Chemistry of

Lipids
Biochemistry
By: Addisu
Addisu w.
W. (MSc)
Hawassa University Dep’t of Biochemistry
By:
 Learning Objectives
After this lectures, you should be able to:
 Define lipid in chemical terms
 Identify structural & functional roles of lipids
 Know the different classes of lipids
 Amphipathic lipids
 Phospholipids
 Lipoproteins structure
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 Introduction to Lipids
 A heterogeneous group of compounds
 Lipids are non-polar (hydrophobic) compounds
 Most membrane lipids are amphipathic, having a non-polar
end and a polar end.
 Insoluble in water, but Soluble in Ether, chloroform, C6H6
 Present in all living organisms.
 Lipids are esters of long-chain fatty acids and alcohols
 “Fats” and “Oils” – crude lipid mixtures from natural sources.
 Fats (solid) & Oil (liquid) By:
1/3/2024
atAddisu
room W.
temperature 3
 Function of Lipids
 Store and provide energy and facilitate the digestive process
 Helps the manufacture of steroids (sex hormones), bile salts
 Protection against traumatic injury and shock absorption
 For transporting fat-soluble vitamins in the blood
 Structural component of cell membrane and protective
barrier
 Intracellular signaling or local hormonal regulation
1/3/2024 By: Addisu W. 4
 Electrical and
Source of fuel
Structural support thermal Insulating
in the body
for cell membrane effect

Padding &
protection of internal
organs
Absorption of
fat soluble
Vitamin Building
(A,D,E,K) Materials
(hormones)

Nervous Supply essential

system: Rich in fatty acids
lipids
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 Classification of Lipids
Based on composition Lipids

Compound
Simple Lipids Derived Lipids
Lipids

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 Classification Definition Examples
Simple Lipids Esters of fatty acids and Neutral fat/oils, waxes,
alcohols triacylglycerol

Compound Lipids Contains other chemical •Phospholipids

groups in addition to •Glycolipids
alcohol and fatty acids •Sulpholipids
•Lipoproteins

Derived Lipids Substances derived from •Fatty acids

simple & compound by •Alcohols other than glycerol
hydrolysis. •Cholesterol, steroids
•Bases (choline, serine)
•Ketone bodies
1/3/2024 By: Addisu W. •MAG & DAG 7
 Classification of Lipids
♯Based on function:
1. Energy-storage lipids (e.g. Fatty acids, TAG)
2. Membrane lipids (e.g. Phospholipids)
3. Emulsification lipids (e.g. Bile acids)
4. Messenger lipids (e.g. Steroid hormones)
5. Protective-coating lipids (e.g. Biological waxes)
 ♯ Based on Functions

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 Fatty acids
 FAs are building block of most lipids.
Have the general formula R-(CH2)n-COOH
One polar carboxyl group (head) &
One non-polar hydrocarbon chain (tail).
♯ Not found freely in nature but found in esterified forms.
♯ Most naturally occurring FA contains even no of carbon.
♯ Saturated or unsaturated, with one or more double bonds.
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 Nomenclature of fatty acids
 IUPAC nomenclature of fatty acids uses number of carbon
atoms and number of double bonds, separated by a colon.
 Example 18-C saturated fatty acid is denoted by 18:0 and
16-carbon monounsaturated fatty acid is denoted by 16:1.
 Positions of any double bonds are specified by superscript
numbers following Δ (delta). 16:1 (Δ9).
 Omega naming system numbering start on ω-carbon by
indicating
1/3/2024 the first double bonds
By: Addisu W. 11
 12
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 Classification of Fatty acids
♯ Based on the Number of Carbon:
A. Short Chain Fatty acids (SCFA)
 < 6 Carbons. Acetate, Propionate, Butyrate
B. Medium Chain Fatty acids (MCFA)
 6 to 12 Carbons. Caproic acid (6), Capric acid (10), Lauric acid (12)
C. Long Chain Fatty acid (LCFA)
 >12 & <20 Carbons, Palmitic acid (16), Stearic acid (18)
D. Very Long Chain Fatty acids (VLCFA)
 ≥20 Carbons. Arachidinoic
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acid (20), Nervonic acid (24)
By: Addisu W. 13
 Different Forms of Fatty acids In Body
1. Free Fatty acid /Unesterified Fatty acid
– Fatty acid who has free Carboxylic group
– FA not reacted and linked to an Alcohol by Ester bond.
2. Esterified Fatty acid/Bound form of Fatty Acid
– Fatty acid has no free Carboxylic group
– Fatty acid is linked to an Alcohol with an Ester bond.
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 Based on double bonds
 Saturated fatty acids:
 C-C-single bond and can not undergo hydrogenation
 Have Higher melting point (solid at RT)
 Unsaturated fatty acids: can undergo further hydrogenation.
Monounsaturated fatty acids (MUFA)
 Has one C-C double bond
Polyunsaturated fatty acid (PUFA)
 Has two or more C-C double bonds
 Have Lower melting point
 Most origin in plants and oily
1/3/2024 fish
By: Addisu W. 15
1/3/2024 By: Addisu W. 16
 Based on Nutritional Requirement
 Essential fatty acids:
PUFA can't be synthesized in the body but obtained from the diet.
 E.g. linoleic (ω -6), linolenic (ω -3)& arachidonic acids (semi).
 Adequate intake of omega-3 and 6 play an essential role in:
 Developing and maintaining good brain function
 The visual process, Immune and inflammatory responses
 The maintenance of normal blood pressure and blood levels of TAG
 Regulate blood clotting and contraction/relaxation of arterial walls
 Nonessential fatty acids. synthesized in the body. E.g. palmitic acid
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 Functions of Fatty Acids
1. Fuel and energy metabolism – free fatty acids and triglyceride. i.e.
Secondary source of energy.
2. Membrane structure – complex lipids
3. PUFA (Arachidonic acid) - Precursor for Eicosanoid Biosynthesis
4. Cholesterol metabolism – cholesteryl ester is the major form in
which cholesterol is transported or stored and excretion.
5. PUFAs build and protect Brain and Heart
6. PUFAs prevents early ageing, prolongs Clotting time.
7. Metabolic regulators – free fatty acids, eicosanoids, complex lipids.
 Alcohols of Lipids
 Three Alcohols Involved In Various Forms of Lipids;
1. Glycerol
(C3-Trihydric Alcohol)

2. Sphingol/Sphingosine
(C18-Dihydric Alcohol)

3. Cholesterol
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(C27-Monohydric Alcohol)
By: Addisu W. 19
 Glycerol/Glycerin
♯ Glycerol [C3 ]is a POLYOL
♯ Glycerol is chemically Trihydric Alcohol (3 –OH groups)
♯ Has a potency to interact with 3 same or different Fas.
♯ Glycerol is a backbone of Glycerol based Lipids:
─ Triacylglycerol CH2OH

H C OH
─ Glycerophospholipids CH2OH
glycerol
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 Source of Glycerol
♯ Glucose is responsible for biosynthesis of Glycerol.
♯ Glucose transforms to Glyceraldehyde,
♯ Glyceraldehyde on reduction forms Glycerol.
♯ Glycerol used for Biosynthesis of Glycerol based Lipids.
♯ Glycerol released from hydrolysis of Glycerol based
Lipids is transformed to Glucose.
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 Sphingosine/Sphingol
♯ Sphingosine is a C18, complex Dihydric, Amino alcohol.
♯ Sphingosine is biosynthesized in human body using amino acid Serine.
♯ Serine provides NH2 group of Sphingosine.
♯ Sphingosine forms Sphingolipids /Compound Lipids with Sphingol
♯ Examples of Sphingolipids:

─Sphingophospholipids
─Sphingoglycolipids
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 Triacylglycerol
♯ Main storage forms of fatty acids in adipose tissue
♯ Glycerol esterified with 3FA.
♯ Types:
─Simple TAG: Glycerol is esterified with same type of FA.
E.g: Simple TAGs of, and, for example, are: Tristearin(16:0),
Tripalmitin(18:0), and Triolein(18:1), respectively.
─Mixed TAG: Glycerol is esterified with different types of FA (≥2
different Fas)
Most naturally occurring TAGs.
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 Triacylglycerols …
♯ TAGs are nonpolar,
hydrophobic
♯ Long chain, saturated TAGs are
solid at RT (fats)
♯ Shorter chain, unsaturated TAGs
are liquid at RT (oils)
♯ Lipids in our diet are usually
1/3/2024 ingested as TAGs (95%)
By: Addisu W. 24
 Important reactions of fats
Hydrogenation
 Triglyceride (C=C) + H2→ Saturated triglyceride
Hydrolysis
 Triglyceride + H2O → Glycerol + 3Fatty acids (acid/lipase)
Saponification
 Hydrolysis of the ester group in the presence of
hydroxide (KOH or NaOH) from glycerol and salts of
fatty acids (soap)
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 Waxes
 Esters of long chain fatty acids with long chain high molecular weight
monohydric aliphatic alcohols.
 They have higher Melting point than triglycerides and have water-
repellent.
 Triacontanoylpalmitate is the major component of bees wax.
 Esters of waxes are more resistant to saponification than fats and oils
 Certain birds have wax secreting glands to prevent their feather from
being wet.
 Waxes have no nutritional values
1/4/2024 Prepared by: Mr. Addisu 26
The leaves of certain tropical plants are also coated with
wax to prevent excessive evaporation of water and for
protection against parasites.
They are widely used in pharmaceutical, cosmetic and
other industries for the manufacture of ointments, polishes,
lubricants, candles and polish.
They form the secretions of insects, leaves and fruits of
plants,
e.g. Lanolin or wool fat, beeswax, whalesperm oil, etc.
1/4/2024 Prepared by: Mr. Addisu 27
Waxes cont…
 Complex lipids Cont…
 Lipids that contain additional substances, besides fatty
acid and alcohol. e.g., sulfur, phosphorus, amino group,
carbohydrate, or proteins.
 Compound lipids: include:
Phospholipids
Glycolipids
Lipoproteins
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 Phospholipids
♯ Phospholipids are compound lipids.
♯ Contains: Phosphoric acid+FA+ Alcohol + Nitrogenous base
♯ Phospholipids are classified into two types:
1. Glycerophospholipids (Phosphoglycerides): contain glycerol.
2. Sphingophospholipids: contain sphingosine as alcohol.

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 1. Glycero-phospholipids

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 Common Phosphoglycerides

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 Phosphatidates
♯ Phospholipids may be regarded as derivatives of phosphatidic
acid in which the phosphate is esterified with the ―OH of a
suitable alcohol.
♯ the simplest phospholipid and doesn’t have specific functions
♯ It is important as an intermediate in the synthesis of:-
─ Triacylglycerols and
─ Phosphoglycerols
♯ But is not found in any great quantity in tissues.
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 Phosphatidylcholines (Lecithin)
♯ Choline is important in nervous transmission, as acetylcholine
♯ It lowers alveolar surface tension and prevents alveolar collapse,
improves gas exchange besides activating macrophages to kill
pathogens.
♯ Preterm babies have immature lung alveoli & and deficient
surfactant respiratory distress syndrome.
♯ Therefore, a small dose of glucocorticoids is injected to mothers
liable to give a preterm baby.
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 Phosphatidyl ethanolamine (Cephalin)
♯ Cephalins are major component of cell membrane,
lipoproteins, brain and nervous tissue
♯ Are located primarily in the inner leaflet
of the cell membrane.
♯ But during cell death by, they become exposed in the outer
leaflet of the cell membrane. apoptosis
♯ Detection of the serine-cephalins on the surface of the cells is
a diagnostic marker for early apoptosis.
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 Phosphatidyl Serine
♯ Phosphatidyl Serine is an important phospholipid which supports cell
integrity
♯ Important in cell signaling specifically for apoptosis
♯ Found in high concentrations in the brain, levels decline with age.
♯ It is essential for normal neuron structure and function and may play a
critical role in maintaining concentration and memory

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 Phosphatidyl inositols
♯ Major components of cell membrane phospholipids.
♯ Plays a major role as second messengers during signal transduction for certain
hormones.
♯ On hydrolysis by phospholipase C, phosphatidyl-inositol-4,5-diphosphate
produces
─ Diacyl-glycerol (DAG) and Act as mediators of the
hormone action.
─ Inositol1,4,5-triphosphate (IP3)
♯ Their major effect is release of calcium from the intracellular stores to mediate
O
the hormone effects. R1 CH2 C
O
O CH2

used in G protein signaling R2 CH2 C O CH myo-Inositol

O OH OH
CH2 O P O 2 3 H
H H
1
OH H OH 4
H 6 5 OH
1/3/2024 By: Addisu W. -Phosphatidylinositol (Inositide) OH 38H
 Cardiolipin
♯ It is an important component of the inner mitochondrial
membrane (20% of lipids)

♯ Two phosphatidic acid are esterified through their phosphate

groups to C-1 and C-3 of an additional glycerol.
♯ This is the only human glycerophospholipid that is antigenic.
♯ Cardiolipin is recognized by antibodies raised against
Treponema pallidum, the bacterium that causes syphylis.
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 Plasmalogens
♯ The plasmalogens make up about 10% of total
phospholipids of brain and nervous tissue, muscle.
♯ Plasmalogens are present in large quantities in the
skeletal muscle, cardiac muscle and in semen.
♯ fatty acid at C1 of a glycerophospholipid is replaced by
an unsaturated alkyl group attached by an ether linkage.
♯ For E.g. phosphatidalethanolamine, is a plasmalogen that
is similar in structure to phosphatidylethanolamine.
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 Platelet-activating factor (PAF)
♯ PAF is synthesized /released by a variety of cell types.
♯ Binds to surface receptors, triggering potent thrombotic and
acute inflammatory events.
♯ PAF activates inflammatory cells and mediates hyper-
sensitivity, acute inflammatory, and anaphylactic reactions.
♯ It causes platelets to aggregate and degranulate the
neutrophils and alveolar macrophages to generate
superoxide radicals to kill bacteria.
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 Degradation of Phospholipids
 Degradation of phosphoglycerides is performed by
phospholipases.
 A number of toxins and venoms have
phospholipase activity, and several pathogenic
bacteria produce phospholipases.
 Sphingomyelin is degraded by the lysosomal
phospholipase, sphingomyelinase.
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 Sites of Action of Phospholipases

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 Function of phospholipids
♯ Enter in the structure of cell membranes
♯ Help triglycerides transport (enter in the synthesis of chylomicron) .
♯ Blood clotting: Cephalins enter in the formation of thromboplastin which is
necessary for blood clotting.
♯ Phospholipids act as lipotropic factors i.e. prevent accumulation of fats in
liver hence prevent fatty liver.
♯ Phospholipids in bile make cholesterol soluble. Their deficiency leads to
cholesterol gallstones
♯ Dipalmitoyl lecithin act as lung surfactant, prevent alveolar collapse and allow
air passage.
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 2. Sphingolipids
♯ Found in large quantities in the membranes of nerve cells in the brain
and in neural tissues.
♯ When sphingosine forms an amide bond to along-chain fatty acid, the
compound is called ceramide , the precursor of the sphingolipids.

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 What Is a Ceramide?
♯ A Fatty acid linked to an amino group of Sphingosine with
an amide linkage form a Ceramide.
♯ Ceramide if linked to Phosphate and Nitrogenous groups
forms Sphingophospholipids.
♯ Ceramide linked to Carbohydrate moieties form
Sphingoglycolipids.
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 2. Sphingolipids…
♯ There are subclasses of
sphingolipids, which are all
derivatives of ceramide, but differ in
their head groups.
I. Sphingomyelins
II. Glycosphingolipids
─ Gangliosides
─ Cerebrosides
─ Globoside
1/3/2024 By: Addisu W. 47
 I. Sphingomyelin
♯ Contain phosphocholine and phosphoethanolamine as their polar head
groups.
♯ Structurally very similar to glycerophospholipids.
♯ Sphingomyelin is an important constituent of the myelin of nerve fibers.
♯ Prominent in myelin, a membranous sheath that surrounds and
insulates the axons of some neurons.

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 II. Glycosphingolipids
♯ These are neutral glycolipids that lack charges in the sugar head
groups, and lack phosphates.
♯ Helps to keep stability of membranes.
♯ An assembly of carbohydrate and lipids
♯ Glycosphingolipids include:
1. Cerebrosides:
2. Globosides
3. Gangliosides:
1/3/2024 By: Addisu W. 49
 Cerebrosides
♯ As the name suggest (cerebral = related to brain), occur in myelin
sheath of nerves and white matter of the brain tissues
♯ They are important for nerve conductance.
♯ They contain sugar, usually -galactose (sometimes glucose or lactose),
sphingosine and fatty acid, but no phosphoric acid. Ceramide

OH O
CH3 (H2C)12 CH CH CH CH NH C R1
Sphingosine Fatty acid
CH2
CH2OH
O
OH H O
Galactose
OH H H
H

H OH

1/3/2024 By: Addisu W. Psychosin 50

Cerebroside
 2. Globosides
 Are composed of ceramide and oligosaccharide
 Produced by attaching additional monosaccharides
(galactose, N-acetylglucosamine) to
glucocerebroside. e.g. lactosylceramide
 They are involved in cell communication,
increase cell adhesion and function as receptors.
 It is an essential structure of the blood group antigen
1/3/2024 By: Addisu W. 51
 Blood Groups Determinants
• Glycosphingolipids as determinants of blood groups.
• Oligosaccharides are attached to certain blood proteins of
individuals of blood types O, A, and B respectively

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 Gangliosides
♯ Present in gray matter of the brain, ganglionic cells, and RBCs.
♯ Gangliosides are the most complex of the glycosphingolipids.
♯ On hydrolysis, gangliosides yield the following:
• A long chain FA (usually C18 to C24)
• Alcohol-sphingosine
• A carbohydrate moiety which usually contains:
─ Glucose and/or galactose,
─ One molecule of N-acetyl galactosamine, and
─ At least one molecule of N-acetyl neuraminic acid (NANA) (called ‘sialic acid’).
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 Sterols
 Lipids contain multiple rings of carbon atoms.
 Are essential components of cell membranes and many
hormones
 Are manufactured in our bodies and therefore are not
essential components of our diet
 All of the steroids have a similar cyclic nucleus
resembling phenanthrene (rings A, B, and C) to which
a cyclopentane ring (D) is attached.
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 Steroids
Estradiol
Cholesterol

Testosterone

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 Steroids play many physiologically important roles
♯ Cholesterol is probably the best-known steroid because of
its association with atherosclerosis.
♯ However, biochemically it is significant because it is the
precursor of a large number of important steroids including:
─ Bile acids,
─ Adrenocortical hormones,
─ Sex hormones,
─ D vitamins, cardiac glycosides
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 Bile Salts
 Are synthesized from cholesterol and stored in the gall
bladder.
 Emulsify fats and oils to give a greater surface area for lipid

digesting enzymes.
cholic acid, a bile acid
O
CH3 CH2
C - +
OH N COO Na
CH3
H
glycine, an amino acid
CH3

HO OH
sodium glycocholate, a bile salt
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 Adrenal Corticosteroids

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 Function of Cholesterol
♯ For bile salts synthesis that are for lipid digestion.
♯ For the synthesis of steroid hormones that are
biologically important like the sex hormones estrogen
and progesterone.
♯ For the synthesis of vitamin D3
♯ It is a major constituent of plasma membrane.
♯ As a component of lipoproteins as transport forms of
lipid based energy.
1/3/2024 By: Addisu W. 59
 Transport Through Cell Membranes
 Diffusion (passive transport)
moves particles from a higher to a
lower concentration.
 Facilitated transport uses protein
channels to increase the rate of
diffusion.
 Active transport moves ions
against a concentration gradient.
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 LIPOPROTEINS
 An assembly of lipids with proteins
 Lipoprotein serve as vehicles for transportation of Neutral and
Amphipathic Lipids through aqueous media blood and lymph.
 Composed of
1. A core of hydrophobic lipids
 CE and TAG
2. Shell of amphiapatic lipids
 PL, Apoproteins and Free cholesterol
1/3/2024 By: Addisu W. 61
 PLASMA LIPOPROTEINS …

Types (Based on density) lipoproteins classified into Four

1. Chylomicrons: Contains apoprotein B-48.

2. VLDL: Main apoprotein is B-100.

3. LDL: Major apoprotein in LDL is B-100.

4. HDL: Major apoprotein in HDL is apo-A.

By: Addisu W.
1/3/2024 64
Lipoproteins
 Chemical composition of different lipoproteins

CM VLDL LDL HDL

85% TAG 60% TAG 8% TAG 3% TAG
2% protein 10% protein 22% protein 50% protein
8% phospholipid 15% phospholipid 20% phospholipid 30% phospholipid
5% Cholesterol-esters 15% Cholesterol 50% Cholesterol 17% Cholesterol

1/3/2024 By: Addisu W. 66

 Lipoproteins in plasma
• Based on Electrophoretic pattern the Lipoproteins are:
Density Mobility Component
CM CM TG rich
VLDL Pre--lipoprotein TG rich
LDL -lipoprotein Cholesterol rich
HDL -lipoprotein Cholesterol/protein rich
 Function of Apoproteins
1.Increases hydrophilicity (Apo B48)

2.Give structural stability to the lipoproteins (Apo B48)

3.Apo C-II: Activate enzymes for lipoprotein metabolism.

Activates extrahepatic lipoprotein lipase in vessel walls; clearance

of TAG from chylomicrons and VLDL

4.Apo E: Act as ligand that target specific receptors on

hepatocytes for hepatic uptake.
1/3/2024 By: Addisu W. 68
 The chylomicron
These are derived from intestinal absorption of TAG
and other lipids and have a very short life span.
Are the largest of the lipoproteins
They have the least density and rich in TAG.
Chylomicrons transport dietary TAG and cholesterol
from the intestine to the liver for metabolism.
1/3/2024 By: Addisu W. 69
 The Chylomicrons…

Patients with a deficiency of LPL or Apo-CII show a dramatic accumulation of

chylomicrons and VLDL in the plasma= type 1 hyperlipoproteinemia
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 VLDL (Very Low Density Lipoproteins)
These are synthesized in the liver from glycerol and fatty acids and
incorporated into VLDL along with hepatic cholesterol, apo-B-
100, C-II and E.
Secreted from liver into the blood stream

Apo-B-100 is the major lipoprotein present in VLDL

Apo-E and C-II are obtained from HDL in plasma.

Used to transport TAG from the liver to extra hepatic tissues.

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VLDL transport from liver to capillaries of
Skeletal muscle
Cardiac muscle
Adipose tissue
Lactating mammary tissues
Activation of LPL by Apo CII

FA’s and glycerol

 Fuel (Muscles)
 Resynthesis of TAG (Adipose tissue)
1/3/2024
 Milk production (Mammary tissue)
By: Addisu W. 72
 LDL (Low Density Lipoproteins)
These are produced from the final stage in the catabolism of
VLDL.
Transport cholesterol synthesized in the liver to peripheral tissues.
The only apoprotein present in LDL is Apo B100
LDL is metabolized via the LDL receptor.
Approximately 30% of the LDL is degraded in extra hepatic
tissues, rest is degraded in liver.
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 Low density lipoproteins…
Reach in free Cholesterol and CE
70% transported back to liver
apoB-100 receptors
30% carried to extrahepatic tissues
Adrenocortical cells, gonadal cells
apoB-100 receptors
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Cholesterol internalized will be used for
 Steroid synthesis
 Membrane synthesis
 Re-esterified and storage
 Excess LDL
Induce an inflammatory response
Initiate atherosclerosis and cardiovascular disease
Therefore, cholesterol in LDL called “bad cholesterol”
Defects in LDL receptor leads to familial hypercholesterolemia
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By: Addisu W.
 HDL (High Density Lipoproteins)
 HDL has the highest density since it contains more protein
and cholesterol than TAG.
 It transports excess cholesterol from peripheral tissues to the
liver for degradation and removal.
 Therefore, HDL cholesterol is good cholesterol
 The higher the ratio of HDL/LDL, the less the chances of CHD
1/3/2024 By: Addisu W. 76
 HDL (High Density Lipoproteins)
HDL has Scavenging role or reverse transport of Cholesterol
HDL clears the body Lipids and do not allow accumulation
of Lipids in blood.
HDLs are inversely related to risk of cardiovascular disease
HDL reduces risk of Atherosclerosis.
Therefore, HDL cholesterol has been called “Good Cholesterol”
1/3/2024 By: Addisu W. 77
 Function of HDL
1. Reverse Cholestrol transport
2. A reservior of apoproteins
VLDL obtains Apo E and Apo C II in circulation from HDL

3. Esterification of cholesterol
4. Uptake of unesterified cholesterol
5. Reducing foam cell formation (Vasculo protective)
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Transport of Lipoproteins in the Body

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 Hawassa University

Hawassa University MEDICAL SCHOOL

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