2023-2024

Fundamentals
of
Biochemistry
BCHE 2030

Prof Kwok Fai LAU

Lipids
School of Life Sciences
CUHK
Lipids (Greek: lipos, fat)
a diverse group of biomolecules that are generally soluble
in organic solvents and largely insoluble in water

General functions of lipids

• Structural components in cell membranes
• Providing energy
• Storage energy for later use
• Insulating the body
• Protecting some organs
• Transporting fat-soluble vitamins
• Signaling molecules 2
Lipid classes
(1) Storage Lipids – contain hydrocarbon chains
e.g. Triacylglycerols, Wax esters
(2) Membrane Lipids – components of biological membrane
e.g. Phospholipids, Glycolipids
(3) Lipids as signals, co-factors and pigment
e.g. Prostaglandins, Steroids

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Fatty acids
• Monocarboxylic acids with variable number of carbon atoms

• Fatty acids with <14 or >20 carbon atoms are uncommon

• Most fatty acids contain even number of carbon atoms

because they are biosynthesized by the concatenation of C2
units

• The properties of fatty acids depend on their hydrocarbon

chains
- Length
- Degree of unsaturation
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• Contain only C-C single bonds -
Saturated

• The melting point of saturated

fatty acids increase with their
molecular mass

• Contain C=C double bonds -

Unsaturated

• C=C double bonds decrease

the melting point fatty acids

• Length of hydrogen carbon chain

influence melting point

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Carboxyl end methyl end

Carbon skeleton / Symbol /Abbreviation

18:1( 9)

No. of Position of
carbon double bond
No. of
double bond
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Unsaturated Fatty Acids

R R R
R

Cis-isomer Trans-isomer

• Monounsaturated – one double bond

• Polyunsaturated – two or more

double bonds
• Most naturally occurring fatty acids are
cis-isomers
Figure 9-1
Principles of Biochemistry 3rd Ed
©2008 Wiley
7
• Degree of unsaturation affects the melting points of fatty acids

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Essential fatty acids
• cannot be synthesized by the body
• Two families of essential fatty acids : -3 and -6

(1) -3 (or omega-3)

– can be found in fish oil eg. Eicosapentaenoic acid
(EPA) and docosahexaenoic acid (DHA)

– polyunsaturated fatty acids

– the first double bond at the third carbon
(counting from the methyl end) 9
 Figure 27.12
Lippincott’s illustrated reviews: Biochemistry 3rd Ed,
© 2005 Lippincott Williams & Wilkins

– Lower blood pressure, reduce serum triacylglycerols,

reduce risk of cardiovascular mortality
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(2) -6 (or omega-6)

linoleic acid

– polyunsaturated fatty acids

– first double bond at the sixth carbon
(counting from the methyl end)
– major -6 is linoleic acid from vegetable oils
– linoleic acid has been found to lower plasma cholesterol

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 Fatty acids form micelles

• Fatty acids are amphipathic

molecules - contain both
hydrophilic and hydrophobic
regions

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Micelle
Triacylglycerols
• consist of three fatty acids esterified to a glycerol backbone

Fatty acids

Condensation

+ 3H2O

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Principles of Biochemistry 3rd Ed
©2008 Wiley
 Guinea pig adipocytes
• the major lipids in our food
• accumulate in adipose tissues and
plant seeds as energy reserve
• insulation in animals
Seed of the plant Arabidopsis
• not a component of membranes
• non-polar molecules
Triacylglycerols

Fats Oils
Solid at room temp. Liquid at room temp.
Large proportion of Large proportion of
saturated fatty acid unsaturated fatty acid
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• Advantages of triacylglycerols as stored fuel

(1) Greater energy yield

Fat 9 kcal/g
carbohydrate/protein 4 kcal/g

(2) Lipid hydrophobicity

Exclude water and form dense droplets
Do not affect osmolarity

The energy reserves for an average person (~ 70kg) are:

100,000 kcal triacylglycerols (~ 11kg)
25,000 kcal protein (muscle)
600 kcal glycogen
40 kcal glucose 15
Special role of Triacylglycerols in Sperm Whales

• Spermaceti oil (TGs + Waxes) – 37oC liquid

• 31oC crystal
• Decrease in buoyancy
• Reduce effort to stay at the
deep sea to wait for their
food (squid)

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Partial hydrogenation of cooking oils
produces trans fatty acids
• TGs in vegetable oils contain large
amounts of unsaturated fatty acids
• Oxidative cleavage of double bonds in
unsaturated fatty acids which produces
volatile aldehydes and carboxylic acids
not suitable for consumption

H H
Hydrogenation
C=C C C
H H high temperatures
with metal catalysts H H
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• partial hydrogenation converts many cis double bonds in the
fatty acids to single bonds

• undesirable effect -- cis double

bonds to trans double bonds

• trans fatty acids increase the

incidence of cardiovascular disease
> increase the levels of "bad"
LDL cholesterol
> reduce “good” high-density
lipoprotein (HDL) cholesterol

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Biological Waxes
• are esters of long chain fatty acids and long chain alcohols

Triacontanoylpalmitate

• chief storage form of metabolic fuel in plankton

• Water repellents – form protective coatings on leaves,

stems, fruits and the skin and fur of animals
• High melting point – 60 -100oC

Honey comb – beeswax

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Membrane Lipids
• 5 – 10% the dry mass of most cells
• Biological membrane is a double layer of lipids
• Every cell has a cell membrane
• Other membrane enclosed organelles in eukaryotes e.g.
nuclei, mitochondria
• Amphipathic – contain both hydrophilic and hydrophobic regions

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 3
1

4 Sphingolipids
Polar head group

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Glycerophospholipids
• are abundant in all biological membrane

phosphodiester bond

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Galactolipids

• Galactolipids are mainly found in plant cells 23

Archaeal Ether lipids
• Archaea – a group of single-celled
microrganisms live in extreme condition.
e.g. high temp., low pH
Ether bond

Ether bond

A typical membrane lipid of archaea

• Ether linkage > more resistant to hydrolysis at low pH and high

temperature
• Branched, saturated hydrocarbon chains > more resistant to
oxidation 24
Sphigolipids
• are derived mainly from the C18 amino 1 2 3

alcohol sphingosine

a phospholipid a glycolipid

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 Glycosphingolipids and blood groups
The carbohydrates of certain sphingolipids define human blood groups

N-acetyl
galactosamine

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Phopholipids and glycolipids readily form
lipid bilayers in aqueous media
• Membrane formation is a consequence of the amphipathic
nature of the molecules
• Polar head groups contact water, hydrocarbon tails
interact with one another
• Form either micelle or lipid bilayer
• Ionized fatty acids readily form micelles
• Fatty acid side chains of a phospholipids
and glycolipids are too bulky to fit into the
interior of a micelle > favour lipid bilayer
formation
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 Signaling Lipids
Hormones
e.g. Eicosanoids
• Paracrine hormones – act on cells near the point of hormone
synthesis
• Derivatives of arachidonic acid
NSAIDs= Nonsteroidal anti-inflammatory drugs (e.g. Asparin, ibuprofen)

Induces contraction of the smooth muscle

Increases body temp. (producing fever) lining the airways to the lung

Acts in blood clot formation

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e.g. steroid hormones

• derived from cholesterol

• Steroids -- lipids characterized by the carbon

skeleton with four fused rings

• Endocrine hormones – move through

the blood stream from their site of
production to target tissues

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Fat soluble vitamins
Vitamin D3
• Fat-soluble vitamin
• Precursor – 7-Dehydrocholesterol
• essential for the regulation of calcium uptake in gut and
reabsorption of calcium in kidney
• Deficiency of vit D > defective bone formation (Rickets)

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Active form
Vitamins A
• an isoprenoid – synthesized by the condensation of
multiple isoprene units (5 carbons)
• furnishes the visual pigment in vertebrate eye
• a regulator of gene expression during epithelial cell growth
• Deficiency of vit A
Skin dryness
Retarded
growth and
development
Night blindness

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 Vitamin E

• an isoprenoid

• an antioxidant – function in protection of membrane lipids

from oxidative damage

• The aromatic ring reacts with oxygen radicals and other free
radicals
• Deficiency of vit E > fragile RBCs
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Vitamin K

• a blood clotting cofactor

• The aromatic ring of vitamin K

undergoes a cycle of oxidation
and reduction during the
formation of prothrombin

Adapted from Smolin & Grosvenor (2000) Nutrition Science &

Applications 3rd Ed, Saunders College Publishing 33
Lipophilic electron carriers
Coenzyme Q (Ubiquinone)
• in mitochondria

Plastoquinone
• in chloroplast

• Both coenzyme and plastoquinone drive the synthesis of

metabolic energy ATP 34
Lipidic pigments
• Many natural pigments are lipidic conjugated dienes

• Conjugated dienes have carbon chains with alternating single

and double bonds

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