Lipids chemistry

(Structure and Functions)

by
Dr/Noha M. Abd El-Fadeal
Lecturer of Medical Biochemistry and Molecular Biology
FOMSCU
Lipids
objectives
• Introduction
• Chemical structure
• Biomedical importance of lipids
• Classification of lipids
Fatty acids:
• Classification of fatty acids
• Nomenclature of unsaturated Fatty acids
 Introduction

▪ Lipids are a heterogeneous group of

compounds.

▪ They have low solubility in water.

▪ They are soluble in nonpolar solvent

(ether, benzene, chloroform).
 Introduction

◼ They includes fats, oils, steroids, waxes, and

related compounds

◼ Lipids are highly reduced forms of carbon yield

large amount of energy upon oxidation in
metabolism (9 kcal/gm)

◼ Lipids are amphipathic (polar and nonpolar)

◼ lipids are important dietary constituents because

of the essential fatty acids and the fat-soluble
vitamins
 Chemical structure

The hydrophobic (water hating) nature of

lipids is due to the predominance of
hydrocarbon chain (-CH2-CH2-CH2) in their
structure
 Biomedical importance of lipids

1- They serve as energy fuel for the body every 1g of fat

produce 9 kcal of energy

2- They protect nerve ending and act as electrical

insulators

3- It act as thermal insulator to keep the body warm in

cold weather

4- They provide structural component of membranes

5- Energy storage (triacylglycerols)
6- inter in the structure of:
- Hormones (sex hormones e.g., Estrogen, testosterone)
- Enzyme cofactors (coenzyme A)
-Electron carriers (coenzyme Q)
-Emulsifying agents (bile salts)
-Intracellular messengers (phosphatidyl inositol)
 Lipids classification
Lipids are classified into three main group:
1. Simple lipids: Esters of fatty acids with various alcohols
Example: (Triglycerols, WAX).
2. Complex lipids: Esters of fatty acids containing groups in
addition to an alcohol and a fatty acid
Example: (Phospholipids, Glycosphingolipids).
3. Derived lipids: they are produced by hydrolysis of the
above two groups or present associated with them in
nature
Example: (Fatty acids, steroids, alcohol, lipid souluble
Examples of simple
lipids

Triacylglycerol
 Triacylglycerol
◼ Triacylglycerol consist of a glycerol esterified with
three fatty acids.
◼ It is the most significant lipid.
◼ It is a major constitute in lipoprotein and a major
storage form of lipid.

O
H2C O

O
CH
O

O
H2C
O
Triacylglycerol
 Waxes
- Esters of long chain fatty acids (C14-36) with long
chain (C16-30) alcohols
O
O

- High melting points (60-100C)

Oleoyl alcohol Stearic acid

Examples of Complex
Lipids
Phospholipids: consist of:
Fatty acids + alcohol + phosphoric acid
 Phospholipids
2 Classes of phospholipids (PL)
(1) Glycerolphospholipids – glycerol backbone
(2) Sphingomyelin – spingosine backbone

Glycerolphospholipids
- essential for membrane structure
- most abundant membrane lipids

Sphingolipids
- Component of a certain membrane
- Sphingosine, fatty acid and glycoside
Glycerolphospholipids: consist of

Fatty acids + alcohol +phosphoric acid

 Sphingolipids: consist of

Fatty acids + sphingosine + nitrogen compound + phosphoric acid

- Phospholipid are amphipathic lipid and fulfill
many important roles
- It is a major constituent of membranes
Amphipathic structure
Glycolipids
Fatty acids +Sphingosine + carbohydrates

An important constituent of nervous tissue such as

brain and the outer leaflet of cell membrane
Examples of derived
lipids
1- Cholesterol, amphipathic lipid, is an important
component of membrane
Cholesterol
Cholesterol
It is the parent molecule from which all other steroids in
the body are synthesized these include sex and
adrenocortical hormone, vitamin D and bile acids.
It is a structural component of plasma membrane and
modulates membrane fluidity
2- Fat soluble vitamins
( Vitamin A , D, E and K)
3- Steroids

- Cholesterol is the most common steroid in

animals and precursor for all other steroids in
animals.
- Other examples of steroids are (Sex hormones
and hormones from adrenal cortex).
- Steroid hormones serve many functions in
animals - including salt balance, metabolic
function and sexual function;
Steroid hormones carry
messages between tissues
4- Fatty acid
Structure and nomenclature

Fatty acids = carboxyl group + a long hydrocarbon chain

Are monocarboxylic acids with hydrocarbon chain

having different chain length.
 Fatty acids (FAs)
Structure and nomenclature

▪Basic formula: CH3(CH2)nCOOH

▪ Carboxylic acids with hydrocarbon chains
of 4-24 carbons
 10 9   1
CH3-(CH2)7-CH-CH-CH2-CH2-CH2-CH2-CH2-CH2-CH2-COOH

▪Free FAs are found in trace quantities in cells

FAs are either:
(i) part of a lipid molecule
(ii) complexed to a carrier protein (e.g.
albumin on blood)
 Classification of fatty acids:

A) According to the chain length into:

1. Short chain FA: (2-6 carbons)
2. Medium chain FA: (8-14 carbons)
3. Long chain FA: (16 carbons and above)
B) According to the degree of saturation of
hydrocarbon chain into:

1-Saturated fatty acids

2-Unstaurated fatty acids
1. Saturated FA:
Fatty acids are single bonds in all carbon-carbon
bonds.
- General formula: CH3 (CH2)n COOH, n is the no of
methylene groups between the methyl and
carboxyl carbon
- Most of them have an even number carbon
atoms, C16,C18,C20 Fatty acids
2.Unsaturated FA:
fatty acids contain one or more double bonds in
hydrocarbon chains.

a. Monounsaturated FA: Example: oleic acid (C18:1)

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

b. Polyunsaturated FA: the double bond are separated by

methylene group
(CH=CH-CH2-CH=CH)
 Naming of fatty acids
C18

 10 9   1
CH3-(CH2)7-CH=CH-CH2-CH2-CH2-CH2-CH2-CH2-CH2-COOH
Cis 9

18:0, stearic acid : octadecanoic acid

18:1 (9), oleic acid : octadecenoic acid

18:2 (9,12), linoleic acid : octadecadienoic acid

18:3 (9,12,15), -linolenic acid : octadecatrienoic acid

 C) According to the body needs
1. Essential fatty acids: cannot be synthesized
by the body
Example :linoleic-linolenic acid
2. Non-essential fatty acids: can be synthesized
by the body
Example oleic acid