Asst. Prof. Dr. Hassan H.

Al-Saeed Biochemistry I
Dr
Lipids
I. Lipids definition:
Lipids are bioorganic compounds either hydrophobic
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(containing only non polar group) or amphipathic (possess both
polar and non polar groups), low solubility in water and high
solubility in non polar solvent, such as chloroform, ether and
benzene.
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II. Lipids functions:
They have many biological functions as divers as their chemistry:
1. High energy storage (many organisms).
2. Structural elements (biological membranes).
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3. As vitamins or hormones.
4. Soluble of different kinds of lipids (Gall bladder acids).
5. Thermal insulator in the subcutaneous tissues and around
certain organs.
6. Electrical insulators, along myelinated nerves.
7. Means of transporting lipids in the blood.

Knowledge of lipid biochemistry is necessary in understanding

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many important biomedical areas, eg, obesity, diabetes mellitus,

atherosclerosis, and the role of various polyunsaturated fatty
acids in nutrition and health.

III. Lipids classification:

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1. Simple lipids.
A. Fats (solid state) and Oils (liquid state):
B. Waxes:
2. Complex lipids:
A. Phospholipids:
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1. glycerophospholipids
2. sphingophospholipids
B. Glycolipids:
1. Glycosphingolipids
2. Galactolipids (sulfolipids)
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C. Lipoproteins:

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 Asst. Prof. Dr. Hassan H. Al-Saeed Biochemistry I
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3. Precursor and derived lipids: These include;
A. Fatty acids,
B. glycerol,
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C. Terpenes
D. Steroids,
Neutral lipids: they are uncharged compounds, and these are
acylglycerols (glycerides), cholesterol, and cholesteryl esters.
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IV. Fatty acids (f.a):
 Structural elements for most lipids.
 Contain two distinct regions, long hydrophobic hydrocarbon
chains (C4 to C36), not chemically active as tail, and terminal
hydrophilic –COOH group as head, which normally ionized
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under physiological conditions.
Fatty acids = carboxyl group + a long hydrocarbon chain.
HO
H2 H2 H2 H2 H2 H2 H2
C C C C C C C C
O C C C C C C C CH 3
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H2 H2 H H2 H2 H2 H2 OH

OH O

16:0 =Palmitic Acid=Hexadecanoic acid 18:1 =Oleic acid=9-Octadecenoic acid

 Most found in nature have an even C number (12-24) and
unbranched, as a results of synthesis mode of these
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compounds, which involves condensation of two carbon units

(acetate).

 Saturated fatty acids: not contain double bonds called

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 Asst. Prof. Dr. Hassan H. Al-Saeed Biochemistry I
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 Unsaturated fatty acids: contain one or more double bonds.
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1. Subdivided of Unsaturated Fatty Acids:
A. Monounsaturated (monoethenoid, monoenoic) acids,
containing one double bond.
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B. Polyunsaturated (polyethenoid, polyenoic) acids,
containing two or more double bonds.
C. Eicosanoids: These compounds, derived from eicosa- (20-
carbon) polyenoic fatty acids, comprise the Prostanoids
[Prostaglandins (PGs), prostacyclins (PGIs) and
Thromboxanes (TXs)], Leukotrienes (LTs), and Lipoxins
(LXs).
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 Hydroxy fatty acids: They contain a hydroxy group

Examples: - Ricinoleic acid and Dihydroxy stearic acid
both are found in castor oil.
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 Cyclic fatty acids: Chaulmoogric acid present in

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chaulmoogra oil which was used previously in

treatment of leprosy.
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 Asst. Prof. Dr. Hassan H. Al-Saeed Biochemistry I
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2. The Naming of Fatty Acids:
A. Common name: as shown in the two tables above.
B. Systematic name:
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1. Derived from the name of its parent hydrocarbon by the
substitution of oic instead of final e. Thus, saturated acids
end with -anoic, eg, octanoic acid (from parent hydrocarbon
octane), and unsaturated acids with one double bonds end in
-enoic, eg, octadecenoic acid (oleic acid), and with two
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double bonds end with -dienoic and with three double bonds
end in -trienoic and so on.

2. Numbering carbon atoms starting at the C carboxyl terminus,

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which takes No. 1. The C atoms adjacent to the carboxyl
carbon (Nos. 2, 3, and 4) are also known as the α, β, and γ
carbons, respectively.
3. The kind of double bond referred as geometric configuration
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cis or trans, and the position number of a double bond,
represent by the lowers number of carbon atom associated
in the double bond.
For example, cis-Δ 9 means that there is a cis double bond
between carbon atoms 9 and 10.
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C. Shorten name:
Number of C fatty acid, then colon (:), then number of
double bonds if presence, represented by the delta symbol
Δ with a superscript number or a number in parentheses,
which represent the lowers number of carbon atom
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associated in the double bond.

For example, 18:0 for stearic acid, and 18:1 Δ9 or 18:1(9)
for oleic acid.

D. Omega name ():

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1. Alternatively, the methyl carbon atom at the distal end of

the chain is called the - (carbon number 1), thus the
carboxyl carbon take the last number.
2. Usually, three series of fatty acids are founds known as
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the ω9, ω6, and ω3 families, respectively.

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 Asst. Prof. Dr. Hassan H. Al-Saeed Biochemistry I
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3. It can obtain the ω series by:
ω series= ω (the number n of fatty acid carbons ) minus
the nearest number of carbon atom on the distant double
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bond from carboxylic group.
For example;
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3. Non essential fatty acids:
They can be synthesized by the body.
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4. Essential fatty acids:
They are not synthesized in the body and hence have to be
provided in the diet.
They are also called polyunsaturated acids. Like;

 Linoleic cid. 18:2 (9,12)

 Linolenic acid. 18:3 (9,12,15)
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 Archidonic acid. 20:4 (5,8,11,14)

5. Properties of fatty acids:

Fatty acids present in nature have the following properties:
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A. They are present in straight chains.

B. They contain even number of carbon atoms.
C. Solubility: This depends on the number of carbon atoms
of the fatty acid.
- If the fatty acid contains from 2--6 carbon atoms, it is
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soluble in water.
- If more than 6 carbon atoms, it is insoluble in water and
soluble in fat solvents e.g. ether.
- The Na or K & salts of fatty acids (soaps) are soluble in
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water.

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 Asst. Prof. Dr. Hassan H. Al-Saeed Biochemistry I
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D. Distillation with steam:
- Short chain fatty acids (from C2 - C6) can be distilled
with steam (volatile).
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- Long chain fatty acids cannot be distilled with steam
(Non volatile).
E. They can form esters with alcohols.
F. Hydrogenation or halogenations
This is a property of unsaturated fatty acids. The
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hydrogen or halogen is added through the double bond.
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G. Oxidation: This is another property of unsaturated fatty
acids. Oxidation occurs at the double bond producing
aldehydes or Ketones.
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H. Melting point:
Depend directly with the length of hydrocarbon chain, and
indirectly with the degree of unsaturation, that's mean;
 Increasing melting point (m.p) if the length of
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hydrocarbon chain increased.

 Decreasing melting point (m.p) if the degree of
unsaturation increased.
Thus the saturation fatty acids of 12-24 C atoms have a waxy
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consistency, whereas the unsaturated fatty acids of these lengths

are oily liquids. Why?
Because saturated fatty acids don’t have a double bond, so its can
pack closely together and interact by vander waals to form ordered rigid
arrays, so they are takes more thermal energy to disorder this arrays.
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 Asst. Prof. Dr. Hassan H. Al-Saeed Biochemistry I
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But unsaturated fatty acids prevent such close packing and their
interaction with each other are therefore weaker however it takes less
thermal energy to disordered these poorly ordered arrays, so they
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have lower m.p than saturated fatty acids of the same length.
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Question: Arrange ascendingly according to the m.p of the following
fatty acids.
1. Palmitic, Myristic, and Stearic acids.
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2. Oleic, Linolenic, and Linoleic acids.
3. Linolenic, Stearic, and Linoleic acids.

6. Isomerization
 Isomerism is possible by varying the position of double bond
in the fatty acid molecule.
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For example; the eighteen carbon fatty acid with a double

bond between C9 and C10 can exist in two forms:
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They called cis-trans isomers.

The naturally occurring fatty acids are the cis-isomer.
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7. Fatty acids derivatives:

The most important example is eicosanoids:
Eicosanoids: are paracrine hormones, substances that act only
on cells near the point of hormone synthesis instead of being
transported in the blood to act on cells in other tissues or organs.
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 They are all derived from arachidonic acid (20:4 Δ5, 8,11,14),
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 Asst. Prof. Dr. Hassan H. Al-Saeed Biochemistry I
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 They take their general name from Greek eikosi (twenty).
 They have a variety of dramatic effects or function on
vertebrate tissues, involved in:
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1) Reproductive function; in the inflammation, fever, and pain.
2) Associated with injury or disease; in the formation of blood
clots and the regulation of blood pressure;
3) In gastric acid secretion; and in a variety of other
processes important in human health or disease.
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 There are three classes of eicosanoids:
- Prostanoids; includes prostaglandins (PGs), prostacyclins
(PGIs), and thromboxanes (TXs).
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- Leukotrienes (LTs).
- Lipoxins (LXs).
A. Prostaglandins (PG):
 Exist virtually in every mammalian tissue, acting as local
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hormones; they have important physiologic and
pharmacologic activities.
 Contain a five-carbon ring derived from the hypothetical fatty
acid, prostanoic acid (Their name derives from the prostate
gland, the tissue from which they were first isolated),
originating from the chain of arachidonic acid.
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Note:
1. The dotted bond between C7 & C8 it's below the plane of the
paper, whereas the thickened bond between C12 & C13 it's
on the top of paper plane.
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2. Prostaglandins divided into nine primary groups PG (A, B,

C, D, E, F, G, H, and I.), and these groups different for each
other according to the nature of pentagonal ring (saturated or
not, and the kind of oxidation), such as the two following
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groups:

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 Asst. Prof. Dr. Hassan H. Al-Saeed Biochemistry I
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3. Prostaglandins groups divided into subgroups, such as
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PGE1, and PGE2 according to the number of double
bonds found in the carbon chain, and also divided to α
when -OH group on C11 behind the paper (dotted line), and
β, when -OH group on C11 above the paper (continuous
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line).
4. All PGs contain double bond between C13 - C14, and –OH
group on C15 joined as α.
 Prostaglandins act in many tissues by:
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- Regulating the synthesis of the intracellular messenger 3´,5´-
cyclic AMP (cAMP). Because cAMP mediates the action of
diverse hormones, the prostaglandins affect a wide range of
cellular and tissue functions.
- Some prostaglandins stimulate contraction of the smooth
muscle of the uterus during menstruation and labor.
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- Others affect blood flow to specific organs, the wake-sleep

cycle, and the responsiveness of certain tissues to hormones
such as epinephrine and glucagon.
- Prostaglandins in a third group elevate body temperature
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(producing fever) and cause inflammation and pain.

B. Thromboxanes (TX):
 Have a six-member ring containing ether (oxygen atom in the
ring to give an oxane ring). They are produced by platelets
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(also called thrombocytes) and act in the formation of blood

clots and the reduction of blood flow to the site of a clot.
 The nonsteroidal anti-inflammatory drugs (NSAIDs) ex.,
aspirin, ibuprofen, and meclofenamate inhibit the enzyme
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prostaglandin H2 synthase (also called cyclooxygenase or

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 Asst. Prof. Dr. Hassan H. Al-Saeed Biochemistry I
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COX), which catalyzes an early step in the pathway from
arachidonate to prostaglandins and thromboxanes.
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C. Leukotrienes (LT):
 First found in leukocytes, contain three conjugated double
bonds. They are powerful biological signals. For example,
leukotriene D4, derived from leukotriene A4, induces
contraction of the muscle lining the airways to the lung.
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 Overproduction of leukotrienes causes asthmatic attacks,
and leukotriene synthesis is one target of anti-asthmatic
drugs such as prednisone.
 The strong contraction of the smooth muscles of the lung
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that occurs during anaphylactic shock is part of the
potentially fatal allergic reaction in individuals hypersensitive
to bee stings, penicillin, or other agents.
Eicosanoids
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V. Simple lipids:
1. Fats (solid state) and Oils (liquid state):
They are esters of fatty acids with glycerol which called
acylglycerols or glycerides.
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 Asst. Prof. Dr. Hassan H. Al-Saeed Biochemistry I
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Glycerol
 It is a polyhydroxy alcohol containing 3 hydroxyl groups:
 Use in medicine:
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- Glycerol enters in all cosmetic preparation.
- Nitroglycerine is used as vasodilator especially for the
coronary arteries. So it is used for treatment of angina pectoris
- Glycerol is used for treatment of glaucoma (increased
intraocular pressure) due to its ability to dehydrate the tissue
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from its water content.
A. Acylglycerols classification:
1. Monoglycerols: contain one fatty acid connected to
glycerol by ester bond.
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2. Diglycerols: contain two fatty acids connected to glycerol
by ester bonds.
3. Triglycerols: contain three fatty acid connected to glycerol
by ester bonds.
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Triacylglycerols (TAG or TG), represent the main
compound in daily fat diets, and it's the form of lipid stored in
adipose tissue or beneath the body skin.
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B.TG kinds:
1. According to the complexity:
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a. Simple triglycerides: contains the same three fatty acids.

eg; TG contains stearic acids, called Tristearoyl glycerol.
b. Mixed triglycerides: consist of different fatty acids.
eg; TG contains stearic acid on C1, C2, and oleic on C3,
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called 1, 2-Distearoyloleylglycerol.
 The name and position of each fatty acid must be specified.
 In nature mixed triglycerides are more abundant than the
simple triglyceride.
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 Asst. Prof. Dr. Hassan H. Al-Saeed Biochemistry I
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2. According to the state:
a. Liquid form: most plant oils contain unsaturated fatty acids
such as oleic, linoleic, and linolenic, so these oils are liquid in
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room temperature.
b. Solid form: obtain from animal sources, contain saturated
fatty acids, such as palmitic and stearic, so these oils are
solid or semi-solid at room temperature.
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C. TG hydrolysis:
TAG can be hydrolyzed to give a mixture of fatty acids and
glycerol by;
1. Pancreatic lipase enzyme.
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2. Acids.
3. Alkaline hydrolysis, to give soap of fatty acid and glycerin.

D. TG roles (functions):
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In animals TG (fat) have several roles;
1. Major storage and transport for fatty acids.
2. Provides insulation against cold temperature (Fat is a
poor conductor of heat).
E. Physical properties:
1. Fats and oils are: colorless, odorless, and tasteless.
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2. The color and the test of some naturally occurring fats are
due to extraneous substances (e.g. butter contains
carotene).
3. They are insoluble in water, but soluble in organic solvents.
4. They have low specific gravity and float in water, oils
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spread in water to form thin monomolecular layers.

5. They have well defined melting points and solidifying points,
the latter temperatures always a few degrees lower.
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2. Waxes:
 Waxes are esters of long chain fatty acids; (C14-36) with
long chain and high number of alcohols (C16-30).
For example; Triacontanoylpalmitate, the major component of
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beeswax, is an ester of palmitic acid with the alcohol triacontanol.

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 Asst. Prof. Dr. Hassan H. Al-Saeed Biochemistry I
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 They have high melting points (60-100C)
 Used as energy storage (Plankton)
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 They are water repellant (in birds and plants).

VI. Complex lipids:

1. Phospholipids (PL):
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A.Glycerophospholipids.
 Glycerol backbone.
 Essential for membrane structure.
 Most abundant membrane lipids.
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1. Carbons 1 & 3 of glycerol are not identical:
It is important to realize that carbons 1 and 3 of glycerol
are not identical when viewed in three dimensions
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Enzymes readily distinguish between them and are

specific for one or the other carbon;
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e.g., glycerol is always phosphorylated on sn-3 by glycerol

kinase to give glycerol 3-phosphate and not glycerol 1-
phosphate.
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To number the carbon atoms of glycerol clearly, the -sn-

(stereochemical numbering) system is used, in which C-1 is, by
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 Asst. Prof. Dr. Hassan H. Al-Saeed Biochemistry I
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definition, that group of the prochiral compound that occupies the
pro-S position. The common form of glycerol phosphate in
phospholipids is, by this system, sn-glycerol 3-phosphate.
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2. General structure:
Glycerophospholipids may be regarded as derivatives of
phosphatidic acid, in which the phosphate is esterified with the -
OH in a C3 of glycerol molecule as a polar head and two fatty
acids in a C1 and C2 as a nonpolar tails,
.
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The X maybe;
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 Asst. Prof. Dr. Hassan H. Al-Saeed Biochemistry I
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as
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If X is;
a. Ethanolamine; the molecule is called
phosphotidylethanolamine (Cephalin).
 Exists in brain tissue.
 Participates in blood clotting.
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b. choline; the molecule is called phosphotidylcholine

(Lecithin).
 The most abundant phospholipids of the cell membrane
 Exists in brain, neural tissue, and in eggs.
 Play an important role in reducing surface tension of the
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moist inner surface of the alveoli.

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 Asst. Prof. Dr. Hassan H. Al-Saeed Biochemistry I
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 Its absence from the lungs of premature infants causes
respiratory distress syndrome.
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c. Inositol (Inositide); the molecule is called
Phosphatidylinositol 4,5-bisphosphate.
 It is an important constituent of cell membrane
phospholipids.
 When stimulation by a suitable hormone agonist, it is
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cleaved into diacylglycerol (DAG) and inositol
triphosphate (IP3), both of which act as internal signals
or second messengers.
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3. Lysophospholipids:
 These are phosphoacylglycerols containing only one acyl
radical, eg, lysophosphatidylcholine (lysolecithin),
 Important in the metabolism and interconversion of
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phospholipids.
 It is also found in oxidized lipoproteins and has been
implicated in some of their effects in promoting
atherosclerosis.
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4. Plasmalogens:
 These compounds constitute as much as 10% of the
phospholipids of brain and muscle.
 Structurally, the plasmalogens resemble phosphatidyl-
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ethanolamine but possess an ether link on the sn-1 carbon

instead of the ester link found in acylglycerols.
 Typically, the alkyl radical is an unsaturated alcohol.
 In some instances, choline, serine, or inositol may be
substituted for ethanolamine.
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 Asst. Prof. Dr. Hassan H. Al-Saeed Biochemistry I
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B. Sphingolipids.
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 Sphingosine, fatty acid and glycoside.
 Component of a certain membrane.
1. General structure:
Sphingolipids; Also have a polar head group and two nonpolar
tails. They are composed of one molecule of the long-chain amino
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alcohol sphingosine (also called 4-sphingenine) or one of its
derivatives, one molecule of a long-chain fatty acid, and a polar
head group that is joined by a glycosidic linkage in some cases
and by a phosphodiester in others.
Carbons C-1, C-2, and C-3 of the sphingosine molecule are
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structurally analogous to the three carbons of glycerol in
glycerophospholipids.
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The X maybe;
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If X is; phosphocholine: the molecule is called sphingomyelin

that found in large quantities in brain and nerve tissue.
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 Asst. Prof. Dr. Hassan H. Al-Saeed Biochemistry I
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2. Glycolipids (glycosphingolipids):
 Glycolipids are widely distributed in every tissue, particularly in
nervous tissue such as brain.
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 They occur particularly in the outer leaflet of the plasma
membrane, where they contribute to cell surface
carbohydrates.
 The major glycolipids found in animal tissues are
glycosphingolipids.
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A. Glycosphingolipids:
They contain ceramide and one or more sugars.
The X sugar maybe;
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1. Galactosylceramide:
 It is a major glycosphingolipid of brain and other nervous
tissue.
 It contains a number of characteristic C24 fatty acids, eg,
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a) Kerasin: containing lignoceric acid and galactose.

b) Phrenosine or cerebron which contains hydroxy lignoceric
acid (cerebronic acid -OH group in C2) and galactose.
c) Nervon: which contains unsaturated lignoceric acid
(Nervonic acid) and galactose.
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 Asst. Prof. Dr. Hassan H. Al-Saeed Biochemistry I
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d) Hydroxy nervon which contains unsaturated hydroxy
lignoceric acid (hydroxyl nervonic acid) and galactose.
The four previous types of glycolipids are present in the white
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matter of cerebral hemispheres and in myelin sheaths of nerves.
 Galactosylceramide can be converted to
sulfogalactosylceramide (sulfatide), present in high amounts
in myelin.

2. Glucosylceramide:
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It is the predominant simple glycosphingolipid of
extraneural tissues, also occurring in the brain in small
amounts.
3. Gangliosides:
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 They are complex glycosphingolipids derived from
glucosylceramide that contain in addition one or more
molecules of a sialic acid.
 Neuraminic acid (NeuAc), is the principal sialic acid found
in human tissues.
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 Gangliosides are also present in nervous tissues in high
concentration.
 They appear to have receptor and other functions.
B. Galactolipids (Sulfolipids):
Predominant in plant cells. They contain two fatty acids
esterified to glycerol and one or two galactose residues are
connected by a glycosidic linkage to C-3 of a 1,2-diacylglycerol,
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but lack the characteristic phosphate of phospholipids.

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 Asst. Prof. Dr. Hassan H. Al-Saeed Biochemistry I
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3. Lipoproteins:
 They are a group of molecular complexes found in the blood
plasma of mammals.
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 Plasma lipoproteins transport lipid molecules
(Triacylglycerols, phospholipids, and cholesterol) through the
blood stream from one organ to another.
 The protein components of lipoproteins are called apo-
lipoproteins or apo-proteins.
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A. Lipoprotein particle contents.
1. Inner core – hydrophobic.
a. Cholesterol esters.
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b. Triglycerides.
2. Outer surface – amphipathic.
a. Amphipathic phospholipids.
b. Free cholesterol.
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c. Apoproteins.

B. Distribution of lipoproteins in
the body:
1. In tissue cells:
a. In cell membrane.
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b. In nucleus.
c. In mitochondria.
d. in microsomes.·
2. In certain oragans e.g.
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a. In the lung tissue: It is regarded as thromboplastic protein.

b. In the eye (layer of rods in the retina) rhodopsin is a lipoprotein.
c. In the blood: Most of the blood lipids are carried as lipoprotein
complexes.
- The lipid fraction in such complexes may be:
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Triglycerides, phospholipids, cholesterol (free or esterified),

Fat - soluble vitamins and steroid hormones.
- The protein fraction in such complexes may be:
α1-globulin and so the lipoprotein formed is called α-
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lipoproteins.

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 Asst. Prof. Dr. Hassan H. Al-Saeed Biochemistry I
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β1-globulin and so the lipoprotein formed is called β-
lipoproteins.
C.Comparison between α- lipoproteins and β-lipoproteins.
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α- lipoproteins β-lipoproteins
Carries 1/3 of total cholesterol in blood Carries 2/3 of total cholesterol in blood
Contains lower concentration of both
Contains higher concentration
free and esterified cholesterol
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Cholesterol: phospholipid ratio is lower Cholesterol: phospholipid ratio is higher

- The normal β to α ratio does not exceed 2.5 / 1.

- Any increase above this ratio. it indicates atherosclerosis.
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The α and β-lipoproteins are the 2 major types of lipoproteins.
D. Classification of lipoproteins; depends on their density;
Lipoproteins can be classified according to the rate of
floatation in sodium chloride solution using ultracentrifugation
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into 6 types:
1. Chylomicrons – large lipoproteins, low density, formed in
the mucosal cells of intestine, used in transport of dietary
triglycerides and cholesterol ester from intestine to tissues.

2. VLDL -Very low density lipoproteins (VLDL or pre β-lipoproteins).

synthesized in the liver, responsible for transport of lipids
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to the tissues, triglyceride rich.

3. IDL – triglycerides and cholesterol.

4. LDL – Low density lipoproteins (LDL or β -lipoproteins).they are

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products of VLDL, they carry cholesterol to the tissues to

be used for the synthesis of cell membranes, steroid
hormones, and bile salts.

Note: When the level of LDL exceeds the amount of cholesterol

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needed by the tissues, the LDLs deposit cholesterol to the arteries,

which can restrict blood flow and increase the risk of developing
heart disease and for myocardial infarctions (heart attacks).

This is why LDL cholesterol is called "bad" cholesterol.

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 Asst. Prof. Dr. Hassan H. Al-Saeed Biochemistry I
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5. HDL – High density lipoproteins (HDL or α -lipoproteins).produced in
the liver, remove excess cholesterol from the tissues and
carry it to the liver where it is converted to bile salts and
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eliminated.

Note: When HDL levels are high, cholesterol that is not needed by
the tissues is carried to the liver for elimination rather than
deposited in the arteries, which gives the HDLs the name of "good"
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cholesterol.

6. Free fatty acids attached to albumin (Alb. -FFA).

 The rate at which each lipoprotein floats may be expressed in
svedberg (Sv) units of floatation. The separation of the different
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lipoproteins by this method is based on the fact that as the
proportion of lipid to protein in lipoproteins increases, the density
decreases.
 Another method of separating the different lipoproteins is by
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electrophoresis.
 Triacylglycerol is the predominant lipid in chylomicrons and
VLDL. On the other hand, cholesterol and phospholipid are the
predominant lipids in LDL and HDL respectively.
 The protein content may be high in some types e.g. 60% in HDL,
99% in Alb. -FFA and as low as 1 % in chylomicrons.
.A

Because high cholesterol levels associated with the onset of

atherosclerosis and heart disease, the serum levels of LDL and
HDL are generally determined in a medical examination.
For adults, recommended levels for;
l-S

Total cholesterol< 200mg/dl.

LDL< 130 mg/dl.
HDL > 40 mg/dl.
A lower level of serum cholesterol decreases the risk of heart
disease.
ae

Higher HDL levels are found in people who exercise regularly and
eat less saturated fat.
E. The apolipoproteins or apoproteins:
 Lipoproteins are characterized by the presence of one or more
ed

of proteins known as apoproteins or apolipoproteins.

22
 Asst. Prof. Dr. Hassan H. Al-Saeed Biochemistry I
Dr
 There are 2 apoproteins of HDL are called A-I and A-II. Apo
protein-Al was found to act as activator of lecithin cholesterol
acyltransferase [LCAT].
.H
 Apoprotein B is the main apoprotein for LDL. It is also found in
VLDL and chylomicrons. Apo-B of chylomicrons [B-48] is
smaller than apo-B of LDL or VLDL and is called [B-100]. B -
48 is formed in the intestine while B-100 is formed in the liver.
apo-B is one of the some lipoproteins containing sugar such
as
as mannose, galactose, fucose , glucose, glucosamine and
sialic acid.
 Another Apoproteins C-I, C-II and C-III are smaller
polypeptides found in VLDL, HDL and chlomicrons. C-
sa
apoproteins can be transferred between VLDL and
chylomicrons on one hand and HDL on the other hand. C-II is
an important activator of lipoprotein lipase clearing
triacylglycerol from circulation. Apoprotein C-I is also a
nH
possible activator of lecithin cholesterol acyltransferase
[LCAT].
 Apoprotein-E. isolated from VLDL is very rich in arginine [10%
of total amino acids].

VII.Precursor and derived lipids:

.A

1. Terpenes:
 The terpenes are a class of lipids formed from combinations
of two or more molecules of 2-methyl-1,3-butadiene, better
known as isoprene (abbreviated C5).
l-S
ae

 Isoprene units can be linked in terpenes to form straight

chain or cyclic molecules, and the usual method of linking
isoprene units is head to tail.
ed

23
 Asst. Prof. Dr. Hassan H. Al-Saeed Biochemistry I
Dr
 Monoterpene (C10) consists of two isoprene units that occur
in all higher plants.
 Diterpene (C20) has four isoprene units, and so on.
.H
 Triterpenes are C30 terpenes and include squalene and
lanosterol, two of the precursors of cholesterol and other
steroids

2. Steroids:
 A cyclic compound of animal or plant origin, the basic
as
nucleus of which consists of three 6-membered rings
resembling phenanthrene (rings A, B, and C) and one 5-
membered ring (ring D), fused together to yield
perhydrocyclopentanophenanthrene.
sa
 The steroids represent a wide variety of compounds,
including sterols, bile acids, adrenocortical hormones,
and sex hormones.
nH
.A

A.Sterol: A steroid in which an alcoholic hydroxyl group is

attached to position 3, and an aliphatic side chain of eight or
more carbon atoms is attached to position 17 of the steroid
nucleus; a steroid alcohol.
l-S

1. Cholesterol:
 Is one of the most important and abundant steroids in the
body.
 Steroid is based on a core structure of sterol.
ae

 It was first isolated from gallstones.

 Rich sources of cholesterol are; brain, nervous tissues,
adrenal glands, egg yolk.
 It has a molecular formula (C27H45OH).
ed

24
 Asst. Prof. Dr. Hassan H. Al-Saeed Biochemistry I
Dr
.H
a. Roles of cholesterol in mammals:
as
1. Structural component of plasma membrane and modulates
membrane fluidity.
2. Precursor of steroid hormones and bile acids.

b. Properties of cholesterol:
sa
1. It is present in blood to the extent 150-250mg/L.
2. Cholesterol is a white crystalline substance showing the
usual solubility properties of the lipids.
3. It has a melting point of 149o.
nH
4. It is usually prepared in laboratory by extraction from brain
or spinal cord with acetone.
5. It is a poor conductor of electricity and functions probably as
an insulating mechanism for the nerve impulses.
6. Cholesterol is considered as a precursor of bile salts,
steroid hormones, and vitamin D3.
.A

c. Cholesterol in the body:

1. Cholesterol is a component of a cell membranes, myelin
sheath, brain, and nerve tissue.
2. It is also found in the liver, bile salts, and skin, where it
forms vitamin D.
l-S

3. It is used to synthesize steroid hormones in the adrenal

gland.
4. Most of the cholesterol in the body is synthesized in the liver
from fats, carbohydrate, and proteins, although some
comes from the diet (meats, milk, and eggs). However, a
ae

person on a high- fat diet reabsorbs cholesterol from the

bile salts causing less cholesterol to be eliminated.
5. In addition, higher levels of saturated fats stimulate the
synthesis of cholesterol by the liver.
ed

6. There is no cholesterol in vegetable and plant products.

25
 Asst. Prof. Dr. Hassan H. Al-Saeed Biochemistry I
Dr
d. Cholesterol levels:
1. If the diet is high in cholesterol, the liver produces less.
2. A typical daily American diet includes 400-500mg of
.H
cholesterol, one of the highest in the world.
3. The American heart Association has recommended that we
consume no more than 300 mg of cholesterol of a day.
4. When cholesterol exceeds its saturation level in the bile,
gallstone may be form.
5. Gallstones are composed of almost 100% cholesterol with
as
some calcium salts, fatty acids, and phospholipids.
6. High levels of cholesterol are also associated with the
accumulation of lipid deposit (plaque) that line and narrow
the coronary arteries.
7. Clinically, cholesterol levels are considered elevated if the
sa
total plasma cholesterol level exceeds 200-220 mg/dl.
8. Some research indicates that saturated fats in the diet may
stimulate the production of cholesterol by the liver.
9. A diet that is low in foods containing cholesterol and
nH
saturated fats appears to be helpful in reducing the serum
cholesterol level.
10. Other factors that may also increase the risk of heart
disease are;
 Family history.
 Lack of exercise.
 Smoking.
.A

 Obesity.
 Diabetes.
 Gender.
 Age.
2. Ergosterol
l-S

 Ergosterol occurs in plants and yeast and is important as a

precursor of vitamin D.
ae
ed

 When irradiated with ultraviolet light, it acquires antirachitic

properties consequent to the opening of ring B.
26
 Asst. Prof. Dr. Hassan H. Al-Saeed Biochemistry I
Dr
B.Bile salts:
 The bile salts are synthesized in the liver from cholesterol
and stored in the gallbladder.
.H
 When bile is secreted into the small intestine, the bile salts
mix with the water-insoluble fats and oils in our diets.
 The bile salts act like soap, breaking apart and emulsifying
large globules of fat.
 The emulsions that form have a large surface area for the
as
lipases, enzymes that digest fat.
 The bile salts also help in the absorption of cholesterol into
the intestinal mucosa.
 If large amounts of cholesterol accumulate in the gallbladder,
cholesterol can precipitate out and form gallstones.
sa
 If gallstones pass into the bile duct, the pain can be severe.
 If the gallstone obstructs the duct, bile cannot be excreted.
 Then bile pigments known as bilirubin enter the blood where
they cause jaundice, which gives a yellow color to the skin
nH
and eyes.
VIII. Biological membranes:
The major function of phosphorus-containing lipids in living
systems is to form biological membranes.

1. The biological membrane functions: Indispensable of life.

 Barriers the separates living systems into various regions.
.A

 Membrane separate cells from their surroundings.

 Semi permeable.
 Control the flow of information.

2. Properties of biological membranes:

l-S

 Most membranes contain 40% lipids and 60% proteins, but

there is considerable variation in these amounts, depending
on the particular cell.
 Certain molecules can pass through selective membrane,
e.g. the nutrients of a cell and its waste product pass through
the membranes. Other compounds are not allowed to pass.
ae

 A semi permeable membrane is a membrane that is highly

selective for the kinds of molecules or ions that is allows
passing.
 Membranes control the flow of information between cells and
ed

their surroundings, by specific receptors that are contain

within the membranes. These receptors are compounds
27
 Asst. Prof. Dr. Hassan H. Al-Saeed Biochemistry I
Dr
usually proteins that undergo specific reaction. For example,
the response of a particular cell to insulin, in a chemical
reaction with a specific receptor molecule in the membrane.
.H
 Another chemical reaction can also occurs in membranes is
photosynthesis.

3. Structure of biological membranes:

Phosphorus-containing lipids form membranes because they all
possess an important common structural feature;
as
A. A polar head and a non-polar tail:
 The non-polar hydrocarbon tail is called hydrophobic (water-
repelling) part.
 The polar head (carboxylic end) is called hydrophilic (water-
sa
loving) part.
 When these lipids are placed in water, only a small fraction
dissolves to form a true solution. The rest form micelles.
 These are aggregates of lipids in which the hydrocarbon tails
gather together to avoid the aqueous solution. In this way,
nH
they form a hydrophobic region in the center of micelle.
.A
l-S
ae
ed

28
 Asst. Prof. Dr. Hassan H. Al-Saeed Biochemistry I
Dr
B. Protein components:
 Biological membranes also contain proteins that are located
either completely or partially in the hydrophobic region of the
.H
bimolecular sheets.
 These proteins carry out the various functions of membrane.
 It is believed that each type of protein has a specific function.
 Some transport ions or molecules across the membrane.
as
 Other act as receptor sites for specific molecules that carry
messages to the cell.
 It is known that proteins carry out the functions of the
membranes, but scientist don't know in detail how they do it.
sa
4. Transport across membranes:
nH
.A
l-S
ae
ed

29