PHYTOCHEMISTRY AND INTRODUCTION TO

SECONDARY METABOLITES
Ananya R. Chavan
CONTENT
❑ Phytochemistry – Definition, History and its scope
❑ Types of Metabolites - Primary and secondary [Short Introduction]
❑ Major Pathway responsible for Biosynthesis of Phytoconstituents- Shikimate Pathway and Mevalonate
Pathway
❑ Classification of Phytoconstituents based on types of metabolites
❑ Definition, Distribution, Properties, Extraction, Isolation and Identification tests of the following
important phytoconstituents:
Alkaloids - Quinine, Nicotine and Caffeine. Glycosides - Coumarins and cardiac glycosides
Flavonoids - Quercetin. Terpenoids - Taxol.
Steroids – Cholesterol Tannins - Embelin
Resins – Podophyllum Lipids [fixed oils and fats]- from Castor oil

06-10-2021 2
 INTRODUCTION
■ Medicinal plants are the richest bio‐resource of drugs for traditional systems of medicine, modern
medicines, nutraceuticals, food supplements, folk medicines, pharmaceutical intermediates and
chemical entities for synthetic drugs.

■ Phytochemistry is the bridge which connects chemistry and botany.

■ How?

■ Once a new compound has been isolated from plant material, the determination of its molecular
structure and a study of its properties are distinctly problems of pure chemistry.

■ On the other hand, chemistry contributes methods of isolation and of quantitative determination of
plant components, by the application of which the necessary data are often secured to give sound
scientific explanations of observed plant responses.
06-10-2021 3
 INTRODUCTION
■ Phytochemicals (from the Greek word phyto, meaning plant) are biologically active, naturally
occurring chemical compounds found in plants, which provide health benefits for humans further
than those attributed to macronutrients and micronutrients.

■ Common sources: Broccoli, cabbage, carrots, onions, garlic, whole wheat bread, tomatoes,
grapes, cherries, strawberries, raspberries, beans, legumes, and soy foods etc.

■ More than 4,000 phytochemicals have been catalogued and are classified by protective function,
physical characteristics and chemical characteristics.

■ About 150 phytochemicals have been studied in detail.

06-10-2021 4
 INTRODUCTION
■ Extraction is the term used for the separation of medicinally significant portions of plant from the

inactive components by using selective solvents in different standard extraction procedures.

■ The solvents are selected carefully on the basis of the nature of phyto‐components present in the

plant.

■ Types of extraction procedures play a decisive role for the qualitative and quantitative composition

of the extracts.

■ These extracts are also utilized for isolation and characterization of therapeutically active chemical

constituents used in modern medicines.

06-10-2021 5
 TYPES OF METABOLITES
■ A substance essential to the metabolism of a particular organism or to a particular metabolic

process is called metabolites.

A plant cell produces two types of metabolites:

■ Primary metabolites involved directly in growth and metabolism (carbohydrates, lipids and proteins),

and

■ Secondary metabolites considered as end products of primary metabolism and not involved in

metabolic activity.

■ Secondary metabolites are accumulated by plant cells in smaller qualities than primary metabolites.

06-10-2021 6
CLASSIFICATION OF METABOLITES
Primary Proteins

Carbohydrates

Other biomolecules

Alkaloid
Secondary
Tannins
Flavonoids
Terpenoids
Saponins
Others

06-10-2021 7
 CONCEPTS OF SECONDARY
METABOLITES
■ Secondary metabolites are compounds biosynthetically derived from primary metabolites.
■ In plant kingdom they are limited to occurrence and may be restricted to a particular
taxonomic group genus, species or family.

06-10-2021 8
06-10-2021 9
CLASSIFICATION OF SECONDARY
METABOLITES
Based on their biosynthetic origins, plant secondary
metabolites can be divided into three major groups:

1. Terpenoids

2. Flavonoids and allied phenolic and polyphenolic

compounds,

3. Nitrogen-containing alkaloids and sulphur-

containing compounds.

06-10-2021 10
Role of secondary metabolites

■ Some of them attract animals for pollination and seed dispersal.

■ They are used by the plants in their defense against herbivores and pathogens.

■ They act as agents of plant-plant competition.

■ They are used in making drugs, insecticides, flavours, pigments, scents, rubber, spices
and other industrial materials like gums, resins for human welfare.

06-10-2021 11
 TERPENOIDS
■ The terpenes, or isoprenoids, are one of the most diverse classes of metabolites.

■ Terpenoids are the largest and most diverse family of natural products, ranging in structure from
linear to polycyclic molecules and in size from the five-carbon hemiterpenes to natural rubber,
comprising thousands of isoprene units.

■ All terpenoids are synthesized through the condensation of isoprene units (C5) and are classified by
the number of five-carbon units present in the core structure.

■ Many flavor and aromatic molecules, such as menthol, linalool, geraniol and caryophyllene are formed
by monoterpenes (C10), with two isoprene units, and sesquiterpenes (C15), with three isoprene units.
Other bioactive compounds, such as diterpenes (C20), triterpenes (C30) and tetraterpenes (C40)
show very special properties.

06-10-2021 12
 TERPENOIDS
■ Hemiterpenoids: Consist of a single isoprene unit. The only hemiterpene is the Isoprene itself, but

oxygen-containing derivatives of isoprene such as isovaleric acid and prenol is classify as

hemiterpenoids.

■ Monoterpenoids: Biochemical modifications of monoterpenes such as oxidation or

rearrangement produce the related monoterpenoids. Monoterpenoids have two isoprene units.

Monoterpenes may be of two types i.e linear (acyclic) or contain rings e.g. Geranyl pyrophosphate,

Eucalyptol, Limonene, Citral, Camphor and Pinene.

■ Sesquiterpenes: Sesquiterpenes have three isoprene units e.g. Artemisinin, Bisabolol and

Fernesol, oil of flowers, or as cyclic compounds, such as Eudesmol, found in Eucalyptus oil.
06-10-2021 13
 TERPENOIDS
■ Diterpenes: It composed for four isoprene units. They derive from geranylgeranyl pyrophosphate.
There are some examples of diterpenes such as cembrene, kahweol, taxadiene and cafestol.
Retinol, retinal, and phytol are the biologically important compounds while using diterpenes as
the base.

■ Triterpenes: It consists of six isoprene units e.g. Lanosterol and squalene found in wheat germ,
and olives.

■ Tetraterpenoids: It contains eight isoprene units which may be acyclic like lycopene, monocyclic
like gamma-carotene, and bicyclic like alpha- and betacarotenes

06-10-2021 14
06-10-2021 15
 PHENOLICS
■ Widely spread throughout the plant kingdom

■ Essential for the growth and reproduction of plants, and are produced as a response for defending
injured plants against pathogens.

■ Phenolics are characterized by having at least one aromatic ring with one or more hydroxyl groups
attached.

■ They can be classified based on the number and arrangement of their carbon atoms and are
commonly found conjugated to sugars and organic acids.

■ The three most important groups of dietary phenolics are flavonoids, phenolic acids, and polyphenols.

■ Phenolics can be classified into two groups: the flavonoids and the non-flavonoids.
06-10-2021 16
 PHENOLICS
Flavonoids
■ Flavonoids are the largest group of plant phenols.

■ Flavonoids are polyphenolic compounds comprising fifteen carbons, with two aromatic rings connected by a three-
carbon bridge.

■ The main subclasses of flavonoids are the flavones, flavonols, flavan-3-ols, isoflavones, flavanones and
anthocyanidins.

■ Hydroxyl groups are usually present at the 4, 5 and 7 positions. Sugars are very common with the majority of
flavonoids existing naturally as glycosides.

■ Both sugars and hydroxyl groups increase the water solubility of flavonoids, other substituents, such as methyl groups
and isopentyl units, make flavonoids lipophilic.
06-10-2021 17
 Generic Structure Of Major Flavonoid

06-10-2021 18
PHENOLICS
Phenolic acids
■ Phenolic acids form a diverse group that includes the widely distributed hydroxybenzoic and hydroxycinnamic
acids.

■ The term “phenolic acids”, in general, designates phenols that possess one carboxylic acid functional group.

■ Hydroxycinnamic acid compounds are produced as simple esters with glucose or hydroxy carboxylic acids.

■ Phenolic compounds in many plants are polymerized into larger molecules such as the proanthocyanidins
(PA; condensed tannins) and lignins.

■ Phenolic acids may arise in food plants as glycosides or esters with other natural compounds such as sterols,
alcohols, glucosides and hydroxyfatty acids.

06-10-2021 19
PHENOLICS

06-10-2021 20
PHENOLICS
Phenolic polymers (tannins)

■ Tannins are a heterogeneous group of high molecular weight polyphenolic compounds with the capacity to form
reversible and irreversible complexes with proteins (mainly), polysaccharides (cellulose, hemicellulose, pectin,
etc.), alkaloids, nucleic acids and minerals, etc.

■ On the basis of their structural characteristics it is therefore possible to divide the tannins into four major groups:
Gallotannins, ellagitannins, complex tannins, and condensed tannins.

06-10-2021 21
ALKALOID
■ The alkaloids are a large and structurally diverse group of compounds; some of them are not
entirely distinguishable from amines.

■ The name of alkaloids derives from the “alkaline” and it was used to describe any nitrogen-
containing base.

■ Many are derived from amino acids, but others result from modification of various classes of
molecules including polyphenols, terpenes, or steroids.

■ The true alkaloids are derived from amino acids, are basic and contain nitrogen in a heteroyclic ring,
e.g. nicotine and atropine.

■ The pseudoalkaloids are basic but are not derived from amino acids, e.g. caffeine and solanidine.

06-10-2021 22
In alphabetical order, these are:
Sr. No. Sr. No.
1 Amaryllidaceae alkaloids 10 Peptide alkaloids
2 Betalain alkaloids 11 Piperidine alkaloids
3 Diterpenoid alkaloids 12 Pyridine alkaloids
4 Imidazole alkaloids 13 Pyrrolidine alkaloids
5 Indole alkaloids 14 Pyrrolizidine alkaloids
6 Isoquinoline alkaloids 15 Quinoline alkaloids
7 Methylxanthines 16 Quinolizidine alkaloids
8 Monoterpenoid alkaloids 17 Steroidal alkaloids
9 Peptide alkaloids 18 Tropane alkaloids

06-10-2021 23
 ALKALOIDS
■ Pyrrolidine alkaloids: they contain pyrrolidine ( tetrahydropyrrole) ring system. E.g Hygrine found in Erythroxylum
coca leaves.

■ Pyridine alkaloids: they have piperidine (hexahydropyridine) ring system. E.g Coniine, piperine and isopelletierine.

■ Pyrrolidine-pyridine alkaloids: the heterocyclic ring system present in there alkaloids is Pyrrolidinepyridine.E.g
Myosmine, Nicotine alkaloid found in tobacco (Nicotiana tabacum) plant.

■ Pyridine-piperidine alkaloids: This family of alkaloids contains a pyridine ring system join to a piperidine ring
system the simplest member is Anabasine alkaloid isolated from poisonous Asiatic plant anabasis aphyllan

■ Quinoline Alkaloids: These have the basic heterocyclic ring system quinoline .E.g Quinine occurs in the bark of
cinchona tree.It has been used for centuries for treatment of malaria.Synthetic drugs such as primaquinine have
largely replace quinine as an anti-malarial.

■ Isoquinoline alkaloids: They contain heterocyclic rig system isoquinoline. E.g Opium alkaloids like narcotine,
papaverine, morphine, codeine, and heroine.

06-10-2021 24
 Saponins
■ They form a stable foam in aqueous solutions such as soap, hence the name “saponin”.

■ Groups: glycosylated steroids, triterpenoids, and steroid alkaloids

■ Two main types of steroid aglycones are known, spirostan and furostan derivatives

■ The main triterpene aglycone is a derivative of oleanane.

■ The carbohydrate part consists of one or more sugar moieties containing glucose, galactose,
xylose, arabinose, rhamnose, or glucuronic acid glycosidically linked to a sapogenin (aglycone).

■ Saponins that have one sugar molecule attached at the C-3 position are called monodesmoside
saponins, and those that have a minimum of two sugars, one attached to the C-3 and one at C-
22, are called bidesmoside saponins

06-10-2021 25
PHYSIOCHEMICAL PROPERTIES OF
SECONDARY METABOLITES
1 Phenolic Acids Increases bile secretion, reduces blood cholesterol and lipid levels and
antimicrobial activity against some strains of bacteria such as
staphylococcus aureus
2 Flavonoids antimicrobial, cytotoxicity, antiinflammatory as well as antitumor activities,
powerful antioxidants
3 Tannins astringents, against diarrhoea as diuretics, against stomach and duodenal
tumours,
4 Alkaloid antimalarial activity (quinine), anticancer actions (dimeric indoles,
vincristine, vinblastine), antihypertensive effects ( many indole alkaloids)
5 Terpanoids growth regulators (phytohormones) of plants

06-10-2021 26
Extraction techniques - Maceration

■ The word 'maceration' means 'softening'.

■ In this process, the material to be extracted is placed in a closed vessel and suitable
solvent (menstruum) is added and left for 7 days with occasional shaking.

■ The liquid is then strained off and the solid residue (Marc) is pressed to remove the
solution as much as possible.

■ The strained and expressed liquids are mixed and clarified by filtration.
Extraction techniques - Maceration

■ In case of vegetable and animal tissues, sufficiently long time is allowed for the
menstruum to diffuse through the cell wall to solubilise the constituents present within
the cells and for the resulting solution to diffuse out.

■ Occasional shaking brings about rapid equilibrium between intra and extra cellular fluids
thereby bringing fresh menstruum to the particle surface for further extraction.

■ A closed vessel is used to prevent the loss of menstrum by evaporation and avoids batch
to batch variations.
Extraction techniques - Maceration

It is essentially used for extracting unorganized drugs. Ex: gums, resins etc.
Modified
maceration This process is quick because the soluble constituents are directly exposed to menstruum due to lack of cellular structure.

The process includes, Comminute the drug with menstruum, place in closed vessel for 2‐7 days, agitate the mixture
occasionally, strain and filter the strained liquid, wash the Marc with fresh menstruum. The filtrate should be collected in a dry
receiver.

Multiple
by using portions of total volume of menstruum for successive maceration.

maceration
Efficiency of extraction increases as the number of maceration's increases.
Extraction techniques - Decoction

■ The decoction is used for active ingredients that doesn´t modify with temperature.

■ In this process the plant is boiled in water for 15 to 60 minutes (depending on the plant or the active
ingredient to extract), it´s cooled, strained and added enough cold water through the plant to obtain the
desired volume.

■ Depending on the consistency of the parts to extract, decoction times will be more or less long; generally
roots, leaves, flowers and leafy stems are boiled in water for about 15 minutes, while the branches and
other hard parts can require up to an hour.

■ Once the decoction is done it is necessary to filter the liquid through a cloth.
Extraction techniques - Percolation
■ Percolation is an extraction process that involves the slow descent of a solvent through a
powdered substance until it absorbs certain constituents and drips out through the filtered
bottom of the container.
■ The main advantages of percolation are a more complete extraction of constituents, shorter
processing time, and increased flexibility in processing. The disadvantages include the need for
more equipment, additional complexity in processing, and the incompatibility of percolation with
certain herbs
■ Percolation depends upon the basic principle of diffusion for extraction: diffusion flows from a
gradient of greater concentration to a lesser concentration.
■ Percolation, however, has the advantage of a continuous gravity driven flow of fresh, unsaturated
solvent that works its way down through the marc.
■ Since the soluble constituents are constantly wicked out of the marc by a less concentrated
solvent the process can continue until the constituents are completely exhausted. This process
does not require any agitation and can usually be completed in two days.
Extraction techniques - Soxhlet
Extraction
■ When active constituents of the drug are not freely soluble in the solvent or
difficult to be displaced from the cells of the drug, then it becomes necessary
to extract the crude drug by the action of hot menstruum for a considerable
length of time.

■ The fixed oils from seeds and alkaloids from the drug are extracted by
continuous hot percolation process using benzene, chloroform, petroleum
ether etc.

■ The drug to be extracted is packed in a paper cylinder made from a filter paper
and it is placed in the body of soxhlet extractor.
Extraction techniques - Soxhlet
Extraction
The apparatus used for continuous hot percolation process is soxhlet
apparatus which consist of three parts:

1. Flask containing boiling solvent.

2. Soxhlet Extractor in which the drug to be extracted is packed. It has a

side tube which carries the vapours of the solvent from the flask to the
condenser and a siphon tube which siphons over the extract from soxhlet
extractor to the flask.

3. A condenser in which the vapours of the solvent are condensed again

into solvent.
Extraction techniques - Soxhlet Extraction

■ The solvent is placed in the flask. When solvent is boiled on heating the
flask, it gets converted into vapours. These vapours enter into the
condenser through the side tube and get condensed into hot liquid which
falls on the column of the drug. When the extractor gets filled with the
solvent, the level of siphon tube also raise up to its top.

■ The solvent containing active constituents of the drug in the siphon tube
siphon over and run into the flask, thus emptying the body of extractor .
Extraction techniques - Soxhlet
Extraction
■ This alternation of filling and emptying the body of
extractor goes on continuously. The soluble active
constituents of the drug remain in the flask while the
solvent is repeatedly volatilized.

■ The process of filling and emptying of the extractor is

repeated until the drug is exhausted. Normally the process
is repeated about 15 times for complete exhaustion of the
drug
Supercritical Fluid Extraction
■ Supercritical Fluid Extraction (SFE) Systems extract chemical compounds using supercritical

carbon dioxide instead of an organic solvent.

■ Supercritical carbon dioxide (s CO2) is a fluid state of carbon dioxide (CO2), where it is held at or

above its critical temperature and critical pressure. CO2 usually behaves as a gas in air at

standard temperature and pressure (STP), or as a solid called dry ice when frozen. If the

temperature and pressure are both increased from STP to be at or above the critical point for

CO2, it can adopt properties midway between a gas and a liquid.

■ Manipulating the temperature and pressure of the fluid can solubilize the material of interest

and selectively extract it.

Supercritical Fluid Extraction
■ The sample is placed in an extraction vessel and pressurized with CO2 to dissolve the
sample.
■ Transferred to a fraction collector, the contents are depressurized and the CO2 loses its
solvating power causing the desired material to precipitate.
■ The condensed CO2 can be recycled.
Extraction techniques - Supercritical
Fluid Extraction
SFE applications in the food, pharmaceutical, and fine chemical industries:
1. Decaffeinating of coffee and tea
2. Extraction of essential oils (vegetable and fish oils)
3. Extraction of flavors from natural resources (nutraceuticals)
4. Extraction of ingredients from spices and red peppers
5. Extraction of fat from food products
6. Fractionation of polymeric materials
7. Extraction from natural products
ISOLATION METHODS
PARTITIONING
■ Possibly the simplest separation method is partitioning, which is widely used as an initial
extract purification and ‘clean up’ step.

■ Partitioning uses two immiscible solvents to which the extract is added; this can be
sequential by using immiscible organic solvents of increasing polarity.

Typically, this may take place in two steps:

■ water/light petroleum ether (hexane) to generate a non-polar fraction in the organic layer;

■ water/dichloromethane or water/chloroform or water/ethyl acetate to give a medium-polar

fraction in the organic layer
■ Size-exclusion chromatography (SEC), also known as molecular sieve
chromatography
■ solution are separated by their size, and in some cases molecular weight
■ when an aqueous solution is used to transport the sample through the column, the
technique is known as gel-filtration chromatography, versus the name gel permeation
chromatography, which is used when an organic solvent is used as a mobile phase.

06-10-2021 41
ION-EXCHANGE CHROMATOGRAPHY

06-10-2021 42
06-10-2021 43
THIN-LAYER CHROMATOGRAPHY

06-10-2021 44
HIGH-PERFORMANCE LIQUID
CHROMATOGRAPHY

06-10-2021 45
Gas CHROMATOGRAPHY

06-10-2021 46
Flash chromatography
■ Flash chromatography is basically an air pressure driven hybrid of medium
pressure and shorter column chromatography which has been optimized
for particularly rapid separation.
1. LPLC - Low pressure liquid chromatography (LPLC) system which operate
around 50 -75 psi
2. MPLC - Medium pressure liquid chromatography (MPLC) systems which
operate above 150 psi.

06-10-2021 47
06-10-2021 48
STRUCTURE ELUCIDATION
■ Structure elucidation of natural products generally employs the classical spectroscopic
techniques of mass spectrometry (MS) and nuclear magnetic resonance (NMR)
spectroscopy.

■ The first steps, however, should be the recording of infrared (IR) and ultraviolet-visible (UV-
Vis) spectra to determine the presence of certain functional groups and conjugation in the
molecule.

■ MASS SPECTROMETRY : This technique allows the measurement of the molecular weight of
a compound and, once a molecular ion has been identified, it is possible to measure this
ion accurately to ascertain the exact number of hydrogens, carbons, oxygens and other
atoms that may be present in the molecule. This will give the molecular formula
Solvent system
■ The only appropriate one-component solvent systems (listed from the least
polar to the most polar):
1. Hydrocarbons: pentane, petroleum ether, hexanes
2. Ether and dichloromethane (very similar polarity)
3. Ethyl acetate

■ The most common two-component solvent systems (listed from the least polar to
the most polar):
4. Ether/Petroleum Ether, Ether/Hexane, and Ether/Pentane: Choice of hydrocarbon
component depends upon availability and requirements for boiling range. Pentane is
expensive and low-boiling, petroleum ether can be low-boiling, and hexane is readily
available.
5. Ethyl Acetate/Hexane: The standard, good for ordinary compounds and best for
difficult separations.
6. Methanol/Dichloromethane: For polar compounds.
7. 10 percent Ammonia in Methanol Solution/Dichloromethane: Sometimes moves
stubborn amines off the baseline.

06-10-2021 50
 ALKALOIDS

06-10-2021 51
Introduction

■ More than 12,000-alkaloids are known to exist in about 20% of plant species and
only few have been exploited for medicinal purposes.
■ Majority of alkaloids exist in solid such as atropine, some as liquids containing
carbon, hydrogen, and nitrogen.

06-10-2021 52
Chemical composition

■ Ammonia compounds
■ Nitrogen bases synthesized from amino acid
■ Various radicals replacing one or more of the hydrogen atoms in the peptide ring,
most containing oxygen.

06-10-2021 53
Physical and chemical Properties

■ Alkaline ( due to 1° , 2° or 3° amines)

■ Turning red litmus paper blue
■ Degree of basicity - depending on the structure of the molecule, and presence and
location of the functional groups
■ Reaction with acids- form crystalline salts without the production of water
■ Readily soluble in alcohol (Majority)
■ Sparingly soluble in water but their salts of are usually soluble
■ Taste – bitter

06-10-2021 54
Function
■ Nitrogenous compounds function in the defense of
plants against herbivores and pathogens

■ Widely exploited as pharmaceuticals, stimulants,

narcotics, and poisons due to their potent biological
activities

■ Pharmacological applications as anesthetics and CNS

stimulants

■ As end product of the metabolism or waste products

■ As storage reservoir of nitrogen for protein synthesis

06-10-2021 55
Examples
■ Analgesics - morphine and codeine

■ Muscle relaxant - tubocurarine

■ Antibiotics - berberine

■ Anticancer- vinblastine

■ Pupil dilator – atropine

■ Amino acids act as precursors for biosynthesis of alkaloids with ornithine and lysine commonly
used as starting materials.

■ Other important alkaloids of plant origin include the addictive stimulants caffeine, nicotine,
codeine, atropine, morphine, cocaine, nicotine

06-10-2021 56
DISTRIBUTION
■ In the plant kingdom, the alkaloids appear to have
a restricted distribution in certain families and
genera.
■ Among the angiosperms, the Apocynaceae,
Papaveraceae, Ranunculaceae, Rubiaceae,
Solanaceae, and Berberidaceae are outstanding
for alkaloid-yielding plants.
■ Amaryllidaceae and Liliaceae are
important alkaloid-yielding plants
among monocotyledons.
■ Specific alkaloids are ordinarily confined to specific
plant families (hyoscyamine in Solanaceae,
colchicine in Liliaceae).
■ Nicotine, which is found in a number of widely
scattered plant families, is an exception to this rule.
Quinine
■ Quinine readily crosses the placental barrier
and is also found in cerebral spinal fluid.

■ Excretion is rapid - 80% of the administered

drug is eliminated by hepatic biotransformation
and the remaining 20% is excreted unchanged
by the kidney.

■ The half-life of quinine ranges between 11-18

hours.

06-10-2021 58
Quinine
■ Quinine is a cinchona alkaloid that belongs to
the aryl amino alcohol group of drugs. It is an
extremely basic compound and is, therefore,
always presented as a salt.

■ Various preparations exist, including the

hydrochloride, dihydrochloride, sulphate,
bisulphate, and gluconate salts; of these the
dihydrochloride is the most widely used. Scientific name: Cinchona
Family: Rubiaceae
■ Quinine is rapidly absorbed both orally and Kingdom: Plantae
parenterally, reaching peak concentrations Higher classification: Cinchoneae
within 1-3 hours. Rank: Genus

06-10-2021 59
Quinine

■ Chloroquine and hydroxychloroquine ─

are 4-aminoquinoline compounds and
derivatives of quinine.
■ Chloroquine phosphate (CQ) was
synthesized in 1934, and introduced into
clinical practice in 1947 for the prophylactic
treatment of malaria.
■ Hydroxychloroquine sulfate (HCQ) was
synthesized in 1946.

06-10-2021 60
❖ C10H14N2,
❖ Poisonous
❖ pale yellow,
❖ oily liquid
❖ pungent odor
❖ an acrid taste.
❖ It turns brown on exposure to air.

❖ Nicotine, a naturally occurring constituent of tobacco, is the active compound

in tobacco smoke.
❖ In tobacco leaves ranges from approximately 2% to 7%.
❖ In concentrated form, it is used as an insecticide

06-10-2021 61
■ Caffeine is a methylxanthine alkaloid found in the seeds, nuts, or leaves of a number of plants.

■ acts primarily as an adenosine receptor antagonist with psychotropic and anti-inflammatory

activities.

■ Some physiological effects associated with caffeine administration include central nervous system
stimulation, acute elevation of blood pressure, increased metabolic rate, and diuresis.

■ Caffeine is rapidly and almost completely absorbed in the stomach and small intestine and
distributed to all tissues, including the brain.

06-10-2021 62
Identification test https://www.youtube.com/watch?v=uMxdSkKcO7U
06-10-2021 64