See discussions, stats, and author profiles for this publication at: https://www.researchgate.

net/publication/346930677

Lipid Chemistry

Presentation · December 2020

DOI: 10.13140/RG.2.2.24865.84324

CITATIONS READS

0 4,278

1 author:

Mohamed_kotb Kotb-El-Sayed
Helwan University
64 PUBLICATIONS 451 CITATIONS

SEE PROFILE

Some of the authors of this publication are also working on these related projects:

natural anticancer products View project

Hemoproteins as a therapeutic targets View project

All content following this page was uploaded by Mohamed_kotb Kotb-El-Sayed on 10 December 2020.

The user has requested enhancement of the downloaded file.

 Lecture 11
Dr. Mohamed Kotb El-Sayed
Associate Professor of Pharmaceutical Biochemistry & Molecular Biology

Lipid Chemistry

1
Dr. Mohamed I. Kotb – Associate Professor of Pharmaceutical Biochemistry and Molecular Biology
Objectives:

By the end of this lecture, you should be familiar with:

 Definition and Functions of Lipids.

 Classification of Lipids.

 Simple Lipids (Oils, Fats, and Waxes).

 Classifications of Fatty Acids.

 Phospholipids, Lipoproteins and Glycolipids.

 Sterols and Steroids.

 Bile Acids and Salts.

 Eicosanoids.
2
Dr. Mohamed I. Kotb – Associate Professor of Pharmaceutical Biochemistry and Molecular Biology
Definition & Functions:
Lipids:
 They are organic compounds, which have the following common properties:
 They are esters of fatty acids or associated with these esters in nature.
 Most of them are insoluble in water and soluble in nonpolar solvent e.g. benzene.
Function of lipids:
1.As a Fuel; Neutral fats in particular are stored in specialized cells, known as
adipocytes (TGs). Of high source of energy when stored in adipose tissues (9
kcal/gm).
2.Acts as medium for fat soluble vitamins (DEKA).
3.It serves as insulating material in the subcutaneous tissues. serve as mechanical,
electrical and thermal insulators.
4.Building block in cell membrane (phospholipids bi-layers).
5.The myelin sheath of the nerves is a phospholipids.
6.Support vital organs, acts as a pad for kidney and liver.
7.Supply our bodies with essential fatty acids.
3
8.They serve as hormones, mediators, and second messengers.
Dr. Mohamed I. Kotb – Associate Professor of Pharmaceutical Biochemistry and Molecular Biology
Classification of Lipids:

I- Simple lipids: They are esters of fatty acids with alcohols and includes;
 Neutral lipid: alcohol is glycerol (Fats & Oils).
 Waxes: higher alcohol is other than glycerol.
II- Compound or conjugated lipids:
 They contain other groups in addition to alcohols and fatty acids.
 Examples; Phospholipids, Glycolipids and Proteolipids.
II- Derived lipids:
 They are produced by hydrolysis of the above two groups or present in
association with them in nature. Examples; Sterol and Bile acid .

4
Dr. Mohamed I. Kotb – Associate Professor of Pharmaceutical Biochemistry and Molecular Biology
Classification of Lipids:

5
Dr. Mohamed I. Kotb – Associate Professor of Pharmaceutical Biochemistry and Molecular Biology
Fatty Acids (FAs):

 They are short, medium or long chain monocarboxylic acids.

 They are obtained from the hydrolysis of fats.
 May be saturated or unsaturated.
 Contain an even (Odd in rare conditions) number of carbon atoms (because
they are synthesized from two carbon units).
Nomenclature of Fatty acids:
 The carbon atoms are numbered from the carboxylic end, which is known
as carbon no. 1
 The carbon atom adjacent to the carboxyl group is known as carbon no. 2
or α-carbon, and the next carbon as carbon 3 or β- carbon and the next
carbon 4 or γ-carbon, …etc.
 The methyl carbon at the other end of F.A. is known as omega carbon (ω-
carbon).
6
Dr. Mohamed I. Kotb – Associate Professor of Pharmaceutical Biochemistry and Molecular Biology
Nomenclature of Fatty Acids:

7
Dr. Mohamed I. Kotb – Associate Professor of Pharmaceutical Biochemistry and Molecular Biology
Types of Fatty Acids:

8
Dr. Mohamed I. Kotb – Associate Professor of Pharmaceutical Biochemistry and Molecular Biology
Saturated Fatty Acids:

9
Dr. Mohamed I. Kotb – Associate Professor of Pharmaceutical Biochemistry and Molecular Biology
Unsaturated Fatty Acids:

A- Monounsaturated fatty acids (MUFAs), (mono-ethenoid):

 e.g. palmitoleic acid (C16) and oleic acid (C18).
B- Polyunsaturated fatty acids (PUFAs):
1. Two double bonds:- e.g. linoleic acid 18:2 ; 9,12 = ω6.
2. Three double bonds:- e.g. linolenic acid 18:3;9,12,15 = ω3.
3. Four double bonds:- e.g. arachidonic acid 20:4;5,8,11,14.

10
Dr. Mohamed I. Kotb – Associate Professor of Pharmaceutical Biochemistry and Molecular Biology
Nutritional Classification of Fatty Acids:

 Fatty acids are classified from this point into two groups (essential and
nonessential).
A- Essential Fatty Acids;
 They are not formed in the animal body, so it is essential to take them in
diet, their
 deficiency produces dermatitis, fatty liver and impaired growth and
reproduction.
 They are linoleic (ω3), linolenic (ω6 ) and arachidonic acids.
B- Nonessential Fatty Acids
 These include the rest of fatty acids because they are formed de novo in
the animal body mainly from carbohydrates.
 It is not essential to take them in diet.
11
Dr. Mohamed I. Kotb – Associate Professor of Pharmaceutical Biochemistry and Molecular Biology
A- Essential Fatty Acids:

 Three polyunsaturated fatty acids (Linoleic, Linolenic and Arachidonic

acids) can't be synthesized by the body.
 They protect against atherosclerosis as they form esters with cholesterol.
 Vegetable oils as corn and olive oils are rich in essential fatty acids and are
beneficial in treatment of hypertension and heart diseases.
 Arachidonic acid is a precursor of Eicosanoids.

12
Dr. Mohamed I. Kotb – Associate Professor of Pharmaceutical Biochemistry and Molecular Biology
Digestion & Absorption of Lipids:

 TAGs digested in stomach by gastric lipase and in intestine by pancreatic lipase.

 The main products of TAGs digestion are glycerol, FAs and monoacylglycerol.
 Cholesterol ester digested by esterase and no digestion for free cholesterol.
 Phospholipids digested by phospholipases A, B, C and D.
 All digestion products form micelles with bile salts for transport from lumen to
intestinal mucosa (step 1 absorption).
 Then apolipoproteins with lipids (cholesterol ester, TAGs, Phospholipids) after
re-synthesis within mucosa forms chylomicron (step 2 absorption).
 Then TAGs of chylomicron by lipoprotein lipase in plasma degrades into free
glycerol and free fatty acids.
 Free fatty acids taken by skeletal muscles to be oxidized into ATP and acetyl CoA
or taken by adipose tissue for esterification again with glycerol to form TAGs.
 Free glycerol taken by liver to be converted into glucose for glycolysis or
glycogenesis.
13
Dr. Mohamed I. Kotb – Associate Professor of Pharmaceutical Biochemistry and Molecular Biology
I- Simple Lipids:

▪ Simple lipids are esters of fatty acids with alcohols. According to the
type of alcohol, they are classified into two main subgroups, neutral
fats and waxes.
I- Neutral Fats:
▪ They are esters of three fatty acids with glycerol, also termed
triglycerides or triacylglycerols (contain three acyl groups).
II-Waxes:
▪ They are esters of fatty acids with higher mono-hydroxy alcohols.
I- NEUTRAL FATS (Triglycerides or Triacylglycerols):
▪ Glycerol which is present in neutral fats is the L-isomer.
▪ It is colorless, odorless and has a sweet taste.
▪ It is liquid and soluble in water.
▪ The fatty acids present in TAG are usually of different types (Mixed).
14
Dr. Mohamed I. Kotb – Associate Professor of Pharmaceutical Biochemistry and Molecular Biology
I- Simple Lipids:
I- Neutral fats are classified into two subgroups:
A- Oils;
▪ They are liquid, due to their high content of USFA e.g. corn, cotton seed
and soya been oils. They have low melting points.
B- Solid Fats:
▪ They have high melting points due to their high content of SFA e.g.,
margarine.
II-WAXES; They are complex mixtures of nonpolar lipids.
▪ They serve as protective coating on leaves, stems and fruits of plants and
the skin and fur of animals.
▪ They are composed of esters of long-chain fatty acids with long-chain
mono-hydroxy alcohols e.g. bees wax which is formed of mericyl alcohol
(C30) esters.
▪ Other types of waxes include esters of cholesterol derivative (lanolin in
15
hair), vitamin D and vitamin A.
Dr. Mohamed I. Kotb – Associate Professor of Pharmaceutical Biochemistry and Molecular Biology
I- Simple Lipids:

16
Dr. Mohamed I. Kotb – Associate Professor of Pharmaceutical Biochemistry and Molecular Biology
II- Compound Lipids:

▪ Results of their hydrolysis yields fatty acids, alcohols, and additional

(prosthetic) groups.
▪ Subclassified according to the type of prosthetic group.
A- Phospholipids:
▪ They are classified according to the alcohol present into two main
subgroups:
1- Glycero-phospholipids: glycerol. 2- Sphingomyelin: sphingosine.

17
Dr. Mohamed I. Kotb – Associate Professor of Pharmaceutical Biochemistry and Molecular Biology
II- Compound Lipids:
1- Glycerophospholipids:
A- Phosphatidic acid:
 It consists of glycerol which is esterified with;
 Saturated F.A. at position. (1),
 Unsaturated F. A at position (2)
 Phosphoric acid at position (3) .
 Phosphatidic acid is formed as intermediate in the biosynthesis of
phospholipids and triglycerides, but not found in tissues to any sufficient
extent.
B- Lecithin:
 Source:
❖ In all body cells.
❖ Egg yolk.
 Importance:
❖ Lipotropic factor (prevent accumulation of fat in liver).
❖ Di-palmityl lecithin act as surfactant in the lung.
❖ Methyl donner.
18
Dr. Mohamed I. Kotb – Associate Professor of Pharmaceutical Biochemistry and Molecular Biology
1- Glycerophospholipids:
C- Lysolecithin & Lysocephalin:
 They are formed by the action of many enzymes on lecithin or cephalins to
form lysolecithins and lyso-cephalins by removal of fatty acid at position 2.
 These enzymes includes →
❖Phospholipase A2 (PLA2) in plasma membrane.
❖(LCAT) lecithin cholesterol acyl-tranferase; present in plasma, and liver.
❖Lecithinase (present in snake venom).
 Excess lysolecithin may cause hemolysis of RBCs.
D- Cephalin:
Sources:
❖In cell membranes.
❖In myelin sheath on nerves.
❖From liver.
19
Dr. Mohamed I. Kotb – Associate Professor of Pharmaceutical Biochemistry and Molecular Biology
2- Sphingo-phospholipids:
Sphingomyelin:
 Source:
❖Brain and nerve cells.
 Niemann-pick’s disease:
❖Deficiency of
sphingomyelinase enzyme
leads to;
▪ Mental retardation
▪ Accumulation of large
amounts of sphingomyelin
in liver.
▪ Death in early life.
20
Dr. Mohamed I. Kotb – Associate Professor of Pharmaceutical Biochemistry and Molecular Biology
Functions of phospholipids:
1.Phosphatidyl inositol acts as a messenger for hormonal action.
2.Phospholipids are amphipathic molecules so they are good emulsifying factors
during digestion they produce emulsification of fats and help digestion of fats by
pancreatic lipase.
3.They are good hydrotropic substances and their presence in bile with bile salts
prevents precipitation of cholesterol and formation of cholesterol stone (biliary
stones or gallstones).
4.They are important constituents of cell membrane lipoproteins.
5.They are important constituent of plasma lipoproteins which act as carrier for
different types of lipids in blood (LDL, HDL).
6.Lung surfactant (lipoproteins) is formed mainly of di-palmitoyl-lecithin, the lack
of which is responsible for respiratory distress syndrome in premature infants.
Lecithin also acts as methyl donner.
7. They provide arachidonic acid for synthesis of eicosanoids.
8.They are essential for blood clotting, as they provide the platelet activating factor
(PAF).
9.Cephalin and lecithin act as lipotropic factor.
21
Dr. Mohamed I. Kotb – Associate Professor of Pharmaceutical Biochemistry and Molecular Biology
B- Glycolipids:
 They are type of conjugated
lipids containing carbohydrates. Importance of Glycolipids
 They do not contain phosphate 1. Glycolipids are found mainly in plasma
group or glycerol. membrane.
2. They are important component of
 FA + sphingosine myelin sheath and red cell membrane.
(Ceramide)+carbohydrate. 3. Many of the cell surface recognition
Example; properties are due to the carbohydrate
radical of glycolipids e.g. cell membrane
❖Cerebrosides, Gangliosides receptors.
and sulpholipid. 4. Generally they are important
1- Cerebroside: constituents of nervous tissues.
 Sphingosine + galactose
 The FA connected to the amino
group of sphingosine in amide
linkage.
 Sugar is connected to the
alcohol group of sphingosine in
glyosidic linkage.
22
Dr. Mohamed I. Kotb – Associate Professor of Pharmaceutical Biochemistry and Molecular Biology
B- Glycolipids:
2- Ganglioside:
 There are similar to cerebrosides but contain a more complex carbohydrate
radical.
 FA is usually stearic or oleic acids.
 They are also found in the brain and spleen.
3- Sulfolipids (Sulfatides):
 They are cerebroside-sulfate, the sulfate is attached at C3 of galactose.

23
Dr. Mohamed I. Kotb – Associate Professor of Pharmaceutical Biochemistry and Molecular Biology
C- Proteolipids or Lipoproteins:
 Lipid with prosthetic group PROTEIN.
 Proteins surrounds the lipids, making the molecule soluble in water.
 They are found in the cell membrane, mitochondria, and blood.
Types:
❖Chylomicrons.
❖Very low density lipoprotein (VLDL).
❖Low density lipoprotein (LDL).
❖High density lipoprotein (HDL).

24
Dr. Mohamed I. Kotb – Associate Professor of Pharmaceutical Biochemistry and Molecular Biology
C- Proteolipids or Lipoproteins:

25
Dr. Mohamed I. Kotb – Associate Professor of Pharmaceutical Biochemistry and Molecular Biology
III- Derived Lipids:

 They are derived from hydrolysis of lipids (simple or complexed) or

precursors of lipids. or they are associated with lipids in nature
Examples:
1. Fatty acids.
2. Fatty alcohols.
3. Fat solubleVitamins
4. Steroids.
5. Glycerol and higher alcohols
6. Carotene pigment
7. Squalene (as in fenugreek oil to increase milk secretion).

26
Dr. Mohamed I. Kotb – Associate Professor of Pharmaceutical Biochemistry and Molecular Biology
Steroids and sterols (Derived Lipids):
 Steroids are derivatives of the C17.
 Cyclopentanoperhydrophenanthrene ring (steroid nucleus).
 Steroids may be classified into 3 groups,
1. Sterols,
2. Bile acid and
3. Steroid hormones.

27
Dr. Mohamed I. Kotb – Associate Professor of Pharmaceutical Biochemistry and Molecular Biology
1- Sterols:

 Phytosterols: present in higher plants, the most important one is

sitosterol.
 Mycosterols: present in fungi, the most important is ergosterol, which
found in yeast and can be converted into vitamin D by irradiation with U.V.
light.
 Zoosterols: present in animals, the most important is cholesterol.

28
Dr. Mohamed I. Kotb – Associate Professor of Pharmaceutical Biochemistry and Molecular Biology
Cholesterol (Animal Sterol): Derived lipid:

 Cholesterol is reduced in the body into dihydroxy-cholesterol

(cholestanol) and reduced also by intestinal bacteria into copro-stanol.
 Oxidation of cholesterol occurs in the liver, intestine and skin forming
7-dehydrocholesterol, which is converted into vitamin D by exposure to
U.V.
 It is the precursor of bile acids and all steroid hormones.

29
Dr. Mohamed I. Kotb – Associate Professor of Pharmaceutical Biochemistry and Molecular Biology
Importance of Cholesterol:

1. It is formed from activated acetic acid (active acetate/acetyl-COA).

Cholesterol acts as precursor of all steroids in animal body.
2. It is widely distributed in all tissues, but higher concentrations are
present in nervous tissue, liver, adrenals, gonads, skin and adipose tissue.
3. Normally it is present in plasma at concentrations ranging from 120 to
200 mg /dL (30 % as free cholesterol and 70 % as cholesteryl esters).
Hypercholesterolemia (increased plasma level) predisposes to
atherosclerosis.
4. It is mainly excreted from the body in bile in the form of bile salts, less
amounts as cholesterol, cholesteryl esters and dihydro-cholesterol. In
large intestine, cholesterol is reduced by bacteria to give copro-stanol.
5. It is converted in the liver to 7-dehydrocholesterol. The later is converted
30
to vitamin D under the skin (by the action of ultra-violet rays).
Dr. Mohamed I. Kotb – Associate Professor of Pharmaceutical Biochemistry and Molecular Biology
Bile Acids & Salts (Oxidation Products of Cholesterol):

 Conjugated with glycine or taurine and are secreted in bile in the form of their
sodium salts.
1. Conversion to bile salts is an important mechanism for removal of
cholesterol from blood.
2. Emulsification of fat in the intestine which is essential for their digestion and
absorption.
3. Prevent precipitation of cholesterol in bile and prevent formation of
cholesterol stones.
4. They stimulate liver cells to secrete more bile (choleretic effect).

31
Dr. Mohamed I. Kotb – Associate Professor of Pharmaceutical Biochemistry and Molecular Biology
Eicosanoids (oxidation products of fatty acids-derived lipids):

 Eicosanoids are
compounds derived
from polyunsaturated
fatty acid that contain
20 carbon atoms
(Arachidonic acid) and
includes →
 Prostanoids:- such
as prostaglandins,
prostacyclin and
thromboxane
 Leukotrienes:
present in leukocytes.
32
Dr. Mohamed I. Kotb – Associate Professor of Pharmaceutical Biochemistry and Molecular Biology
A- Prostanoids:

 Prostaglandin E2 (PGE2), It has protective function in GIT thus prevent

peptic ulcer, also can be used in treatment of bronchial asthma.
❖It is also has vasodilatation effect and smooth muscle relaxation action.
 Prostaglandin F2α (PGF2α): causes vasoconstriction and smooth muscle
contraction, stimulate the uterine contraction and induction of labor.
 Prostacyclin (PGI2): acts as vasodilator particularly for coronary
arteries.
❖It is also inhibits platelet aggregation and adherence to the endothelial
surface of vessels.
 Thromboxane A2 (TX2): Produced by platelets to promote platelet
aggregation, vasoconstriction and contraction of smooth muscle.
 Thus the action of thromboxane and prostacyclin are physiologically
antagonist.
 Aspirin: It acts as anti-inflammatory and antithrombotic agent because it
inhibits prostaglandin synthase and decreases formation of prostaglandins
and thromboxane.
33
Dr. Mohamed I. Kotb – Associate Professor of Pharmaceutical Biochemistry and Molecular Biology
B- Leukotrienes:

 They are synthesized in leukocytes and contain typical triene

structures (i.e. 3 double bonds).
 They are involved in chemotaxis, inflammation and allergic
reactions.
 Leukotriene D4 (LTD4): are components of slow-reacting
substance of anaphylaxis (SRS-A), which cause smooth muscle
contraction, about 1000 times more potent than histamine in
constricting the pulmonary airways (causing asthma) and increase
fluid leakage from small vessels (causing swelling) and constricts
coronary arteries.
 Leukotriene B4 (LTB4): attracts leukocytes (neutrophils and
eosinophils), which are found in large number at the site of
inflammation.
34
Dr. Mohamed I. Kotb – Associate Professor of Pharmaceutical Biochemistry and Molecular Biology
References:
•• .Lieberman M, Marks AD. Marks’ Basic Medical Biochemistry: A Clinical Approach.
3rd Ed. Baltimore: LippincottWilliams &Wilkins, 2009,
• Pelley, John W. Rapid review biochemistry / John W. Pelley, Edward F. Goljan. – 3rd
ed. p. ; cm. – (Rapid review series) Rev. ed. of: Biochemistry. 2nd ed. c2007. ISBN
978-0-323-06887-1

mohamed.kotb71524@gmail.com
WhatsApp: 00201140400767
https://www.facebook.com/moh.elsayed.925/
https://www.researchgate.net/profile/Mohamed_kotb_Kotb-El-Sayed2

35
Dr. Mohamed I. Kotb – Associate Professor of Pharmaceutical Biochemistry and Molecular Biology
View publication stats