ST.

LIDETA HEALTH SCIENCE AND BUSINESS COLLAGE

DEPARTMENT OF PHARMACY
CHEMISTRY OF NATURAL PRODUCT(CNP)
CHAPTER 4
LIPIDS

Instructor: Yilkal.M
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 OUTLINES
* Definition and classification.
* Fatty acids.
* Triglycerides neutral fats and oils.
* Triglycerides reactions.
* Waxes.
*Phospholipids.
*Prostaglandines.

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 INTRODUCTION
 Lipid is organic substances with widely different
compositions and structures .
 It defined in term of physical property (solubility)
, insoluble in water but soluble in non polar
solvents (ether, chloroform, acetone & benzene).
 Lipids are the waxy, greasy or oily compounds
found in plants and animals.
 lipid repel water ,a useful characteristic of
protective wax coatings found in some plants.

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CLASSIFICATION OF LIPIDS
Derived
Simple lipid Complex lipid
lipids

 Simple: fats, oils, waxes

 Complex: phospholipids, sulfolipids, glycolipids.

 Derivatives: FA, hormones, fat-solubile vitamins

 Miscellaneous: Terpenes

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FATTY ACIDS
 The fundamental building blocks of many lipids
 Fatty Acids are long chain of carboxylic acid.

 Hydrocarbon chain length may vary from 10-30

carbons (most usual is 12-18).
 The long nonpolar tail of F.A. that are responsible for
most of the fatty or oily characteristics of fats.
 Carboxylic group, polar head of F.A is very hydrophilic
under conditions of physiological pH and it exists as the
carboxylate anion -COO¯.
CH3—CH2—CH2—CH2—CH2—CH2—CH2—COOH
↓ ↓
Non polar hydrophobic Polar hydrophilic head
tail water insoluble (water soluble) 7
 The F.As found in natural lipids have several
characteristics:
1. They are usually straight chain carboxylic acids (no
branching).
2. F.As usually have even number of carbon atoms
including carbonyl carbon.
3. F.As can be saturated (no double bonds)or
unsaturated contain one or more double bonds and
found in cis configuration.
 Saturated Fatty acids have no carbon–carbon double
bonds)

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 Unsaturated fatty acid have one or more carbon–carbon
double bonds.

Unsaturated/
common name
16 palmitoleic (9 Z )-hexadecenoic
acid
acid
18 oleic acid (9 Z )-octadecenoic
acid

18 linoleic acid (9 Z,12Z )-

octadecadienoic acid

18 linolenic acid (9 Z,12Z,15Z )-

octadecatrienoic acid

20 arachidonic (5 Z,8 Z,11Z,14Z )-

eicosatetraenoic acid
acid
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20 EPA (5 Z,8 Z,11Z,14Z,17Z )-
eicosapentaenoic acid
 Human body can synthesis all F.As except two (linoleic
acid , linolenic acid) which are polyunsaturated F.As
that contain 18 C atom, it must be obtained from the
diet they are called Essential F.As.
 A fatty acid needed by the body but not synthesized
within the body ,it distributed in plants and fish oils.
linolenic acid (fish oil)
CH3─CH2─(CH=CH─CH2)3─(CH2)6─COOH
 In body ,both acids used to produce hormone like
substances that regulate a wide range of functions and
characteristic including:
 blood pruessre
 blood clotting
 blood lipid level 11
 immune response to injury and infections.
OMEGA FATTY ACIDS
 Omega is used to indicate the position of the first double
bond from the methyl end in an unsaturated fatty acid.
 linoleic acid is called omega-6 fatty acid.

 Linolenic acid is called omega-3 fatty acid.

 Linoleic acid and linolenic acids, therefore, are essential

fatty acids for mammals.
 In other words, the acids must be included in the diet 12
because, although they cannot be synthesized, they are
required for normal body function.
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TRIGLYCERIDES(TGS)
 Triglyceride: an ester of glycerol with three fatty acids
 Triglycerides (TGs) are
 the main constituent of animal fat
 play an important role as transporters of fatty acids
 serving as an energy source.

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 TYPES OF TRIGLYCERIDES
A. Simple triglycerides:
 Three fatty acids connected to glycerol are of the same
type, e.g., tripalmitin.

B. Mixed triglycerides:
 If the three fatty acids connected to glycerol are of
different types.
 Natural fats are mixtures of mixed triglycerides with15
a
small amount of simple triglycerides
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FAT AND OILS
 Fatis a triglyceride that is a solid at room
temperature.
 Mostly from animal sources
 It contain long chain saturated F.As (higher melting
points) or fatty acids with only one double bond.
 Fats are a type of nutrient that you get from your
diet.
 It is essential to eat some fats,
 it is also harmful to eat too much.
 The fats you eat give your body energy that it needs
to work properly.

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 Oils
is a triglyceride that is a liquid at room
temperature
 Mostly from plant and fish sources
 primarily of triacylglycerols with unsaturated fatty
acids (lower Mp)

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 Vegetable oil such as corn, sunflower oils
consists of unsaturated F.A(lower melting point).
 Example Olive oil
 Contains a high percentage of oleic acid, which is a
monounsaturated fatty acid with one cis double bond

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 CHEMICAL PROPERTIES OF FATS AND OILS
1. Hydrolysis
2. Saponification
3. Addition:
 Hydrogenation

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 1. HYDROLYSIS
 The most important reaction in fats and oils it’s the
reveres to ester formation.
 Hydrolysis of a fat or oil produces a mixture of fatty
acids

O
CH2 O C (CH2)14CH3
O
H+
CH O C (CH2)14CH3 H2O
O
CH2 O C (CH2)14CH3 CH2 OH O
CH OH HO C (CH2)14CH3

CH2 OH 21
Enzymes (lipases) of the digestive system also catalyze the hydrolysis to
supply energy.
2. Saponification:(soap making)
 Saponification of Triacylglycerols is the alkaline
hydrolysis of triacylglycerols, leading to glycerol and a
mixture of salts of long-chain carboxylic acids.
 soap: A salt of a F.A often used as a cleaning
agent.
 Sodium salts →hard salt .

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 Potassium salts →soft salt →sharing creams and liquid
soap.
O
H2 C OH
H2 C O C R O
O +
+ 3 KOH HC OH 3 R C OK
HC O C R
O
H2 C OH
H2 C O C R

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 O
CH2 O C (CH2)14CH3
CH2 OH
O
O
CH O C (CH2)14CH3
+ CH OH Na+ -O C (CH2)14CH3
3NaOH
O
“soap”
CH2 O C (CH2)14CH3 CH2 OH

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3. Hydrogenation:
 double bond can be reduced to single bond by
treatment with hydrogen H2 in the presence of catalyst .
 The C=C bonds in vegetable oils can be reduced by
catalytic hydrogenation, to produce saturated solid or
semisolid fats.

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 It is commercial reaction of fats and oils and therefore
increase the melting point
 it is most often used in the production of semisolid
cooking shortening (margarines) from liquid vegetable
oils.

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HYDROGENATION:

O
CH2 O C (CH2)5CH CH(CH2)7CH3 Ni
O + 3H2
O
CH O C (CH2)5CH CH(CH2)7CH3
O CH2 O C (CH2)14CH3
CH2 O C (CH2)5CH CH(CH2)7CH3 O
CH O C (CH2)14CH3
glyceryl tripalmitoleate
O
(tripalmitolean)
CH2 O C (CH2)14CH3

glyceryl tripalmitate
(tripalmitin)
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 During hydrogenation reaction is accompanied by some
cis–trans isomerization
 producing fats with about 10% to 15% trans
unsaturated fatty acids.
 Dietary intake of trans fatty acids increases cholesterol
levels in the blood
 Increasing the risk for heart problems

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WAXES
 Waxes are esters of long-chain fatty acids and long-
chain alcohols (13-32 carbon).
 Waxes insoluble in water and not as easily hydrolyzed
as fat and oil ,they occur naturally in nature as
protective coating on feathers, skin , fruits, leaves.

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 PHOSPHOGLYCERIDES (PHOSPHOLIPIDS)
 phosphoglycerides(Phosphoacylglycerols) are the major
components of cell membranes.
 A complex lipid contains glycerol, F.As, phosphoric acid ,
and an amino alcohol component.
 terminal OH group of glycerol is esterified with
phosphoric acid.

Fatty acid

Fatty acid
Glycerol
Amino
PO4
alcohol
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 Phosphoglycerides have different amino alcohol
groups the most commonly used are ethanolamine,
choline, and serine

CH3
│+ +
HO−CH2−CH2−N−CH3 HO−CH2−CH2−NH3
│
choline CH3 ethanolamine
+
NH3
│ Amino alcohols
HO−CH2−CH−COO−
serine

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 Phosphatidylethanolamines are also called cephalins,
and phosphatidylcholines are called lecithins .
 Lecithin and cephalin are glycerophospholipids
 Abundant in brain and nerve tissues.
 Found in egg yolk, wheat germ, and yeast.

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 Sphingolipids: A complex lipid contain sphingosine compound
along-chain unsaturated amino alcohol ,an 18-carbon alcohol,
F.As, phosphoric acid , and an amino alcohol component.
 they found in cell membrane like: sphingomyelin , glycolipid.

fatty acid
sphingosine
PO4 Amino
alcohol

CH3−(CH2)12 −CH=CH−CH−OH
│
sphingosine CH−NH2
│
CH2−OH
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Sphingomyelin:
 Sphingolipid found in brain and nerve tissue and in
protective myelin sheath that surrounds nerves.
 It is a complex lipid contain a siphingosin , F.A, cholin.
 There is an amide bond between a fatty acid and
sphingosine.

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Glycolipids:
 A complex lipid contain a siphingosin ,F.A ,a carbohydrate
(glucose or galactose)and often called cerebrosides because
of their abundance in brain tissues.

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PROSTAGLANDINS
 Prostaglandins have five-membered ring with a seven-carbon
carboxylic acid substituent and an eight-carbon hydrocarbon
substituent.
 The two substituents are trans to each other.

 Prostaglandins are named PGX, where X designates the functional

groups of the five-membered ring.
 PGAs, PGBs, and PGCs all contain a carbonyl group and a double
bond in the five-membered ring.

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 PGDs and PGEs are ketones, and PGFs are 1,3-diols.

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 Prostaglandins are found in all body tissues.
 Clinically, PGs have many functions for regulating
a variety of physiological responses, such as
inflammation, blood pressure, blood clotting, fever, pain,
the induction of labor, and the sleep– wake cycle.

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 Biosynthesis of prostaglandins, thromboxanes, and
prostacyclins

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Prostaglandins are:
• Produced by injured tissues.
• Involved in pain, fever, and inflammation.
• Not produced when anti-inflammatory drugs such as
aspirin inhibit their synthesis.

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 Aspirin (acetylsalicylic acid) inhibits the cyclooxygenase
activity of prostaglandin endoperoxide synthase.
 Aspirin, therefore, inhibits the synthesis of
prostaglandins.

 decreases the inflammation produced by these com-

pounds
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 Other anti-inflammatory drugs, such as ibuprofen and
naproxen also inhibit the synthesis of prostaglandins.

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