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Chapter 3 Lipids

Lipids are organic compounds primarily made of alcohol and fatty acids, characterized by their insolubility in water and solubility in organic solvents. They play crucial biological roles, including energy storage, providing essential fatty acids and fat-soluble vitamins, and forming cell membranes. Lipids can be classified into simple, compound, and derived lipids, with various types such as triglycerides, fatty acids, and sphingolipids, each serving specific functions in the body.

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0% found this document useful (0 votes)
23 views61 pages

Chapter 3 Lipids

Lipids are organic compounds primarily made of alcohol and fatty acids, characterized by their insolubility in water and solubility in organic solvents. They play crucial biological roles, including energy storage, providing essential fatty acids and fat-soluble vitamins, and forming cell membranes. Lipids can be classified into simple, compound, and derived lipids, with various types such as triglycerides, fatty acids, and sphingolipids, each serving specific functions in the body.

Uploaded by

derartuelias1
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
Available Formats
Download as PPTX, PDF, TXT or read online on Scribd
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1

LIPIDS

01/31/2025
Introduction
2

Definition:
 Lipids are organic compounds formed
mainly from alcohol and fatty acids
combined together by ester linkage.

O
H2O O
R CH 2 OH
+ HO C R R CH 2 O C R
Fatty alcohol Fatty acid Esterase (lipase) ester (lipid)
01/31/2025
3

 - Lipids are insoluble in water, but soluble


in organic solvents (ether, chloroform,
benzene, acetone).

 - Lipids include fats, oils, waxes and


related compounds.

 They are widely distributed in nature both


in plants and in animals.
01/31/2025
4

Biological Importance of Lipids:


1. They are more palatable and storable.
2. they provide more energy per gram than
(25% of body needs) carbohydrates and
proteins but carbohydrates are the preferable
source of energy.
3. Supply the essential fatty acids.
4. Supply fat-soluble vitamins (A, D, E and K).
5. Tissue fat is an essential constituent of cell
membrane and nervous system.
6. A pad for the internal organs to protect them
from outside shocks.
01/31/2025
Classification of Lipids
5

1. Simple lipids (Fats &


Waxes)
2. Compound or conjugated
lipids
3. Derived Lipids

01/31/2025
Fatty alcohols

1-Glycerol:
 It is a trihydric alcohol (i.e., containing three OH
groups) and has the popular name glycerin.
 It is synthesized in the body from glucose.
 Properties:
1. Colorless, viscous oily, liquid with sweet taste.
2. On heating with sulfuric acid or it gives acrolein
that has a bad odour.
 This reaction is used for detection of free
glycerol or any compound containing
01/31/2025
glycerol.
7

CH 2 OH 2 H 2O CHO

HO CH CH
Heating, KHSO4
CH 2 OH CH 2
Glycerol Acrolein

3-It combines with three molecules of nitric acid to form


trinitroglycerin (TNT) that is used as explosive and
vasodilator.
4-On esterification with fatty acids it gives:
• Monoglyceride or monoacyl-glycerol: one fatty acid +
glycerol.
• Diglyceride or diacyl-glycerol: two fatty acids + glycerol.
• Triglyceride or triacyl-glycerol: three fatty acids + glycerol.
5-It has a nutritive value by conversion into glucose and
01/31/2025
enters in structure of phospholipids.
Uses of Glycerol:
8

1. Glycerol enters in pharmaceutical and


cosmetic preparations.
2. Reduces brain edema in cerebrovascular
disease.
3. Nitroglycerin is used as vasodilator
especially for the coronary arteries, thus it
is used in treatment of angina pectoris.
Also, enters in explosives manufacturing.
4. Glycerol is used in treatment of glaucoma
(increased intraocular pressure)due to its
ability to dehydrate the tissue
01/31/2025
from its
water content.
9

2-Sphingosine:
 - It is the alcohol present in sphingolipids.
 - It is synthesized in the body from serine and

palmitic acid.
 It is not positive with acrolein test.

OH
CH 3 (CH 2)12 CH CH CH CH NH 2

CH 2 OH
Sphingosine
01/31/2025
Fatty Acids

10

 Fatty acids are long-chain organic acids having


usually from 4 to 30 carbon atoms; they have a
single carboxyl group and a long, nonpolar
hydrocarbon ‘tail’, which gives most lipids their
hydrophobic and oily or greasy nature.
 Fatty acids which occur in natural fats are usually
monocarboxylic and contain an even number of C
atoms as these are synthesized from 2 carbon units.
 Fatty acids are stored as an energy reserve (fat)
through an ester linkage to glycerol to form
triglycerides.
 If free, the carboxyl group of a fatty acid will be
ionized. 01/31/2025
Fatty Acids
11

 Fatty acids are aliphatic mono-carboxylic acids


 mostly obtained from the hydrolysis of natural
fats and oils.
 Have the general formula R-(CH2)n-COOH
 In this formula "n" is mostly an even number of
carbon atoms (2-34) with a few exceptions that
have an odd number.
 mostly have straight chain.

01/31/2025
Fatty acids are classified according to several
bases as follows:
12
I. According to presence or absence of double
bonds
 A-Saturated Fatty Acids
contain no double bonds with 2-24 or
more carbons.
solid at room temperature except if
they are short chained.
may be even or odd numbered.
have the molecular formula,
CnH2n+1COOH. 01/31/2025
Saturated fatty acids
13

A-Short chain Saturated F.A. (2-10 carbon).

a-Short chain Saturated volatile F.A.(2-6


carbon).

b- Short chain Saturated non volatile F.A.(7-10


carbon).

B-Long chain Saturated F.A.(more the10 carbon)


01/31/2025
a-Volatile short-chain fatty acids:
14
 They are liquid in nature and contain

(1-6) carbon atoms.


 water-soluble and volatile at room

temperature, e.g., acetic, butyric,


and caproic acids.
 Acetic F.A. (2C ) CH3-COOH.
 Butyric F.A. (4C ) CH3-(CH2)2-COOH.
 Caproic F.A. (6C ) CH3-(CH2)4-COOH.
01/31/2025
b-Non-volatile short-chain fatty
15
acids:

 They are solids at room temperature and


contain 7-10 carbon atoms.
 They are water-soluble and non-volatile at
room temperature include caprylic and
capric F.A.

 Caprylic (8 C ) CH3-(CH2)6-
COOH.
 Capric (10 C ) CH 3-(CH2)8-
01/31/2025
B-Long-chain fatty acids:
16
 They contain more than 10 carbon atoms.
 They occur in hydrogenated oils, animal fats,
butter and coconut and palm oils.
 They are non-volatile and water-insoluble
 Include palmitic, stearic, and lignoceric F.A.

 Palmitic(16C) CH3-(CH2)14-COOH
 Stearic (18 C ) CH3-(CH2)16-COOH
 lignoceric (24C ) CH3-(CH2)22-
COOH 01/31/2025
B-Unsaturated Fatty Acids:
Based on Degree of Unsaturation they are

17 Monoethenoid acids: They contain one double bonds .
Molecular Formula :(CnH2n-1 COOH) Ex: Oleic acid.
 Diethenoid acids : They contain two double bonds .
Molecular Formula :(CnH2n-3 COOH) Ex: Linoleic acid.
 Triethenoid acids : They contain three double bonds .
Molecular Formula :(CnH2n-5 COOH) Ex: Linolenic acid.
 Tetraethenoid acids : They contain four double bonds .
Molecular Formula :(CnH2n-7 COOH) Ex: Arachidonic acid.
 Monoethenoid acids are commonly called as
monounsaturated fatty acids (MUFAs) and the remaining
ones as polyunsaturated fatty acids (PUFAs).

01/31/2025
18
 linoleic, linolenic and arachidonic acid - On account
of the important physiological role, these 3 acids
are collectively called as essential fatty acids (EFA)
1-Monounsaturated fatty acids:
1-Palmitoleic acid :
 It is found in all fats.
 It is C16:1∆9, i.e., has 16 carbons and one double
bond located at carbon number 9 and involving
carbon 10.

CH3-( CH2 )5CH = CH-(CH2)7 –COOH


01/31/2025
2-Oleic acid
19

 Is the most common fatty acid in


natural fats.
 It is C18:1∆9, i.e., has 18 carbons

and one double bond located at


carbon number 9 and involving
carbon 10.

CH3-(CH2)7- CH=CH – (CH2)7-COOH


01/31/2025
2-Polyunsaturated fatty acids :
(Essential fatty acids):
20

Definition:
 They are essential fatty acids that
can not be synthesized in the
human body and must be taken in
adequate amounts in the diet.

 They are required for normal


growth and metabolism.
01/31/2025
21

 Source: vegetable oils such as corn oil, linseed oil,


peanut oil, olive oil, cottonseed oil, soybean oil and
many other plant oils, cod liver oil and animal fats.
 Deficiency: Their deficiency in the diet leads to
nutrition deficiency disease.
 Its symptoms include: poor growth and health
with susceptibility to infections, dermatitis,
decreased capacity to reproduce, impaired
transport of lipids, fatty liver, and lowered
resistance to stress. 01/31/2025
 Function of Essential Fatty Acids:
22

1. useful in the treatment of atherosclerosis


(transporting blood cholesterol and triglycerides).
2. The hormones are synthesized from them.
3. They enter in structure of all cellular and
subcellular membranes and the transporting
plasma phospholipids.
4. They are essential for skin integrity, normal growth
and reproduction.
5. They have an important role in blood clotting
(intrinsic factor).
6. Important in preventing and treating fatty liver.
7. Important role in health of the retina and vision.
8. They can be oxidized for energy production.
01/31/2025
1-Linoleic:
23

 C18:29, 12.
 It is the most important since other essential
fatty acids can be synthesized from it in the
body.

CH3-(CH2)4-CH = CH-CH2-CH=CH-
(CH2)7-COOH

01/31/2025
2-Linolenic acid:
24

 C18:39, 12, 15,


 in corn, linseed, peanut, olive,

cottonseed and soybean oils.

CH3-CH2-CH=CH-CH2-CH=CH-CH2-
CH=CH-(CH2)7-COOH

01/31/2025
3-Arachidonic acid:
25

 C20:45, 8, 11, 14.


 It is an important component of
phospholipids in animal and in peanut oil
from which prostaglandins are synthesized.

CH3-(CH2)4-CH=CH-CH2-CH=CH-CH2-
CH=CH-CH2-CH=CH-(CH2)3-COOH

01/31/2025
I. Simple Lipids
26

A. Neutral Fats and oils (Triglycerides)


 They are called neutral because they are
uncharged due to absence of ionizable groups in it.
 The neutral fats are the most abundant lipids in
nature.
 They are esters of glycerol with various fatty acids.
Since the 3 hydroxyl groups of glycerol are
esterified, the neutral fats are also called
“Triglycerides”.

 Esterification of glycerol with one molecule of fatty


acid gives monoglyceride, and that with 2
molecules gives diglyceride. 01/31/2025
27

O O
HO C R 1 CH 2 OH H 2C O C R1
O
O
HO C R 2 + HO C H R2 C O C H
O
O
CH 2 OH 3 H 2O H 2C O C R3
HO C R 3
Glycerol Triglycerides
Fatty acids (Triacylglycerol)

01/31/2025
Types of triglycerides
28

1-Simple triglycerides: If the three fatty acids


connected to glycerol are of the same type
the triglyceride is called simple triglyceride,
e.g., tripalmitin.
2-Mixed triglycerides: if they are of different
types of fatty acids connected to glycerol, it
is called mixed triglycerides, e.g., stearo-
diolein and palmito-oleo-stearin.
 Natural fats are mixtures of mixed
triglycerides with a small amount of simple
triglycerides. 01/31/2025
O
CH 2 O C (CH 2 )14 CH 3
O
CH 3 (CH 2 )14 C O C H
O
CH 2 O C (CH 2 )14 CH 3
Tripalmitin
(simple triacylglycerol)
O
CH 2 O C (CH 2 )16 CH 3
O
CH 3 (CH 2 )7 CH CH (CH 2 )7 C O C H
O
CH 2 O C (CH 2 )7 CH CH (CH 2 )7 CH 3
1-Stearo-2,3-diolein
(mixed triacylglycerol)
O
CH 2 O C (CH 2 )14 CH 3
O
CH 3 (CH 2 )7 CH CH (CH 2 )7 C O C H
O
CH 2 O C (CH 2 )16 CH 3
1-palmito-2-oleo-3-stearin
29 01/31/2025
(mixed triacylglycerol)
30

 The commonest fatty acids in animal fats


are palmitic, stearic and oleic acids.
 The main difference between fats and oils
is for oils being liquid at room
temperature, whereas, fats are solids.
 This is mainly due to presence of larger
percentage of unsaturated fatty acids in
oils than fats that has mostly saturated
fatty acids.

01/31/2025
Physical properties of fats and
31
oils:

1. Freshly prepared fats and oils are colorless,


odorless and tasteless.
 Any color, or taste is due to association with
other foreign substances, e.g., the yellow color
of body fat or milk fat is due to carotene
pigments(cow milk).
2. Fats have specific gravity less than 1 and,
therefore, they float on water.
3. Fats are insoluble in water, but soluble in organic
solvents as ether and benzene.
4. Melting points of fats are usually low, but higher
01/31/2025
than the solidification point.
Chemical Properties of fats and oils:
1-Hydrolysis:
32

 They are hydrolyzed into their constituents (fatty


acids and glycerol) by the action of super heated
steam, acid, alkali or enzyme (e.g., lipase of
pancreas).
 - During their enzymatic and acid hydrolysis glycerol
and free fatty acids are produced.
O O
CH 2 O C R1 H 2C OH R1 C OH
O Lipase or Acid O
R2 C O C H HO C H +R C OH
2
O
O
CH 2 O C R3 3 H 2O H 2C OH
R3 C OH
Triacylglycerol Glycerol Free fatty acids
01/31/2025
2-Saponification.
33

Alkaline hydrolysis produces glycerol and salts of fatty


acids (soaps).
 Soaps cause emulsification of oily material this help

easy washing of the fatty materials


O O
CH 2 O C R1 H 2C OH R1 C ON a
O O
R2 C O C H HO C H +R C ON a
2
O
O
CH 2 O C R3 3 NaOH H 2C OH
R3 C ON a
Triacylglycerol Glycerol Sodium salts of
fatty acids (soap)

01/31/2025
3-Halogenation
34

 Neutral fats containing unsaturated fatty acids have


the ability of adding halogens (e.g., iodine or
iodination) at the double bonds.
 It is a very important property to determine the
degree of unsaturation of the fat or oil that
determines
CH (CH ) CH
its biological
CH CH CH
value.
CH (CH ) COO H
3 2 4 2 2 7
Linoleic acid
2 I2

CH 3 (CH 2 )4 CH CH CH 2 CH CH (CH 2 )7 COO H


I I I I
Stearate-tetra-iodinate
01/31/2025
4-Hydrogenation
35
or
hardening of oils:
 It is a type of addition reactions accepting hydrogen
at the double bonds of unsaturated fatty acids.
 The hydrogenation is done under high pressure of
hydrogen and is catalyzed by finely divided nickel or
copper and heat.
 It is the base of hardening of oils (margarine
manufacturing), e.g., change of oleic acid of fats
(liquid) into stearic acid (solid).
 It is advisable not to saturate all double bonds;
otherwise margarine produced will be very hard, of
very low biological value and difficult01/31/2025
to digest.
5-Oxidation(Rancidty)
 This toxic reaction of triglycerides
36

leads to unpleasant odour or taste


of oils and fats developing after
oxidation by oxygen of air,
bacteria, or moisture.

 Also this is the base of the drying


oils after exposure to atmospheric
oxygen.
Example is linseed oil, which is
used in paints and 01/31/2025
varnishes
Rancidity
Definition:
37

 It is a physico-chemical change in the


natural properties of the fat leading to the
development of unpleasant odor or taste
or abnormal color particularly on aging
after exposure to atmospheric oxygen,
light, moisture, bacterial or fungal
contamination and/or heat.

 Saturated fats resist rancidity more than


unsaturated fats that have unsaturated
double bonds.
01/31/2025
Prevention of rancidity is achieved
by:
38

1. Avoidance of the causes (exposure to light,


oxygen, moisture, high temperature and bacteria
or fungal contamination).
 By keeping fats or oils in well-closed
containers in cold, dark and dry place (i.e.,
good storage conditions).
2. Removal of catalysts such as lead and copper
that catalyze rancidity.
3. Addition of anti-oxidants to prevent peroxidation
in fat (i.e., rancidity). They include phenols,
naphthols, tannins and hydroquinones.
 The most common natural antioxidant is
vitamin E that is important in vitro and in vivo.
01/31/2025
B. Waxes
39
 Waxes are solid simple lipids containing a
monohydric alcohol (with a higher molecular
weight than glycerol) esterified to long-chain
fatty acids. Examples of these alcohols are
palmitoyl alcohol, cholesterol, vitamin A or D.
 Properties of waxes: Waxes are insoluble in
water, but soluble in fat solvents and are
negative for acrolein test.
 Waxes are not easily hydrolyzed as the fats and
are indigestible by lipases and are very resistant
to rancidity.
 Thus they are of no nutritional value.
01/31/2025
Type of Waxes:
40

 Waxes are widely distributed in nature such as


the secretion of certain insects as bees-wax,
protective coatings of the skins and furs of
animals and leaves and fruits of plants. They
are classified into true-waxes and wax-like
compounds as follows:

A-True waxes: include:


 Bees-wax is secreted by the honeybees that

use it to form the combs. It is a mixture of


waxes with the chief constituent is mericyl
01/31/2025
palmitate.
41

O O
C 15 H 31 C OH + C 30 H 61 OH C 15 H 31 C O C 30 H 61

Palmitic Mericyl Mericyl


H2O
acid alcohol palmitate

B-Wax-like compounds:

Cholesterol esters: Lanolin (or wool fat) is
prepared from the wool-associated skin
glands and is secreted by sebaceous glands
of the skin.
 It is very complex mixture, contains both
free and esterified cholesterol, e.g.,
cholesterol-palmitate and other sterols.
01/31/2025
Differences between neutral lipids and waxes:

Waxes Neutral lipids


1.Digestibility: Indigestible (not hydrolyzed Digestible (hydrolyzed by lipase).
by lipase).
2-Type of alcohol: Long-chain monohydric alcohol + Glycerol (trihydric) + 3 fatty acids
one fatty acid.

3-Type of fatty Fatty acid mainly palmitic or Long and short chain fatty acids.
acids: stearic acid.

4-Acrolein test: Negative. Positive.


5-Rancidability: Never get rancid. Rancidible.
6-Nature at room Hard solid. Soft solid or liquid.
temperature.

7-Saponification Nonsaponifiable. Saponifiable.


8-Nutritive value: No nutritive value. Nutritive.

9-Example: Bee & carnuba waxes. Butter and vegetable oils.


42 01/31/2025
II. Compound Lipids
43

Definition:
 They are lipids that contain additional substances,
e.g., sulfur, phosphorus, amino group, carbohydrate,
or proteins beside fatty acid and alcohol.
 Compound or conjugated lipids are classified into the
following types according to the nature of the
additional group:
1. Phospholipids

2. Glycolipids.

3. Lipoproteins

4. Sulfolipids and amino lipids. 01/31/2025


1-Phospholipids
44

Definition: Phospholipids or phosphatides are compound lipids, which


contain phosphoric acid group in their structure.

Importance:

1. They are present in large amounts in the liver and brain as well as
blood. Every animal and plant cell contains phospholipids.

2. The membranes bounding cells and subcellular organelles are


composed mainly of phospholipids. Thus, the transfer of substances
through these membranes is controlled by properties of phospholipids.

3. They are important components of the lipoprotein coat essential for


secretion and transport of plasma lipoprotein complexes. Thus, they are
lipotropic agents that prevent fatty liver.
01/31/2025
4. Myelin sheath of nerves is rich with phospholipids.
45

 Classification of Phospholipids are classified into 2 groups according


to the type of the alcohol present into two types:

A-Glycerophospholipids: They are regarded as derivatives of


phosphatidic acids that are the simplest type of phospholipids and
include:
1. Phosphatidic acids.
2. Lecithins
3. Cephalins.
4. Plasmalogens.
5. Inositides.
6. Cardiolipin.

B-Sphingophospholipids: They contain sphingosine as an alcohol and


01/31/2025
are named Sphingomyelins.
B-Sphingophospholipids
1-Sphingomyelins

46

 Definition: Sphingomyelins are found in brain and


nerves ,in lung, spleen, kidney, liver and blood.
 Structure: Sphingomyelins differ from lecithins and
cephalins in that they contain sphingosine as the
alcohol instead of glycerol, they contain two nitrogenous
bases: sphingosine itself and choline.
 Thus, sphingomyelins contain sphingosine base, one

long-chain fatty acid, choline and phosphoric acid.


 To the amino group of sphingosine the fatty acid is

attached by an amide linkage.

01/31/2025
2-Glycolipids
47
 Definition: They are lipids that contain
carbohydrate residues with sphingosine as the
alcohol and a very long-chain fatty acid (24 carbon
series).
 They are present in cerebral tissue, therefore are
called cerebrosides
 Classification: According to the number and nature
of the carbohydrate residue(s) present in the
glycolipids the following are
 Cerebrosides. They have one galactose molecule
(galactosides).
 Sulfatides. They are cerebrosides with sulfate on the
sugar (sulfated cerebrosides).
 Gangliosides. They have several sugar and sugar-
amine residues. 01/31/2025
3-Lipoproteins
48

 Definition: Lipoproteins are lipids combined with


proteins in the tissues.
 The lipid component is phospholipid, cholesterol
or triglycerides. The holding bonds are
secondary bonds.
 They include:
1. Structural lipoproteins:
 These are widely distributed in tissues being present
in cellular and subcellular membranes.
 In lung tissues acting as a surfactant in a complex of
a protein and lecithin.
 In the eye, rhodopsin of rods is a lipoprotein complex.
01/31/2025
49

2. Transport lipoproteins:
 These are the forms present in blood

plasma.
 They are composed of a protein called

apolipoprotein and different types of


lipids.
 (Cholesterol, cholesterol esters,
phospholipids and triglycerides).
 As the lipid content increases, the density

of plasma lipoproteins decreases.

Grp-2 01/31/2025
 Plasma lipoproteins can be separated by
two methods:
50

1. Ultra-centrifugation: Using the rate of floatation


in sodium chloride solution leading to their
sequential separation into chylomicrons, very
low density lipoproteins (VLDL or pre--
lipoproteins), low density lipoproteins (LDL or -
lipoproteins), high density lipoproteins (HDL or -
lipoproteins) and albumin-free fatty acids
complex.
2. Electrophoresis: is the migration of charged
particles in an electric field either to the anode
or to the cathode. It sequentially separates the
lipoproteins into chylomicrons, pre--, -, and -
lipoprotein and albumin-free fatty01/31/2025
acids complex.
51

a) Chylomicrons: They have the largest


diameter and the least density.
 they contain 1-2% protein and 98-99% fat.
The main lipid fraction is triglycerides
absorbed from the intestine and they contain
small amounts of the absorbed cholesterol
and phospholipids.
b) Very low-density lipoproteins (VLDL) or
pre--lipoproteins: Their diameter is smaller
than chylomicrons.
 They contain about 7-10% protein and 90-93%
lipid. The lipid content is mainly triglycerides
formed in the liver. They contain phospholipid
and cholesterol more than chylomicrons.
01/31/2025
52

c) Low-density lipoproteins (LDL) or -


lipoproteins: They contain 10-20% proteins in
the form of apolipoprotein B.
 Their lipid content varies from 80-90%. They
contain about 60% of total blood cholesterol and
40% of total blood phospholipids. As their
percentage increases, the liability to
atherosclerosis increases.
d) High-density lipoproteins (HDL) or -
Lipoproteins: They contain 35-55% proteins in
the form of apolipoprotein A.
 They contain 45-65% lipids formed of cholesterol

(40% of total blood content) and phospholipids


(60% of total blood content).
Grp-2 01/31/2025
53

 They act as cholesterol scavengers, as their


percentage increases, the liability to
atherosclerosis decreases.
 They are higher in females than in males. Due
to their high protein content they possess the
highest density.

e) Albumin-free fatty acids complex:


It is a proteolipid complex with 99% protein
content associated with long-chain free fatty
acids for transporting them. 01/31/2025
III. Derived Lipids
54

 Prostaglandins
 Synthesized from arachidonic acid
 Several metabolic functions
 Steroids
 Cholesterol, ergosterol, bile acids
 Terpenes
 Made by plants
 Carotenoids, xanthophylls

01/31/2025
55

Cholesterol Vitamin D3
(a sterol) (cholecalciferol)

Testosterone
(a steroid hormone) Stigmasterol
(a phytosterol)
01/31/2025
Cholesterol:
 Importance: -
56

 It is the most important sterol in animal tissues as free


alcohol or in an esterified form (with linoleic, oleic,
palmitic acids).
 Steroid hormones, bile salts and vitamin D are
derivatives from it.
 Tissues contain different amounts of it that serve a
structural and metabolic role, e.g., adrenal cortex
( 10%,), brain ( 2%), others 0.2-0.3%.
 Source: - It is synthesized in the body from acetyl-CoA
(1gm/day)
 cholesterol does not exist in plants.
 It is also taken in the diet (0.3 gm/day as in, butter,
01/31/2025
milk, egg yolk, brain, meat and animal fat).
Propeties:
57
It has a hydroxyl group on C3, a double bond between
C5 and C6, asymmetric carbon atoms and a side
chain of 8 carbon atoms.
 It is found in all animal cells, corpus luteum and

adrenal cortex, human brain .


 In the blood (the total cholesterol amounts about

200 mg/dL of which 2/3 is esterified, chiefly to


unsaturated fatty acids while the remainder
CH 3 occurs
18
as the free 12
cholesterol.
CH 3 CH 3
CH 3

19 17 16 CH 3
11 13
CH 3 C D CH 3
1 9 14 15
2
A 5 10 B 8
HO 3 4 6 7
HO
Steroid ring
Cholesterol
01/31/2025
Ergosterol
58

differs from 7-dehydrocholesterol in the side chain.


Ergosterol is converted to vitamin D2 by irradiation
with UV. Ergosterol and 7- dehydrocholesterol are
called Pro-vitamins D or precursors of vitamin D.
 It was first isolated from ergot, a fungus then from

yeast. Ergosterol is less stable than cholesterol


(because of having 3 double bonds).
CH 3 CH 3
CH 3 CH 3
CH 3 CH 3
CH 3 CH 3 CH 3
CH 3 CH 3

HO HO
7-dehydrocholesterol Ergosterol 01/31/2025
59
Steroids
 Steroids constitute an important class of biological
compounds.
 Steroids are usually found in association with fat.
They can be separated from fats after saponification
since they occur in the unsaponifiable residue.
 They are derivatives of cholesterol that is formed of
steroid ring or nucleus.
 Biologically important groups of substances, which
contain this ring, are:
1. Sterols.
2. Adrenal cortical hormones.
3. Male and female sex hormones.
4. Vitamin D group.
5. Bile acids.
6. Cardiac glycosides. 01/31/2025
General consideration about naturally occurring
steroids:
60

C19 becomes a methylene group (=CH2) and the ring B


is A typical member of this group is cholesterol.
Certain facts have to be considered when drawing
steroid formula:
1) There is always oxygen in the form of hydroxyl or
ketone on C3.
2) Rings C and D are saturated (stable).
3) Methyl groups at C18 C19. In case of vitamin D, the
CH3 group at opened, whereas, this methyl group is
18
absent in female sex hormones (estrogens). 12 CH 3
19 17 16
4) In estrogens (female sex hormones) ring
CH 3A is
C aromatic
11 13
D
15
and there is no methyl group on C10.
2
1
A
9
10 B 8
14
5 7
HO 3 4 01/31/2025
6
Steroid ring
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