Lipids

By/ Ibraheem Al-nawd

BSc. Medical Laboratory
MSc. Clinical Biochemistry
I. Introduction to lipids:
A. Definitions:
1. Lipids are a heterogeneous
group of compound related to
fatty acids.
2. Lipids are relatively insoluble
in water.
3. They are soluble in nonpolar
solvents such as ether, chloroform or benzene.
B. The hydrophobic (water-hating) nature of lipids is
due to the predominance of hydrocarbon chains (-CH2-
CH2-CH2-) in their structure.
C. Classification: lipids are classified into simple,
complex (compound) and derived lipids:
1. Simple lipids: are esters of fatty acids with various
alcohols.
(Ester bond = -COO-). They are either fats or waxes.

a) Fats: are esters of fatty acids with glycerol (Acylglycerols).

b) Waxes: are esters of fatty acids with higher alcohols.

2. Complex (compound) lipids: are esters of fatty acids
with alcohol in addition to other groups. They include:
a) Phospholipids: They contain phosphate. They
include:
1) Glycerophospholipids: the alcohol is glycerol.
2) Sphingophospholipids: the alcohol is sphingosine.
b) Glycolipids : They contain carbohydrate:
c) Lipoproteins: They consist of lipids conjugated with
proteins.
3. Derived and precursor lipids: which include:
a) Substances which are given by hydrolysis of
simple and complex lipids e.g. fatty acids and
alcohols.
b) Substances which are insoluble in water but
soluble in nonpolar solvents as:
1) Steroids.
2) Carotenoids.
3) Cholanthrenes.
4) Ketone bodies.
5) Fat soluble vitamins
D. Functions (biomedical importance):
1. In diet: Lipids are important constituent of diet due to:
a) They are a source of high energy value.
b) They contain fat soluble vitamins.
c) They contain essential fatty acids.
d) They make diet palatable.
2. In the body:
a) Lipids in adipose tissue serve as storage form of energy.
b) They serve as thermal insulator in the subcutaneous tissues.
c) Nonpolar lipids act as electrical insulator, allowing rapid
propagation of waves along myelinated nerves.
d) Lipoproteins (a combination of fat and proteins) are important
because :
1) They enter in the structure of cell membranes.
2) They serve as a transport form of energy in the blood.
E. Neutral lipids: are those which carry no charges and include:
1. Neutral fats (acylglycerols).
2. Cholesterol and cholesteryl esters.
• Chemistry of fatty acids, alcohols and simple lipids
Fatty acids: R.COOH
I. Introduction:
A. Fatty acids are water-insoluble long chain hydrocarbons.
B. Fatty acids may be saturated (containing no double bonds) or
unsaturated (containing one or more double bonds).
C. They are mostly monocarboxylic i.e. having one carboxyl
group at the end of the chain (-COOH).
D. They are mostly aliphatic (i.e. not branched). A few branched
chain fatty acids are present in animals and plants.
E. Fatty acids occur mainly as esters in natural fats and oils.
F. Fatty acids may also present as free fatty acids in the plasma.
II. Saturated fatty acids:
A. Have no double bonds in the chain.
B. Their general formula is CH3-(CH2)n-COOH where (n)
equals the number of methylene (-CH2 ) groups between the
methyl and carboxylic groups.
C. The systemic name of saturated fatty acids ends by the
suffix (-anoic) e.g. palmitic acid (16C) has systemic name
hexadecanoic acid (Hexa =6, Deca =10).
D. Example of the formula of some saturated fatty acids:
1. Butyric acid (4C) = CH3 - CH2 - CH2 -COOH.
2. Caproic acid (6C) = CH3- CH2- CH2- CH2- CH2- COOH.
3. Palmitic acid (16C) = CH3- (CH2)14- COOH.
4. Stearic acid (18C) = CH3- (CH2)16- COOH.
E. Numbering of carbon atoms: Many methods are used to
number the carbon atoms e.g. palmitic acid.

1. Counting starting from carboxylic (-COOH) group = carbon

No.1 is that of carboxylic group, carbon No. 2 is the carbon
adjacent to the carboxyl carbon and so on.
2. Counting from carbon adjacent to carboxyl carbon i.e.
carbon No.2: carbons may be numbered as α, β, γ and so on.
3. Counting from last methyl carbon (CH3) which is called
omega carbon (Ѡ). The carbon adjacent to it is carbon No.2
and so on.
III. Unsaturated fatty acids:
A. The general formula is Cn- H2n-1 -COOH.
B. The systemic name of unsaturated fatty acids ends by the suffix
(-enoic) e.g. oleic acid (18 carbons) has systemic name
octadecenoic acids (Octa = 8, Deca = 10).
• System of numbering and position of double bonds:
a- Numbering of carbon atoms; same as in saturated fatty acids.
b- Position of double bonds; The most commonly used systems
for designating the position of double bonds in unsaturated fatty
acids are:
(1) The delta (∆) numbering system e.g. palmitoleic acid, C 16: 1
∆9 means that this acid contains 16 carbons (16) and one double
bond (1) and the position of double bond is between carbon
number 9 and carbon number 10 starting from carboxyl carbon 1.
(2) Omega (Ѡ) system e.g. the palmitoleic acid may be written as: C
16:1 ,Ѡ7 which indicates a double bond on seventh carbon counting
from the Ѡ-Carbon atom i.e. last –CH3 carbon.
Cis and trans double bonds: Double bonds in naturally occurring fatty
acids in mammals are always in a cis form (configuration) not as trans
form: polyunsaturated acids:
a) Cis form means that the groups are on the same side.
b) Trans form means that the groups are on the opposite sides.
Trans fatty acid may be present in certain foods, during hydrogenation
of oils to manufacture margarine.
C. Unsaturated fatty acids are either
monounsaturated or polyunsaturated acids:
1. Monounsaturated (monothenoic, monoenoic) fatty acids i.e.
contain one double bond e.g. palmitoleic (16:1 ∆9) and oleic acid
(18:1 ∆9).
IV. Branched-chain fatty acids:
Almost all fatty acids present in mammalian tissues are aliphatic i.e. straight
chain. However, branched-chain fatty acids are found in nature.
A. phytanic acid (18C): Some milk products contain branched chain fatty acid
called phytanic acid (18C). It contains 4 methyl groups at position 3, 7, 11
and 15 carbons.
B. Refsum's disease:
1. It is caused by inability of oxidation of phytanic acid. This leads to its
accumulation in plasma and tissues.
2. Manifestations: nervous tissue damage in the form of blindness and
deafness.
V. Essential and nonessential fatty acids:
A. Non-essontial fatty acids:
1. These are fatty acids which can be synthesized in the body. Thus they
are not necessary to be obtained from the diet.
2. They include all saturated and monounsaturated (one double bond) fatty
acids as palmitoleic and oleic acid.
3. They can be synthesized from acetyl CoA (active acetate) derived from
glucose oxidation.
B. Essential fatty acids:
1. Definition:
a) These are fatty acids that cannot be synthesized in the body.
They must be obtained from the diet.
b) They include fatty acids that contain more than one double
bond (polyunsaturated fatty acids), e.g. lenoleic, lenolenic
and arachidonic acids.
c) A type of essential fatty acids are Ѡ-3 fatty acids (omega-3
fatty acids) which are a family of unsaturated fatty acids that
have double bond in the Ѡ -3 position; that is, the third bond
from the methyl end of the fatty acid. Examples of Ѡ-3 fatty
acids include linolenic acid and arachidonic acids.
d) The human body has enzyme system that can form only one
double bond at the ninth carbon atom (∆ 9).
2. Sources:
a) Plant oils e.g. corn oil, soya bean oil, safflower oils, sunflower,
linseed oil and cotton seed oil.
b) Fish oils: shark liver oils, which particularly contain the Ѡ3
polyunsaturated fatty acids.
3. Importance (functions): Essential fatty acids are important for:
a) Normal growth.
b) They enter in the structure of phospholipids and cholesterol
esters.
c) They enter in the structure of cell membranes and are required
for the fluidity of membrane structure.
d) They protect against atherosclerosis and coronary heart
disease (CHD) by decreasing free cholesterol and LDL.
e) Arachidonic acid (20C) is a precursor of a group of compounds
called: eicosanoids.
VI. Properties of fatty acids:
A. Physical properties:
1. Solubility :
a) Short chain fatty acids e.g. acetic (2C), butyric (4C) and
caproic (6C) are soluble in water.
b) Long chain fatty acids are insoluble in water but soluble in
nonpolar fat solvents.
2. Melting point : It depends on the length of the chain of
fatty acids and the degree of unsaturation, so :
a) Short chain and unsaturated fatty acids are liquid at room
temperature.
b) Long chain saturated fatty acids are solid at room
temperature.
B. Chemical properties:
1. Hydrogenation, halogenation and oxidation: These are

2. Salt formation (soap): Fatty acids form soap (salts) with alkalies as NaOH,
KOH, Ca(OH)2:
R-COOH + NaOH → R-COONa + H2O
Fatty acid Sodium hydroxide Sodium salt
3. Ester formation:
a) Fatty acids form esters (R.COO.R) with alcohols:
R-COOH + R1-OH → R-COOR1 + H2O
1) Esters of fatty acids with glycerol → Neutral fats (Acylglycerols).
2) Esters of fatty acids with higher alcohols → waxes
VII. Eicosanoids:
A. Definition: These are cyclic compounds that derived from arachidonic acid
(eicosatetraenoic) (20 C) after cyclization of its carbons chain to form a ring.
B. Components of eicosanoids:
1. Prostanoids:
which comprise prostaglandins, prostacyclins and
thromboxanes:
a) Prostaglandins (PG):
1) (A, B, D, E, F, H, G and I).
2) They have hormonal like action.
3) They cause vasodilatation, contraction of the uterus
and intestine.
b) Prostacyclines:
They cause vasodilatation and inhibit platelets
aggregation.
c) Thromboxane:
They cause aggregation of platelets.
2. Leukotriens (LT):
a) They are present in leucocytes, platelets and
mast cells.
b) They cause chemotaxis i.e. Collection of
white blood cells at the site of inflammation.
Alcohols: R.OH
I. Introduction: Alcohols associated with lipids include glycerol, cholesterol
and higher alcohols (e.g. cetyl alcohol, C16H33OH) usually found in the wax.
II. Glycerol: It is polyhydric alcohol containing 3 (-OH) groups:
A. Properties:
1. Glycerol is colorless, odorless, hygroscopic and has sweet taste.
2. It is soluble in water and alcohol, insoluble in nonpolar solvents.
3. It combines with one fatty acid to form monoacylglycerol, two fatty acids
to form diacylglycerols and three fatty acids to form triacylglycerols. This
combination is through ester linkage.
4. Acrolein: It is an aldehyde with a substance characteristic odour. It derives
from glycerol by losing 2 water molecules.

B. Uses of glycerol:
1. Nitroglycerol is used - as a drug - for dilatation of coronary artery.
2. Glycerol enters in manufacturing of creams and lotions for dry skin.
III. Cholesterol: is an alcohol and derived lipids (will be studied later).
IV. Higher alcohol: They contain one (-OH) group i.e. monohydric alcohols.
Simple lipids:
I. Introduction:
A. They are called simple because they are formed only
from alcohols and fatty acids. There are two classes of
simple lipids (according to the type of alcohol):
acylglycerols and waxes.
Acylglycerols are esters of one, two or three fatty acids
with glycerol.
B. Numbering of carbons of glycerol is either: α, β and γ
or 1, 2 and 3. Notice that carbon 1 and 3 of glycerol in
triacylglycerols are not identical when viewed in 3
dimensions. Enzymes can differentiate between the two
positions.
II. Triacylglycerols (triglycerides):
A. They are called neutral fat because they carry no charge.
B. Body triacylglycerols:
1. Location: They are stored mainly in cytoplasm of adipose
tissue cells (which is located subcutaneously and around kidney
and other organs).
2. Body fat is important source of energy. Each gram fat gives
9.3 kcal.
3. Human fat is liquid at room temperature and contains high
contents of oleic acid.
C. Dietary sources of triacylglycerols:
1. In animals e.g. butter and lards.
2. In plants e.g. cotton seed oil, linseed oil, sesame oil and olive
oil.
3. Marine oils e.g. cod liver oil and shark liver oil.
 D. Types of triacylglycerols: simple or mixed.
1. Simple triacylglycerols: similar 3 fatty acids are attached to glycerol.

2. Mixed triacylglycerols: 3 different fatty acids are attached to glycerol.

E. Properties of triacylglycerols:
1. Physical properties:
a) Solubility: All triacylglycerols are insoluble in water, soluble in fat
solvents.
b) Melting point:
1) Triacylglycerols rich in unsaturated fatty acids are liquid at room
temperature. They are called oils.
2) Triacylglycerols rich in saturated fatty acids are solid at room
temperature. They are called fats.
c) Specific gravity: It is less than one. Specific gravity of water is one.
Therefore, triacylglycerols float on the surface of water.
d) Grease stain test: All Triacylglycerols give positive grease stain test.
2. Chemical properties:
a) Acroline test: All triacylglycerols contain glycerol. So all give
positive acroline test.
b) Hydrolysis: Lipase enzymes present in digestive and other
systems can hydrolyze triacylglycerols into fatty acids and
glycerol. (Note: hydrolysis means breakdown of substance by
addition of water).
c) Saponification: Alkalies as NaOH and KOH can react with
triacylglycerols breaking them into glycerol and salts of fatty
acids. These salts are called soaps and the process is called:
saponification. Soaps cause emulsification of oily material
(i.e. breaking down large fat particles into small ones). This
helps easy washing the fatty materials away.
 d) Halogination: This depends on the presence of
unsaturated fatty acids in the triacylglycerol
molecules.

e) Hydrogenation: This also depends on the presence

of unsaturated fatty acids in the molecules.
Hydrogen is usually added at high temperature in the
presence of nickel as a catalyst. This reaction is the
base of conversion of oils into margarine (Harding of
oils).
f) Oxidation = Rancidity:
1. Definition: It is a toxic reaction of triacylglycerols. It is due
to oxidation of its unsaturated fatty acids content by oxygen
of the air, bacteria or moisture. It leads to unpleasant odor or
taste of oils and fats.
2. Types of rancidity:
a. Oxidative rancidity: Fatty acids are oxidized at double
bonds giving peroxide.

b. Ketonic rancidity: Produces aldehyde and ketone with

characteristic taste:
c. Hydrolytic rancidity: triacylglycerols are hydrolyzed by bacterial enzymes
into glycerol and fatty acids. The free fatty acids can then undergo further
auto-oxidation with a free radicals.

3. Enhancement of rancidity: This can be done by certain substances as:

a) Free radicals as reactive oxygen species.
b) Lead or copper.
c) Heme compounds.
d) The enzyme: lipooxygenase found in platelets.
4. Detection of rancidity: By copper acetate test that detects the free
hydrolyzed fatty acids.
5. Prevention of rancidity: The addition of antioxidant delays or prevents the
process of rancidity. Examples of antioxidants are:
a) Vitamins: as vitamins E and C.
b) Substances containing -SH group, e.g. cysteine amino acid.
c) Avoidance of oxygen of the air, bacteria or moisture.
III. Waxes: These are esters of fatty acids with long chain alcohol other than
glycerol. These alcohols contain one (-OH) group, i.e., monohydric alcohols
e.g. bee wax.
A. Sources: Waxes are excreted extracellularly in some plants and animals
and has a protective function as in:
1. Bee wax.
2. Sebaceous secretions.
3. Cuticles of leaves.
B. Properties:
1. They have the same physical properties as fat.
2. They give negative acrolein test because they contain no glycerol.
3. They are not digested by lipase enzyme. Thus they are not utilized by the
body.
4. They are solids at room temperature.
Complex (compound) lipids
I. Introduction: These include phospholipids, glycolipids,
lipoproteins, sulpholipids and aminolipids.
A. Phospholipids: They contain phosphoric acid residues. They are
classified into glycerophospholipids (contain glycerol) and
sphingophospholipids (contain sphingosine).
Phospholipids include:
1. Phosphatidic acid (diacylglycerolphosphate):
a) Structure: Glycerol + Saturated fatty acid (attached to 1 (α)
position), Unsaturated fatty acid (attached to 2 (β) position) +
phosphoric acid residue at position 3(γ).
b) Function: It has no function. It is produced as an intermediate
in the synthesis of triacylglycerols and phospholipids.
2. Cardiolipin (diphosphatidylglycerol):
a) Structure: It is formed of two phosphatidic acids linked together
by glycerol.
b) Function:
1) Cardiolipin is the major lipid in mitochondrial membrane.
2) It stimulates antibody formation i.e. antigenic.
3. Lecithin (phosphatiyl choline):
a) Structure:
1) Glycerol.
2) Saturated fatty acid (attached to 1 (α) position.
3) Unsaturated fatty acid (attached to 2 (β) position.
4) Phosphoric acid (attached to 3(γ) position.
5) Choline base (attached to phosphoric acid).
b) Functions:
1) Lecithin enters in the structure of cell membrane. It is the most
abundant phospholipid in cell membrane.
2) Lecithin acts as lipotropic factor i.e. prevent accumulation of fat
in liver (fatty liver).
3) Lecithin forms cholesterol esters: Lecithin reacts with
cholesterol, giving cholesterol ester and lyso-lecithin in the
presence of LCAT enzyme (lecithin cholesterol acyl transferase).
Cholesterol esters is transported to the liver and excreted with
bile. This prevents atherosclerosis.
4) Lecithin acts as body store of choline. Choline is important for:
I- Nerve transmission.
II- Transmethylation: It acts as methyl donor in transmethylation reaction.
5) Lecithin prevents gall stones: lecithin in bile solubilizes cholesterol and
prevent cholesterol stones in gall bladder.
6) Dipalmityl lecithin (i.e. lecithin which contains 2 palmitic acid residues)
acts as a surfactant in the lung.
i- Dipalmityl lecithin is continuously secreted by the lung cells in the
alveolar wall, forming a monolayer over the watery surface of the alveolus
and so lowers the surface tension. This helps expiration and inspiration.
• During expiration, the surfactant becomes solid under pressure. This
prevents the adherence of alveolar wall.
• During inspiration, the surfactant makes the lung easier to expand.
ii- Respiratory distress syndrome (hyaline membrane disease):
• In premature babies, lungs do not secrete enough surfactant. This leads
to lung collapse and death from respiratory failure. Treatment: putting the
premature babies in incubator and administration of surfactant in the lung.
4. Cephalin (phosphatidyl ethanolamine):
a) Structure: Like lecithin but it contains ethanolamine instead of choline.
b) Function: It is one of activating factors of coagulation mechanism.
5. Lysophospholipids (lysolecithin and lysocephalin):
a) Structure: Like lecithin and cephalin, but contains only one fatty acid in
position 1 (α).
b) Functions:
1) Lysolecithin is important in the metabolism and inter-conversion of
phospholipids.
2) Lycocephalin is strong surface-active substance. It is used in manufacturing
most types of chocolates.
6. Phosphatidylserine:
a) Structure: like lecithin but it contains serine instead of choline.
(Notice that phospholipids containing threonine are also present).
7. Lipositol (phosphatidylinositol):
a) Structure: Like lecithin but it contains inositol instead of choline.
b) Function: It is present in cell membrane. It acts as precursor of second
messenger (inositol triphosphate), mediating hormonal action inside cells.
8. Plasmalogens:
a) Structure: Like lecithin but it contains unsaturated alcohol attached to
glycerol at position 1 (α) by other linkage instead of unsaturated fatty acid.
b) Function: They constitute about 10% of the phospholipids present in brain
and muscles.
9. Sphingomyelins:
a) Structure:
1) Sphingosine.
2) Fatty acid (attached to amino group at position 2(β).
3) Phosphoric acid residue (attached to 3 (γ) position).
4) Choline base (attached to phosphoric acid).
b) Function: It is present in high concentrations in brain and nerve tissue.
c) Niemann Pick's disease:
1) It is accumulation of large amounts of sphingomyelin in liver due to
deficiency of sphingomyelinase enzyme.
2) It leads to mental retardation and death in early life.
10. Ceramide: It is not a phospholipid, but found in glycosphingolipids.
a) Structure: Sphingosine + fatty acid (usually polyunsaturated).
B. Glycolipids:
These are complex lipids containing carbohydrate.
They also contain sphingosine (therefore, glycolipids
together with sphingomyelin may be classified as
sphingolipids). Glycolipids include cerebrosides,
ganglioside, ceramide oligosaccharides and sulpholipids.
1 . Cerebrosides: They are called simple glycolipids.
a) Upon hydrolysis ,they give:
1) Sphingosine.
2) Fatty acid.
3) Sugar (usually galactose or glucose).
b) According to the type of fatty acid, they may be classified into:
1) Kerasin: The fatty acid is lignoceric acid (C24: saturated).
2) Narvon: The fatty acid is nervonic acid (C24- unsaturated ,Ѡ9).
3) Oxynervon: The fatty acid is
oxynervonic acid (hydroxy nervonic acid).
4) Cerebron: The fatty acid is cerebronic
acid (C24-hydroxy saturated).
c) Functions of cerebrosides:
1) Cerebrosides are present in many tissues especially in the
brain and myelin of nerve fibres.
2) They act as insulators of nerve impulse.

d) Gaucher’s disease:
1) Accumulation of cerebrosides (sphingolipids) in phagocytes due to
deficiency of β glucocerebrosidase enzyme.
2) Manifestations: mental retardation, hepatomegaly and bone
disorders.
2. Sulpholipids (sulphatides): are cerebrosides containing sulphate
group (attached to sugar).
3. Gangliosides: They are called complex glycolipids, because they
contain in addition to hexose, one or more sialic acid molecules.
a) Upon hydrolysis they give:
1) Ceramide (sphingosine and fatty acid).
2) Hexoses (glucose and galactose).
3) Hexosamines:
• Sialic acid (N-acetylneuraminic
acid).
• N-acetylgalactosamine.
b) Functions of gangliosides:
1) They act as receptors at cell membrane.
2) They are present in high concentration in brain.
c) Degradation: By hexosaminidase enzyme.
d) Tay sachs disease:
1) Accumulation of gangliosides in brain and intestine
due to deficiency of hexosaminidase enzyme.
2) Manifestations: mental retardation, hepatomegaly,
blindness and death in early life.
4. Ceramide oligosaccharides: They contain sphingosine
base, fatty acid (C24) and many glucose and galactose
units. They are present in heart and kidney.
C. Lipoproteins: These are complex lipids formed of lipids
conjugated with protein.
1 . They are present in cell membrane, mitochondria and
plasma (plasma lipoproteins).
2. Plasma lipoproteins convert water insoluble lipids into water
soluble complexes. This facilitates transport of lipids between
blood and different tissues.
3. The plasma lipids (360 - 820 mg/dl) are triacylglycerols,
phospholipids, cholesterol (free and esterified) and free fatty
acids.
4 . Methods used for separation of plasma lipids:
These methods include electrophoresis , ultracentrifugation, gas
liquid chromatography and thin layer chromatography:
a) By electrophoresis, plasma lipoproteins can be separated into
chylomicrons, β-lipoproteins, pre-β- lipoproteins and α-lipoproteins.
b) By ultracentrifugation, plasma lipoproteins can be separated into
chylomicrons , VLDL, LDL and HDL.
5. The protein fractions are called apolipoproteins. They include
apolipoproteins A, B48 , B100, C, D and E. All are globulins.
Derived lipids B. The ring is characterized by
I. Substances which are insoluble in the presence of the following
water but soluble in nonpolar solvents. atoms or groups:
They include: 1. At C3: oxygen in the form of
1. Steroids and sterols.
hydroxy (-OH) or ketone (=O)
group.
2. Carotenoids
2. At C17: Side chain.
3. Cholanthrenes 3. At C10 and C13: Methyl
4. Ketone bodies. groups.
5. Fatty aldehydes. 4. Steroids and sterols differ
II. Steroids and sterols: from each other in the nature
of side chain (at C11).
A. These are a group of compounds that
contain ring called cyclopentano-
perhydrophenanthrene ring.
III. Types of steroids and sterols are:
 A. Cholesterol:
1. Structure: It contains:
a) Cyclopentano-perhydrophenanthrene ring.
b) -OH group at C3 (so it is an alcohol).
c) 2 methyl groups at C10 & C13 (-CH3 = 1).
d) Long side chain at C17.
2. Body cholesterol:
a) It is present in every body cell (cell membrane) especially in:
1) Adrenal cortex.
2) Gonads.
3) Liver and kidney.
4) Brain and nerve tissue.
b) Blood cholesterol:
1) It occurs in the blood in 2 forms: free form
and esterified form (combined to fatty acids
to form ester).
2) The level of blood cholesterol is normally
less than 220 mg/dl. Any increase above this
level is called: hypercholesterolemia.
3. Properties:
a) It is an alcohol, insoluble in water, soluble in fat solvents.
b) It forms characteristic crystals with broken corner.
c) It gives positive Lieberman's test, which runs as follows:
Cholesterol + Acetic acid + cone. sulphuric acid → Bluish green
color.
d) It is present only in animals and not in plants.
4. Functions of cholesterol: It is important for:
a) It enters in the structure of every body cell particularly:
1) Cell membranes.
2) In nervous tissue.
b) Synthesis of steroid hormones.
c) Synthesis of bile salts.
d) Synthesis of vitamin D3.
5. Coprastanol (coprosterol): Some cholesterol is synthesized in the
intestine and reduced by intestinal bacteria into coprastanol before
excretion (by reduction of double bond of cholesterol between C5
and C6).
B. Ergosterol:
1. Structure: Similar to cholesterol but differs in:
a) Extra double bond between C7, C8.
b) The side chain is unsaturated and has extra methyl group.
2. Properties: It is a plant sterol, poorly absorbed from small intestine.
3. Functions: It gives vitamin D2 by ultraviolet rays.
C. Vitamin D group:
1. Structure:
a) Vitamin D3 is derived from 7-dehydrocholesterol by the rupture of second
ring by ultraviolet rays.
b) Vitamin D2 is derived
from ergosterol by the
rupture of second ring by
ultraviolet rays.
2. Functions: will be
studied in vitamins.
D. Bile acids and salts: Bile acids are hydroxyl derivatives of
C24 steroid termed cholanic acid.
1. Types of bile acids:
1. Types of bile acids:
a) Primary bile acids: these are formed in the liver from
cholesterol and include cholic acid (3, 7,12 trihydroxy cholanic
Acid) and chenodeoxy cholic acid (3, 7 dihydroxy cholanic acid).
b) Secondary bile acids (no -OH at C7): These are formed by
the action of intestinal bacteria that contain 7 α dehydroxylase
which removes the hydroxyl group at C7, with production of 2
types of secondary bile acids : deoxycholic acid (3, 12 dihydroxy
cholanic acid) and lithocholic acid (3 monohydroxy cholanic acid).

2. Bile salts are bile acids (=cholic acid) conjugated with glycine
(80%) and taurine (20%), they are excreted by liver in bile as
sodium salts e.g. sodium glycocholate and sodium taurocholate.
Bile salts pass to the intestine where they are reabsorbed and
return back to the liver to be excreted again in bile (enterohepatic
circulation of bile salt).
3. Function: Bile salts are amphipathic and important for digestion
and absorption of lipids:
a) Digestion of lipids: by emulsification of fat in the intestine and
activation of lipase enzyme.
b) Absorption of lipids: by forming micelles.
c) Excretion of cholesterol: Half of cholesterol is excreted after
its conversion into bile salts.
d) Choleretic effect: i.e. bile salts stimulate liver cells to secret
more bile.
e) Prevent formation of cholesterol stones by keeping
cholesterol in soluble state.
E. Hormones of steroid nature:
1. Female sex hormones:
a) Estrogens: There are 3 types: estrone (E1), estradiol
(E2) and estriol (E3). E2 is the most active member.
1) Structure:
i- Hydoxyl group at C3.
ii- Ring A is unsaturated.
iii- Methyl group at C13
iv- Ketone group at C17 (E1 ), hydroxyl group at C17 (E2)
and 2 hydroxyl groups at C16 & C17 (E3).
2) Synthesis: From cholesterol.

3) Site of production:
i- Mainly: ovary and placenta in female.
ii- Minor amounts:
• Adrenal cortex in both male and female.
• Testes in males.
4) Functions:
I- They stimulate the development of female secondary sex characters
and organs e.g. voice, distribution of hair, distribution of fat, ...etc.
II- They stimulate the development of female sex organs e.g. uterus.
III- E2 has anabolic effect on bone and cartilages.
5) Contraception: synthetic estrogens can be used as contraceptives.
6) Fate: End product E3 are produced in the liver and conjugated with
sulphuric acid and glucuronic acid and then excreted in the urine.
b) Progesterone:
1) Structure:
i- Ketone group at C3.
ii- Double bond between C4 and C5.
iii· Methyl group at C10 & C13.
iv- Methyl ketone at C17.
2) Site of production:
i- Ovary and placenta in female.
ii- Adrenal cortex in both male and female.
3) Functions of progesterone:
i- It prepares the uterus for implantation of the ovum.
ii- It stabilizes pregnancy (it prevents abortion).
iii- It stimulates breast acini during puberty and pregnancy.
iv- It inhibits milk production in late pregnancy.
Progesterone decreases sharply after delivery causing lactation.
v- Antagonizes the action of estrogens at various tissues.
4) Fate: In the liver, the end product is pregnadiol which is conjugated with
sulphuric acid and glucuronic acid and then excreted in urine.
2. Male sex hormones:
a) Androgens (testosterone and
dihydrotestosterone, DHT):
1) Structure:
i- Ketone group at C3.
ii- Double bond between C4 and C5.
iii- 2 methyl group at C10 & C13.
iv- -OH at C17·
v- Dihydrotestosterone (DHT) has the same
structure of testosterone without double bond
between C4 and C5. It is the active form of
testosterone at tissues.
2) Site of production:
i- Interstitial cells of leyding of the testes in male.
ii- Adrenal cortex in both male and female.
3) Functions:
I- They stimulate the development of male sex character and
organs as voice, distribution of hair, distribution of fat, …etc.
II- They stimulate sperms formation (spermatogenesis).
III- They have anabolic effect on proteins.
4) Fate: The end products are 17-keto steroids (compounds having
= O instead of -OH at C17) which is excreted in the urine.
i- 17 Ketosteroids include dehydro-epiandrosterone acetate
(DHEA), androsterone, and epiandrosterone.
ii- Variations in urinary 17 ketosteroids:
• Increased in testicular tumors and hyperfunctions of adrenal
cortex e.g. Cushing syndrome.
• Decreased in hypogonadism and hypofunction of adrenal cortex
e.g. Addison disease.
3. Adrenal cortical hormones (= Glucocorticoids and mineralocorticoids):
a) Structure:
1) All have a ketone group at C3.
2) All have double bond between C4 ,C5.
3) All have a methyl groups at C10.
4) All have a methyl groups at C13 (except aldosterone which has -CHO
group).
5) All have a ketol group at C17.
6) All have an -OH group or oxygen at C11 ,(except DOC).
b) Site of production: are derived from cholesterol in adrenal cortex of
suprarenal glands.
c) Types:
1) Glucocorticoids: include corticosterone, cortisol, cortisone and 11-
dehydrocorticosterone.
2) Mineralocorticoids: include aldosterone and deoxycorticosterone (DOC).
Note: The synthetic derivative of DOC is called deoxycorticosterone acetate
(DOCA), which is used in treatment of Addison disease (=cortical
hypofunction).
d) Functions:
1) Glucocorticoids: Control the metabolism of carbohydrate, protein and fat.
i- Have catabolic effect (breakdown) on proteins and lipids.
ii- Have anabolic effect on carbohydrate: have anti-insulin effect, inhibit
glucose oxidation and stimulate gluconeogenesis.
2) Mineralocorticoids: Control the metabolism of minerals. They act mainly on
kidneys where it promotes secretion of K+ and H+ and reabsorption of Na+.
e) Variations:
1) Hyperfunctions: ↑ Glucocorticoids → Cushing disease.
2) Hypofunctions: ↓ Glucocorticoids and mineralocorticods → Addison's
disease.
IV. Other derived lipids:
Carotenoids, Cholantherene and Polyprenoids
A. Carotenoids (terpenes):
1. Definition:
a) Carotenoids are among the most common and most important
natural pigments.
b) They have yellow to red color.
2. Types and structure:
a) Many types are present e.g. α, β and γ carotene.
b) All are hydrocarbons formed only of carbons and hydrogen.
c) Generally each carotene is formed of two ionone rings. Each
ionone ring is connected to two isoprene units, both are
interconnected by methane group (-CH=CH-).
3. Sources:
a) Plant sources: They are responsible for many colors of fruits and
vegetables e.g. carrots, orange, apricot, apple and tomato.
b) Animal sources: fats, butter, milk and egg yolk.
4. Functions:
a) They have antioxidant and antimalignant properties.
b) Provitamin A: They are converted into vitamin A in intestine (Will
be studied in vitamins).
B. Cholantherene:
1. These are derived lipids similar in structure to steroids with
extramethyl group. They are highly carcinogenic.
C. Polyprenoids: These are compounds related to steroids because
they are synthesized like cholesterol from 5-carbon isoprene unit.
1. They include upiquinone, a member of the respiratory chain in
mitochondria, and the long alcohol dolichol which takes part in
glycoprotein synthesis.
2. Isoprenoid compounds derived from plants include rubber,
camphor, the fat soluble vitamins (A, D, E and K) and α-carotene
(provitamin A).
V. Methods of separation and Identification of lipids in
biologic material: Many methods may be used, which
include:
A. Thin layer
chromatography.
B. Gas liquid
chromatography.
C. Extraction of lipid
by a mixture of
chloroform and
methanol (2:1 ). This
method is an old one
and not used now.
VI. Amphipathic lipids:
A. Amphipathic molecules are those formed of two parts:
1. Water insoluble part: nonpolar or hydrophobic part.
2. Water soluble part: polar or hydrophilic part.
B. Lipids are insoluble in water except polar lipids like
phospholipids and glycolipids.
C. Lipid bilayer: Phospholipids and glycolipids possess both polar,
hydrophilic groups (glycerol, phosphate, nitrogen bases and
inositol), and nonpolar hydrophobic groups (hydrocarbon chains of
fatty acids and sphingosine). A bilayer of these lipids has been
suggested as a basic structure in biologic membranes; the plasma,
nuclear, mitochondrial and lysosomal membranes. In such
membranes, the lipid molecules arrange themselves so that the
nonpolar groups of the 2 layers are towards each other, while the
polar groups are towards the surrounding aqueous phase.
D. Micelles: These are spheres of polar lipids, less than 0.5 μm in
diameter, in which the nonpolar groups are at the centre, while the
polar groups are at the periphery of the sphere, towards the
aqueous phase. This process appears to be important in the
absorption of fats from the intestine.
E. Loposomes: These are spheres of lipid bilayers enclosing a very
small quantity of an aqueous phase. They are probably involved in
the processes of pinocytosis (uptake of particles by the cell) and of
exocytosis or emiocytosis (secretion of particles by the cell).
F. Emulsions: Relatively stable emulsions of nonpolar lipids in water
can be obtained if we add small amounts of a polar lipids (e.g.
phospholipids) before shaking. The molecules of the polar lipid
surround the emulsion particles of the nonpolar lipid so that the
nonpolar groups are towards inside, while the polar groups are
towards the surrounding aqueous phase. Emulsification of fats is
important in their digestion by the enzyme lipase in the intestine.