structures), alcohol, dilute alkali, and glycerin.
• 4. Sparingly soluble in ethyl acetate.
• 5. Insoluble in organic solvents, except acetone.
• 6. Molecular weight ranging from 500 to >20,000.

251
9)TANNINS NOTES BY BILAL MALIK

7. Oligomeric compounds (In chemistry, an oligomer ( i/əˈlɪɡəmər/) (oligo-, "a


few" + -mer, "parts") is a molecular complex that consists of a few monomer
units, in contrast to a polymer, where the number of monomers is, in principle,
not limited.)with multiple structure units with free phenolic groups.
• 8. Can bind with proteins and form insoluble or soluble tannin—protein
complexes.

The tannin compounds can be divided into two major groups on the basis of
Goldbeater’s skin test.

252
9)TANNINS NOTES BY BILAL MALIK

Catechin /ˈkætᵻtʃɪn/ is a flavan-3-ol, a type of natural phenol and antioxidant. It


is a plant secondary metabolite. It belongs to the group of flavan-3-ols (or
simply flavanols), part of the chemical family of flavonoids.

253
9)TANNINS NOTES BY BILAL MALIK

254
9)TANNINS NOTES BY BILAL MALIK

255
9)TANNINS NOTES BY BILAL MALIK

256
9)TANNINS NOTES BY BILAL MALIK

257
9)TANNINS NOTES BY BILAL MALIK

BIOSYNTHESIS OF TANNINS:
• Tannins belong to the phenolics class of secondary metabolites. All
phenolic compounds; either primary or secondary are in one way or
another formed through shikirnic acid pathway (phenylpropanoid
pathway). Hydrolysable tannins and condensed tannins (Pro-
anthocyanidins) are the two main categories of tannins that impact animal
nutrition.
Common tannins are formed as follows
 Gallic acid is derived from quinic acid.
 Ellagotannins are formed from hexahydroxydiphenic acid esters by the
oxidative coupling of neighbouring gallic acid units attached to a D-
glucose core.
 Further oxidative coupling forms the hydrolysable tannin polymers.
 Proanthocyanidin (PA) biosynthetic precursors are the leucocyanidins
(flavan-3,4-diol and flavan-4-ol) which on autoxidation, in the absence of
heat, form anthocyanidin and 3-deoxyanthocianidin, which, in turn,
polymerize to form PAs

258
9)TANNINS NOTES BY BILAL MALIK

KINO (pterocarpus):
• Biological Source
• It consists of dried juice obtained by making vertical incisions to the stem
bark of the plant Pterocarpus marsupium Linn., belonging to family
Leguminosae.
• Geographical Distribution
It is found in various parts of the world.

Chemical Constituents:
• Kino contains about 70–80% of kinotannic acid, kino-red, k-pyrocatechin
(catechol), resin and gallic acid.
• Kinotannic acid is glucosidal tannin, whereas kino-red is anhydride of
kinoin.
• Kinoin is an insoluble phlobaphene and is produced by the action of
oxydase enzyme. It is darker in colour than kinotannic acid.
• Chemical Tests
1. When the solution of drug is treated with ferrous sulphate, green colour is
produced.
• 2. With alkali (like potassium hydroxide) violet colour is produced.

259
9)TANNINS NOTES BY BILAL MALIK

Uses:
• Kino is used as powerful astringent and also in the treatment of diarrhoea
and dysentery, passive haemorrhage, toothache, and in diabetes.
• It is used in dyeing, tanning, and printing.
• The aqueous infusion of the wood is considered to be of much use in
diabetes.
• The alcoholic, as well as, aqueous extracts of heartwood are known to
possess hypoglycaemic action.
• The bark exhibited hypotensive properties in pharmacological trials.
• Bark also showed antiviral effects.

Catechu:
Gambir or pale catechu of the BP 1989' BP (Vetelinary), 2000 is a dried,
aqueous extract prepared from the leaves and young twigs of a climbing
shrub,
• Botanical source: Uncaria gambier
• Family: Rubiaceae
• Geographical Source
• The tree is cultivated in tropical India, Sri Lanka, Malay States, South
China, Philippine Islands and parts of East Africa (including Zanzibar
and Tanzania).

260
9)TANNINS NOTES BY BILAL MALIK

Chemical Constituents:
 Pale catechu contain from about 7 to 30% of pseudotannin catechin and
22 to 55% of a phlobatannin catechutannic acid. Both of the about
component constitute over 60% of the drug.
 It also contains catechu red, gambier fluorescin and quercetin.
 It contains indole alkaloid up to 0.05%, which includes gambir-tannin and
its derivatives. Gambirtannin gives a strong fluorescence under UV light.
 Catechin forms white, needle like crystals, which dissolves in alcohol and
hot water. Catechutannic acid gives green colour with ferric chloride
Uses
• Pale catechu is medicinally used as local astringent.
• In diarrhoea, it is used as general astringent. It is largely used in various
countries of east for chewing with betel leaf.
• Gambirine is reported to be hypotensive; d-catechu constricts blood
vessels.
• Catechins protect the liver from infection.
• Large proportion of gambier is used in dyeing and tanning industries. It is
used for tanning of animal hides to convert it to leather.

Nutgall:
• Synonyms (Nutgalls, blue galls, Turkish galls)
• Biological source
• Nutgall consists of the pathological outgrowth obtained from the young
twigs of the dyers oak, Quercus infectoria
• Olivier, belonging to family Fagaceae.
• Outgrowth is caused by the puncture of ovums of insect Cynipstinctoria
or Adleria gallaetinctoriae Olivier Family Cynipidae
Geographical Source
Oak galls are obtained principally from Turkey. Dyers
oak is found in Turkey, Syria, Iran, Cyprus, and Greece.

261
9)TANNINS NOTES BY BILAL MALIK

Chemical Constituents:
• Nutgalls contains about 50–70% tannin mainly gallotannic acid which is
official tannic acid.
• It also consists of 2–4% gallic acid, ellagic acid, sitosterol, methyl
belulate and methyl oleanolate which are methyl esters of betulic and
oleanolic acid. Recently few more compounds such as roburic acid, and
syringic acids have been reported from galls. It contains abundant starch.
• Syringic acids exhibited hepato-protective, antibacterial effects,
antidiabetic effects, antiglycating properties,
• Syringic acids induced motor dysfunction, dopaminergic markers
expression and neuro-inflammation in mice
• Tannic acid of commerce is a hydrolysable tannin which yields gallic
acid and glucose. The molecule of tannic acid may contain the gallic acid
up to pentagalloyl glucose. It is isolated by fermentation and subsequent
extraction of galls with water-saturated ether.
Uses:
• Nutgall is the major source of tannic acid, which is largely used in
tanning and dyeing industry and for the manufacture of ink.
• It is used medicinally as a local astringent in ointments and suppositories.
• Antibacterial effect of Quercus infectoria is reported
• No cytotoxic effect
262
9)TANNINS NOTES BY BILAL MALIK

• Showed potent antileishmanial and antioxidant activity


• Strong anti-inflammtory effects in vivo
• Strong larvicidal effects

Castanea sativa Mill:


• Synonym: Spanish Chestnut, Sweet Chestnut C. vulgaris Lam.
• Family : Fagaceae.
• The leaves contain tannins (8–9%) flavone glycosides, triterpenoids,
ursolic acid, lupeol and betulin.
• Heartwood contains 61.4% tannins and 27.7% nontannins. The wood and
bark contain 7–14 and 8–14% tannins respectively.
• Nuts are eaten raw, roasted or boiled like potatoes. Nuts contain protein
calcium, phosphorus, thiamine, riboflavin and niacin; also tocopherols.
Uses :
 Leaves—astringent, antitussive and antipyretic and diseases of the
respiratory tract).
 An infusion is used as a gargle in pharyngitis, proxysmal coughs, catarrh
and whooping cough.
 Nuts—extract, as platelet inhibitor in thrombosis and atherosclerosis.
Nuts, crushed with vinegar and barley flour, are used against indurations
(Indurations:The hardening of tissue, usually because of the accumulation of
cells from an inflamed or infected site. Also called. sclerosis when caused by
inflammation)of breast.
Leaves are inhibitors of pectinolytic enzymes(Pectin is a structural
heteropolysaccharide contained in the primary cell walls of terrestrial plants.)

Krameria:
Botanical origin: Krameria triandra
• Family : Krameriaceae.

263
9)TANNINS NOTES BY BILAL MALIK

• Habitat: Peru, Bolivia. Reported to be imported into India.


Actions
Astringent, wound healing, antidiarrhoeal. Used for
menorrhagia(Menorrhagia is the medical term for menstrual periods with
abnormally heavy or prolonged bleeding.); topically for wounds, haemorrhoids
and chilblains(Chil-blains (sometimes called pernio) are small, itchy, painful,
red swellings on the skin. Chilblains are caused by an abnormal skin reaction to
cold. They tend to occur on 'extremities' that easily become cold); as a lozenge,
gargle or mouthwash for gingivitis(Gingivitis is a common and mild form of
gum disease (periodontal disease) that causes irritation, redness and swelling )
and pharyngitis.
• The astringency of the drug is due to condensed tannins composed of pro-
cyanidins and propel-argondins.

Myrobalan:
• The common name myrobalan can refer to several unrelated fruit-
bearing plant species:
• Cherry plum, myrobalan plum (Prunus cerasifera)
• Amla, Amalaki, emblic myrobalans (Phyllanthus emblica)
• Bibhitaki, Belliric myrobalans (Terminalia bellirica)
• Haritaki, Chebulic myrobalans (Terminalia chebula)
• Arjuna, Arjun myrobalans (Terminalia arjuna)
• Myrobalan extracts (at least from Terminalia chebula) are used
for tanning

264
11)NUTRACEUTICALS AND COSMECEUTICALS BY BILAL MALIK

Cosmeceuticals
• Cosmeceuticals are cosmetic products with biologically active
ingredients having medical or drug‐like benefits.

 A cosmeceutical is an ingredient with medicinal properties that


manifests beneficial topical actions and provides protection against
degenerative skin conditions.
 The word "Cosmeceuticals" was popularized by Albert M. Kligman in
the late 1970s.
 It encompasses cosmetic actives with therapeutic, disease fighting, or
healing properties, serving as a bridge between personal care products
and pharmaceuticals.
 Like cosmetics, cosmeceuticals are topically applied, but they contain
ingredients that influence the biological function of the skin.
 Cosmeceuticals typically claim to improve skin tone, texture, and
radiance, while reducing wrinkling.
 There are skin‐care products that go beyond coloring and beautification
of the skin. These products improve the functioning/texture of the skin by
encouraging collagen growth by combating harmful effects of free
radicals, thus maintaining keratin structure in good condition and making
the skin healthier.

Moisturizing Agents:
 Stratum corneum is the primary barrier of the skin whose one of main
purpose is to keep inside in & outside out. This barrier is rich in
cholesterol, free fatty acids, and ceramides.
 Water from the stratum corneum gets evaporated very quickly leading to
dehydration. This dehydration of skin can be averted by using
moisturizers which provide flexibility to the skin.
 Moisturizers by hydrating the skin, make the stratum corneum softer &
can even alter physiology of skin.

279
11)NUTRACEUTICALS AND COSMECEUTICALS BY BILAL MALIK

 Ceramide containing moisturizers are very popular as these contain the


same balance of lipids as our skin.
 Besides these, soy extract, and vitamins A and E also help in
augmenting the skin's natural moisture balance.

Sunscreen Agents:
• Use of sunscreen agents and limiting the exposure to sun prevents early
wrinkling and skin cancer.
• Sunscreen agents are used to prevent sunburns.

Kinds of sunscreen agents


chemical and physical:

280
11)NUTRACEUTICALS AND COSMECEUTICALS BY BILAL MALIK

• Chemical sunscreen agents protect the skin from the sun by absorbing the
ultraviolet (UV) and visible sun rays, while physical sunscreen agents
reflect, scatter, or block the rays.
• Chemical sunscreens mainly based on para‐amino benzoic acid, its
derivatives, cinnamates, various salicylates etc. are frequently employed
as sun blocking agents.
• Direct physical blockers include metal containing compounds such as
iron, zinc, titanium, and bismuth.

Vitamins:
• Exposure to the UV radiations accelerates the aging effect of the skin.
• Damage is initiated by the generation of reactive oxygen species (free
radicals). It is a progressive process whose consequences are damage to
DNA.
• The topical treatment of acne vulgaris with vitamin A, is very well
supported by evidence.
• Vitamin B3, commonly known as nicotinamide is available in
cosmeceutical products and can be used as a complementary agent for
some types of acne, as well as aging skin.
Vitamin A:
• The human epidermis contains significant amounts of vitamin A (alltrans‐
retinol). It has been observed that both UVB and UVA can damage the

281
11)NUTRACEUTICALS AND COSMECEUTICALS BY BILAL MALIK

metabolism and transport of vitamin A. This may lead to vitamin A


deficiency in the skin.
• Topical retinoids have successfully been used to treat acne. The useful
concentration of topical retinol ranges from 0.3% to 1%.
• Most of the over‐the‐counter products available usually contain lower
levels of retinol (about 0.08% or less).
Vitamin E:
• The physiological function of vitamin E, if applied dermally is to
contribute to the antioxidant defense of the skin, because of its tendency
to absorb UV light in the solar spectrum region that is responsible for
most of the harmful biologic effects of the sun.
• Vitamin E blocks lipid peroxidation in cells & tissues & it is a good
antioxidant. It helps to enhance the performance of UV filters, softens
skin & moisturizes within. Vitamin E is the body's major lipid‐soluble
antioxidant.
• Vitamin E as alphatocopherol or tocopherol acetate is used in topical
OTC products in concentration (1% ‐ 5%).
• Alphatocopherol has been found to be beneficial in reducing minimal
erythema and the number of epidermal sunburn cells, which marks skin
damage related to oxidative stress caused by UV.
Vitamin B3:
• Nicotinamide is a part of the coenzymes nicotinamide adenine
dinucleotide (NAD), NAD phosphate (NADP), and its reduced forms are
NADH and NADPH. These molecules are important in many cellular
metabolic enzyme reactions. The reduced forms mainly act as
antioxidants.
• Nicotinamide is one of the newly discovered vitamin‐based components
of cosmeceutical products. It is found to possess anti inflammatory and
anti acne actions.
Vitamin C:
• The increase of vitamin C in skin concentration is limited even with huge
oral supplementation. Vitamin C has become a popular topically applied
cosmeceutical because topical application of L -ascorbic acid is the only
way to further increase skin concentration.
282
11)NUTRACEUTICALS AND COSMECEUTICALS BY BILAL MALIK

• L‐ascorbic acid is the active form of vitamin‐C, which was first used as
cosmeceutical creams.
• Previous formulations ( L‐ascorbic acid) were very unstable due to the
oxidation of the vitamin exposed to air. So to overcome this problem,
esterified derivatives of L‐ascorbic acid in topical formulations have been
used to improve stability.
• The most commonly used derivatives are ascorbyl‐ 6‐palmitate and
magnesium ascorbyl phosphate.

Skin Whitening Agents:


• Hyperpigmentation is the changing of colour intensity of the skin to
darker hue, which is due to an increased amount of melanin in the
epidermis, the dermis, or both.
• This change can be due to 2 pathophysiologic processes:
Melanocytosis (increased number of melanocytes) Melanosis
(increased amount of melanin).
• Standard dermatologic agent for skin lightening is hydroquinone but its
safety is questionable, leading to the use of alternative agents such as
retinoids, mequinol, azelaic acid, arbutin, aleosin, licorice extract,
ascorbic acid, soy proteins, and N ‐acetyl glucosamine.

Chemical Peeling Agents:


• Alpha‐hydroxy acids have been shown to lighten melasma, solar
lentigines, and post‐inflammatory hyper pigmentation.
• Glycolic acid is derived from sugar cane and is used as an ingredient in
skin lightening products in low concentrations. It may also be used as a
peeling agent in concentrations of 30‐70% to increase the efficacy of
other lightening agents such as hydroquinone by removal of the dead
skin, thus enhancing the penetration of hydroquinone.
• Other chemical peels include 50% trichloroacetic acid (TCA) peels and
20‐30% salicylic acid peels used for various pigmentary disorders,
including melasma, on darker skin types.

283
11)NUTRACEUTICALS AND COSMECEUTICALS BY BILAL MALIK

Nutraceuticals
“bio-actiVe products presented as 'dietary supplements' or similar”
Introduction:
• Nutraceuticals, a term first coined by Stephen DeFelice in 1989.
• These are natural plant products that are not only the source of nutrient-
rich foods, but also have therapeutic effects with virtually no adverse
reactions.
• Because of their beneficial effects on the prevention and treatment
of several diseases, major biotechnology companies and academia have
ventured into the screening and large-scale production of the next-
generation pharmaceuticals from plants
• Nutraceuticals may be defined as—‘any substance that may belong to a
plant, food or an essential component of food providing definitive
medicinal usefulness and health promotion as well as physiological
benefits, and ultimately minimise the possible risk of the prevailing
chronic disease significantly.
• Products of which one would have heard rarely some l0 or 20 years
ago are now objects of daily discussion. The lack of licensing of
these products is a point of major concern
• One of the significant outcomes of such a search is the identification of a
medicinal plant, Echinacea purpurea, as a rich source of nutraceuticals.
The plant extract has been reported to prevent viral infection and reduce
tumor progression.
• In addition, daily use of the extract is known to significantly abate
leukemia as well as extend the life span of both leukemic and aging mice.
• Functional Food may be defined as—“the food usually prepared by the
aid of ‘scientific intelligence’ using definite knowledge about its
anticipated merit/usefulness.”In this manner, the functional food
essentially caters to the body with the necessary quantum of vital
carbohydrates, fats, proteins and vitamins, etc, required for its normal as
well as healthy survival.
• Examples: Vegetables, rice, wheat, fruits, pulses, fish, eggs, poultry
products, beef, meat etc

284
11)NUTRACEUTICALS AND COSMECEUTICALS BY BILAL MALIK

• Nutraceutical may be defined as—“a food (or a portion of a food) that


essentially provides distinct health and medical benefits, even including
the prevention and/or treatment of a particular disease
• Examples: Fortified ‘dairy products’ e.g., milk powder, baby food, malted
milk food; vitamic C enriched citrus fruits e.g., orange juice, grape juice
• Carotenoids refer to natural compounds that usually render corn yellow,
carrots reddish-orange, and tomatos red. Besides, they impart typical
natural characteristic colours to gold fish, flamingo, salmon, and also the
autumn leaves (i.e., when the nature’s green chlorophyll get depleted
significantly, the carotenoids and phenols remain.
• α-carotene possesses essentially 50-54% of the antioxidant activity of β-
carotene, whereas epsilon carotene bears 42-50% of the said activity.
• Carotenes, in general, also increase appreciably the immune response and
afford adequate protection to skin-cells against UV-radiation(i.e.,
incorporated in ‘Sun-Creams’ profusely).
• Polyphenolics (or Polyphenol Extracts) essentially represent a host of
natural antioxidants, used as nutraceuticals, and found in apples, green-
tea, and red-wine for their enormous ability to combat cancer and are also
thought to prevent heart ailments to an appreciable degree.
• Flavonoids are actually flavone-like substances which are invariably
antioxidants and sometimes as anti-inflammatory agents.
• Mechanism of Action: Flavonoids exert their activity by carefully
scavenging the ‘free-radicals’ thereby giving rise to a fairly ‘stable
radical’ which in turn would undergo reaction with another ‘flavonoid
radical’ to yield two non-radicals

285
11)NUTRACEUTICALS AND COSMECEUTICALS BY BILAL MALIK

286
11)NUTRACEUTICALS AND COSMECEUTICALS BY BILAL MALIK

287
11)NUTRACEUTICALS AND COSMECEUTICALS BY BILAL MALIK

288
12)TUMOUR INHIBITORS FROM PLANTS BY BILAL MALIK

TUMOUR INHIBITORS FROM PLANTS


• The cells in our bodies all have certain jobs to do. Normal cells divide in
an orderly way. They die when they are worn out or damaged, and new
cells take their place.
• Cancer is when the cells start to grow out of control. The cancer cells
keep on growing and making new cells. They crowd out normal cells.
This causes problems in the part of the body where the cancer started.
• When cancer cells spread, it’s called metastasis
• A tumor, also known as a neoplasm, is an abnormal mass of tissue which
may be solid or fluid-filled.
• A tumor does not mean cancer - tumors can be
• benign (not cancerous),
• pre-malignant (pre-cancerous),
• or malignant (cancerous).

Natural anticancer:
• Natural products have played a major beneficial role in cancer
chemotherapy for over 50 years, both in terms of providing
established drugs and new lead compounds for synthetic optimization,
and in furnishing substances for probing cellular and molecular
mechanisms of action relevant to cancer inhibition.
• Out of 175 small-molecule anticancer drugs introduced into therapy over
an approximately 70-year period, about 49% were either obtained from
organisms directly or were derived from natural products .

Catharanthus roseus:
• Vinblastine is isolated from the dried entire plant of Catharanthus roseus
Linn (Apocynaceae).
• It is indigenous to Madagascar but is now widely distributed
throughout warm regions and is much cultivated as an ornamental; it
grows profusely in southern Florida. Commercial supplies of the

289
12)TUMOUR INHIBITORS FROM PLANTS BY BILAL MALIK

drug are obtained from both wild and cultivated plants produced in
various locations, including Africa, India, Thailand, Taiwan, eastern
Europe, Spain, USA and Australia.
Constituents:
• About 150 alkaloids have now been isolated from C. Roseus .Of
particular interest is a group of about 20 bisindole alkaloids which
contains those having antineoplastic activity, including vincristine and
vinblastine
• vincristine is obtained in about 0.0002% yield from the crude drug.
Uses:
• Uses. vinblastine is used mainly for the treatment of generalized
Hodgkin's disease, and non-hodgkin's lymphomas. Vincristine is
used principally in the treatment of acute lymphocytic leukaemia in
children.
• It has other applications for lymphomas, small cell lung cancer,
cervical and breast cancers.
• The semi-synthetic vindesine is also used in the treatment of acute
lymphoid leukaemia in children. vincristine has a superior antitumour
activity compared to vinblastine, but is more neurotoxic.
• Vinorelbine is a newer, orally active, semi-synthetic
anhydroderivative of 8‘-norvinblastine with a broader anticancer
activity and lower neurotoxic side-effects than the other
Catharanrthus alkaloids.

Podophyllum peltatum:
• Synonyms: Podophyllum, American Mandrake, May-apple root.
• Geographical Source
Podophyllum peltatum is indigenous to Eastern part of the United States and
Canada. It grows wildly in Virginia, North Carolina, Kentucky, Indiana, and
Tennessee
Chemical Constituents:

290
12)TUMOUR INHIBITORS FROM PLANTS BY BILAL MALIK

• Podophyllum rhizomes contain 2–8% resinous material termed as


podophyllin. The major constituents of podophyllum resin are the lignan
derivatives which are characterized as podophyllotoxin, α- and β-peltatin.
• The lignans are found in the form of glycosides and also as their free
aglycones. It also contains desmethyl-podophyllotoxin, des-oxy-
podophyllotoxin, podophyllotoxone, a flavonoid quercetin and starch.
Uses:
Podophyllum resin or podophyllin shows cytotoxic activity. It is used for
the treatment of venereal(Venereal spreading through sexual contact)
and other warts.
Podophyllotoxin is semisynthetically converted to a potent anticancer
agent etoposide which is mainly used for the treatment of lung and
testicular cancer.
Podophyllum resin is a strong gastrointestinal irritant. It acts as a drastic
purgative in moderate doses but it has been mostly replaced by other
purgative drugs.

Rifampicin:
• Rifampicin, also known as rifampin, is an antibiotic used to treat several
types of bacterial infections. This
includes tuberculosis, leprosy(Leprosy is an infectious disease that
causes severe, disfiguring skin sores and nerve damage in the arms and
legs).
• Rifampicin was discovered in 1965, marketed in Italy in 1968, and
approved in the United States in 1971.
• It is on the World Health Organization's List of Essential Medicines, the
most effective and safe medicines needed in a health system.
Angiogenesis:
• Tumor growth beyond a certain prevascular size depends on the
production of new capillaries from preexisting vessels.
• This complex process, called angiogenesis, involves enzymatic and
signal transduction cascades that affect extracellular matrix
degradation, fibrinolysis, hemodynamic control of oxygenation,

291
12)TUMOUR INHIBITORS FROM PLANTS BY BILAL MALIK

microvascular endothelial cell proliferation and migration, and


subsequent formation of the vascular lumen.
• Tumors unable to elicit angiogenesis remain in a dormant state and
fail to grow beyond a few millimeters in size.
{ Rifampicin at concentrations of <40 µg/ml, which induce potent gene inhibitory
activity, showed remarkable antiproliferative effects on endothelial cells exponentially
growing in the presence of fetal bovine serum and growth supplements. The effects were
very profound and appeared to reflect its activity to down regulate a variety of genes
related to growth and angiogenesis.}

Antitumor effects:
• Rifampicin, exerts potent inhibitory effects on hepatic tumors when
administered orally at low doses. The in vitro effects of rifampicin to
rapidly downregulate angiogenesis- and mitogenesis-related genes in
cultured endothelial cells are reminiscent of endostatin, one of the most
well-studied angiogenesis inhibitors.
• However, rifampicin at the expected hepatobiliary concentrations after
low oral doses showed more complete antiproliferative effects on
endothelial cells, which make rifampicin favorable as an adjunct
anticancer regimen.
{ Vascular endothelial growth factor (VEGF), is a signal protein produced by cells that
stimulates vasculogenesis and angiogenesis. It is part of the system that restores the oxygen
supply to tissues when blood circulation is inadequate such as in hypoxic conditions. VEGF's
normal function is to create new blood vessels. When VEGF is overexpressed, it can
contribute to disease. Solid cancers cannot grow beyond a limited size without an adequate
blood supply; cancers that can express VEGF are able to grow and metastasize. It also has
inhibitory effect on VEGF.}

• Since rifampicin undergoes hepatic accumulation resulting from the


enterohepatic circulation, it may be especially beneficial for
targeting hepatobiliary tumors.
• Rifampicin only elicits its direct antitumor activities at high
concentrations that far exceed the plasma levels, but can be attainable
in the hepato-biliary system, especially in patients with liver cirrhosis.

292
12)TUMOUR INHIBITORS FROM PLANTS BY BILAL MALIK

Macrolides as antitumor:
• The macrolides are a class of natural products that consist of a
large macrocyclic lactone ring to which one or more deoxy sugars may be
attached.
• The lactone rings are usually 14-, 15-, or 16-membered. Macrolides
belong to the polyketide class of natural products. Some macrolides
have antibiotic or antifungal activity and are used as pharmaceutical
drugs.
• Azithromycin
• Clarithromycin
• Erythromycin
Bryostatins are a group of macrolide lactones first isolated in the 1960s from
extracts of a species of bryozoan, Bugula neritina.
The structure of bryostatin 1 was determined in 1982. To date, 20 different
bryostatins have been isolated; further, certain analogs of bryostatin have been
referred to as "bryologs". Bryostatins are potent modulators of protein kinase C.
They are currently under investigation as
 Anti-cancer agents,
 Anti-aids/Hiv agents and
 a memory-enhancing agent.
{ Hodgkin disease (Hodgkin lymphoma) is a type of lymphoma, a cancer that starts in white
blood cells called lymphocytes. Lymphocytes are part of the immune system.
https://www.youtube.com/watch?v=FcvqEsLb23s}

• In in vitro trials, bryostatin-1 was able to induce apoptosis in human


leukaemia [HL-60] chronic lymphocytic leukaemia.
• Bryostatin 1 acts synergistically in combination with other anti-cancer
drugs. Drug combination was effective against a large variety
of tumor cells including lung, prostate and non-Hodgkin's
lymphoma tumor cells.
• Although animal studies were promising, bryostatin 1 as a single drug has
failed to demonstrate significant activity in tumor patients in phase II
trials in a wide range of tumor types, including melanoma and colorectal
cancer.

293
12)TUMOUR INHIBITORS FROM PLANTS BY BILAL MALIK

• {Non-Hodgkin lymphoma (NHL) is a group of blood cancers that includes all types
of lymphoma except Hodgkin's lymphomas
• https://en.wikipedia.org/wiki/Protein_kinase_C}

• Additionally severe side-effects, mainly myalgia, were observed after


bryostatin administration
• As a consequence research focus has shifted to an investigation of
combination therapy with other chemotherapeutic antitumor agents such
as gemcitabine, vincristine, cisplatin. As of 2016 about 30 clinical trials
for various cancers have been completed.

294
13. INTRODUCTION TO CLINICAL PHARMACOGNOSY BY BILAL MALIK

Clinical Pharmacognosy
Introduction:
 Natural medicines have been used to enhance human health since
time immemorial and the success of modern medical science largely
depends on drugs originally obtained from natural resources.
 Medical science has exploited plants, animals, microorganisms and
minerals as the potential sources of drugs to prevent and cure
human health problems.
 Even today, the traditional medicinal practices and natural remedies
are equally relevant in modern pharmaceutical practices worldwide.
 In the modern pharmacy, about 50% of drugs and drug substances
are derived from natural products.
 Clinical pharmacy requires optimum use of medications, therapeutic
knowledge, counseling, clinical experience, therapeutic drug monitoring
and disease good diagnosis.
 Clinical pharmacists should monitor patient outcomes according to the
patient’s situation and the probable risks associated with therapy.
 Recognition of therapeutic systems and patient records are principles of
this field.
 Clinical pharmacists should prepare a nice atmosphere and consultation
area and have a good communication skill as well as should know the
patient’s quality of life that can be obtained via interview of patients
 While clinical pharmacy significantly progressed, a gap between this
science and herbal and traditional medicines fields is evident. As the use
of herbals increased in the recent years, new kinds of demands are raised.
 There are several potential problems associated with herbal remedies like
lacking of systematic reviews and evidence-based data about their
efficacies.
 One of the reasons behind increase in use of herbal medicines is the belief
that they have lower toxicities but the fact is that herbal medicines may
cause unwanted effects, allergic or toxic reactions
 Herbs can even cause drug-drug, drug-food and herb-drug interactions if
not properly used specially in use of OTC drugs.

295
13. INTRODUCTION TO CLINICAL PHARMACOGNOSY BY BILAL MALIK

 Clinical pharmacognosy should deal with above problems and find the
best solutions for them. Although this term has been used in a workshop
in the United States entitled, “Clinical Pharmacognosy: Contribution of
pharmacognosy to clinical trials of botanicals and dietary supplements”,
which took place at the American Society of Pharmacognosy meeting in
Portland, Maine, on July 2007 and in a Japanese journal on March 2011,
there has not been any comprehensive definition yet
 The revival of herbal medicine in the world creates a demand for studies
in the field of pharmacognosy, traditional medicine and some related
fields.
 From a practical perspective this includes quality control (identity, purity,
consistency), efficacy (therapeutic indications, clinical studies,
pharmacological investigations), documentation and safety (adverse
reactions, drug interactions, contraindications, precautions and toxicities).
 There are huge capacities of research topics in the herbal and traditional
medicine fields which this new discipline can design and perform them
clinically. This new borderline discipline may extend the scope of clinical
aspects of pharmacognosy and play a progressive role in the safe, rational
and efficient use of traditional and herbal medicine
 Clinical pharmacognosy is a bridge between clinical research and
botanicals knowledge providing clinical and pharmaceutical researchers,
physicians and other healthcare professionals with the key information
they need to assist the progress of herbal and traditional medicines.
 Clinical pharmacognosist should ask the patients about the herbal drugs
or other supplements they have had taken before and about the history of
possible allergic reactions.
 He should also evaluate the patient recovery process after using each kind
of synthetic, herbal or traditional drugs and should focus on resolving a
wide range of challenging problems
 It seems that in the third millennium, we need education of clinical
pharmacognosists for providing more details regarding different aspects
of clinical applications of natural health products. In order to use rational
herbal and traditional medicines and adding standard clinical values to
them, establishing and spreading of clinical pharmacognosy feature may
help to improve health to all.

296
13. INTRODUCTION TO CLINICAL PHARMACOGNOSY BY BILAL MALIK

 Clinical pharmacognosist can provide full and correct information about


all pharmaceutical and medical aspects of plants, natural health products
and dietary supplements. This field may plays leading and interesting
roles in identifying, analyzing, standardizing, controlling, documentation
and determining of these natural health products evidence based
medicines.
 It increases more the findings of effective naturals especially by doing
systematic review of randomized controlled trials evaluated herbal
therapies for different diseases

297
14. CLINICAL USE OF HERBS & HERBAL MEDICINE BY BILAL MALIK

1)Clinical Use of Herbs and Herbal Medicine


Cardiac diseases
a) DIGITALIS SPECIES:
Botanical Origin:
Digitalis purpurea
Digitalis lanata
Family:
Plantigenaceae
Part used:
Dried leaves
Collection:
Leaves collected from 2nd year growth of plant in June before opening of
flower.
Drying is done by applying artificial heat (temperature not more than 65°C).
 Geographical Sources
 It is mainly found in England, Germany, France, North America, India,
Iraq, Japan, Kurdistan, Mexico, Nepal, Spain, Turkey.
Plant:
 Perreneal or bieneal herb, 1.5 m tall In 1st year radical rises
 In 2nd year shoot grows and bears bell shaped flowers.
Purpurea, purple flowers, Fruits are big lobular capsule with many seeds
Lanata, small, 1 meter tall, yellowish creamy flower.
Leaves bears hairs.

Mechanism:
Increase the force of systolic contraction
Shorten length of systole
As a result
299
14. CLINICAL USE OF HERBS & HERBAL MEDICINE BY BILAL MALIK

Heart have more time to rest between contraction.


Therapeutic activity depends upon;
1. Chemical nature of aglycone
2. Number of sugars
Clinical Uses:
 As cardiotonic glycosides
 In CHF
 It has also been employed in the treatment of internal haemorrhage, in
inflammatory diseases, in delirium tremens, in epilepsy, in acute mania
and various other diseases.
 Digitalis has a cumulative effect in the body, so the dose has to be
decided very carefully Safety of the herb cannot be established due to
variable amounts of cardiac glycosides. The powder is toxic at 520mg.
 Cardiac glycosides are extensively used as anticancer agents.

b) Convallaria majalis :
Family:
Liliaceae
Part Used:
Rhizomes/roots or aerial parts
Constituents:
The principal glycoside is convalla-toxin, which on hydrolysis gives
strophanthidin and rhamnose.
Uses:
 Cardio-active (same as digitalis).
 Convallatoxin, a Dual Inducer of Autophagy and Apoptosis, Inhibits
Angiogenesis In Vitro and In Vivo exerts cytotoxic effects on a number of
cancer and normal cell lines and induces apoptosis by increasing caspase-
3 and poly ADP ribose polymerase (PARP) cleavage.

300
14. CLINICAL USE OF HERBS & HERBAL MEDICINE BY BILAL MALIK

c) Urginea indica:
 Synonym: Sea onian, Indian squill, scilla

Dried slices of the bulb of Urginea indica

 Family: Liliaceae

 WORLD WIDE especially in India

 CHEMICAL CONSTITUENTS

 Cardiac glycosides: scillaren A, Scillaren B

 Glucoscillaren A

 Enzyme scillarenase

 Mucilage

 Calcium oxalate

PHARMACOLOGICAL ACTIVITY

 Cardiac stimulant action

 In small dose act as diuretic

 In large dose act as emetic & cathartic

 Resembles Digitalis in action

 Also possess anticancer activity.

Uses:

Digitalis like action on Heart

In small doses used as expectorant

Diuretic and anticancer.

The squill has shown to have cardiac effects similar to digoxin, including
positive inotropic and negative chronotropic effects.

301
14. CLINICAL USE OF HERBS & HERBAL MEDICINE BY BILAL MALIK

The aglycones in squill are poorly absorbed from the GI tract and are
therefore less potent than digitalis cardiac glycosides. Additional
cardiovascular properties include reducing left ventricular diastolic
pressure and reducing pathologically elevated venous pressure.

Large amounts of squill are gastric irritants; small amounts expectorant

d) (Garlic) Allium sativum:


 Cultivated all over the world

 Popular for use as;

a. food flavoring

b. medicine

 Garlic, Allium sativum, is a root crop (meaning the bulb grows


underground) of the family Liliaceae

 It is among the oldest of all cultivated plants

 The leaves are long, narrow and flat like grass

 It is a member of the same group of plants as the Onion.

Garlic Bulb:

 The bulb of Allium sativum is the only part of the plant eaten

 The cloves are grouped together between the membranous scales and
enclosed within a whitish skin, which holds them as in a sac

History:

 In China, garlic tea has long been recommended for fever, headache, and
cholera.

 In Japan, garlic is used as remedy for the common cold with headache,
fever and sort throat.

302
14. CLINICAL USE OF HERBS & HERBAL MEDICINE BY BILAL MALIK

 The Egyptian: an effective remedy for a variety of ailment including heart


problems, headache, bites, worms and tumors.

 Roman: garlic poultices were used to prevent wound infections

Common Uses:

 Common cold prevention

 Heart disease prevention

 Antiseptic

 Antimicrobial activities

 Insect repellent

 Anticancer effects

 Strengthen Immune System

 Vaginal Infections

 Antioxidant effects

 Anti coagulation effects

 High cholesterol

 Hypertension

Medical Uses:

The Ayurvedic Pharmacopoeia of Indiaindicates the use of the bulb as

a brain tonic in epilepsy and psychic disorders.

 Heavy consumption of garlic prior to surgery led to increased


clotting time or reduced platelet aggregation (in human case
reports).

 Garlic tablets at a dose of 400 mg twice daily for 12weeks reduced


platelet aggregation 59% compared with placebo in 80 patients (in
human clinical study).

303
14. CLINICAL USE OF HERBS & HERBAL MEDICINE BY BILAL MALIK

 Garlic cloves are high in sulphur containing amino acids known as


alliin (no taste, no smell, no medicinal action)

 Prevention of certain cancers (stomach and colon cancer)

 Standardized Allium sativum bulbs is used as Hypo-cholesterolemic /


Antirheumatic Powder/Paste: Alliin 1.5%–2.5% by HPLC

 The antibiotic effect is attributed to allicin;

 Hypoglycaemic effect to allicin and allyl-prophyl-disulphide

 Anticarcinogenic activity to diallyl-monosulfide;

 platelet aggregation inhibitory effect to diallyl-di- and tri-sulphides.

 Ajoene inactivated human gastric lipase, which is involved in digestion


and absorption of dietary fats

 DosageBulb—3g

e) PUNICA GRANATUM:
Pomegranate:

Family:

Punicaceae

Cultivation:

Mostly in India and Afghanistan

Plant:

 Short (less than 5 m), spiny shrub with

shiny leaves of 4-6 cm

 Bears red/orange bell shaped flowers

 Produces red spherical fruits approx

10 cm in diameter

304
14. CLINICAL USE OF HERBS & HERBAL MEDICINE BY BILAL MALIK

◦ Each fruit contains numerous seeds

covered in fleshy arils (seed packets)

contained in walls of membranous tissue.

Constituents:

 Fruit

◦ Antioxidants

 Polyphenols

 Tannins (Ellagitannins)

 Anthocyanins

◦ Steroid estrogen estrone (one of the few plants in nature)

 Roots, Bark, Leaves

◦ Piperidine alkaloids

 Pelletierine, Isopelletierine (Active)

 N-methylisopelletierine, pseudopelletierine (Inactive)

◦ Punico tannic acid

Historic Uses:

o Greek physicians advised women

of childbearing age to ingest the seeds of pomegranate to prevent

pregnancy

o Giambattista della Porta suggest (Italian scholor)

eating the seeds to

strengthen teeth.

Traditional Uses:

305
14. CLINICAL USE OF HERBS & HERBAL MEDICINE BY BILAL MALIK

 Pomegranates have astringent properties because of the alkaloids


(pelletierine tannate) present in the bark of the stems and roots and have
been used for many years as an anthelmintic.

 Dysentery and chronic diarrhea

 Seed packets used in dyes

Modern Uses:

 Juice of Leaves and Fruits

◦ Antioxidant (free radical scavenging)

◦ Lower LDL-level in blood

◦ Gastroenterological ailments including diarrhea and Ulcers

◦ Antiathersceloris

◦ Prevent cancers

◦ Hypertension

◦ Diabetes

◦ Rind and Bark of stem and roots

◦ Anthelmintic

◦ Antidiarrheal

◦ Promotes mucous discharge

◦ Dried Flowers

◦ Hematuria, hemorrhoids, dysentery, chronic diarrhea, and


bronchitis

306
14. CLINICAL USE OF HERBS & HERBAL MEDICINE BY BILAL MALIK

2)Herbs used in Respiratory Diseases


a) Ficus religiosa:
• Family Moraceae.

• Habitat Pakistan, India, west bengal

• English Peepal, Bot-tree.

• Unani Peepal.

Constituents:

 The bark contains β-sitosteryl D-glucoside, Vitamin K, n-octacosanol,


methyl oleanolate, lanosterol, stigmasterol and lupen-3-one. saponin
gluanol acetate, β-sitosterol, stigmasterol and lupeol, leuco-
anthocyanidin, and leuco-anthocyanin.

 A hypoglycaemic response is reported for β-sitosterol-D-glucoside


obtained from the bark.

 Aerial roots are given to women, also used in prescriptions, for inducing
conception.

 The dried fruits are used as a uterine tonic.

 The fruits contain 4.9% protein having the essential amino acids,
isoleucine and phenyl-alanine.

Medicinal Uses

Bark

Astringent, Antiseptic, Laxative, Haemostatic,

Vaginal disinfectant, diabetes, diarrhoea, leucorrhoea,

menorrhagia, nervous disorders, skin diseases, ulcers and wounds.

 Antiviral activity in vitro is reported

 Antifungal activity of plant against Candida albacans


307
14. CLINICAL USE OF HERBS & HERBAL MEDICINE BY BILAL MALIK

 In vitro antimicrobial activity against a no of pathogens has been


reported.

 The crude bark extract of the plant also showed protection in acute
animal models of convulsions, which was found to be due to GABA
aminotransferase inhibitory activity of its bioactive metabolites

Leaves and twigs

 Laxative

 Its leaf extract was studied in acute animal models of convulsion, but was
found to be ineffective

Fruits

Respiratory disease, Antitumour, antibacterial bleeding piles, haematuria


and haemorrhages

Roots

The crude root extract and fractions were studied for anticonvulsant activity
only saponins has shown significant effect.

 Latex of the plant has shown Hepatoprotective effect on cisplatin


induced liver injury in Wistar rats.

Anticancer activity; The apoptotic effect of copper oxide nano-particles is


mediated by the generation of reactive oxygen species (ROS) involving the
disruption of mitochondrial membrane potential.

Effects on Respiratory:

 The alcoholic bark extract at 300, 375, 450 mg/kg;i.p. and 75 mg/kg;i.v.
doses inhibited the acetylcholine and histamine. The extract exhibited
more pronounced effect against asthma induced by acetylcholine as
compared to histamine, suggesting strong involvement of
parasympatholytic and weak antihistaminic mechanisms.

 Moreover, the bark extract showed relaxation of the bronchial muscles of


dog when injected at 35–70 mg/kg;i.v. dose. The study proved the
bronchodilatory effect of the bark and validated its traditional use in
asthma.

308
14. CLINICAL USE OF HERBS & HERBAL MEDICINE BY BILAL MALIK

 Leaves of the plant In guinea pigs at a dose of 150 and 300 mg/kg
significantly delay the onset tine of histamine and acetylcholine induced
pre-convulsive dyspnea.

 Potent Mast cell stabilizing effect was observed and was comparable to
ketotifen at 20 µg/ml of

Dosage: Bark, fruit 50–100 ml decoction.

Further details?????????

Pharmacokinetic profile??????

Side /unwanted effects/ Toxicity

 The long history of traditional use, with no reports of any serious side
effect suggests that F. religiosa can be considered as safe.

 In majority of toxicity studies carried out on F. religiosa, no sign of


toxicity was observed.

 In acute toxicity studies carried out on male Swiss albino mice, the
methanolic fruit extract of F. religiosa was found to be safe at 10 times of
its effective doses (up to 1000 mg/kg; i.p.).

b) Adhatoda vasica Nees:


• Synonym A. zeylanica Medic.

Justicia adhatoda Linn.

• Family Acanthaceae.

• Habitat India, Pakistan

• English Malabar Nut, Vasaca

• Unani Arusaa

Constituents:

309
14. CLINICAL USE OF HERBS & HERBAL MEDICINE BY BILAL MALIK

Actions/Uses:

The chief quinazoline alkaloid vasicine is reported in all parts of the plant.
Which have the following properties

• Bronchodilator,

• Respiratory stimulant,

• Hypotensive,

• Cardiac depressant,

• Uterotonic

• Abortifacient

• Expectorant

• Bronchial, asthmatic and pulmonary infections

• Antispasmodic

• Febrifuge

• smooth muscle-relaxant properties of airways.

• protection against allergin-induced bronchial obstruction.

• activate the digestive enzyme trypsin

• Antifungal activity

Dosage

• Leaf—10–20 ml juice.

• Dried leaves—10–20 g for deoction.

• Root—3–6 g powder.

310
14. CLINICAL USE OF HERBS & HERBAL MEDICINE BY BILAL MALIK

3)HERBS USED IN Skin Diseases


• A) Aloe barbadensis Mill:
• Synonym _ A. vera Tourn. ex Linn., A. indica Royle, A. littoralis
Koening

• Family _ Liliaceae; Agavaceae.

• Habitat _ Throughout India, Pakistan

• English _ Curacao Aloe, Barbados Aloe, Indian Aloe,

• Unani _ Gheekwaar, Sibr.

Constituents

 Anthraquinone glycosides, known as aloin, in small doses act as a tonic to


the digestive system, and at higher doses become a strong purgative, as
well as increase colonic secretions and peristaltic contractions.

 Resin fraction is also as important as aloin in cathartic action.

 Aloe produces pelvic congestion and is used for uterine disorders,


generally with Fe and carminatives. The pulp is used in menstrual
suppressions.

 A molecule in the Aloe vera gel, acemannan, stimulates macrophages and


releases immune system potentiators; enhances function of T cells and
interferon production.

 Animal studies have shown promising results in sarcoma(Sarcoma: a


malignant tumour of connective or other non-epithelial tissue).

 Strong Antibacterial effect against various pathogenic bacteria.

 Strong and antioxidant effect is also reported

 25 known anthraquinones and related compounds from Aloe has shown


antioxidant and anti-osteoporotic activities.

 The carboxy-peptidase and salicylate components of Aloe gel can inhibit


bradykinin, a pain-producing agent; C-glycosyl chromone appears to
reduce topical inflammation.
311
14. CLINICAL USE OF HERBS & HERBAL MEDICINE BY BILAL MALIK

 Aloe gel also slows or inhibits the synthesis of thromboxane, which may
accelerate the healing of burns.

Uses:

• As purgative, Constipation, Emmenagogue (blood to pelvic),


dysmenorrhoea, liver diseases, Antihyperglycaemic,

• Gel—topically emollient, anti-inflammatory, antimicrobial (used for


wound healing, sunburn).

Toxicity reports

 solutions of nondecolorized extracts of Aloe vera leaves in the drinking


water to groups of rats and mice, caused cancers of the large intestine in
male and female rats and

 also caused hyperplasia of the large intestine, small intestine, stomach,


and lymph nodes in male and female rats.

 Aloe vera extract also caused hyperplasia of the large intestine in male
and female mice and hyperplasia of the mesenteric lymph node in male
mice and hyperplasia of the stomach in female mice

 Aloe vera extracted in methanol and given to mice at 100 mg/kg in


drinking water for 3 months caused significant sperm damage compared
to controls.

 Aloe barbadensis extracted with water and given to pregnant albino rats
on gestational days (GDs) 0 through 9 was an abortifacient and produced
skeletal abnormalities.

 Aloin (an anthraquinone) did not produce tumors when included in the
feed of mice for 20 weeks,

 Other animal data also suggest that components of Aloe inhibit tumor
growth and improve survival.

 Diarrhea was the only adverse effect of note with the use of Aloe-derived
ingredients to treat asthma, ischemic heart disease, diabetes, ulcers, skin
disease, and cancer.

 Case reports include acute eczema, contact urticaria, and dermatitis in


individuals who applied Aloe-derived ingredients topically.
312
14. CLINICAL USE OF HERBS & HERBAL MEDICINE BY BILAL MALIK

 In Aloe-derived ingredients used in cosmetics, regardless of species,


anthraquinone levels should not exceed 50 ppm.

 The Cosmetic Ingredient Review Expert Panel advised the industry that
the total polychlorobiphenyl (PCB)/pesticide contamination of any plant-
derived cosmetic ingredient should be limited to not more than 40 ppm,
with not more than 10 ppm for any specific residue and that limits were
appropriate for the following impurities: arsenic (3 mg/kg maximum),
heavy metals (20 mg/kg maximum), and lead (5 mg/kg maximum).

 Contraindications:

 Contraindicated in intestinal obstruction and acutely inflamed intestinal


diseases, ulcerative colitis, appendicitis

 Dosage:

 Leaf pulp juice—10–20 ml.

 Dried leaf pulp juice— 125–500 mg powder

b) Angelica archangelica Linn:


• Family _ Umbelliferae; Apiaceae.

• Habitat: Native to Syria; now grown in Kashmir.

Constituents:

 The roots from Kashmir yield furocoumarins, phenol compounds and


flavonoids.

 Xanthotoxol exhibited antihistamintic and antinicotinic activities on


guinea-pig ileum.

 Furocoumarins, especially psoralen and 8-methoxypsoralen, are used in


the photochemotherapy of psoriasis and vitiligo.

 Most of the coumarins have shown significant calcium antagonistic


activity in vitro. Angelicin, a resin, is stimulating to the lungs and skin.

Uses:

313
14. CLINICAL USE OF HERBS & HERBAL MEDICINE BY BILAL MALIK

• Expectorant, carminative, digestant, cholagogue (bile), antispasmodic,


diaphoretic (pores), diuretic, anti-inflammatory, smooth muscle relaxant,
antifungal, antibacterial, In flatulence, peptic discomforts, for menstrual
irregularity, lack of menstruation and painful menstruation.

Contraindications:

• In bleeding disorders, peptic ulcers and pregnancy.

Dosage:

• Root—1–3 g powder.

c) Mentha piperata Linn:


• Family _ Labiatae; Lamiaceae.

• Habitat _ Native to Europe; cultivated in India, Pakistan.

• English _ Peppermint, Brandy Mint.

Constituents:

 The major constituents of the essential oil are: menthol, menthone,


pulegone, menthofuran, 1,8-cineole, menthyl acetate, isomenthone. The
leaves contain flavonoids, glycosides, eriocitrin, luteolin 7-O-rutinoside,
hesperidin, isorhoifolin, diosmin, eriodictyol 7-O-glucoside and narirutin,
besides rosmarinic acid, azulenes, cholene, carotenes.

Uses:

 Oil—digestive, carminative, chloretic (stimulate bile), antispasmodic,


diuretic, antiemetic, mild sedative, diaphoretic, antiseptic, antiviral, used
in many mixtures of indigestion, colic, cough and cold remedies, Irritable
colon, irritable bowel syndrome, Respiratory tract discomfort,
inflammation of the oral mucosa, antibacterial, antiviral and antifungal .

 Externally, for myalgia, neuralgia, rheumatic complaints, pruritus,


urticaria, and pain in irritable skin conditions

314
14. CLINICAL USE OF HERBS & HERBAL MEDICINE BY BILAL MALIK

 Leaf—internally for spastic complaints of the gastrointestinal tract,


gallbladder and bile ducts. dyspepsia, flatulence, intestinal colic, and
biliary disorders.

d)Citrus limon (Linn.):


• Family _ Rutaceae.

• Habitat _ Cultivated all over India and Pakistan.

• English _ Lemon.

• Unani _ Utraj

Constituents:

• The fruits contain flavonoids and limonoids. The flavonoids comprise


three main groups—flavanones, flavones and 3-hydroxyflavylium
(anthocyanins).

• Lemon juice is a richer source of vitamin (contains 40– 50 mg/100 g of


vitamin C), and a fair source of carotene and vitamin B1. Volatile oil
(about 2.5% of the peel) consists of about 75% limonene, alpha-and beta-
pinenes, alpha-terpinene and citral. The fruit juice also contains
coumarins and bioflavonoids.

• The bioflavonoids strengthen the inner lining of blood vessels, especially


veins and capillaries, and help counter varicose veins, arteriosclerosis,
circulatory disorders and infections of liver, stomach and intestines.
Major flavonoid glycosides, isolated from citrus peels and juices, include

• Hesperidin. Flavanone glycosides contained in lemon and lime juices are


eriocitrin 47 and 94; hesperidin 84 and 196 mg/l, respectively.
Monoterpene alcohols and their esters, aldehydes—geraniol, geranial and
neral, contribute to the characteristic aroma of lemon.

Uses:

• Fruit—antiscorbutic, carminative, stomachic, antihistaminic,


antibacterial. Used during coughs, colds, influenza and onset of fever
(juice of roasted lemon), hiccoughs, biliousness.

315
14. CLINICAL USE OF HERBS & HERBAL MEDICINE BY BILAL MALIK

• Externally for ringworm (mixed with salt), erysipelas (infection of


dermis), also in the treatment of leprosy (bacterial infection) and white
spots.

Dosage:

• Fruit—6–12 g

(Juice—5– 10 ml).

e) Balsamodendron mukul:
• Synonym _ Commiphora mukul,

C. wightii (Arn.).

• Family _ Burseraceae.

• Habitat _India

• English _ Indian Bdellium, Gum Guggul.

• Unani _ Muqallal yahood, Muql, Bu-e-Jahudaan

Constituents:

• Guggul resin contains steroids—gugglsterones Z and E, guggulsterols I–


V, diterpenoids; volatile oil, terpene hydrocarbon cembrene A. E- and Z
guggulsterones.

Uses:

• Oleo-gum-resin—used for reducing obesity and in rheumatoid arthritis,


osteoarthritis, sciatica (pain by spinal nerve), hyperlipidemia,
hypercholesterolaemia, inhibits platelet aggregation, anti-inflammatory
and activates the thyroid gland.

• The gum is also used in hemiplegia (one side paralysis) and


atherosclerotic disorders; as a gargle in chronic tonsillitis and pharyngitis.
Fumes are recommended in hay fever and chronic bronchitis.

Dosage : Oleo-gum-resin—2–4 g

316
14. CLINICAL USE OF HERBS & HERBAL MEDICINE BY BILAL MALIK

4) Herbs used for the Treatment of

Musculo-skeletal disorders :
Musculoskeletal Disorders or MSDs are injuries and disorders that affect
the human body’s movement or musculoskeletal system (i.e. muscles,
tendons, ligaments, nerves, discs, blood vessels, etc.).

a)Nigella sativa Linn [kalonji]:


• Family: Ranunculaceae.

• Habitat: Cultivated in India and Pakistan.

• English: Black Cumin, Small Fennel.

• Unani: Kalonji, Kamaazaruus.

• Part used: Seeds

Constituents

 The essential oil contains nigellone, 2-methyl-4-isopropyl-p-quinone,


carvone, d-limonene, cymene, fatty acids including palmitic, myristic,
stearic, oleic, linoleic, linolenic and β-sitosterol.

 Nigellone inhibits the release of histamine.

 Antifungal; antidiabetic, antimanic effect and Anticonvulsant like effects


in epilepsy model of carvone and is reported

 . The seeds are reported to contain a fatty oil rich in unsaturated fats,
mainly linoleic acid (50-60%), oleic acid (20%), eicodadienoic acid
(3%) and dihomolinoleic acid (10%)

 The extracts have used to treat nervous system diseases such as memory
impairment, epilepsy, neurotoxicity, as antispasmodic, analgesic effects
on experimental animals.

 Thymoquinone- the major active ingredient of the volatile oil of Nigella


sativa seeds, provided protection against Pb-induced renal antioxidant
capacity impairment and suggest that this component might be a
clinically promising alternative in Pb nephrotoxicity.

317
14. CLINICAL USE OF HERBS & HERBAL MEDICINE BY BILAL MALIK

 Thymoquinone has also shown an anti-anxiety-like effect in mice


through modulation of γ-aminobutyric acid (GABA) and nitric oxide
(NO) levels in the brain or plasma

 Nigella sativa seed administration caused significant prevention of febrile


neutropenia during chemotherapy among children with brain tumors.

 N. sativa extract showed analgesic and anti-inflammatory effects by


stabilizing dural mast cells in rats.

 The topical application of Nigella sativa oil was effective in reducing


pain in patients with knee osteoarthritis; therefore, it is recommended as a
safe supplement for these elderly.

 It also modulate ulcer inducing agents and thus could be helpful as


antiulcer.

 The methanol extract modifies amino acid levels in the rat brain regions
and thus could be helpful in some neurodegenerative diseases which is
related to amino acid level imbalances in the central nervous system.

Other uses:

• diuretic,

• antihypertensive,

• anti-diabetic,

• immune-modulatory,

• antimicrobial,

• anthelmintic,

• bronchodilator,

• antiinflammatory,

• anti-tussive,

• gastroprotective,

• hepato-protective,

318
14. CLINICAL USE OF HERBS & HERBAL MEDICINE BY BILAL MALIK

• Low density lipoprotein

• Cholesterol decreasing

• Renalprotective and

Anti-oxidant properties

Traditional Uses:

• Skeletal muscular prob.

• Stimulant,

• Carminative,

• Diuretic,

• Puerperal fever.

• Common cold,

• Cough

• Bronchospasm.

• Sexual diseases,

• Diarrhea

• Skin disorders

Dosage: 1-3g, 3-5g

b) Trigonella foenum-graecum Linn:


• Family: Papilionaceae; Fabaceae.

• Habitat: Widely cultivated in India.

• English: Fenugreek.

• Unani: Hulbaa, Methi.

• Part Used: Seeds


319
14. CLINICAL USE OF HERBS & HERBAL MEDICINE BY BILAL MALIK

Constituents:

• Alkaloids (trigonelline, gentianine and carpaine)

• Saponins (sapogenins, diosgenin and its isomer yamogenin, gitogenin and


tigogenin) (reduce cholesterol)

• Flavonoids (vitexin)

• Glycosides

• Esters

• Luteolin

• mucilage (galactomannan)

• C-steroidal sapogenin peptide ester, fenugreekine, exhibited


hypoglycaemic activity.

• 4-hydroxy-isoleucine (stimulate insulin)

Uses:

• Loss of appetite,

• Flatulence,

• Dyspepsia,

• Colic;

• Diarrhoea,

• Dysentery;

• Enlargement of liver and spleen

• Galactagogue

• Secretolytic,

• Antiseptic

• Demulcent

• Hypoglycaemic,
320
14. CLINICAL USE OF HERBS & HERBAL MEDICINE BY BILAL MALIK

• Diabetes mellitus,

• Hypercholesterolaemia.

• Healing of gastric ulcers,

• Smooth muscle relaxant

• Skeletal muscle problems

• Increased bile secretion

• Hair growth stimulant.

Dosage: Seed 3-5 g powder

c)Zingiber officinale Rosc.:


• Family: Zingiberaceae.
• Habitat: Native to Southeast Asia; india, Pakistan, West Bengal.
• English: Ginger.
• Unani: Fresh rhizome—Zanjabeele- Ratab, Al-Zanjabeel. Dried
rhizome—zanjabeel, Zanjabeel-eyaabis.
• Part Used: Rhizome
Constituents:
• Essential oil (monoterpenes, mainly geranial and neral)
• Sesquiterpenes (beta-sesquiphellandrene, betabisabolene, ar-curcumene
and alphazingiberene
• Gingerols, shogaols and related phenolic ketones which have sedative,
anti-inflammatory, antipyretic, analgesic, hypotensive and
hepatoprotective and cardiotonic effects.
• Diarylheptenones, di-terpenes, gingesulphonic acid and
monoacyldigalactosyl glycerols.
Uses:
• Antiemetic,
• Antiflatulent,
• Hypocholesterolemic,
321
14. CLINICAL USE OF HERBS & HERBAL MEDICINE BY BILAL MALIK

• Anti-inflammatory,
• Antispasmodic,
• Skeletal muscular disorders
• Expectorant,
• Circulatory stimulant,
• Diaphoretic,
• Irritable bowel
• Diarrhea,
• Colds and influenza
• Migraine and cluster headache.
• Dyspepsia,
• Loss of appetite,
• Tympanitis,
• Anaemia,
• Cough
• Dyspnoea
• Constipation,
• Colic,
• Edema
• Throat infections
• Motion sickness
• Vomiting of Pregnancy, post-Operative Antiemetic
• Anorexia,
• Bronchitis
• Rheumatic complaints
• Suppress gastric contractions and secretions

322
14. CLINICAL USE OF HERBS & HERBAL MEDICINE BY BILAL MALIK

5)Herbs used for the T.T of Diabetes:

a)Gymnema sylvestre B. Br:


 Family: Asclepiadaceae.
 Habitat: Mostly found in India.
 English: Australian Cow Plant, Ipecacuanha (Indian).
 Unani: Gurmaar Buuti.
 Gymnemagenin, the main sapogenin in the leaves, yielded 3.9–4.6% of
total gymnemic acids.
 Gymnemic acids are anti sweet principles and exhibit inhibitory effect on
levels of plasma glucose.
 The extract of dried leaves, given to diabetic rats at a dose of 20 mg/day
per rat for 8 weeks, was found to bring about blood glucose homoeostasis
by increasing serum insulin levels. Increased glycoprotein level and the
resultant nephropathy, retinopathy and micro-and macro-angiopathy were
also controlled.
 The leaf extract (25–100 mg/kg), when orally administered to
experimentally induced hyperlipidaemic rats for 2 weeks, reduced the
elevated serum triglyceride and total cholesterol in a dose-dependent
manner. The efficacy and anti-atherosclerotic potential of the extract (100
mg/kg) were comparable to that of a lipid lowering agent, clofibrate.
 In homoeopathy, a drug obtained from the leaves and roots is prescribed
for diabetes
 Gymnemic acid is reported to inhibit melanin formation in vitro. It also
inhibits dental plaque formation.
Action:
 Leaf—antidiabetic. Stimulates the heart and circulatory system, activates
the uterus. Used in parageusia (bad taste) and furunculosis (bact. Skin
inf).
 Plant—diuretic, antibilious.
 Root—emetic, expectorant, astringent, stomachic.

323
14. CLINICAL USE OF HERBS & HERBAL MEDICINE BY BILAL MALIK

Dosage: Root, leaf—3–5 g pwd, 50–100 ml decoction.

b) Azadirachta indica A. Juss.:


 Synonym: Melia azadirachta Linn.
 Family: Meliaceae.
 Habitat: found all over India and Pakistan.
 English: Neem tree, Margosa tree.
 Unani: Aazaad-Darakht-e-Hindi.
 Plant tetranortriterpenoids have been examined extensively for their
antibiotic, antitumour, insecticidal, antibacterial and antifungal activities.
 The methanolic extract of the bark shows antimalarial activity against
Plasmodium falciparum.
 The aqueous extract of leaves exhibited antiulcer and anti-inflammatory
activity.
 The water-soluble portion of alcoholic extract of leaves reduces blood
sugar in glucose-fed and adrenaline-induced hyperglycaemic rats (but not
in normal and streptozotocin-induced diabetic rats).
 A volatile fraction of the Neem oil is reported to be responsible for
spermicidal activity at a dose of 25 mg/ml for human sperm.
 The oil has been found to retard the growth of human immunodeficiency
virus.
 Neem oil has caused mitochondrial injury in mice; poisonous in high
doses.
Actions:
 Leaf, bark—antimicrobial, antifungal, anthelmintic, insecticidal, antiviral,
antipyretic, antimalarial, antiperiodic, mosquito larvicidal, anti-
inflammatory, antifertility, spermicidal, hypoglycaemic; used in
inflammation of gums, gingivitis, periodonitis, sores, boils, enlargement
of spleen, malarial fever, fever during childbirth, measles, smallpox, head
scald and cutaneous affections.
 Oil—used as a contraceptive for intra-vaginal use, for the treatment of
vaginal infections, and as a mosquito repellent.
324
14. CLINICAL USE OF HERBS & HERBAL MEDICINE BY BILAL MALIK

Dosage:
 Dried leaf—1–3 g powder; 10–20 g for decoction.
 stembark—2–4 g powder decoction for external use.
 Leaf juice—10–20 ml; oil—5–10 drops.
 Bark decoction—50–100 ml

c)Momordica charantia Linn:


 Family: Cucurbitaceae.
 Habitat: Cultivated all over India
 English: Bitter Gourd, Balsam Pear, Carilla.
 Unani: Karelaa
 Immature fruits gave several non bitter and bitter momordicosides.
 Fruits, seeds and tissue culture gave a polypeptide containing amino
acids.
 Fruits also gave 5-hydroxytryptamine, charantin (a steroidal glucoside),
diosgenin, cholesterol, lanosterol and betasitosterol. Bitter principles are
cucurbitacin glycosides.
 Hypoglycaemic effects of the fruit have been demonstrated by blood tests
in both humans and animal studies.
 Researchers have warned that the fruit extract leads to a false negative
test for sugar in the urine (due to its ability to maintain the indicator dye
in the glucose oxidase strips and the alkaline copper salts in a reduced
state).
 Chronic administration of the fruit extract (1.75 g/day for 60 days) to
dogs led to testicular lesions with mass atrophy of the spermatogenic
elements.
 The extract reduced the testicular content of RNA, protein and sialic acid
as also the acid-phosphatase activity.
 The fruits and seeds yielded a polypeptide, p-insulin, which was
considered similar to bovine insulin.

325
14. CLINICAL USE OF HERBS & HERBAL MEDICINE BY BILAL MALIK

 The seed and fruit contain an inhibitor of HIV, MAP-30 (Momordica


anti-HIV-protein) which exhibited antiviral and antitumour activity in
vitro.
 The seeds yield alpha-and beta momorcharins (glycoproteins). When
these glycoproteins were co-cultured with isolated hepatocytes,
morphological changes in hepatocytes were observed, indicating
hepatotoxicity. Another principle with antilipolytic and lipogenic
activities, found along with the alpha-and beta-momorcharin in the seed
extract, did not show toxic effect.
 Vicine is the hypoglycaemic constituent in the seed. Pure vicine has been
found to possess 32.6% hypoglycaemic activity as against 22.2% shown
by fresh juice, when tested on albino rats. The vicine is non-haemolytic.
 Actions: Seed/fruit—improves diabetic condition. Fruit—stomachic,
laxative, antibilious, emetic, anthelmintic. Used in cough, respiratory
diseases, intestinal worms, skin diseases, also for gout and rheumatism.
Powdered fruit—applied to wounds and ulcers.
 Leaf—emetic, antibilious, purgative.
 Fruit, leaf and root—abortifacient.
 Leaf and seed—anthelmintic.
 Root—astringent; applied to haemorrhoids.
Dosage:
 Fresh fruit—10–15 ml
 juice 10–20 ml

D) Syzygium cuminii(Linn.) Skeels:


 Synonym: S. jambolanum(Lam.) DC. Eugenia jambolana Lam.
 Family: Myrtaceae.
 Habitat: Cultivated throughout India and Pak
 English: Java Plum, Jambolan, Black Plum.
 Unani: Jaamun

326
14. CLINICAL USE OF HERBS & HERBAL MEDICINE BY BILAL MALIK

 The aqueous alcoholic extract of the bark contains bergenin, gallic acid
and ethyl gallate.
 The fruit contains anthocyanins and yielded citric, malic and gallic acids.
 Gallic acid and tannins account for astringency of the fruit. Malic acid is
the major acid of fruit; a small quantity of oxalic acid is reported to be
present. Glucose and fructose are principal sugars in the ripe fruit;
sucrose was not detected.
 The seeds contain tannin, ellagic acid, gallic acid, beta-sitosterol,
essential oil, myricyl alcohol is present.
 The stem bark yielded friedelan- -alpha-ol, kaempferol, quercetin,
betasitosterol and its glycoside, kaempferol- -O-glucoside, gallic acid,
friedelin and betulinic acid. It contained eugenin and epi-friedelanol.
tannins were reported.
 The leaves contain aliphatic alcohols, sitosterols, betulinic acid and
crategolic (maslinic) acid.
 The flowers contain triterpenic acids—oleanolic acid and crategolic acid.
The oleanolic acid is a strong protector against adriamycin-induced lipid
peroxidation in liver and heart microsomes.
 Phenols, including methylxanthoxylin and, -dihydroxy- -
methoxyacetophene have been isolated from the plant (also from the
seed).
 Seeds in normal and alloxanized rabbits exhibited hypoglycaemic
activity. The chloroform fraction of seed extract exhibited potent anti-
inflammatory action. Water extract exhibited antibacterial properties.
 Action Fruit—stomachic, carminative, diuretic.
 Bark and seed—anti-diarrhoeal. Seed—hypo-glycaemic.
 Leaf—antibacterial, anti-dysenteric.
 Key application: Bark—in nonspecific acute diarrhoea and in topical
therapy for mild inflammation of the oral-pharyngeal mucosa; externally
in mild, superficial inflammation of the skin. The seed has been included
among unapproved herbs by German Commission E, as the blood sugar-
lowering effect could not be established by several researchers.

327
14. CLINICAL USE OF HERBS & HERBAL MEDICINE BY BILAL MALIK

 Claimed applications: in diabetes, also in combination preparations for


tonic and spastic constipation, diseases of the pancreas, gastric and
pancreatic complaints.
 The Ayurvedic Pharmacopoeia of India recommends the bark in acute
diarrhoea and haemorrhagic diseases; the seed in hyperglycaemia and
polyuria.

328
14. CLINICAL USE OF HERBS & HERBAL MEDICINE BY BILAL MALIK

6)Herbal Medicine Used in CNS disorders

a)Nux Vomica:
Synonyms:
Poison Nut, Dog Button, Quaker Button

Bot Name: Strychnos nux-vomica


Family: Loganiaceae

Part Used: Dried ripe seeds.


Habitat: India and South East Asia.
 It is a major source of the highly poisonous intensely bitter alkaloids
Strychnine and Brucine, derived from the seeds inside the tree's round,
green to orange fruit.
 The seeds contain approximately 1.5% strychnine, and the dried blossoms
contain 1.0%.
 The tree's bark also contains brucine and other poisonous compounds.
 The use of strychnine is highly regulated in many countries, and is mostly
used in baits to kill feral mammals including wild dogs, foxes, and
rodents.

Description:
 S. nux-vomica is a medium-sized tree with a short thick trunk.
 The leaves are about 4 inches long and 3 inches wide.
 The flowers are small with a pale green colour with a funnel shape.
 The fruit are about the size of a large apple with a smooth and hard shell
which when ripened is a mild shade orange colour.
 The flesh of the fruit is soft and white with a jelly-like pulp containing
five seeds covered with a soft woolly substance.
 The seeds are removed from the fruit when ripe.

329
14. CLINICAL USE OF HERBS & HERBAL MEDICINE BY BILAL MALIK

 They are then cleaned, dried and sorted.


 The seeds have the shape of a flattened disk completely covered with
hairs.
 The seeds are hard.
Constituents:
 Nux Vomica contains the alkaloids Strychnine , Brucine and traces of
strychnicine.
 The glucoside Loganin, about 3 per cent fatty matter, caffeotannic acid
and a trace of copper.
 The pulp of the fruit contains about 5 per cent of loganin together with
the alkaloid strychnicine.
Medical uses:
 There are no uses in modern medicine, although it was widely used in
medicine before World War II.
 Strychnine is a deadly poison with a lethal dose to humans of about 30 to
120 mg.
 The properties of Nux Vomica are those of the alkaloid strychnine.
Strychnine is eliminated with a half-life of about 12 hours.
 The most direct symptom caused by strychnine is violent convulsions due
to a simultaneous stimulation of the motor or sensory ganglia of the
spinal cord. During the convulsions there is a rise in blood pressure.
 Brucine closely resembles strychnine in its action, but is slightly less
poisonous as it only causes paralysis of the peripheral motor nerves.
Action
Nervine tonic and a potent CNS stimulant.
 Seeds—used in emotional disorders, insomnia, hysteria (emotional
excess), epilepsy, retention or nocturnal incontinence of urine, sexual
debility (loss of strength) and impotence, general exhaustion; as antidote
to alcoholism; GIT disorders. antiulcer
 Bark—juice given in acute dysentery, diarrhoea and colic.
 Root—given in intermittent fevers.

330
14. CLINICAL USE OF HERBS & HERBAL MEDICINE BY BILAL MALIK

 In Chinese medicine; a paste made of Nux vomica seeds is applied


topically for treating facial paralysis.
 The detoxified seeds in paralysis, facial paralysis, sciatica and impotency.
 Orally, 30–50 mg Nux-vomica (5 mg strychnine) is toxic.
Dosage: Detoxified seed—60– 125 mg.

b)DATURA:
Jimson Weed
Syn : Jimson weed, Thorn Apple, Mad Apple

Bot Name : Datura stramonium


Family : Solanaceae
Parts Used : Leaves, seeds.
Habitat : Throughout the world, except the colder or Arctic regions.

History:
 The name “Jimson” comes from the word “Jamestown.” Early colonists
were known to have found the weed growing in abundance in Jamestown.
 Dating and analysis of remains show 4000 years of use.
 Was used as an aphrodisiac in the Middle Ages.
 Very toxic and can cause hallucinations

Description:
 Grows to about 1.5m tall.
 Annual shrub that grows mainly in the summer months (July – October).
 Requires sunlight to grow.
 Prefers neutral or basic, dry soils.

331
14. CLINICAL USE OF HERBS & HERBAL MEDICINE BY BILAL MALIK

 Large, white, funnel shaped flowers grow to about 5-10cm long.


 Its fruits are large, thorny pods filled with seeds.
. Traditional Uses:
 Aphrodisiac
 Wound and burn healer
 Treating colds and asthma
 Recent uses include treatments of epilepsy, acute mania
 Over-the-counter powders and cigarettes were sold for asthma
treatment.Banned in 1968 as an over-the-counter drug.

Preparations:
 Leaves are rolled into cigarettes for asthma treatment
 Seeds can be crushed and used in drinks or teas
 Flowers can be boiled
 Leaf extracts or seeds can be made into pill form
Constituents:
 Atropine
 Scopolamine (main cause of hallucinations)
 Hyoscyamine
 Other tropanes

332
14. CLINICAL USE OF HERBS & HERBAL MEDICINE BY BILAL MALIK

Scopolamine:
 Central nervous system depressant
 Antimuscarinic effects similar to atropine
 Commonly used to prevent motion sickness
 Blocks short-term memory
 Also used as a gastrointestinal and urinary antispasmodic

Hyoscyamine:
 Has similar, but more potent, antimuscarinic effects as atropine and
scopolamine
 Used as an adjunct in treatments of peptic ulcer disease and Zollinger-
Ellison syndrome
 Antidote to cholerinesterase inhibitors

Contraindications:
 Due to the dangerous effects of datura, its use is not recommended, but is
still used in many areas.
 The accumulation of acetylcholine leads to persistent stimulation of
nicotinic receptors, possibly altering fetal development.
Adverse Effects:
 All parts of Datura are toxic
 Overdosing on Jimson weed will lead to:
 Visual hallucinations
 Disorientation
 Speech incomprehension
 Dilated pupils
 Can be fatal
 Delirium, agitation and seizures
 Scopolamine is known to be the main cause of hallucinations

333
14. CLINICAL USE OF HERBS & HERBAL MEDICINE BY BILAL MALIK

c) Cannabis sativa Linn:


 Synonym C. indica Linn.
 Family Cannabinaceae.
 Habitat Cultivated all over the India and Pakistan
 English Hemp, Indian Hemp.
 Unani Bhang, Charas, Qinnab.
Actions: Hallucinogenic, hypnotic, sedative, analgesic, anti-inflammatory,
glaucoma, antiemetic in cancer chemotherapy. All variants produce initial
excitement followed by depression.
 Cannabis yields cannabinoids, cannabispirans and alkaloids.
 Toxic constituents are readily absorbed, excreted in urine and feces,
stored in lipid tissues, especially CNS, crosses placenta.
 High doses in animals have damaged developing embryos and resulted in
birth defects.
Dosage: Dried leaves, after removing turbidity—125–250 mg pwd.

d) Papaver somniferum Linn:


 Family Papaveraceae.
 Habitat Native to Asia
 English Opium Poppy.
 Unani Afyum. Tukhm-ekhashkhaash(seed).
 Opium contains isoquinoline alkaloids; morphine with narcotine, codeine,
papaverineand thebaine.
 The seeds contain thiamine, riboflavin, folic acid, pantothenic acid and
niacin.
 The seed oil (from Turkey) contains gamma-tocopherol, alpha-tocopherol
and beta-tocopherol.
 Some low-molecular proteins along with cysteine, glutamic acid and
arginine were also isolated.

334
14. CLINICAL USE OF HERBS & HERBAL MEDICINE BY BILAL MALIK

 The seeds yield a fatty oil containing palmitic, stearic, oleic, linoleic and
linolenic acids.
Actions
 Opium is obsolete as a drug. Narcotic, sedative, hypnotic, analgesic,
sudorific (promote sweating), anodyne (releive pain), antispasmodic,
hypoglycemic and antitumor.
 Poppy seed—nutritive, demulcent, emollient, spasmolytic, against
constipation, also used in catarrh of the bladder.
 Poppy seed oil is also free from narcotic properties.
 Used against diarrhoea, dysentery and scalds (burns).

e)Atropa . belladonna:
 Synonym A. acuminata
 Family Solanaceae
 Habitat Kashmir
 English Indian Belladonna, Indian Atropa.
 Unani Luffaah, Luffaah-Barri, Yabaruj, Shaabiraj.
 The herb contains tropane (tropine) or alkaloids including hyoscamine
and atropine; flavonoids; coumarins; volatile bases (nicotine).
 Tropane alkaloids inhibit the parasympathetic nervous system, which
controls involuntary bodily activities; reduces saliva, gastric, intestinal
and bronchial secretions, and also the activity of urinary tubules.
 Tropane alkaloids also increase the heart rate and dilate the pupils. These
alkaloids are used as an additive to compound formulations for
bronchitis, asthma, whooping cough, gastrointestinal hypermotility,
dysmenorrhoea, nocturnal enuresis and fatigue syndrome.
 Atropine provides relief in parkinsonism and dystonia (neurological
movement disorders).
 The root is most poisonous,
 Actions

335
14. CLINICAL USE OF HERBS & HERBAL MEDICINE BY BILAL MALIK

 Highly poisonous; sedative, narcotic, antispasmodic (used in


paralysis); parkinsonism; encephalitis (acute inflammation of brain);
carcinoma; spastic dysmenorrhoea; whooping cough, spasmodic asthma;
colic of intestines, gall bladder or kidney, spasm of bladder and ureters;
 Contraindicated in enlarged prostate, Tachycardia, arrhythmias,
glaucoma, acute oedema of lungs.
 Dosage Leaf, root—30–60 mg, pwd

336
14. CLINICAL USE OF HERBS & HERBAL MEDICINE BY BILAL MALIK

7)Herbs used in GIT DISORDERS

a) Foeniculum vulgare Mill. :

 Family: Umbelliferae; Apiaceae.


 Habitat: Throughout India and Pakistan
 English: Fennel.
 Unani: Baadiyaan, Saunf
 Fennel seed contain about 8% volatile oil (about 50–60%anethole, among
others 10–15% fenchone and methylchavicol), flavonoids, coumarins
(including bergapten) and sterols.
 The extract of seeds inhibits the growth of micro-organism, especially
Streptococcus mutans.
 The essential oils have antibacterial, antifungal, antioxidant,
emmenagogue, oxytocic, abortifacient and exhibits anticarcinogenic
activity used as a chemoprotective agent and for decreasing the side
effects of chemotherapy and increasing the immune function.
 Anethole and fenchone have secretolytic action in respiratory tract.
 The fatty acid, petroselenic acid, obtained from the oil, exhibited
antimicrobial activity.
 Anethole, a major constituent of fennel seed/oil has been found to be an
active estrogenic agent with minimal hepatotoxicity and no teratogenic
effect.
USES:
 As Carminative,
 stomachic,
 antispasmodic,
 promotes gastrointestinal motility,
 emmenagogue,
 galactagogue,
337
14. CLINICAL USE OF HERBS & HERBAL MEDICINE BY BILAL MALIK

 anti-inflammatory,
 diuretic
 Relieves bloating,
 nausea,
 settles stomach
 stimulates appetite
 Amenorrhoea
 Enuresis
 Dyspepsia
 flatulence.
 catarrh of the upper respiratory tract.
Dosage:fruit. 3-6 g pwd
Contraindications: Pregnancy

b) Ferula foetida Regel.:


 Synonym F. assafoetida Linn.
 Family Umbelliferae; Apiaceae.
 Habitat Native to Iran, Afghanistan and Pakistan.
 English Asafoetida.
 Unani Hilteet, Hing.
Constituents:
 Resins about 40–60%, consisting of asaresionotannols and their esters;
farnesiferols, ferulic acid and other acids;
 about 25% gum;
 about 6–17% volatile oil, major constituent being sec-propenylisobutyl
disulphide; sulphated terpenes, pinene, cadinene and vanillin;
sesquiterpenoid coumarins.
 Some compounds from Ferula sp. exhibit anti-fertility activity.

338
14. CLINICAL USE OF HERBS & HERBAL MEDICINE BY BILAL MALIK

USES:
 Olea-gum-resin: stimulates the intestinal and respiratory tracts and the
nervous system bark.
 Used for simple digestive problems such as bloating, indigestion,
constipation; for congested mucus, bronchitis, whooping cough, also for
neurological affections, epilepsy, cramps and convulsions, In dyspepsia,
chronic gastritis, irritable colon; as spasmolytic.
Contraindications: bleeding disorders, pregnancy, infectious or inflammatory
GI diseases
Dosage: oleo gum-resin—125–500 mg.

c) Cuminum cyminum Linn. :


 Family Umbelliferae; Apiaceae.
 Habitat: Throughout India, Pakistan
 English Cumin.
 Unani Safed Jeeraa, Kamun.
Constituents:
 Seeds contains up to 14.5% lipids, 14 flavonoid glycosides; 7 belong to
apigenin, 5 to luteolin and 2 to chrysoeriol group. Major constituents of
the essential
 oil include cuminaldehyde (20–40% of the oil) and p-cymene.
 Cumin is considered superior is comforting carminative qualities to
Fennel.
 Cumin oil and cumin-aldehyde have been reported to exhibit strong
larvicidal and antibacterial activity. Fine grinding of the seed can cause
loss of 50% of volatile oil, most within one hour.
USES:
 Carminative,
 antispasmodic
 in dyspepsia

339
14. CLINICAL USE OF HERBS & HERBAL MEDICINE BY BILAL MALIK

 diarrhoea,
 stimulant,
 diuretic,
 antibacterial,
 emmenagogue,
 galactagogue,
 hypotensive

Dosage
 Fruit—1–3 g pwd.

d) Aegle marmelos (L.) Correa ex Roxb.:


 Family Rutaceae.
 Habitat Throughout India
 English Bael tree, Bengal Quince.
 Unani Bael.
 A number of coumarins (including xanthotoxol and alloimperatorin
methyl ether), flavonoids (including rutin and marmesin), alkaloids
(including alpha-fagarine), sterols and essential oils have been isolated
from plant parts. Pectin is an important constituent of the fruit.
 Alkaloid aegeline, present in the leaves, is efficacious in asthma. The
active principle in aqueous extract of leaf shows hypoglycaemic activity
similar to insulin. Leaves are also given in jaundice. Alcoholic extract of
seeds shows antiallergic activity.
 Marmin, a coumarin isolated from the roots, shows anti-inflammatory
effects experimentally. Marmin also inhibited gastric haemorrhagic
lesions in rats and exhibited antiulcer effects.
 Seed oil showed beneficial effects in regeneration of tumour cells.
 Aurapten is found to be the most potent inhibitor of heart rate. Rootbark
is used for palpitation of the heart.

340
14. CLINICAL USE OF HERBS & HERBAL MEDICINE BY BILAL MALIK

Uses:
 Stomachic,
 antimicrobial
 diarrhoea,
 colitis,
 dysentery
 enteric infections,
 digestive,
 astringent,
 spasmolytic,
 hypoglycaemic.
 Roots in dysuria;
 Stem bark in diabetes and lipid disorders.

Dosage
 Pulp of unripe/ half ripe fruit—3 g Pwd
 Roots—6 g Pwd.

e) Prunus domestica Linn. :


 Synonym P. communis Huds.
 Family Rosaceae.
 Habitat Cultivated in Kashmir,
 English Prune.
 Unani Aaluuchaa.
Constituents:
 The fruit pulp contains about 44% sugar and malic acid as major
constituents.

341
14. CLINICAL USE OF HERBS & HERBAL MEDICINE BY BILAL MALIK

 Kernel contains fixed oil about 45% and amygdalin and benzoic acid
among others.
 The crude extract of the fruit was found effective in controlling centrally
induced emesis in dogs. The action was comparable to that of
Metoclopramide (Maxolon) and chlorpromazine (Largactil).
Uses:
Fruit

 laxative
 Nutritive
 Improves haemoglobin levels in iron deficiency
 Promotes excretion of excess calcium by the kidneys
 An adjuvant for atherosclerosis and arthritis
Root
 Astringent

342
14. CLINICAL USE OF HERBS & HERBAL MEDICINE BY BILAL MALIK

8)Medicinal Herbs Used For the treatment of Hepatitis


a) Berberis vulgaris Linn:
 Family: Berberidaceae:
 Habitate: India and Pakistan
 English: Common barberry, True barberry
 Part Used: Roots and bark
Uses: ailments of;
 GIT,
 Liver,
 gall bladder,
 Kidney and Urinary tract,
 febrifuge,
 Blood purifier,

The main alkaloid berberine berbamine and jatrorrhizine which are;


 bactericidal, trypanocidal,
 antidiarrhoeal,
 stimulate bile secretion
 sedative, hypotensive,
 anticonvulsant
 uterine stimulant activity,
 increase WBC and platelets,
 many alkaloids have antineoplastic activity
 Combined with pyrimethamine-more effective in treating chloroquine
resistance malaria.
Dosage: berbamine 50mg TID for 1-4 weeks reverse leukopaenia

343
14. CLINICAL USE OF HERBS & HERBAL MEDICINE BY BILAL MALIK

b) Picrorhiza kurroa:
Family: Scrophulariaceae
Habitat: Kashmir
English: Picrorhiza
Unani: Kutki
Part Used: Roots, Rhizome
Uses:
 Stomachic
 Antidiarrhoeal
 Hepatoprotective (in Jaundice)
 Used in hepatitis
 Chronic dysentery, Amoebiasis.
 Intermittent fever, Dyspnea and Skin Diseases.
Family: Scrophulariaceae
Habitat: Kashmir
English: Picrorhiza
Unani: Kutki
Part Used: Roots, Rhizome
Uses:
 Stomachic
 Antidiarrhoeal
 Hepatoprotective (in Jaundice)
 Used in hepatitis
 Chronic dysentery, Amoebiasis.
 Intermittent fever, Dyspnea and Skin Diseases.

344
14. CLINICAL USE OF HERBS & HERBAL MEDICINE BY BILAL MALIK

c) Lawsonia inermis Linn. :


 Family: Lythraceae.
 Habitat: Native to Arabia and Persia;
 English Henna
 Unani Hinaa, Mehndi.
 Part used: Leaves, stem bark
Constiuents: The leaves contain naphthoquinones,
in particular lawsone; coumarins (laxanthone, I, II
and III); flavonoids, luteolin and its 7-O-glucoside,
acacetin-7-O-glucoside; beta-sitosterol- 3-O-
glucoside; all parts contain tannins.
Uses:
 Hepato-protective against CCl4 induced toxicity, (Jaundice)
 Antibacterial,
 Antifungal,
 Anti-inflammatory
 Astringent,
 Antihaemorrhagic,
 Antispasmodic,
 Oxytocic,
 Antifertility,
 Dysuria,
 Bleeding disorders
 Ulcers,
 Prurigo
 Vertigo
Dosage Leaves—5–10 ml juice

345
14. CLINICAL USE OF HERBS & HERBAL MEDICINE BY BILAL MALIK

9) Herbs Used in REPRODUCTIVE DISORDERS


a)Saraca asoca(Roxb.):
• Synonym S. indica auct.
• Family Caesalpiniaceae.
• Habitat Throughout Asia.
• English Ashoka tree.
• Unani Ashoka.
• The flowers contain fatty acids and gallic acid; apigenin-7-O-betaD-
glucoside, cyanidin-3,5-diglucoside, kaempferol 3-O-beta-D-glucoside,
pelargonidin-3,5-diglucoside, quercetin and its 3-O-beta-D-glucoside and
sitosterol.
• The bark yields alkanes, esters and primary alcohols. It gave n-
octacosanol, tannin (6%), catechin, (+)-catechol, (−)-epicatechin, (−)-
epicatechol, leucocyanidin, leucopelargonidin, procyanidin derivatives,
methyl-and ethylcholesterol derivatives.
• Quercetin and its 3-O-rhamnoside, kaempferol-3-O-alpha-L-rhamnoside,
amyrin, ceryl alcohol and beta-sitosterol have been isolated from leaves
and stem.
• The aqueous extract has been found to enhance the life span of mice
infected with Ehrlich ascites carcinoma by 24%.
• Pure phenolic glucoside, isolated from stem bark, exhibited highly potent
oxytocic activity on different mammals and was similar in nature to
pitocin and ergometrine.
Uses/Actions:
• Bark—uterine tonic, used for suppressed menses, leucorrhoea, menstrual
pain, menorrhagia (regular prolong menstural peroid), complaints of
menopause (opposite of menarche). Also used for dyspepsia, biliousness,
colic, burning sensation. Antibacterial
• Flower-- used in haemorrhagic dysentery, bleeding piles and retention of
urine.

346
14. CLINICAL USE OF HERBS & HERBAL MEDICINE BY BILAL MALIK

• The Ayurvedic Pharmacopoeia of India recommends the bark in


metrohhagia (uterine bleeding at irregular interval), menorrhagia, chronic
lymphadenitis and inflammations.
Dosage Dried stem bark—20–30 g for decoction.

b) Ruta graveolens Linn.:


• Family Rutaceae.
• Habitat cultivated all over India.
• English Garden Rue.
• Unani Sudaab, Suddaab.
Constituents:
• Volatile oil, with 2-undecanone (30.73) 2-nonanone (18.06), 2-nonyl
acetate (11.03), psoralen (1.28) and bergapten and xanthotoxin (7.24%);
rutin (about 2%).
• The flavonoids include quercetin; coumarins include bergapten,
daphnoretin, isoimperatorin, naphthoherniarin, psoralen, pangelin,
rutamarin, rutarin, scopoletin and umbelliferone. Tissue culture of the
plant gave furacridone alkaloids. Tissue culture of the root gave
gravacridondiol and its glucoside.
• The spasmolytic activity of the herb is attributed to the presence of
bergapten, xanthotoxin and the essential oil.
• Anti-inflammatory and antitumour activity is due to rutin. The
furocoumarins are responsible for the herb’s phototoxicity.
• The herb is hepatotoxic, and is contraindicated in kidney diseases and
bleeding disorders.
• Maximum safe level is 0.001% for Rue and 0.0002% for the oil. (Natural
Medicines Comprehensive Database, 2007.)
Uses/Action:
• Herb—stimulating, antispasmodic, stomachic; irritant, abortifacient. Used
as an emmenagogue, cough, colic and flatulence.
• Leaf—used in as tonic amenorrhoea and colic. Externally, used for
sciatica, headache, muscular chest pain, bronchitis and arthritis.
347
14. CLINICAL USE OF HERBS & HERBAL MEDICINE BY BILAL MALIK

• Fresh juice of leaves, internally, can lead to painful irritations of the


stomach and intestines.
• Oil— antispasmodic, antiepileptic, emmenagogue, rubefacient. (Toxic in
large doses.)

c)Nigella sativaLinn. :
• Family: Ranunculaceae.
• Habitat: Cultivated in India and Pakistan.
• English: Black Cumin, Small Fennel.
• Unani: Kalonji, Kamaazaruus.
• Part used: Seeds
Constituents:
• The essential oil contains nigellone, 2-methyl-4-isopropyl-p-quinone,
carvone, d-limonene, cymene, fatty acids including palmitic, myristic,
stearic, oleic, linoleic, linolenic and Beta-sitosterol. Nigellone inhibits the
release of histamine.
• The extracts have antispasmodic, CNS depressant and analgesic effects
on experimental animals.
Uses:
• Skeletal muscular prob.
• stimulant,
• carminative,
• diuretic,
• lactiferous,
• emmenagogue (stimulate uterine)
• puerperal fever.
• common cold,
• cough
• bronchospasm.

348
14. CLINICAL USE OF HERBS & HERBAL MEDICINE BY BILAL MALIK

Dosage: 1-3g, 3-5g

d)Glycyrrhiza glabra Linn.:


• Family Papilionaceae; Fabaceae.
• Habitat Native to Kashmir, India and Pakistan.
• English Licorice, Liquorice.
• Unani Asl-us-soos, Mulethi.
Constituents:
• Glycyrrhizin, a triterpene saponin with low haemolytic index.
• Glycyrrhetinic (glycyrrhetic) acid, the aglycone of glycyrrhizin is also
present in the root.
• Isoflavonoids, chalcones, coumarins, triterpenoids and sterols, lignans,
amino acids, amines, gums and volatile oils.
• Hypokalemia is the greatest threat when glycyrrhizin are prescribed for
prolonged periods. causes fluid retention. Patients should be placed on a
high potassium and low sodium diet. Special precautions should be taken
with elderly patients and patients with hypertension or cardiac, renal or
hepatic disease.
• A special liquorice extract known as DGL (deglycyrrhizinated liquorice)
is used in the treatment of peptic ulcer.
• Oral liquorice preparations, containing glycyrrhetinic acid, are used for
the treatment of viral infections—viral hepatitis, common cold.
• Topical preparations, containing glycyrrhetinic acid, are used for herpes,
eczema, psoriasis.
USES/ACTIONS:
• Demulcent, expectorant, anti-allergic, anti-inflammatory, spasmolytic,
mild laxative, anti-stress, anti-depressive, antiulcer, liver protective,
estrogenic, emmenagogue, antidiabetic.
• Used in bronchitis, dry cough, respiratory infections, catarrh,
tuberculosis; genitourinary diseases, urinary tract infections; abdominal
pain, gastric and duodenal ulcers, inflamed stomach, mouth ulcer.

349
14. CLINICAL USE OF HERBS & HERBAL MEDICINE BY BILAL MALIK

• Also used for adrenocorticoid insufficiency.


• Key application In catarrh of the upper respiratory tract, gastric and
duodenal ulcers, bronchitis, inflammation, chronic gastritis, rheumatism
and arthritis, adrenocorticoid insufficiency, and to prevent liver toxicity.
• Dosage: Root—2–4 g pwd.

e) Claviceps purpurea:
• Family Hypocreaceae.
• Habitat A fungous parasite on a number of grasses particularly in rye,
cultivated in the Nilgiris and at Chakrohi farm in Jammu.
• English Ergot of Rye. Fungus of Rye.
• Unani Argot.
• The fungus gave indole alkaloids. The ergometrine or ergonovine group
includes ergometrine and ergometrinine. The ergotamine group includes
ergotamine and ergotaminine. The ergotoxine group includes
ergocristine, ergocristinine, ergocryptine, ergocryptinine, ergocornine and
ergocorninine.
• The fungus also contains histamine, tyramine and other amines, sterols
and acetylcholine.
• Ergotamine is used to relieve migrainous headaches as it is a
vasoconstrictor and has anti-serotonin activity.
• Ergometrine is used after childbirth and for post-partum haemorrhage, as
it is a powerful uterine stimulant, particularly of the puerperal uterus.
(Both the constituents are used under medical supervision).
• Ergocornine significantly inhibited the development of induced
mammary tumours in rats. The derivatives of ergot alkaloids are known
to have suppressing effect on human breast cancer in initial stages. This
activity is linked to prolactin inhibitory action.
• The extract is toxic at 1.0–3.9 g, ergot alkaloids at 1 g in adults, 12 mg in
infants. (Francis Brinker).
USES/ACTION:

350
14. CLINICAL USE OF HERBS & HERBAL MEDICINE BY BILAL MALIK

• Uterine stimulant, Oxytocic, abortifacient, parturient, vasoconstrictor,


haemostatic.
• Used in obstetrics (difficult childbirth, for exciting uterine contractions in
the final stages of parturition).
• Also used after abortion for removal of the placenta. It is no more
employed in internal haemorrhages, as it has been found to raise blood
pressure in pulmonary and cerebral haemorrhage.

Dosage: Whole plant—10–30 ml infusion.

f)Myristica fragrans Houtt. :


• Family Myristicaceae.
• Habitat Native to the Moluccas Islands; grown in the Nilgiris, Kerala,
Karnataka and West Bengal.
• English Nutmeg, Mace.
• Unani Jauzbuwaa (seed), Bisbaasaa (mace).
• The hexane extract contains myristicin, an anti-inflammatory principle,
and licarin-B and dehydro diisoeugenol which exhibited CNS depressant
properties. The extracts of nutmeg decreased kidney prostaglandin levels
in rats. They also inhibited platelet aggregation (due to eugenol and
isoeugenol).
• The anti-inflammatory activity observed in carrageenan-induced oedema
in rats and enhanced vascular permeability in mice, are attributed to
myristicin present in mace.
• Mace also activates hepatic detoxification process. Monomeric and
dimeric phenyl propanoids (myristicin, dehydro diisoeugenol) from mace,
on p.o. administration in mice, produced suppression of lipid peroxidation
in liver.
• Seeds contain about 0.24% myristicin, whereas volatile oil about 3.12%.
The resorcinols, malabaricones B and C, isolated from the seed coat
(mace) exhibited strong antibacterial and antifungal activities. Neoplasm
inhibitors, phenylpropyl derivatives, have been isolated from pulverized
mace.

351
14. CLINICAL USE OF HERBS & HERBAL MEDICINE BY BILAL MALIK

Uses/Action
• Nutmeg—carminative, spasmolytic, antiemetic; used in flatulency,
diarrhoea, nausea and vomiting; topically anti-inflammatory.
• stimulant carminative, Narcotic in high doses, used in rheumatism,
chronic bowel complaints and asthma. When roasted, both nutmeg and
mace are used for diarrhea, colic, flatulence, antispasmodic, inhibit
prostaglandin synthesis and used in dyspepsia.
• Fruit in spermatorrhoea.
Dosage dried seed—0.5–1 g pwd

352
14. CLINICAL USE OF HERBS & HERBAL MEDICINE BY BILAL MALIK

10)Medicinal Herbs Used For Renal Disorders

a)Cucumis melo:
 Synonym: C. utilissimus Roxb
 Family: Cucurbitaceae
 Habitate: Cultivated in India, Pak, Afghanistan
 English: Snake Cucumber
 Unani: Kakari
 Part used: seeds
 Uses: Cooling,
 diuretic (in painful micturation)
 Dysurea,
 lithiasis
 Dosage: seeds 3-6 g.

b) Berberis vulgaris Linn :


 Family: Berberidaceae:
 Habitate: India and Pakistan
 English: Common barberry, True barberry
 Part Used: Roots and bark
Uses: ailments of;
 GIT,
 Liver,
 gall bladder,
 Kidney and Urinary tract,
 febrifuge,

353
14. CLINICAL USE OF HERBS & HERBAL MEDICINE BY BILAL MALIK

 Blood purifier,

The main alkaloid berberine berbamine and jatrorrhizine which are;


 bactericidal,
 trypanocidal,
 antidiarrhoeal,
 stimulate bile secretion
 sedative,
 hypotensive,
 anticonvulsant
 uterine stimulant activity,
 increase WBC and platelets,
 many alkaloids have antineoplastic activity
 Combined with pyrimethamine-more effective in treating chloroquine
resistance malaria.
Dosage: berbamine 50mg TID for 1-4 weeks reverse leukopaenia

c)Zea mays:
 Family: Gramineae, Poaceae
 Habitat: South america, India, Pak,
Kashmir
 English: Maize, Corn
 Unani: Makka, Zurraa Makka
Constituents:
 Saponins,
 alantoin,
 sterols (beta-sisterol and stigmasterol),

354
14. CLINICAL USE OF HERBS & HERBAL MEDICINE BY BILAL MALIK

 alkaloids hordenine,
 polyphenols,
 mucilage,
 potassium,
 vit-C,
 Vit-K,
 Cryptoxanthin,
 anthocyanins,
 plant acids,
 tannin

USES:
 diuretic,
 urinary demulcent,
 antilithic,
 cystitis,
 urethritis,
 prostatitis,
 irritation of UT,
 nephritis,
 uncontrollable bladder,
 bed-wetting.
 Antiviral
 antitumor

d)Tribulus terrestris Linn.:


 Family: Zygophyllaceae.

355
14. CLINICAL USE OF HERBS & HERBAL MEDICINE BY BILAL MALIK

 Habitat: India
 English: Land-Caltrops, Puncture Vine
 Unani: Khaar-e-Kkasak Khurd
 Part used: Fruit, leaves and seeds
Constituents:
 Sapogenins
 diosgenin,
 gitogenin,
 chlorogenin,
 ruscogenin,
 D-spirosta-diene,
 Flavonoids—rutin,
 quercetin,
 kaempferol,
 kaempferol
 glucoside,
 rutinoside,
 tribuloside
 alkaloids
 (harmane and harmine)
 Harmol
Uses:
 diuretic,
 demulcent,
 anti-inflammatory,
 anabolic,
 spasmolytic,

356
14. CLINICAL USE OF HERBS & HERBAL MEDICINE BY BILAL MALIK

 muscle relaxant,
 hypotensive,
 hypoglycaemic,
 strangury,
 urolithiasis,
 crystallurea,
 urinary discharge,
 pruritis,
 sexual inadequacy,
 support medicine of cough and asthma.
 haemostatic.
 stomachic,
 cardiotonic
 for treating angina pectoris
 hypotensive,
 hypolipidaemic,
 hypoglycaemic.
Dosage:
Fruit— 3-6 g powder

357

You might also like