LIPID

Syllabus Content
1. Fatty Acids
a. Essential fatty acids

2. Physical and chemical properties of

fatty acids
3. Classification of fatty acids

IMPORTANT
Definition of lipid, classification
General structure of triacylglycerol,
phosphoacylglycerol, sphingolipid
Fatty acid definition
Fatty acid structure, amphiphatic, identify
polar/nonpolar end
Fatty acid identify saturated/unsaturated, draw fatty
acid from info: degree of unsaturation or abbreviation
symbol, chemical formula

What is Lipid
Lipids: insoluble in water, but soluble in organic solvents
including diethyl ether, chloroform, methylene chloride, and
acetone
Has one polar and nonpolar end
Amphipathic: hydrophobic in nature
Lipids include:
Open Chain forms
fatty acids, triacylglycerols, sphingolipids,
phosphoacylglycerols, glycolipids,
lipid-soluble vitamins
prostaglandins, leukotrienes, and thromboxanes
Cyclic forms
cholesterol, steroid hormones, and bile acids

Lipid: Structure
1. Open chain:

eg. A fatty acid

OH

long nonpolar tail with a polar head

Saponifiable

2. Cyclic forms/Fused ring:

- based on the steroid ring
skeleton

C
A

LIPID: CLASSESS
1.
2.
3.
4.
5.
6.
7.
8.

Fatty acids and their derivatives

Triacylglycerols
Phosphoacylglycerol, phosphoglycerides
Sphingolipids (Eg: Ceramide, ganglioside)
Wax esters
Steroids (Eg: Cholestrol, Pytosterol, Hormones)
Isoprenoids (Eg: Vitamin E, K & -carotene)
Eicosanoids (Eg: prostaglandin & leukotrienes)

LIPID: Structural features

/ phosphoacylglycerol

GENERAL
STRUCTURE
The structural features of storage and membrane lipids. (a) The storage lipids are composed
of nonpolar triacylglycerol. (b) The membrane lipids are composed of glycerophospholipids
and sphingolipids which have polar and nonpolar regions

Fatty Acids
Fatty acid: a molecule with a carboxyl group as the
polar end and a hydrocarbon chain as the
hydrophobic/nonpolar end.
an unbranched-chain carboxylic acid, mostly in even numbers
of carbon

Nonpolar hydrophobic tail

Polar hydrophilic head

Fatty Acids
derived from hydrolysis of animal fats, vegetable oils, or
phosphodiacylglycerols of biological membranes
Amphiphatic

Nonpolar hydrophobic tail

Polar hydrophilic head

Fatty Acids
Length of fatty acid plays a role in its chemical character
Usually contain even numbers of carbons (can contain
odd, depending on how they are biosynthesized)
FA - C=C bonds, are unsaturated fatty acid
- C-C bonds, are saturated fatty acid

Fatty Acids

Fatty Acids
Unsaturated fatty acids have lower melting
points than their saturated counterparts; the
greater the degree of unsaturation, the lower
the melting point

Fatty Acids
In most unsaturated fatty acids, the cis isomer
predominates; the trans isomer is rare

16:19

Palmitoleic acid
Cis double bond results
in a bent chain and lower mp.

Fatty Acids
Palmitoleic 16:19 degree of unsaturation
or abbreviation symbol

CH3(CH2)5CH=CH (CH2)7COOH chemical

formula
9

1
11

13

15

Palmitoleic acid

Fatty Acids

Stearic acid

Oleic acid

18:0

18:19

structure

Effect of Double Bonds on the

Conformations of Fatty Acids
Kink in hydrocarbon
chain
Causes disorder in
packing against other
chains
This disorder causes
greater fluidity in
membranes with cisdouble bonds vs
saturated FA chains

kink

Fatty Acids

Fatty Acids - examples

1. Stearic

18:0

CH3(CH2)16COOH

2. Oleic acid

18:19 / 18:19 / 18:1- 9

CH3(CH2)4CH2CH2CH2CH=CH(CH2)7COOH
3. Palmitoleic

16:19

CH3(CH2)5CH=CH (CH2)7COOH
4. Linolenic

18:29,12

CH3(CH2)4CH=CHCH2CH=CH(CH2)7COOH
5. Arachidonic 20:45,8,11,14
CH3(CH2)3(CH2CH=CH)4(CH2)3 COOH

Triacylglycerols
Triacylglycerol (triglyceride): an ester of
glycerol with three fatty acids
Nonpolar class of lipid, very hydrophobic

O
CH2O C R1
Glycerol
O
part
CH O C R2
O
CH2O C R3

Fatty acid
chains

Triacylglycerols (TAGs)
TAGs which are solids at room temperature are
rich in saturated acids and are called fats.
TAGs which are liquids at room temperature
are rich in unsaturated acids and are called oils.
e.g. oil seeds include peanut, corn,
safflower, palm, olive and soybean.

Triacylglycerols (TAGs)
Hydrolysis of TAGs will produce 1 glycerol
and 3 fatty acids.
Biologically this is done by lipases.
Chemically base hydrolysis is called
saponification.

Hydrolysis of
Triacylglycerols (TAGs)

Glycerol

Free fatty acids

Saponification
CH2OH
O
CH2O C R3
CH OH
O
3 NaOH
CH
OH
2
CH O C R3
O
+
O
CH2O C R3
3 NaO C R3
a soap, Na or K
salt of a fatty acid
Saponification reactions of
triacylglycerol with NaOH or KOH to
produce soap, which is the sodium salt

LIPID

Triacylglycerols

Storage lipid energy metabolism,

(storage of fatty acid)

LIPID: Structural features

/ phosphoacylglycerol

GENERAL
STRUCTURE
The structural features of storage and membrane lipids. (a) The storage lipids are composed
of nonpolar triacylglycerol. (b) The membrane lipids are composed of glycerophospholipids
and sphingolipids which have polar and nonpolar regions

Phosphoacylglycerols
(Phospholipids)
O
CH2O C
O
CH O C
O
CH2O P
O

Phosphatidic acid
When one alcohol group of glycerol is
esterified by a phosphoric acid rather
than by a carboxylic acid,
R2 phosphatidic acid produced
Phosphatidyl ester =
OH phosphoacylglycerol
Phosphoacylglycerol the phosphoric
acid (in phosphatidic acid) is esterified
to second alcohol

R1

Phosphoacylglycerols =
glycerophospholipids
Phosphoacylglycer
ols amphiphatic,
polar, hydrophilic
The second most
abundant group of
naturally occurring
lipids, and they are
found in plant and
animal membranes

Phospholipids

second alcohol

Phosphatidyl esters = phosphoacylglycerol

= glycerophospholipids

O
CH2O C R1
O
CH O C R2
O
CH2O P OR
O

Fatty acid

R=
+

CH2 CH2 NH3

phosphatidylethanolamine
CH2 CH2 N(CH3)3
phosphatidylcholine
(lecithin)

O
O
OH
CH2 CH CH2 O P O CH O C R3
O CH2 O C R4
O
diphosphatidylglycerol

Functions
The functions of phosphoglycerides include:
Structure of cell membranes
Reservoir for intracellular messengers
Anchors of some proteins for cell membranes
Stabilization of protein structure
Cofactors of enzymes
Biological detergents

Surfactants in lungs
Solubilization of non polar lipids in lipoproteins.

Phospholipids

Phospholipids

The Basic Structural Component of the Membrane:

Phospholipid Molecule

Phospholipids

The Fluid-Mosaic Model of the Membrane Structure

Sphingolipids
No glycerol
Contain sphingosine, a
long-chain amino alcohol
Found in plants and
animals
Abundant in nervous
system
Bares structural similarity
to phospholipids

phosphocholine

Sphingolipids
(simplest)

Amide
bond

Fatty
acid

Primary alcohol group

esterified to phosphoric
acid which esterified to
choline

Sphingolipids + sugar residue =

Glycolipids glycosphingolipid
Glycolipid: a compound in
which a carbohydrate is
bound to an -OH of the lipid
In most cases, sugar is either
glucose or galactose
many glycolipids are
derived from ceramides
Glycolipids with complex
carbohydrate moiety that
contains more than 3 sugars
are known as gangliosides

ceramide

Polar?

Ganglioside

Most complex
glycosphingolipid

Waxes
A complex mixture of esters of long chain carboxylic acids (fatty acids)
and alcohols
Found as protective coatings for
plants and animals
Polar?

Steroids
Steroids: a
group of lipids
that have fusedring structure of
3 six-membered
rings, and 1
five-membered
ring.

Cholesterol
ONLY IN ANIMAL
The steroid of most interest in our discussion
of biological membranes is cholesterol
Amphiphilic
but more hydrophobic than
glycerophospholipids
and sphingolipids
OH

CH3

CH3
CH3

C O

OH at C3 - polar

progesterone
CH3

Sterol
O

testosterone

CH3

Phytosterol
Plant steroid

Isoprenoids
Based on isoprene structures

Vitamins E, K,
-carotene

Example
isoprene

Eicosanoids
A family of compounds that have the 20carbon skeleton
Arachidonic acid as precursor
Example: prostaglandins and leukotrienes

Arachidonic Acid and Some

Prostaglandins

Leukotrienes (Contd)

Lipid soluble vitamins

Lipid: Functions
1.
2.
3.
4.

Storage molecules for energy

Membrane components
Messenger
Mediate the hormonal response and synthesis of hormones