 Introduction to lipids; General characteristics

 Classification of lipids
 Fatty acids:- structures, nomenclature and sources of
fatty acids of physiological significance.
 Structures, nomenclature and source of triacylglycerol
of physiological importance.
 Structures, sources and functions of phospholipids.
Glycolipids: -structures, sources and functions.
 Structure and functions of vitamins (Fat soluble)
 Structures and functions of some steroids and
sterols.
General properties
 Lipids are non-polar (hydrophobic) heterogeneous
compounds(are hydrocarbons). No common structure
 Lipids are a class of biological molecules defined
by low solubility in water and high solubility in
organic /nonpolar solvents e.g chloroform,
methanol, acetone
 Most membrane lipids are amphipathic, having a non-
polar end and a polar end.

31-Mar-25 Njoroge V.K 2

Functions of lipids
 ENERGY: Act as Energy source mainly as triacylglycerols (Beta
oxidation of fatty acids).
As molecules that are largely hydrocarbon in nature, lipids
represent highly reduced forms of carbon and, upon oxidation
in metabolism, yield large amounts of energy. Lipids are thus
the molecules of choice for metabolic energy.
 STRUCTURAL: Phospholipids & glycolipids act as structural
components of cell membranes.
 PROTECTION: Waxes acts as protective coverings e.g. plants
or arthropods. Fats Insulates the body against cold.
 SIGNALLING: Some lipids e.g. steroids, prostaglandins,
vitamins acts as hormones.

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 Classes of Lipids

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 Classes of lipids

fatty acids
Fat soluble
vitamins eicosanoids

*
steroids

triacylglycerols

glycolipids
waxes
* fatty acids absent phospholipids
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Classification of lipids
a) By structure:
1. Simple: fats, oils, waxes, steroids.
2. Complex: phospholipids, spingolipids, glygolipids.
3. Their derivatives: hormones, fat-solubility vitamins
b) On the basis of whether they undergo hydrolysis
reactions in alkaline solution:
1. Saponifiable lipids can be hydrolyzed under
alkaline conditions to yield salts of fatty acids.
2. Nonsaponifiable lipids do not undergo hydrolysis
reactions in alkaline solution.
Saponifiable vs unsaponifiable
 Lipids can also be broadly subdivided as either saponifiable
or nonsaponifiable.
Saponifiable lipids
Triglycerides
Glycolipids
Sphingolipids
Waxes (some)
Phospholipids
Nonsaponifiable lipids
Steroids
Prostaglandins
Leukotrienes
Terpenes
1 FATTY ACIDS
 LONG CHAIN CARBOXYLIC ACIDS
 Insoluble in water
 Contain 12-24 carbon atoms.
 Most fatty acids contain an even number of carbon
atoms.
 Some contain double bonds
 Corn oil contains 86% unsaturated fatty acids and 14%
saturated fatty acids
 Physical Properties of Fatty Acids:
1. Fatty acids are long chain carboxylic acids and are therefore weak
acids.
2. Fatty acids do not dissolve in water; instead they are dispersed by the
formation of micelles in water.
3. As the fatty acid carbon chain length increases, the melting point and
boiling point increases.
4. Unsaturated fatty acids have lower melting points and boiling points
than saturated fatty acids. This is because the cis C=C cause "kinks"
in the hydrocarbon chains, which reduce the extent of association of
the molecules. Less energy is required to separate the molecules.
5. They Contain 12-24 carbon atoms.
6. Most fatty acids contain an even number of carbon atoms.(Why?)
Functions of FAs
 Acts as a component of membrane lipids.
 Are components of stored fat in the form of
acylglycerols. (a good source of energy, beta
oxidation to acetyl CoA).

31-Mar-25 Njoroge V.K 10

Fatty acids-Structure
 Long chain carboxylic acids.
 Contain a carboxyl (-COOH) group at
one end (right).
 Have a methyl (CH3) group on the other
end (left).
 CH3(CH2)nCOOH

31-Mar-25 Njoroge V.K 11

 Types of fatty acids
 Saturated fatty acids- contain no carbon-
carbon double bonds.
 Unsaturated fatty acids-contain one or
more double bonds.
 Divided into 2 classes:
1. Mono-unsaturated –Contain one C-C
double bond.
2. Poly-unsaturated – contain 2 or more
C-C double bonds

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Saturated and unsaturated FAs

Saturated : C–C bonds

Unsaturated: one or more C=C bonds

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 Properties of saturated FA
 Contain only single C–C bonds
 High melting points hence exists as
solids (fats) in room temperature.

COOH
COOH
COOH
 Common biological saturated FA
Symbol common systemati structure mp(C)
name c name
12:0 Lauric acid dodecanoic CH3(CH2)10 44.2
acid COOH

14:0 Myristic Tetradecan CH3(CH2)12 52

acid o-ic acid COOH

16:0 Palmitic Hexadecan CH3(CH2)14 63.1

acid o-ic acid COOH

18:0 Stearic acid Octadecano CH3(CH2)16 69.6

-ic acid COOH

20:0 Arachidic Eicosanoic CH3(CH2)18 75.4

aicd acid COOH
 Properties of unsaturated FA
 Contain one or more double C=C bonds in cis
Configuration
 Double bonds of poly unsaturated fatty acids are never
conjugated i.e. they are separated by methylene
groups.
 Low melting points that increases with length.
 Exists as Liquid (oils) at room temperature.
H H
C C

cis double bond COOH

Common biological unsaturated FA
Symbol commo systematic structure Mp
n name name (C)

16:1 Palmitoleic
acid
Hexadecenoic
acid
CH3(CH2)5CH=CH- -0.5
(CH2)7COOH

18:1 Oleic acid 9-

Octadecenoic
CH3(CH2)7CH=CH- 13.4
(CH2)7COOH
acid
18:2 Linoleic
acid
9,12 -
Octadecadien
CH3(CH2)4(CH=CHCH2)2(C -9
H2)6COOH
oic acid

18:3 Linolenic
acid
9,12,15 -
Octadecatrien
CH3CH2(CH=CHCH2)3(CH2 -17
 )6COOH
oic acid

20:45,8, arachidon
ic acid
5,8,11,14-
Eicosatetraeno
CH3(CH2)4(CH=CHCH2)4 -49
11,14 (CH2)2COOH
ic acid

20:55,8,11, EPA 5,8,11,14,17- CH3CH2(CH=CHCH2)5(CH2 -54

14,17 Eicosapentaen )2COOH
oic- acid
22:6 DHA Docosohexaen Draw the structure
4,7,10,13,16,19
oic acid
Cis and trans configuration

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Acylglycerols (Acylglycerides)
 They are esters of fatty acids and glycerol.
 They are formed thro a condensation
process where water is eliminated.
 There are of 3 types:-
 Monoglycerides (monoacylglycerols)
 Diglycerides (diacylglycerols)
 Triglycerides (triacylglycerols)

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General structure of TGs

Glycerol Ester 3 FAs, R1,R2,R3

backbone bonds
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.

Diglyceride

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Triacylglycerols
 The most common are the triacylglycerols (TGs).
 They consist of glycerol esterified with three fatty
acids
 They are also referred to as neutral fats, fats or
triacylglycerides.
 TGs are non polar, hydrophobic molecules
essentially insoluble in water.

31-Mar-25 Njoroge, VK 23
Reactions of Triglycerides
 Hydrogenation
 Unsaturated FA in TGs react with H2
 In the reaction C=C bonds are converted to C–C bonds
 Hydrolysis
 TGs can be hydrolysed by water, an acid or enzyme
catalyst to produce glycerol and 3 fatty acids

31-Mar-25 Njoroge V.k 24

Functions of TGs
 Stores energy as fat deposits in adipocytes
(or fat cells).
 TGs are stored in the seeds of plants
providing energy during seed germination
 Fats also acts as body insulator in animals (e.g. seals).

31-Mar-25 Njoroge, VK 30
2. INSULATION
 Animals living in cold regions such as seals, penguins
and bears store a lot of fat below the skin which serve
insulation purposes.
 Humans as well utilize adipose fats below skin to
regulate body heat in cold weather.
 Hibernators accumulate huge fat reserve before cold
season. This is used as insulation but mainly as energy
store.

31-Mar-25 Njoroge VK. 31

Phospholipids
 Are lipids of biological membranes
 Are phosphate-containing lipids.
 Have a glycerol backbone and two FA moieties
and are called phosphoglycerides

31-Mar-25 Njoroge V.K 33

 Structure Phosphoglycerides

FA

FA
Glycerol

PO4 X

Phosphatidic Acid

31-Mar-25 Njoroge V.K 34

Phosphatidic acid
R’ & R”=FA
moieties

Glycerol backbone Phosphoric acid

31-Mar-25 Njoroge V.K 35
Structure of phospholipids
 The carbons C1 and C2 are attached to a FA.
 The Carbon C3 is attached to Phosphate group
(forming Phophatidic acid).
 The –OH of phosphatidic acid can be linked to other
functional groups (polar groups e.g. glycerol, serine,
choline).

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General structure of a Phospholipid

FAs

X:Ethanolamine,
Choline, Serine,
Inositol

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Properties of phospholipids
 Phospholipids are amphipathic.
 The polar head is hydrophilic.
 The fatty acid in the 1st and 2nd carbon atoms of
glycerol are normally nonpolar and hydrophobic.

Njoroge V.K
31-Mar-25 38
The most common glycerophospholipids are:

1- Phosphatidic acid:
it is the simplest phosphlipid and doesn’t have specific functions

2- Lecithin: It is formed of glycerol, two fatty acids, phosphate and choline which is
a nitrogenous base. It is phosphatidic acid + choline so it is called
phosphatidylcholine , readily available sources, such as egg yolk or soy beans. They
are a major component of biological membranes

Lecithin Phosphatidic acid

Cephalins: Their chemical structure is exactly as lecithin but they differ only in the
base which may be:
a) Ethanol amine so called: phosphatidyl ethanol amine
b) Serine and so called phosphatidyl serine

Phosphatidyl serine
Phosphatidyl Serine is an important
phospholipid which supports cell integrity
- Found in high concentrations in the
brain, levels of which decline with age.
- It is essential for normal neuron
structure and function and may play a
critical role in maintaining
concentration and memory
 Phosphatidyl ethanolamine (cephalin)

Sources: brain tissues.

Phosphatidyl inositol: structure

It is one of cell membrane

lipids (but less common)

In addition it plays a role

in cell signaling
 Examples of Phospholipids

Phosphatidylserine (PS)

Phosphatidylinositol (PI)

31-Mar-25 Njoroge V.K 44

Each
derivative
is named
for the
head-
group
alcohol
(X) with
the pre-fix
"phosphati
dyl-".
GLYCEROPHOSPHOLIPIDS

Each derivative is named for the head-group alcohol (X) with the
pre-fix "phosphatidyl-".
In caridiolipin, two phosphatidic acids share a single glycerol,
hence it is also called diphosphatidly-glycerol.
GLYCEROPHOSPHOLIPIDS
2. The fatty acids can vary greatly between organisms, tissues
and cells.
In general, they contain a saturated C16 or C18 fatty acid at
C1 and a C18 to C20 unsaturated fatty acid at C2.
GLYCEROPHOSPHOLIPIDS

3. Common components of cell membranes.

STRUCTURES OF SOME COMMON
GLYCEROPHOSPHOLIPIDS

(lecithin)
 SOME PHOSPHOLIPIDS HAVE
ETHER LINKED FATTY ACIDS
1. Plasmalogens have an ether-linked alkenyl chain where
most glycerophospholipids have an ester-linked fatty acid. The
head group alcohol is choline. ~50% of the heart phospholipids
are plasmalogens.(perhaps resistance to phospholipases?)

ETHER
ESTER
2. Platelet-activating factor has a long ether-linked alkyl chain
at C1. Acetic acid is ester-linked at C2, which makes it more
water soluble than most glycerophospholipids. The head-group
alcohol is choline.
Platelet-activating factor is a potent molecular signal released
from leucocytes that stimulates platelet aggregation and serotonin
release. It also has a variety of effects on many tissues including
roles in inflammation and the allergic response.
Functions of phospholipids
1- Enter in the structure of cell membranes
2- Help triglycerides transport (enter in the synthesis of chylomicron) .
3- Blood clotting: Cephalins enter in the formation of thromboplastin which
is necessary for blood clotting.
4- Phospholipids act as lipotropic factors i.e. prevent accumulation of fats in
liver hence prevent fatty liver.
5- Phospholipids in bile make cholesterol soluble. Their deficiency leads to
cholesterol gallstones .
6- Dipalmitoyl lecithin act as lung surfactant, prevent alveolar collapse and
allow air passage
 Sphingolipids

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Sphingolipids
 2nd biggest class of membrane lipids
 Have a polar head and two non polar tails, one of
long chain FA and the other a long chain amino
alcohol called sphingosine

31-Mar-25 Njoroge V.K 56

 SPHINGOLIPIDS

The 3-carbon
backbone is
analogous to the
3-carbons of
glycerol.
At C3 there is the
long chain amino
alcohol
sphingosine.
 SPHINGOLIPIDS

At C2 there is a
fatty acid which is
usually saturated or
monounsaturated,
and can be either
16,18, 22, or 24
carbons long.
 SPHINGOLIPIDS

Ceramide is the
parent compound.
Other polar head
groups can be
attached at position
X.
 SPHINGOLIPIDS

Glycosphingolipids
are a sub-group of
sphingolipids that
contain sachharide
headgroups
 Waxes

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Waxes
 Waxes are esters of long chain fatty acids and alcohols.

 Use one alcohol instead of glycerol

 Esters of:
 Long-chain fatty acid
 Long-chain alcohol
 The longer the chains, the higher the melting point
 Protects the skin of plants and fur of animals
 The FA is generally 16-36 carbons.
 The alcohols is 24-36 carbons (even #'s).
 Beeswax is 30-carbon alcohol and 16-carbon acid.

31-Mar-25 Njoroge V.K 62

Properties of wax
 Waxes are found in several places in nature.
 Fruits - surface.
 Leaves - surface.
 Animal furs,hair, skin.
 Feathers.
 All properties of repelling water, it protects the skin
from dehydration

31-Mar-25 Njoroge V.K 63

Structure of beeswax (myricyl
palmitate)

31-Mar-25 Njoroge V.K 64

 Waxes
 Waxes are esters that combine a long-chain fatty acid with
a long-chain alcohol (14-30 carbons in each chain,
unbranched)
 Plants produce waxes on the surfaces of their leaves, stems
and fruits to prevent water loss and protect against pests
 Animals produce waxes on their fur or feathers to provide a
water-proof coating (ducks, polar bears, etc.)
 Waxes are used commercially to produce many products,
such as car wax, candles and cosmetics
 Steroids

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Steroid Compounds
 Includes steroid hormones
 Progesterone, estrogen (estradiol), testosterone
 corticosteroids such as cortisol (cortisone),
 aldosterone
 vitamin D
 Bile acids
 Cholesterol is the precursor to steroid hormones
and vitamin D.

31-Mar-25 Njoroge V.K 67

 Steroids
 Based on a core structure consisting of three 6-
membered rings and one 5-membered ring, all
fused together.
 Cholesterol is the most common steroid in
animals and precursor for all other steroids in
animals.
 Steroid hormones serve many functions in
animals - including salt balance, metabolic
function and sexual function.
Figure 1. The structure of cholesterol,
shown with steroid ring designations and
carbon numbering.
Summ Structure of cholesterol

31-Mar-25 Njoroge V.K 70

Functions of Cholesterol
 Cholesterol is primarily found in
membranes - increasing the fluidity of the
membrane
 Cholesterol is utilized by the body as a
precursor for:
1. Bile salts.
2. Vitamin D.
3. Steroid hormones.

31-Mar-25 Njoroge V.K 71

Steroid hormones
Pregnenolone (C-21)

produced directly from cholesterol, the

precursor molecule for all C18, C19 and C21
steroids
Progesterone (C-21)
• A progestin, produced directly from
pregnenolone.
• Secreted from the corpus luteum.
• Maintains (with estradiol) the uterine
endometrium for implantation.
• Differentiation factor for mammalian
glands.

Estradiol (C-18) • Female: regulates gonadotrope secretion in

ovarian cycle.
• Maintains (with progesterone) uterine
endometrium.
• Differentiation of mammalian gland.
• Responsible for secondary female sex
characteristics.
•Male: negative feedback inhibitor of Leydig
cell synthesis of testosterone.
 Testosterone (C-19)

• After conversion to dihydrotestosterone,

production of sperm proteins in Sertoli cells.
• Responsible for secondary male sex
characteristics.
• Produced from progesterone.

Dehydroepiandrosterone

• Week androgen, which can be converted

to estrogen.
• Various protective effects. It may play a
role in the aging process.
• Regulates NAD+ coenzymes.
Aldosterone (C-21)
• The principal mineralocorticoid.
• Produced from progesterone in the zona
glomerulosa of adrenal cortex.
• Causes sodium ion uptake via
conductance channel.
• Occures in high levels during stress.
Rises blood pressure and fluid volume.

• Dominant glucocorticoid in humans,

Cortisol synthesized from progesterone in the zona
fasciculata of the adrenal cortex.
(C-21) • Stress adaptation through various cellular
phenotypic expression, stress adaptation.
• Slight elevation of liver glycogen. Numerous
effects on the immune system, killing effect on
certain T cells in high doses.
• Na+ uptake in epithelia lumen.
1, 25-Dihydroxyvitamin D3 (Calcitriol)

• Causes synthesis of Ca2+ transport protein.

• Regulates calcium and phosphorus homeostasis.
 Fat Soluble Vitamins (ADEK)

31-Mar-25 Njoroge V.K 79

Vitamin D
 Vit. D is formed under he skin by the by the
action of UV light in sunlight
 Vit. D plays a crucial role in the control of
calcium and phosphorous metabolism
 Deficiency of Vit. D causes rickets in young
children and osteomalacia in adults

Njoroge V.K
31-Mar-25 80
ADEK
 SHOW THE STRUCTURE, FUNCTIONS AND
DEFICIENCY OF VITS A,E AND K
 Eicosanoids: Prostaglandins,
Leukotrienes and Thromboxanes
 Fatty acids which can’t be synthesized by the
body are essential fatty acids
 Linoleic acid is an essential fatty acid required to
make arachadonic acid
 Arachidonic acid (20 C) is the eicosanoid
precursor
 Eicosanoids are three groups of structurally
related compounds -
 Prostaglandins COO
17.2 Fatty Acids

 Leukotrienes
 Thromboxanes
arachadonic acid
Prostaglandins
 Potent biological molecules
 They act like hormones in controlling the
body’s processes
 Structure
 Synthesized from 20-carbon unsaturated fatty acids
 Cyclic compounds including a 5-carbon ring
 Names are based on ring substituents and
number of side-chain double bonds
 Made in most tissues
 Exert their effects on cells that produce them and
cells in the immediate vicinity
 Structures of Four Prostaglandins
17.2 Fatty Acids
Thromboxane and Leukotriene
Structure
 Other Complex Lipids
Complex lipids are those bonded to other types of
molecules
Lipoproteins
 Molecular complexes found in blood plasma
 Contain:
 Neutral lipid core of cholesterol esters and/or TAGs
 Surrounded by a layer of:

 Phospholipid
 Cholesterol
 Protein
Classes: chylomicrons, VLDL, LDL, HDL
Lipoproteins
• Chylomicron:
• 85% TAG, 4% chol., 8% protein
• 80 -500nm
•formed in intestinal epithelial cells
• deliver exogenous TAGS to tissue
• ApoCII activates lipases in capillary cell
walls releasing FFA to tissue
• chylomicron remnants return to liver where
they bind to ApoE receptor and are taken up
• 1/2 life in blood - 4-5 minutes
• VLDL:
• 50% TAGs, 22% choles., 10% protein
• 30 -100 nm
• formed in liver
• deliver endogenous lipids to other tissues
(mainly muscle and fat cells)
• ApoCII activates lipases in capillary cell
walls releasing FFA to tissue
• converted to IDLs and LDL as lipids are
released
Lipoproteins
• IDL: (31% TAGs, 29% choles., 18% protein)
• formed from VLDLs as lipids removed
• some IDLs return to liver
• rest converted to LDLs by further removal
of lipids
• LDL: “bad” cholesterol
• 10% TAGs, 45% choles., 25% protein
• 25 - 30 nm
• formed as lipids removed from VLDLs
and IDLs.
• all apolipoproteins lost except ApoB100
• bind to LDL receptor via ApoB100 and
taken up by endocytosis by hepatic and other
tissues (50-75% taken up by liver).
• Primary mode of cholesterol delivery to tissues.
• Synthesis of LDL receptor is inhibited by
high levels of intracellular cholesterol and
stimulated by low levels of cholesterol.
Therefore, cholesterol uptake is closly
matched to intracellular cholesterol levels.
Lipoproteins
• HDL: “good” cholesterol
• 8% TAGs, 30% choles., 33% protein
• 7.5 - 10 nm
• formed in liver
• scavenge cholesterol from cell surfaces
and other lipoproteins and deliver it to liver.
• Convert cholesterol to cholesterol ester
• bind to “scavenger receptor” on liver cell
surface - cholesterol esters taken up and
HDLs released and reenter circulation.