ABSTRACT

It is now known that lipids play a much more

important role in the body than previously
believed. It was previously known that lipids
played the role of storage of energy or forming
cell membranes alone. Researchers have
found that lipids have a much more diverse
and widespread biological role in the body in
terms of intracellular signalling or local
hormonal regulation etc. – Dr. A. Mandal

Prof. Minda Aquino

MC 2 Biochemistry

https://www.livescience.com/
3505-chemistry-life-human-
body.html

MODULE 3
Bioorganic Compounds: Lipids
Title: Module 3
Bioorganic Compounds: Lipids

Overview:
Found in living organisms, lipids are a family of substances that are insoluble in water
but soluble in nonpolar solvents and solvents of low polarity, such as diethyl ether. Unlike the
case with carbohydrates, we define lipids in terms of a property and not in terms of their
structure. (Bettelheim, F.A., Brown, W.H., and Campbell, M.K. () Introduction to Organic and
Biochemistry, 6th ed.,)

Learning Outcome:
1.Describe the characteristics and properties of lipids in living organisms.
2.Describe and classify lipids according to their structure, functions and properties.
5. Differentiate fats, oils, and waxes according to their properties, structure, and uses.
6. compare and contrast phospholipids, sphingolipids, and glycolipids based on their:
• backbone component
• fatty acid component
• sources
7. Differentiate the lipoproteins according to their density and functions.
8. Compare the structure and biological roles of prostaglandins, leukotrienes, and steroids.
9. Explain the roles of cholesterol, sex hormones, and fat-soluble vitamins in living organism.

Objectives:
At the end of the module the students shall be able to:
1. Define lipids;
2. Classify lipids according to functions and structure;
3. Enumerate and describe some properties of triglycerides;
4. Describe the mechanism and transport of LDL and HDL.
5. Identify chemistry connection among humans.
6. Enumerate physiological roles of steroid hormones.

Reference:
Bettelheim, F.A., Brown, W.H., and Campbell, M.K. () Introduction to Organic and Biochemistry,
6th ed.,
**images taken from google

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I. LIPIDS
- Are family of substances that are insoluble in water but are soluble in non-polar
solvent.
CLASSIFICATION OF LIPIDS
1. Simple Lipids (Fats and waxes)
2. Complex Lipids, include the
a. Phospholipids (glycerophospholipids and spingolipids)
b. Glycolipids
3. Steroids (Cholesterol, Lipoprotein, Adrenocorticoid, Sex hormones
4. Prostaglandins, Thromboxane, Leukotriene
CLASSIFICATION OF LIPIDS BY FUNCTION
Major roles of lipids
1. They store energy within the fat cells.
2. They separate compartments of aqueous solutions from each other.
3. They serve as chemical messenger like steroid hormones and deliver signals from one
part of the body to another.
CLASSIFICATION OF LIPIDS BY STRUCTURE
- Animal fats and plant oils are triglycerides. Triglycerides are tri esters of glycerol and
long chain of carboxylic acids called fatty acids.
- Illustration:

or

Glycerol

- In triglycerides, all the three groups of glycerol are esterified thus, a typical triglyceride
molecule is a combination of oleate, palmitate and stearate.
- Illustration:

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SOME PROPERTIES OF TRIGLYCERIDES

A. Physical State
- Excepts fats that come from animals, they are generally solid at room temperature.
Plant or fish oils are usually liquids.
- What is usually the structural difference between solid fats and liquid oils? It is the
degree of unsaturation; solid animal fats contain mainly of saturated fatty acids while
vegetable oils contain high amount of unsaturated acids.
- Some unsaturated fatty acids (linoleic and linolenic acids are called essential fatty
acids because the body cannot synthesize them from precursors hence, they must
therefore be consumed as part of the diet.
B. Hydrogenation
- Involve the reduction of C, C double bonds to a single bond.
- It is difficult to convert unsaturated liquid oils to solid, partial but not complete
hydrogenation result to a product with just right consistency for cooking.
Example. Margarine result from the partial hydrogenation of vegetable oil.
C. Saponification
- It is a base hydrolysis of fats and oil producing glycerol and a mixture of fatty acid
salts called soap. It has been used for thousand of years and saponification is one of
the oldest known chemical reaction.

II. COMPLEX LIPIDS

- The complex lipids constitute the main components of membranes, they are classified
into 2 groups:
1. PHOSPHOLIPIDS
- Contain an alcohol, two fatty acids and a phosphate group.
- Include the glycerophospholipids and the sphingolipids.
a. GLYCEROPHOSPHOLIPIDS
• Are membrane components of cells throughout the body. The alcohol is
glycerol.
• Include lecithin, cephalins, and phosphatidylinositol.
• Lecithin is a major component of egg yolk because it has a polar and
nonpolar part and it is an excellent emulsifier used in making mayonnaise.
• Cephalin is similar to lecithin except that instead of choline, it contains
other alcohol like ethanolamine or serine.
• Another group glycerophospholipid is phosphatidylinositols or PI, bounded
phosphate ester bond. It is integral structural part of biological membrane.
b. SPH INGOLIPIDS
• It is the myelin coating of nerve axon having an alcohol part called
sphingosine. It is associated with diseases such as multiple sclerosis.
2. GLYCOLIPIDS
- are complex lipids containing carbohydrates and ceramides.

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III. STEROIDS
- Is the third major class of lipids which are compounds containing a ring system.

- Steroids include the following:

1. CHOLESTEROL
• Most abundant steroid in the human body.
• Cholesterol serves as a plasma membrane component in all animal cells. Its
important function is to serve as a raw material for the synthesis of steroids
such as sex and adrenocortico hormone.
• The correlation between high serum cholesterol level, many people became
afraid of cholesterol and regard it as some kind of poison. But far from being a
poison, it is necessary for human life. In essence, our liver manufacture
cholesterol that satisfies our need even without dietary intake.
2. LIPOPROTEINS
• Cholesterol along with fat is transported by lipoproteins.
• There are four kinds of lipoproteins.
a. High-density lipoprotein (HDL) or good cholesterol – consist of 33% protein
and about 30% cholesterol.
b. Low-density lipoprotein (LDL) or bad cholesterol – contains 25% protein
and 50% cholesterol.
c. Very low-density lipoprotein (VLDL) carries triglycerides (fats) synthesized
by the liver.
d. Chylomicrons carry dietary lipids synthesized in the intestines.

MECHANISM AND TRANSPORT OF LDL

• The transport of cholesterol from the liver starts out as a large VLDL particles (55
nanometers in diameter). The core of VLDL contains triglycerides and cholesteryl esters
mainly cholesteryl linoleate. It is surrounded by a polar coat of phospholipids and
proteins. The VLDL is carried in the serum.
• When the capillaries reach the muscle or fat tissues, the triglycerides and all proteins
except apoB-100 are removed from VLDL. At this point, the diameter of the lipoprotein
shrinks to 22 nanometers and its core contains only cholesterol esters. Because of the
removal of fat, the density increases and it becomes LDL. LDL lipoproteins stays in the
plasma for about 2.5 days.
• The LDL carries cholesterol to the cells where specific LDL receptor molecules line the
cell surface in certain concentrated areas called coated pits. The apoB-100 protein on
the surface of the LDL binds specifically to the LDL receptor molecules in the coated
pits.

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 • As such binding, the LDL is taken inside the cell (endocytosis) where enzymes break
down the lipoprotein. This is the normal fate of LDL.

TRANSPORT OF CHOLESTEROL IN HDL

• High density lipoprotein transport cholesterol from peripheral tissues to the liver and
transfers cholesterol to LDL. While in the serum, the free cholesterols in HDL are
converted to cholesteryl esters. These esters feed cholesterol is delivered to the liver for
the synthesis of bile acids and steroid hormones.
• The cholesterol uptake from HDL differs from that noted with LDL. This process does not
involve endocytosis and degradation of the lipoprotein particle, instead in a selective lipid
uptake, the HDL binds to the liver cell surface and transfers its cholesteryl esters to the
cell. The HDL depleted from its lipid then reenters the circulation.
• It is desirable to have a high level of HDL in the blood because it removes cholesterol
from the blood stream.

CHEMISTRY CONNECTION: Levels of LDL and HDL

All lipids, cholesterol is insoluble in water. If its level is elevated in the blood serum, plaque like
deposits may form in the inner surfaces of the arteries resulting in the decrease of diameter of
blood vessels thereby decreasing also the flow of blood. This is termed atherosclerosis along
with the accompanying high blood pressure may lead to heart attack or kidney dysfunction.
Atherosclerosis along with accompanying high blood pressure may lead to heart attack, stroke.
It may exacerbate the blockage of some arteries by a clot at the point where the arteries are
constricted by plaque.
Furthermore, the blockage may deprive cells from oxygen causing them to cease to function
and consequently, the death of heart muscles due to lack of oxygen is called myocardial
infarction.
In certain cases, if there are not enough LDL receptors, a disease called familial
hypercholesterolemia where the cholesterol level may be as high as 680 mg/ 100 mL
compared to 175 mg/ 100 mL in normal subjects. This high level of cholesterol can also lead to
premature atherosclerosis and heart attack.

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PHYSIOLOGICAL ROLES OF STEROID HORMONES
- Cholesterol is the starting material for the synthesis of steroid hormones. In this process,
the phenanthrene side chain or the D is shortened by the removal of a 6 C unit while the
secondary alcohol group or C3 is oxidized to ketone to form a molecule of progesterone
and adrenocorticoid hormone.
A. ADRENOCORTICOID HORMONES
- They are the product of adrenal glands. Adrenal means “adjacent to renal”. In
terms of function, there are two groups:
1. Mineralocorticoids – regulate the concentration of ions Na+ and K+.
2. Glucocorticoids - control the carbohydrate metabolism. The term corticoid
indicates that the site of secretion is the cortex.
- Cortisol is the major glucocorticoid and its function is to increase the glucose and
glycogen concentrations in the body.
- Cortisol and its ketone derivative cortisone have remarkable anti-inflammatory
effects, similar synthetic derivatives such as prednisolone are used to treat
inflammatory diseases of many organs like rheumatoid arthritis and bronchial
asthma.
B. SEX HORMONES
- The most important male sex hormone is testosterone which promotes the
normal growth of male genital organ, it is synthesized in the testes from
cholesterol.
- During puberty, increased in testosterone production lead to the male secondary
characteristics like deep voice and appearance of facial and body hair.
- The female sex hormone is estradiol. It regulates the cyclic changes occurring in
the uterus and ovaries known as the menstrual cycle. As the cycle begins, the
level of estradiol in the body rises, which in turn causes the lining of the uterus to
thicken.
- Another hormone called Luteinizing hormone (LH) triggers ovulation. If the ovum
is fertilized, progesterone level increases inhibiting further ovulation. Both
estradiol and progesterone promote further preparation of the uterine lining to
receive the fertilized ovum.

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ILLUSTRATION SHOWING THE CYCLES

IV. BILE SALTS

- Bile salts are oxidation products of cholesterol. First the cholesterol is oxidized to
trihydroxy derivative then oxidized further to carboxylic acid. They are powerful
detergents. They can disperse dietary lipids in small intestines thereby facilitating
digestion. The dispersion of dietary lipids of bile salts is similar to the action of soap in
dirt.
PROSTAGLANDINS, THROMBOXANES AND LEUKOTRIENES
Prostaglandins
- group of fatty acids like substances isolated from human semen. The seminal glands
secrete 0.1 mg of prostaglandin per day in a mature male.
- It is synthesized in the body from the arachidonic acid by an enzyme cyclooxygenase
or COX enzyme.
- There are 2 forms of COX, COX-1 and COX-2.
COX-1 catalyzes the normal physiological production of prostaglandins. Examples:
PGE2 and PGF2a stimulate uterine contraction and induce labor.
COX-2, by contrast, is responsible for the production of prostaglandins in inflammation.
When a tissue is injured or damaged, special inflammatory cells invade the injured

7|Module 3
 tissue and interact with resident cells—for example, smooth muscle cells. This
interaction activates the COX-2 enzyme, and prostaglandins are synthesized.
Thromboxanes
- These substances are derived from PGH2, but their ring is a cyclic acetal.
Thromboxane is known to induce platelet aggregation. When a blood vessel is
ruptured, the first line of defense is the platelets circulating in the blood, which form an
incipient clot. Thromboxane A2 causes other platelets to clump, thereby increasing the
size of the blood clot.
Leukotrienes
- act to mediate hormonal responses. Like prostaglandins, they are derived from
arachidonic acid by an oxidative mechanism.
- Leukotrienes occur mainly in white blood cells (leukocytes) but are also found in other
tissues of the body. They produce long-lasting muscle contractions, especially in the
lungs, and can cause asthma-like attacks. In fact, they are 100 times more potent than
histamines.
- Both prostaglandins and leukotrienes cause inflammation and fever, so the inhibition of
their production in the body is a major pharmacological concern.

Now, click the link and watch some videos related to the
topic.
Lipids
https://www.youtube.com/watch?v=5BBYBRWzsLA
Lipids | Fats, Steroids, and Phospholipids | Biological
Molecules Simplified #4
https://www.youtube.com/watch?v=69-eGO7XDfU
Cholesterol Metabolism, LDL, HDL and other Lipoproteins,
Animation
https://www.youtube.com/watch?v=9dghtf7Z7fw

Study your lesson for now, exercise will be posted in your

classroom. Your instructor will update you on this.
All the best.

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