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LIPIDS CONTAINING GLYCEROL

A. Triacylglycerols (neutral fats)
1. At least 10% of the body weight (even in slim persons) consists of
neutral fats.
2. They are insoluble in water and do not tend to form highly dispersed
micelle. However, diacyl and monoacyl have appreciable polarity because
of free OH groups.
3. Strong alkali will hydrolyze all ester bonds in a process called
saponification, releasing free glycerol, and salts of fatty acids (soaps).
Both soap and glycerol are soluble in water and insoluble in nonpolar
solvents such as ether.

CH2 – O – CO – C15H31 CH2 – O – CO – C17H35

CH – O – CO – C15H31 CH - O – CO – C17H35

CH2 – O – CO – C15H31 CH2 – O – CO – C17H35

Palmitin Stearin

CH2 – O – CO – C17H33 CH2 – O – CO – C15H31

CH – O – CO – C17H33 CH – O – CO – C17H33

CH2 – O – CO – C17H33 CH2 – O – CO – C17H35

Olein Palmito – oleo- stearin

B. Phosphoglycerides or Phospholipids
They are found in cells of both plants and animals. In the body, they play
an important role in the transport of fats to the different tissues and
appear to be involved in its utilization.

Characteristics:
1. They are the most polar of all lipids and are amphipathic.
2. They are amphoteric, bearing both negatively charged and positively
charged groups.
3. Phospholipids are major constituents of cellular membranes. They
comprise about 40% of the lipids in the erythrocytes membrane. About
20% of the lipids of the inner mitochondrial membrane are cardiolipin.
4. Phosphoglycerides are also referred to as phosphatid. Not all
phosphorous containing lipids are phosphoglycerides like sphingomyelin.
5. Phospholipids that are found in biological membranes are:
a. Lecithin – phosphatidic acid with choline as nitrogenous base
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b. Cephalin – phosphatide of ethyl amine

c. Lipositol – phosphotidyl inositol
d. Phosphotidyl serine
O

O CH-O-C-R1

R2-C-O-CH O

CH2-O-P-O-X

O-
C. Cardiolipin
It consists of 2 molecules of phosphatidic acid connected by a glycerol
bridge; it is of immunological importance.
Structure: CH

CH2 – C – CH2

O H O

O = P-O O=P-O

O- O-
D. Plasmalogens
They make up 10% of phospholipids of the brain and muscles. They are
phospholipids where alkyl ether is attached at alpha position of glycerol.
Structure:
CH2- O – CH – CH- R

O
CH – O – C – R

CH2 – O – P – O – (CH2-CH2-NH3)

1. The three principal classes of plasmalogens are:

- phosphotidal choline
- phosphotidal serines
- phosphotidal ethanolamines
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2. Alpha-beta unsaturated ether linkage in this compound is stable in dilute

alkali but in dilute acid, the linkage is hydrolyzed to yield an aldehyde of
the corresponding alpha-beta unsaturated alcohol.

V. LIPIDS NOT CONTAINING GLYCEROL

A. SPHINGOLIPIDS

1. They are complex lipids containing sphingosine or a related base, as their

backbone.
2. The naturally occurring form is D-erythro form
3. All sphingolipids contain three characteristics; building block
component: 1 molecule of fatty acid, 1 molecule of sphingosine or 1 of
its derivatives and a polar head group.
4. D-4 sphingosine and dihydrosphingosine are the major bases of various
species.
5. The greatest concentration of sphingolipids is found I the CNS,
particularly in the white matter, although nearly all human tissues
contain some. Only traces of sphingolipids are found in depot fats.
6. Kinds of sphingolipids:
a. Ceramide – the characteristic parent structure of all sphingolipids
and a major component of membrane in neural tissues.

b. Sphingomyelin – the only sphingolipid that contains phosphate and

has no sugar moiety

c. Glycosphingolipids – lack of phosphorous and an additional

nitrogenous base but they contain 1 molecule or more
of carbohydrates.
1. Cerebroside – or neural glycosphingolipid – contains a group
of sugar or monosaccharide bound in beta-glycosidic
linkage to OH group (primary alcohol) of ceramide. It
occurs abundantly in myelin sheath of nerves.
2. Glucosylceramide
3. Trihexoside
a. Galactocerebroside- all of the cerebrosides in the normal
brain type.
b. Glucocerebrosides- present in small amount in the brain
and in certain pathological conditions as well as immature
brain.
4. Ganglioside-(acidic glycosphingolipid)-
a. the most complex glycosphingolipid
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b. It contains in their oligosaccharides head groups one or

more residues of a sialic acid.
c. The sialic acid that is usually found in human ganglioside
d. They are found in high concentration in ganglion cells of
the PNS and in lower concentration in membranes of
most cells.

B. ALIPATHIC ALCOHOL AND WAXES

1. They are naturally occurring fatty acids esters of any alcohol other than
alcohol. They are water-insoluble, solid esters of higher fatty acids with
long chain monohydroxylic fatty alcohols or with sterols.
2. Cholesterols in one of the most important of these alcohols. Its ester,
cholesteryl palmitate is one of the common waxes in blood plasma. In
pathological condition like Schuller-christian disease, large amount of
cholesterol are found in the liver, spleen and other tissues.
3.Waxes are found as the protective coat of skin, fur and feather and on
leaves and fruits.

C. TERPENES
Terpenes and steroids are two major classes of nonsaponifiable lipids.
Terpenes are polymers of isoprene units (C5). Vitamins A, E and K which are lipid
soluble, belong to this class of lipids, as well as alcohol phosphates that function
in glycoprotein synthesis. Cholesterol and vitamin D are derived from terpene.

CH3

CH2 = C – CH2 – CH3

Examples: phytol, squalene, cartenoids, natural rubber, ubiquinone or

coenzymes Q

D. STEROIDS
Steroid nucleus

Characteristic features;
a. They have some structural resemblance to terpenes, and they
contain the cyclopentanperhyrophenanthrene ring.
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b. There is an oxygenated substituent on C1 which is shared by

almost all naturally occurring steroids.

Biologically important Steroids:

A. Sterols
They are derivatives of the saturated tetracyclic hydrocarbon Steroid
nucleus is found in Vitamin D, sex hormones, certain hormones, drugs, bile
and sterols.

Members under Sterols:

1. Cholesterol { C27 }
2. 7 – Dehydrocholesterol
3. 3 – Ergosterol {yeast steroid}
4. Lanosterol

Cholesterol
1. The most abundant representative of sterol in animal tissue. It is
particularly abundant in the brain, nerve tissue and glandular
tissue.
2. Presence of beta OH at C3 , double bond at5,6 position mostly
unsaturated fatty acids, 2/3’s are free alcohol.
3. Melts at 150o , insoluble in water but can be extracted from
organic solvents.
4. Occurs in plasma membrane and lipoprotein of blood.
5. Precursor of many steroids in animal tissues including bile acids,
androgen, estrogen, and adrenocortical hormones.
6. The chief component of gall stones.
7. Its normal value in the blood is 200 mg/100 ml of blood.

Test for Cholesterol:

1. Liebermann – Burchard Test – cholesterol produces emerald
green color when dissolved in chloroform and conc. H2SO4 and
acetic anhydride. This is the basis for colorimetric quantitative
determination of cholesterol.
2. Salkowski’s test – reddish blue color to purple color.
3. When crystallized, cholesterol forms white crystals with
characteristic notch in one corner.

B. Bile Acids
Bile salts are steroids in nature. Four different salts occur in human bile.
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1. Side chain at C17 consists of 5 C atoms terminating in a COOH group.

2. Because of the presence of extra OH and COOH groups on the side
chains, they are excellent emulsifying agents that aids in the absorption
of lipids in the small intestines.

Glycoholic acid Deoxyalcoholic acid

Cholic acid Lithocholic acid

C. Adrenocortical Hormones
1. Isolated from the adrenal cortex (derived from cholesterol)
2. Conjugated double bond at C atom 3 and 4, the so called unsaturated
ketone and hydroxysubstituent at position 11.
3. The parent compound is corticosterone; physically active modification
of the molecule is 17-hydrocorticosterone (cortisol)
4. Aldosterone is a hormone which plays an important role in water and
electrolyte metabolism
Corticosterone Cortisol Aldosterone (C12 )

D. Androgens and Estrogens (C19 and C18 steroids)

1. Androgens or male sex hormones are C steroids and belong to the class
of steroids devoid of carbon side chain at C.
e.g. testosterone (synthesized from the testis)

2. Estrogen differ from all the steroids in that ring A is aromatic

a. There is no available valence for a methyl group at position C10 .
b. Hydroxyl group at position 3 is phenolic rather than alcoholic.
c. Because of this fact, estrogens behave like weak acids and are
extractable from benzene solution with aqueous alkali.

Testosterone
C19 steroid

E. Vitamin D
Conversion of a steroid in the skin to Vit. D is done by irradiation by
ultraviolet light.

Two forms of Vitamin D:

1. Vitamin D2 or calciferol
2. Vitamin D3 is formed by irradiation of 7-dehydrocholesterol

Structure of Vitamin D3
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Functions of Vitamin D:
1. It is required for the proper deposition of calcium phosphate in bone.
2. It aids in supersaturating fluids with calcium phosphates by inducing a
calcium transport system in the intestines and mobilizing old or deep
bone.
3. Increased reabsorption of phosphate by the kidney tubule and
increased phosphatase activity.

Vitamin D3 is transported from the skin to the liver where it is converted

into 25 – dihydrocholecalciferol

F. Other Steroids
1. Digitoxigenin – it is a cardiac stimulating glycoside
2. Ecdysone – is an insect steroid hormone that influences molting and
metamorphosis.
3. Methylcholanthrene – is an aromatic compound similar to steroid and a
potent carcinogen.

E. PROSTAGLANDINS
1. They are a family of fatty acids derivatives which have a variety of potent
biological activities of a hormonal or regulatory nature.
2. There are many different prostaglandins which function as regulators of
metabolism in a number of tissues and in a number of ways.
3. Fourteen prostaglandins occur in human seminal plasma.
4. The best known prostaglandins are E1 ,F1a , F2a abbreviated as PGE1 , PGF18 and
PGF2a .
5. The prostaglandins differ from each other with respect to their biological
activity, although all show at least some activity in lowering blood pressure
and inducing muscle to contract.

Example: PGE1 – antagonize the action of certain hormones

PGE2 and PGE3 – have their clinical use in inducing labor and
bringing about therapeutic abortion

Prostanoic acid
(parent cells of all prostaglandins)

Cyclopentane ring with 2 tails (PGE3)

F. LIPOPROTEINS
1. Lipoprotein are lipids combines with proteins.
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2. They are involved in the transport of lipids in the blood

3. Blood concentration of lipoprotein changes in disease condition.

Types of lipoproteins: as transport form in the blood:

1. High density lipoprotein (HDL) – mostly phospholipids
2. Low density lipoprotein (LDL) – cholesterol
3. Very low density lipoprotein (VLDL) – triglycerides from the liver
4. Chylomicrons – triglycerides from the diet.

MISCELANNEOUS TESTS: for the detection and qualitative measurement of

choline, cholesterol and bile acids.

Test for Cholesterol:

1. Liebermann – Burchard Test – cholesterol produces emerald
green color when dissolved in chloroform and conc. H2SO4 and
acetic anhydride. This is the basis for colorimetric quantitative
determination of cholesterol.
2. Salkowski’s test – reddish blue color to purple color.
3. When crystallized, cholesterol forms white crystals with
characteristic notch in one corner.