THOUGHT FOR THE WEEK

The Fear of the Lord is the

Beginning of Wisdom
 UNIT 3: BIOCHEMISTRY OF LIPIDS
Outcomes: Upon completion of this unit you will
be able to:
i. Identify the classes of lipids.
ii. State and explain the different functions of
lipids.
iii. Describe the formation & decomposition of
triglycerides through condensation &
hydrolysis reactions.
iv. Describe the composition of lipid.
 Introduction
Lipids
• Predominantly carbon and hydrogen and some oxygen
• insoluble in water
• soluble in organic solvents e.g. acetone (one important
character)
• comprise glycerol + fatty acids
• joined by condensation reaction between hydroxyl groups on
glycerol and on fatty acid = anabolic or synthesis reaction
• results in ester bond and release of water
• parted by hydrolysis reaction with use of water = catabolic or
degradation reaction
• hydrocarbon chains are non-polar
• carboxyl end group is polar
• chains can be saturated or unsaturated
• unsaturated fatty acids lower melting point so oils (liquid at
room temp) have more unsaturated FA than fats (solid at
room temp)
• Whether in solid or liquid form, one gram of
lipid contains 2.25 times as much energy as
one gram of carbohydrate.
 Lipid Composition
• Lipids contain the chemical elements carbon,
hydrogen, and oxygen.
• They are built up from two basic types of
subunits: fatty acids and glycerol.
 A: Fatty Acids
• They consist of a carboxyl group (–COOH) attached to one
end of a hydrocarbon (H-C) chain.
• The molecule has a polar hydrophilic end, and a non-
polar hydrophobic end that is insoluble in water.
• The hydrocarbon chains contain
 4 – 24 carbon atoms and
 is normally unbranched,
 may be saturated or unsaturated,
 may be attached to functional groups containing oxygen,
halogens, nitrogen and sulfur.
• The fundamental and building block for more complex
lipids.
• Structures called mono, di-, and tri glycerides are formed
when a single glycerol molecule is joined to one, two, or
three of the fatty acid subunits.
Fig1: Free Fatty Acid Structure
 Saturated & Unsaturated Fatty Acids
• Saturated chains contain
repeating CH2 groups
joined by single bonds
(eg. stearic acid),

• unsaturated chains
contain double bonds in
the form of –CH=CH-
groups (e.g. linoleic
acid).
• Here two and no more
than six carbon atoms in Figure .2: (top) This fatty acid is saturated with
the hydrocarbon chain hydrogen. (bottom) This fatty acid has room for
two more hydrogen atoms, one on each of the
are linked together by highlighted carbon atoms. Such a fatty acid is
double bonds. called unsaturated.
 Differences
• The fatty acids that contain as many hydrogen atoms as possible on
the carbon chain are called saturated fatty acids and are derived
mostly from animal sources.

• Unsaturated fatty acids are those that have some of the hydrogen
atoms missing; this group includes monounsaturated fatty acids,
which have a single pair of hydrogens missing, and polyunsaturated
fatty acids, which have more than one pair missing.
Polyunsaturated fats are found mostly in seed oils.

• Saturated fats in the bloodstream have been found to raise the

level of cholesterol, and polyunsaturated fat tends to lower it.

• Saturated fats are generally solid at room temperature;

polyunsaturated fats are liquid.
 B: Glycerol/Glycerol lipid

• Figure 3: .Glycerol is a linear chain of three

carbons
• The central carbon is bound to one hydroxyl
radical and to one hydrogen and
• the two other carbons in the extremities are
bound to a hydroxyl radical and to two
hydrogens.
 Characters
• Glycerol is a clear, colourless, odourless, viscous, low of
toxicity, sweet-tasting liquid.
• It belongs to the alcohol family of organic compounds
• and the molecular formula is HOCH2CHOHCH2OH.
• It is commonly used in pharmaceutical formulations. It is a
simple polyol compound.
• Glycerol has three hydrophilic hydroxyl groups that are
responsible for its solubility in water
• The glycerol backbone is central to all lipids known as
triglycerides. In triglycerides, the three hydroxyl groups of
glycerol are each esterified by three different fatty acids.
• The hydrolysis of the ester bonds of triglyceride and the
release of glycerol and fatty acids from adipose tissue is
called fat mobilization.
 Classes of Lipids
1. Triglyceride

• The most common storage form of fat in many organisms.

• Created via the esterification of three fatty acids to a
single glycerol molecule.
• Triglycerides are an efficient storage medium because their
highly hydrophobic nature allows them to be stored as part
of droplets (in which they have little or no contact with
water molecules).
• They vary in molecular composition according to the
identities of the fatty acids used in their synthesis .
• Fatty acids that have been esterified to the glycerol moiety
of the triglyceride may be unsaturated (containing double
bonds) or saturated (containing no double bonds).
.
• The number of double bonds in the fatty acids affects
the melting temperature of the triglyceride.
• Saturated fats have higher melting points and are often
solids at room temperature.
• Unsaturated fats have lower melting points and are
often liquids at room temperature.

• In animals, triglycerides are either ingested as part of the

diet or synthesized in the liver.
• Triglycerides are transported in blood as part of
lipoprotein particles.
• Triglycerides synthesized in the liver are transported as
part of lipoprotein particles called very low density
lipoproteins or VLDLs.
• Triglycerides are then removed from lipoprotein particles
as they move through the circulatory system.
• Tissues either utilize this transported
triglyceride immediately, or it is stored in
adipose tissue (as fat) .

• Triglycerides are the most abundant form of

stored potential fuel in the human body.
For example: A typical 70-kilogram man will
have approximately 15 kilograms of stored
triglyceride, representing several months of
stored fuel.
• When physiologic conditions necessitate the use
of triglycerides stored in adipose tissue, a
hormone or neurotransmitter signals their
release.
• Exercise or stress triggers the release of the
neurotransmitter norepinephrine from nerve
terminals in the adipose tissue, thereby
stimulating triglyceride release.
• Fasting also initiates the release of triglycerides. Insulin
and glucagon, two hormones produced by the
pancreas, control this release of triglycerides.
• During fasting, blood glucagon levels increase and
insulin levels decrease.
• The combination of increased glucagon and decreased
insulin levels in the blood is the hormonal signal that
triggers the release of triglycerides from the adipose
tissue.
• However, triglycerides do not exit adipose tissue
intact. Hormonal signaling activates an enzyme called
a lipase that hydrolyzes a triglyceride molecule into a
glycerol molecule and three fatty acids.
• The glycerol and fatty acids are then transported
within the circulatory system to tissues that will utilize
them as fuel.
• Fatty acids are transported in the blood bound to the
serum protein albumin, as their hydrophobic natures
would otherwise make them insoluble in the blood.
Triglycerides formation/decomposition in
Condensation/Hydrolysis Reaction

Figure 4: Condensation and hydrolysis of a fat molecule. When a fat

molecule forms, three fatty acids combine with glycerol and three
water molecules are produced. Unsaturated fats have double bonds
(shown in yellow) between carbon atoms.
Triglycerides formation in Condensation Reaction
• Fats and oils (lipids) are made from sub-units: fatty acids and glycerol.
•
• Below, three molecules of fatty acids bound to one molecule of glycerol.
Hydroxyls of each one of the three fatty acids and each hydrogen of the
hydroxyls of the glycerol bind to form three molecules of water that are
liberated. Three ester linkages are formed as a result.
• The resulting compound is a triglyceride, or a neutral fat. Note that the
molecule has a large number of carbon atoms with associated hydrogen atoms
(as in hydrocarbons), and no -OH groups. This explains why fats do not dissolve
in water, and also the large number of C-C and C-H bonds explain why lipids
are a high energy store.
• Unlike the comparable situation in carbohydrates and proteins (the
condensation of sugars into polysaccharide and amino acids into
polypeptides), in lipids the condensation reaction is not capable of proceeding
beyond the stage shown here, because there are only 3 sites for fatty acids to
attach to glycerol.

Hydrolysis of a Triglyceride
• One molecule of lipid - triglyceride - is hydrolysed (digested) to give 1 molecule
of glycerol and 3 molecules of fatty acid. Here 3 molecules of fatty acid and 1
molecule of glycerol are formed when 3 water molecules are added to the
compound. The –H and –OH groups break the ester bonds. The bonds are
broken with the help of the enzyme lipase.
 2. Phospholipids/ Glycerophospholipids
• Consists of a hydrophilic polar
head group and a hydrophobic tail.

• The polar head: one or more

phosphate groups.

• The hydrophobic tail: two fatty acyl

chains.

• Similar structure to lipids but only 2

FA
• third hydroxyl (glycerol) has a
phosphate group attached
• phosphate group is polar

Orientation:
• hydrophilic phosphate head group
towards water
• hydrophobic FA tails away from
water
• function is as component of
membranes
 Bilayer
• When many phospholipids
molecules are placed in
water, their hydrophilic
heads tend to face water
and the hydrophobic tails
are forced to stick together,
forming a bilayer.
• The lipid bilayer is a thin
membrane made of two
layers of lipid molecules.
• Forms:
The cell membrane: living
organisms ,many viruses.
membranes: cell nucleus &
sub-cellular structures.
 The lipid bilayer (membrane components)

1. is the barrier that keeps ions, proteins and other molecules where
they are needed and prevents them from diffusing into areas where they
should not be.

2. suited to this role because, even though they are only a few nanometers
thick, they are impermeable to most water-soluble (hydrophilic)
molecules.
•
3. Steroid

• Steroids contain four cycloalkane rings that are

joined to each other.

• They do not contain fatty acids but they form

plasma membrane, influencing the latters’
structure and function in transport and
permeability.

• They have widely different physiological

properties. Few examples are listed in the table
 Structure
• Seventeen carbon atoms form the core of steroids. The
carbons joined together to form four fused rings: 3
cycloheane (A,B,C rings) and 1 cyclopentane ring (D ring).

• The steroids vary by the functional groups attached to this

four ring core and by the oxidation state of the rings.

• For example, the eighteen-carbon (C18) steroids include

the estrogen family whereas the C19 steroids comprise the
androgens such as testosterone and androsterone.
Some Steroid hormones of veterbrates
 Table: Some Important Steroids
Steroid Function
Cholesterol Major component of cell membranes,
raw material for many other steroids
Bile acids In the form of bile salts, they help in
emulsifying fats during digestion
Corticosteroi Hormones manufactured in the cortex
ds region of the adrenal gland. They are
involved in stress responses
Oestrogens, Reproductive hormones in female
Progesterone mammals
s
Testosterone Reproductive hormone in male
mammals
Calciferol Promotes calcium and phosphate
(Vitamin 12) absorption from the small intestine
 Cholesterol
• Cholesterol is the most well known steroid and is abundant in the body
when compared to other steroids.
• Other steroids are used as hormones and vitamins.
• High levels of cholesterol in the blood are an indicator for diseases such as
heart problems
LDL are bad
cholesterols &
HDL are good
cholesterol
 Activity 1
1. What are the constituents of lipids?
2. Structurally, what is the difference between
saturated and unsaturated fatty acids?
3. What are the main types/classes of lipids?
4. What is the structural formula of glycerol? To
which organic function do these molecules
belong?
5. How are triglycerides made?
6. What are phospholipids?
7. What are steroids? What are some examples of
steroids with a biological function?
 Biological functions

1. Membranes

• The glycerophospholipids are the main structural

component of biological membranes, such as the
cellular plasma membrane and the intracellular
membranes of organelles.

• In animal cells the plasma membrane physically

separates the intracellular components from the
extracellular environment.
2. Energy storage

• Triacylglycerols, stored in adipose tissue, are a major form of

energy storage in animals.

• The adipocyte/fat cell, is designed for continuous synthesis

and breakdown of triacylglycerols, with breakdown controlled
mainly by the activation of hormone-sensitive enzyme lipase.

• The complete oxidation of fatty acids provides high caloric

content, about 9 kcal/g, compared with 4 kcal/g for the
breakdown of carbohydrates and proteins.

• Migratory birds that must fly long distances without eating

use stored energy of triacylglycerol to fuel their flights.
3. Signaling
• lipid signaling is a vital part of the cell signaling.

• members of several different lipid categories have

been identified as signaling molecules and cellular
messengers.

• Examples:
the steroid hormones such as estrogen, testosterone
and cortisol, which modulate a host of functions such
as reproduction, metabolism and blood pressure.
 Activity2
1. What are hydrophobic molecules (or hydrophobic molecular
regions)? What are hydrophilic molecules? How can they be
characterized in relation to their polarity?

2. Regarding solubility, how are lipids classified?

3. What is meant by saturation or unsaturation of oils and fats?

4. How are lipids used as an energy source by the organism?

5. Explain the functions of lipids as biological membranes and

cell signalling and messengers.