IDS

LIPIDS
A class of biological molecules
defined by low solubility in water and
high solubility in non-polar solvents
(such as chloroform)

They are largely hydrocarbon in

composition, thus represent highly
reduced forms of carbon, and upon
oxidation in metabolism, yield large
amounts of energy.
Examples of Lipids
FATS and OILS, certain VITAMINS &
HORMONES, and most NON-PROTEIN
MEMBRANE COMPONENTS.

Lipids, per se, are not bad; they are

indispensable to metabolism & cell
structure.
Functions

Energy storage, mobilization, and

utilization
Prostaglandin, cytokine synthesis
Cell differentiation and growth
Cell membrane structure, myelination
Signal transmission
Hormone synthesis
Bile acid synthesis
Classification
Fatty Acids
Fatty acids are long-chain hydrocarbon
molecules containing a carboxylic acid
moiety at one end.
They rarely occur in free form and are
usually found in esterified form as the
major components of various lipids.
Fatty acids with less than 12 and more
than 24 carbon atoms are uncommon in
biological systems. The most abundant
species are those with 16 and 18 carbon
atoms.
Most of the fatty acids have even number
of carbon atoms as they are synthesized in
biological systems by condensation of two-
carbon acetate units.
Fatty Acids
Fatty acids are long-chain hydrocarbon
molecules The numbering of carbons in
fatty acids begins with the carbon of the
carboxylate group.

As their name suggests, all of them are

acids with pKa value in water of
approximately 4.5. Hence at
physiological pH, the carboxyl group is
readily ionized, rendering a negative
charge onto the fatty acids.
Fatty Acids
are carboxylic acids with long-
chain hydrocarbon chains

are rarely 'free' (uncomplexed) in

nature [except arachidonic acid]

are usually in esterified form as

major components of other lipids
Fatty Acids
are often complexed in
triacylglycerols (TAGs)

most have an even number of carbon

atoms (usually 14 to 24)

are synthesized by concatenation of

C2 units.

C16 & C18 FAs are the most common FAs

in higher plants and animals.
Interactions between fatty
acids
Fatty Acids
Are either:

saturated (all C-C bonds are single

bonds) or
unsaturated (with one or more double
bonds in the chain)
monounsaturated (a single double
bond)
polyunsaturated (more then one
double bond)

the number of double bonds in FAs varies

from 1 to 4 (usually),but in most bacteria
Fatty Acids
Nomenclature

A : X (Y)
A number of carbons present in the
fatty acid
X number of double bonds
Y the carbon number having the
double bond
Fatty Acids
Nomenclature

Ex. Oleic Acid 18:1 (9)

The first double bond in an

unsaturated FA usually occurs
between C(9) and C(10) counting
from the carboxyl C atom (the
-COOH at the end of the molecule).
Fatty Acids
The cis double bonds of unsaturated
FAs put a rigid 30 bend in the
hydrocarbon chain of unsaturated
fatty acids that interferes with
packing in space.
This causes reduced van der Waals
interactions which cause melting
points to decrease lipid fluidity
like vegetable oil (and don't "clog
your arteries")
Essential Fatty Acids
1. Linoleic acid - required for the
synthesis of arachidonic acid
2. Linolenic acid

. Both are (poly)unsaturated

. Therefore, absolute requirements for fat in
the diet applies only to unsaturated fat
Essential Fatty Acids
Waxes
 Triacylglycerol

Triacylglycerols, also called

triglycerides, are the simplest of lipids
composed of three fatty acids each in
ester linkage with a single glycerol
molecule.
 Triacylglycerol
Physical properties:
non-polar, hydrophobic and essentially
insoluble in water since the polar
hydroxyls of glycerol and the polar
carboxylates of fatty acids are bound in
ester linkage
densities lower than that of water and do
not mix with water but form a separate
phase and float on water.
 Triacylglycerol
Chemical properties:
1. Hydrolysis
2. Saponification hydrolysis of ester linkage in
alkaline conditions
3. Saponification number amount of soap
formed
4. Rancidity of Fats - due to hydrolysis of
component glycerides of a fat into free fatty
acids and glycerol
5. Acid Number amount of base needed to
neutralize the acid
6. Reicher-Meissel Number/volatile fatty acid number
amount of base required to neutralize the soluble
volatile fatty acids derived from five grams of fat that
has been saponified
7. Iodine number measures the degree of
Reactions of Triglycerides
Phospholipids
 Phospholipids
amphipathic molecules with nonpolar
tails and a polar phosphoryl-X head.

They differ from triacylglycerols in

possessing a highly polar head group in
addition to their hydrocarbon tails.

All the glycerophospholipids have a

negative charge on the phosphate
group at pH 7.0.
Phospholipids
 Phospholipids
Phospholipids get their name from
the fact that the phosphate ion
(PO43-) is one of the components used in
their formation.
There are two classes of phospholipids:
1) glycerophospholipids
2) sphingophospholipids
 Glycerophospholipids
Made by
combining
glycerol, two
fatty acids, a
phosphate
group, and an
alcohol.
Glycerophospholipids
Glycerophospholipids
Sphingolipids

Made by
combining
sphingosine +
fatty acid +
phosphate
Sphingolipids
Sphingolipids
Glycolipids
 Glycolipids

GLYCEROGLYCOLIPID SPHINGOGLYCOLIPIDS
S
Lipoproteins
Lipoproteins
Lipoproteins are classified according to
density.
High protein to phospholipid ratio =
high density.
Low protein to phospholipid ratio =
low density
Lipoproteins
LDLs and HDLs
The major function of Low density
lipoproteins (LDLs) is to transport
cholesterol and phospholipids from
the liver to the cells, where they are
incorporated into membranes or, in the
case of cholesterol, transformed into other
steroids.
High density lipoproteins (HDLs)
transport cholesterol and
phospholipids from the cells back to
the liver.
Low HDL and high LDL levels in the blood
are warning signs of atherosclerosis, the
buildup of cholesterol-containing deposits
Steroids
Steroids are a class of lipids that share
the same basic ring structure - three
fused 6-carbon atom rings and one 5-
carbon atom ring.

There are three important types of steroids:

1) cholesterol 2) steroid hormones 3)
Steroids
Cholesterol is the steroid found most
often in humans and other animals.

In cholesterol, the nonpolar rings and

hydrocarbon chain are hydrophobic and the
-OH group, which makes up a much smaller
part of the molecule, is hydrophilic.
Steroids
Hormones, molecules that
regulate the function of organs
and tissues, come in a variety of
forms.

Some, such as sex hormones and

adrenocorticoid hormones, are
steroids.

Steroid hormones are made from

cholesterol.
Steroids
Bile salts, produced from cholesterol,
are glycocholate and taurocholate

They are released from the gallbladder

into the small intestine, where they aid
digestion by forming emulsions with
dietary lipids.
Eicosanoids

Eicosanoids are fatty acid derivatives with

a variety of extremely potent hormone like
actions on various tissues of vertebrate
animals.

They are all derived from arachidonic acid

[20:4(5,8,11,14)]
Eicosanoids
 Eicosanoids
Prostaglandins
cause pain
cause
inflammation
cause fever
affects blood
pressure
induces labor
(PGE2)
Eicosanoids
Thromboxanes and
Leukotrienes
Thromboxanes, such
as thromboxane A2,
are involved in blood
clotting.
Leukotrienes,
including leukotriene
A4, induce muscle
contractions in the
lungs and are linked
to asthma attacks.
Some anti-asthma
drugs block the
Eicosanoids
Nonsteroidal Anti-inflammatory
Drugs (NSAIDs)
NSAIDs such as aspirin,
acetaminophen, and ibuprofen reduce
pain, fever, and inflammation by
blocking the action of an enzyme
involved in the conversion of
arachidonic acid into prostaglandins
and thromboxanes.

There are two forms of this enzyme: