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 Learning objectives
After this lectures, you should be able to:
• Define lipids in chemical terms
• Identify structural & functional roles of lipids
• Classify lipids into their major classes with examples of
each group
• Describe the structure & biochemical composition and
functions of biological membranes
• Describe types of membrane transports
 Introduction
The lipids are a heterogeneous group of compounds, including
fats, oils, steroids, waxes, and related compounds, which are
related more by their physical than by their chemical
properties.

Lipids (Greek: lipos, fat) are naturally occurring compounds

They have the common property of being:
(a) Relatively insoluble in water and
(b) Soluble in non polar solvents such as ether and chloroform.
 Nonpolar lipids act as electrical insulators, allowing
rapid propagation of depolarization waves along
myelinated nerves.

 Combinations of lipid and protein (lipoproteins) are

important cellular constituents, occurring both in the
cell membrane and in the mitochondria, and serving
also as the means of transporting lipids in the blood

Knowledge of lipid biochemistry is necessary in

understanding many important biomedical areas, e. g,
obesity, diabetes mellitus, atherosclerosis, and the role of
various polyunsaturated fatty acids in nutrition and
health.
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 Lipids
• Lipids constitute a very important heterogenous group of
organic substances in plant and animal tissues.
• They are formed of
– Long--chain hydrocarbon groups but
– May also contain oxygen, phosphorus, nitrogen, and
sulfur
• They are a group of structurally diverse compounds
defined by their hydrophobicity
• They are not very soluble in water but soluble in organic
solvent
 Lipids cont’d..

• They differ from other organic compounds in their

potential to be utilized by the living organisms.
• Lipids represent highly reduced forms of carbon and,
– upon oxidation in metabolism, yield large amounts of
energy.
• Lipids are thus the molecules of choice for metabolic
energy storage
Physiological and Biological Importance of Lipids

Lipids:
– Are second chief concentrated storage form of
energy; 1 gm of fat gives 9 [Link] energy on hydrolysis.
– Provide shape to the organs and body.
– Serve as Insulators and Heat conservation
– Serve as Intracellular messengers
– Serve as transport vehicles
– Act as precursors for hormones (steroid hormones)
– Also dissolve fat-soluble vitamins and assist their
digestion
 Cont.….

Serve as structural components of biological membranes

(the turnover about 2 g / d in adult humans)
 Provide energy reserves, predominantly in the form of
triacylglycerols (turnover about 100 g per day in adult
humans)
 Both lipids and lipid derivatives serve as vitamins and
hormones
 Lipophilic bile acids aid in lipid solubilization
 Biomedical Importance of Lipids
Source
of energy

Lipoproteins
Protection

Thermal & Electrical

Bile salts insulator

Hormones
Prostaglandins
Vitamins
 Importance of dietary Lipids
• Lipids are a major source of energy for the body
• Enter in bilayer structure of biological membranes
• Triglycerides in adipose tissue
• Cholesterol enters in
Membranes
component of lipoproteins
Steroid and sex hormones
Bile acid synthesis
Vitamin D synthesis
•Prostaglandins are synthesized from arachidonic acid
• Fat-soluble vitamins have wide scale of functions.
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 Dietary Lipids
 90% triacylglycerol.(TAG)

 10%: cholesterol (most dietary cholesterol is

unesterified)

+ cholesteryl esters (only 10 % of diet cholesterol)

+phospholipids

+ non-esterified fatty acids (NEFAs).

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Lipids are a heterogeneous group of water- insoluble (hydrophobic)
Organic molecules.
Hydrophobicity is due to the long – hydrocarbon chains.

Common classes of lipids include:

1. Fatty acids.
2. Triacylglycerols. (triglycerides) ( 3 fatty acids esterified to
glycerol).
3. Phospholipids. ( phosphoglycerides), (the alcohol moeity
glycerol +phosphate + 2 fatty acids + other groups)
4. Steroids. (cholesterol, steroid hormones, bile acids, vitamin D)
5. glycospingolipids. ( the alcohol moiety is sphingosine + fatty
acid + carbohydrate). tilish4ayane@[Link] 13
 Classification of lipids
• According Bloor’s, Depending on lipid
composition Classified in to:-
Classification of lipids
 Derived lipids: Fatty acids(Fas)

• They are the fundamental building blocks of lipids.

• FAs are obtained from hydrolysis of fats.
• FAs are carboxylic acids with hydrocarbon chains
ranging from 4 to 36 carbons long (C4 to C36)
– The general formula of fatty acid is R-COOH
• They are in a low oxidation state, and thus
conversion to CO2 and H2O is highly exergonic.
 Fatty acid cont’d

• A fatty acid molecule contains

– Both polar (hydrophilic) and
– Non-polar (hydrophobic) regions;
such molecules are called amphipathic molecules
• Fatty acids are simplest of all amphipathic substances
in the body
 Classification
A. Simple lipid - ester of fatty acids with various alcohols
1. Natural fats and oils (triglycerides)
2. Waxes
(a) True waxes: cetyl alcohol esters of fatty acids
(b) Cholesterol esters
(c) Vitamin A esters
(d) Vitamin D esters
B. Compound lipid - esters of fatty acids with alcohol plus other groups
1. Phospholipids and sphingomyelin: contains phosphoric acid and often a nitrogenous
base
2. Sphingolipids (also include glycolipids and cerebrosides): contains aminoalcohol
sphingosine, carbohydrate, N-base; glycolipids contains no phosphate
3. Sulfolipids : contains sulfate group
4. Lipoproteins : lipids attached to plasma/other proteins
5. Lipopolysaccharides: lipids attached to polysaccharides
C. Precursor and Derived lipids – hydrolytic
products of simple & complex, with lipid characters
1. Saturated & unsaturated fatty acids
2. Monoglycerides and diglycerides
3. Alcohols (β-carotenoid ring, e.g., vitamin A,
certain carotenoids)
 Based on functional organization

Storage Lipids (80%)

Structural Lipids in Membranes (5-10%)
Lipids as Signals, Cofactors, and Pigments

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 1. Storage Lipids
• The fats and oils used almost universally as stored
forms of energy in living organisms are derivatives
of fatty acids.
• The fatty acids are hydrocarbon derivatives, at
about the same low oxidation state (that is, as highly
reduced).
• Two types of fatty acid–containing compounds,
triacylglycerols and waxes

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Fatty acids:-
- Fatty acids are carboxylic acids with hydrocarbon chains
ranging from 4 to 36 carbons long, usually C12-C20
- May be saturated or unsaturated (double bonds), almost
always at C18-C20, usually in cis configuration
- Non-conjugated DB System: DB interrupted by a methylene
group (-CH2-)
- C-C and C-H bonds non-polar (hydrophobic) character even
with the COOH group (hydrophilic)= amphipathic
-Naturally occurring saturated FA that have 1-8 atoms are
liquid; more C = solid
-Fatty acids occur mainly as esters
- Free FA (unesterified ) are few in nature, at physiological pH
= FA are ionized
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 Physical Properties

• Chain Length and Degree of Unsaturation

– ↑Chain length = ↑ Boiling point (BP) and Melting point (MP)
– ↑ Unsaturation = ↓MP (due to structure of unsaturated FA:
kinks (Unwanted to twist or bent)
– Fully saturated compounds - pack tightly
– Unsaturated fatty acids – kink – weak interaction - lower
melting Points and Boiling point
– ↑ Chain length = ↓ Solubility
• The membrane lipids, which must be fluid at all
environmental temperatures, are more unsaturated than
storage lipids.
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 Unsaturated Fatty Acids
Contain One or More Double Bonds
Fatty acids may be further subdivided as follows:
(1) Monounsaturated (MUFA) acids, containing one double bond.
(2) Polyunsaturated (PUFA) acids, containing two or more double
bonds.
(3) Eicosanoids: These compounds, derived from eicosa- (20-
carbon) polyenoic fatty acids, comprise the prostanoids,
leukotrienes (LTs), and lipoxins (LXs).
Prostanoids include prostaglandins (PGs), prostacyclins (PGIs),
and thromboxanes (TXs). 24
 Omega-3 Fatty Acids
• Group of polyunsaturated fatty acids
• Essential–must be obtained in the diet
• Component of cell membranes
• Mediate inflammation, regulate blood clotting and
contraction/relaxation of arterial walls
• May be helpful in relieving symptoms in rheumatoid arthritis and age-
related macular degeneration

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Polyunsaturated fatty acids (n-6 and n-3)
are essential for animals
In higher animals, only the desaturases are known which generate double bonds at
carbons 9, 6, 5, and 4.
Fatty acids containing double bonds beyond C-9 (acids n-6 and n-3) are synthesized by
plants. They are essential dietary constituents for animals and serve as precursors of
eicosanoids (prostanoids and leukotrienes).
Providing the dietary intake is sufficient (vegetable seed oils, resp. fish), linoleate and α-
linolenate act as precursors of other essential polyenoic acids such as arachidonate (n-6) and
eicosapentaenoate (n-3), from which eicosanoids are formed.

Linoleate 18:2 (9,12) α-Linolenate 18:3 (9,12,15)

6-desaturation 6-desaturation

γ-Linolenate 18:3 (6,9,12) Octadecatetraenoate 18:4 (6,9,12,15)

elongation elongation

Eicosatrienoate 20:3 (8,11,14) Eicosatetraenoate 20:4 (8,11,14,17)

5-desaturation 5-desaturation

Arachidonate 20:4 (5,8,11,14) Eicosapentaenoate 20:5 (5,8,11,14,17)

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 1.1 Triacylglycerols Are Fatty Acid Esters
of Glycerol
• The simplest lipids constructed
from fatty acids
• Three fatty acids each in ester
linkage with a single glycerol
• Simple - containing the same
kind of fatty acid
• Mixed - contain two or three
different fatty acids
• essentially insoluble in water
• Lipids have lower specific
gravities than water 29
• Solid / semisolid at room temp = fats (neutral fats);
in animals;
• liquid = oils (neutral oils), in plants, fish

• Plant triglycerides = ↓MP, liquid at RT due to

↑unsaturated FA

• Animal triglycerides = ↑saturated FA, ↑MP

• Palmitic and stearic acid = most abundant saturated

FA
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 TAG Function

Provide Stored Energy (in adipocytes & seeds of plants)

There are two significant advantages to using TAG’s
as stored fuels
i. The carbon atoms of fatty acids are more reduced
(contains less O2)
ii. TAG’s are hydrophobic
as insulation against low temperatures.

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 Reactions
o Hydrolysis: strong acid + H2O to cleave ester bonds, produces
free FA
Saponification: alkaline hydrolysis of ester; produces glycerol and
soap
Enzymatic hydrolysis (lipase catalyzed): in vivo digestion of fats
• Cleaves sn-1 and sn-3: diacylglycerol + 1 FA →
monoacylglycerol +2 FA glycerol + 3FA)
o Transesterification: rearrangement of acyl groups; modifies
physical and nutritional properties
• Hydrolysis to remove → Esterification to reattach

o Hydrogenation – producing oleomargarine and shortening

o Slow Hydrolysis of Fat: yields FFA and oxidation of DB

producing peroxides causing rancidity of fats
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Partial Hydrogenation of Cooking Oils Produces
Trans Fatty Acids
• When lipid-rich foods are exposed too long to the
oxygen in air, they may spoil and become rancid -
unpleasant taste and smell
• result from the oxidative cleavage of double bonds in
unsaturated fatty acids
• To improve the shelf life vegetable oils are subjected to
partial hydrogenation.
• dietary intake of trans fatty acids -
 Raise the level of TAG and of LDL
 Increase the body’s inflammatory response
 A higher incidence of cardiovascular disease
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 Nomenclature
Genevan system - names the FA after the hydrocarbon the
final -e. end in -anoic, eg, octanoic acid, and -enoic, eg,
octadecenoic acid.
a. Standard nomenclature
Carbon atoms are numbered as 1,2,3… and α, β, γ the terminal
methyl carbon is known as the ω or n-carbon.
Delta system: ∆x y:z
x = location of double bonds y = number of C, z = number of
double bonds
n system – defined with respect to C
18:2 ∆ 9,12 (n-6)
b. For polyunsaturated fatty acids (PUFAs)
assigning the number 1 to the methyl carbon
three series of fatty acids known as ω 9 , ω 6 and ω 3 series
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families.
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 Nomenclature of fatty acids
• The most frequently used systemic nomenclature is
based on naming the fatty acids after the hydrocarbon
with the same number of carbon atoms, “oic” being
substituted for the final “e” in the name of the
hydrocarbon.
• Saturated acids end in “anoic” e.g. octanoic acid and
• Unsaturated acids with double bonds end in enoic,
e.g. octadecenoic acid (oleic acid).
 Nomenclature cont’d

 There are two systems of numbering the carbon

atoms in a fatty acid
1. Numbering starts from carboxyl carbon. The last
carbon is the "n" carbon
2. The second carbon is the "α"and the third the "β"
Carbon. The last carbon atom is omega.
n 3 2 1
CH3 (CH 2)n CH = CH CH2 CH2 CH2 COOH
ω β α
 Nomenclature cont’d

A widely used convention is to express the fatty acids

by formula to indicate:
• The number of carbon atoms
• The number of double bonds and
• The positions of the double bonds.
For example, oleic acid, C18:1, ∆9 or 18:1(9)
C18 indicates 18 carbons
1 indicates the number of double bonds
delta 9(∆9) indicates the position of double bond
between 9th and 10th carbon atoms.
 Classification of fatty acids
1. Based on the presence / absence of double bond
– Saturated fatty acid
– Monounsaturated fatty acid
– Polyunsaturated fatty acid
2. Based on the numbers of carbon atom in the chain
– Short chain fatty acids (4-6)
– Medium chain fatty acids (8-12)
– Long chain fatty acids ( 12-22)
– Very long chain fatty acid (>22)
3. Based on biological importance
– Essential
– Non-essential fatty acids
 Saturated fatty acids

 Contain only single C–C bonds.

 Have the general formula : CH3 – (CH2)n – COOH
 Have high melting points.
 Are solids at room temperature.
 But short-chain saturated fatty acids are liquid at
room temperature
 Table 1 : Common saturated fatty acids

Carbon chain Chemical name Common name Melting point (0c)

C 10:0 Decanoic acid Capric acid 31.6

C 12:0 Dodecanoic acid Lauric acid 44.2

C 14:0 Tetradecanoic acid Myristic acid 54.4

C 16:0 Hexadecanoic acid Palmitic acid 62.9

C 17:0 Heptadecanoic acid Margaric acid 60.9

C 18:0 Octadecanoic acid Stearic acid 69.6

C 20:0 Eicosanoic acid Arachidic acid 75.4

C 22:0 Docosanoic acid Behenic acid 80

 Unsaturated fatty acids
 unsaturated fatty acids contain one or more cis
double C=C bonds
– Have kinks in the fatty acid chains.
– Have few attractions between chains.
– Have low melting points.
– Are liquids at room temperature

Mono unsaturated fatty acids :Contains one double bond

( Eg. Oleic acid, 18:1, ω9 )
Omega C 10 9
CH3 – (CH2)7 – CH = CH – (CH2)7 –COOH
Poly unsaturated fatty acid: contain two or more double
bonds
 Unsaturated fatty acids cont’d..
• Example of PUFA: Linoleic acid (18C:2Δ 9,12, ω6)
Omega C 13 12 11 10 9
CH3 – (CH2)4 – CH = CH – CH2 – CH = CH – (CH2)7 – COOH
PUFA, linolenic acid (18C:3Δ 9,12, 15 ω3)
Omega C 16 15 14 13 12 11 10 9
CH3–CH2–CH=CH–CH2–CH=CH–CH2–CH=CH–(CH2)7–COOH
Table : lists of some unsaturated fatty acids
Carbon chain Chemical name Common name Melting point(0c)

C 16:1 9-hexadecenoic acid Palmitoleic acid -

C 18:1 9-octadecenoic acid Oleic acid 16.3

C 18:2 9,12-octadecadienoic acid Linoleic acid -6.5

C 18:3 9,12,15-octadecatrienoic acid Linolenic acid -12.8

 Unsaturated fatty acid cont’d..

Unsaturated fatty acid can exist as:

 Cis-fatty acid: H‘s on same side of the double bond; fold into
U-like formation; naturally occurring.
 Trans-fatty acid: H‘s on opposite side of double
bond; more linear; occur in partially hydrogenated
foods
Essential fatty acids are poly unsaturated fatty acid
,which cannot be synthesised in the body and must
be provided in the diet.
– This includes linoleic acid and linolenic acid.
 2. Simple lipids

• They are called neutral lipids .

• They are the most abundant lipids and serve as the
storage form of lipids in animals as well as the plants
• Simple lipids are esters of fatty acids with different
types of alcohols
– If the alcohol is glycerol, the simple lipids are called
Triacyglycerol, neutral fats or oils.
– If the alcohol is of higher molecular weight than
glycerol, the simple lipids are called waxes
 Fats and oils(neutral fats)
• They are esters of fatty acids with glycerol.
• They are similar chemically, but they differ in physical
properties:
– as oils are liquid while fats are solid at room
temperature.
• They are called triglycerides because they are triesters
formed of glycerol and 3 fatty acids.
 Triacylglycerols (TAG)

Triacylglycerols (Triglycerides or Neutral Fats)

– are Triesters of Glycerol and 3 Fatty acid
– present in many foods (eg vegetable oil).
– Provide Stored Energy and Insulation

ester bond
TAG cont’d…..
 Triglycerides…
• TAGs that contain:
– similar fatty acids are simple triglycerides

– Different fatty acids are mixed triglycerides

 2- Waxes

They are esters of

fatty acids + Long chain Monohydric alcohol.
• are solid at room temperature.
• serve as energy stores and water repellents
 Reading assignment

Phosphatides
Cardiolipin
Sphingolipids
Steroids
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