Lipid -1

Structure & Function of Lipids

Mr. Wong Gou Rean

9 October 2023
Learning Outcomes:
• At the end of the lectures, student should be able to:
i. define lipids and state its important functions.
ii. classify and state important properties of lipids.
iii. explain the nomenclature used in classifying lipids.
Lipid
• A heterogeneous group of compounds of biochemical importance
• Solubility:
• insoluble in water
• soluble in non-polar organic solvents
• High energy value: major source
of energy
• Glucose: 2 acetyl CoA vs Lipid:
many acetyl CoA
• Fat is stored in adipose tissue,
thermal insulator in the
subcutaneous tissue and organs
• Additional function:
• essential fatty acids, fat-soluble
vitamin, coenzyme functions,
prostaglandins, steroid hormones
Lipids
• Compartmentalized in human body:
• Membrane
• Droplet
• lipoprotein
• Amphipathic properties
• Hydrophobic and hydrophilic region
• Hydrophobic barrier
Lipid Chemistry
Lipid is ester= alcohol+ carboxylic acids

Carboxylic Acid (R-COOH)

COOH =carboxyclic group
R- hydrocarbon group

Fatty acid general formula: CH3-(CH2)n-COOH

Triacylglycerols
High energy value: major source of energy (TAG)
• Glucose: 2 acetyl CoA vs Lipid: many acetyl CoA
Classifications
1. Simple lipids: fats/oil (FA with glycerol) and waxes (FA with
monohydric alcohols)
2. Complex lipids
1. Phospholipids: sphingolipid, lecithin, cardiolipins etc
2. Glycolipids
3. Other complex lipids: sulfolipids, amino lipids, lipoproteins
3. Derived lipids: fatty acids, hydrocarbons (glycerol, alcohol) ,steroids,
ketone bodies, hormones
- Some of these (free FA etc) also act as precursors lipids
Fatty acids
Saturated (no double bond) vs unsaturated (one or more double bond)

• Double bond 3 carbons apart

• Fatty acids that occur in natural
fats usually contain an even
number of carbon atoms
• The melting points of fatty acids
increase with chain length
• The melting points of fatty acids
decrease according to
unsaturation
Cis–trans isomers for fatty acids with
double bond(s)
Arachidonic acid. Four double
bonds in the cis configuration
bend the molecule into a U
shape.
Classification of Fatty acid by length of carbon
• Short chain (3-10 carbons)
• Medium chain (8-18 carbons)
• Long chain (16-24 carbons)
• Very long-chain (Longer than 24 carbons)
Transport of lipid
• long-chain fatty acids (LCFAs): These molecules are highly water
insoluble and must be transported in the circulation in association
with protein.
• More than 90% of the fatty acids found in plasma are in the form of
fatty acid esters (primarily TAG, cholesteryl esters, and phospholipids)
contained in circulating lipoprotein particles
• Unesterified (free) fatty acids are transported in the circulation in
association with albumin (made in liver).
Other unsaturated fatty acids
Eicosanoids: derived from eicosa (20-C) polyenoic fatty acids
prostanoids, leukotrienes (LTs), and lipoxins (LXs)

• Prostanoids- prostaglandins, thromboxanes

• Cyclization of the 20C polyunsaturated fatty acids
• Exist in every mammalian tissue
• Act as local hormones
Nomenclature names of the fatty acid
• Commonly used systematic nomenclature names the FA after the
hydrocarbon with the same number of arrangement of carbon atoms
• Saturated acids ends in –anoic. E.g octanoic acid (caprylic acid) (C8)
• Unsaturated acids end in –enoic. Eg. ocatadecenoic acid (oleic acid) (C18)

Carboxyl end
C5 C3 C1
Methyl end COOH also known as the α, β, and γ
carbons, respectively, and the
C16 C4 C2 terminal methyl carbon is known
as the ω- or n-carbon.
Other nomenclature:
• arachidonic acid, 20:4(5,8,11,14), is 20 carbons long and has 4 double
bonds (between carbons 5–6, 8– 9, 11–12, and 14–15).
Essential fatty acids
• Dietary essentials in humans because we lack the enzymes needed to
synthesize them. Plants provide us with these essential fatty acids.
• Linoleic (18:2) and α-linolenic acids (18:3) are the only fatty acids
known to be essential for animals including humans.
• Conditional essential fatty acid: arachidonic acid
• can be formed from linoleic acid.
• Essential fatty acid deficiency (rare) can result in a dry, scaly
dermatitis as a result of an inability to synthesize molecules that
provide the water barrier in skin.
Cholesterol
• Precursor of many steroids
• Bile acids, hormones, vitamin D
• Constituent of tissue: Basic structure
• plasma membrane and lipoproteins
• Often found as cholesteryl ester
• Esterified with a long chain fatty acids
• It occurs in animals but not in plants or
bacteria.

cholesterol
Clinical Importance
• Essential roles in nutrition and heath
• Obesity
• Atherosclerosis and cardiovascular diseases
• diabetes mellitus
Obesity
• Excessive fat deposits cause
obesity
• a risk factor for increased
mortality, hypertension, type 2
diabetes mellitus,
hyperlipidemia, hyperglycemia,
and various endocrine
dysfunctions
Atherosclerosis

• Abnormality in cholesterol and

lipoprotein metabolism leads to
atherosclerosis and
cardiovascular diseases.
• Atheros (paste) +sclerosis
(hardness)
• Hardening of the arteries
• Formation of fibrofatty lesions in
the intimal lining of arteries
• Accumulation of lipid in the vessel
wall leads to atherosclerotic
plaque formation
Diabetes mellitus
• Glucose and lipid metabolism are
associated to each other.
• diabetes mellitus, the metabolisms
of fatty acids and lipoproteins are
deranged, leading to ketosis
• Many patients with DM have
dyslipidaemia
• Elevation of plasma cholesterol and
TAGs
Summary
• Lipids have the common property of being relatively insoluble in
water (hydrophobic) but soluble in nonpolar solvents.
• 3 major classes of lipid: simple, complex and derived lipid
• Long-chain fatty acids may be saturated, monounsaturated, or
polyunsaturated.
• Nomenclature names of the fatty acid
• Cholesterol, an amphipathic lipid, is an important component of
membranes and the parent molecule from which all other steroids in
the body.
• Biology importance of lipid
Reference text book
• Ferrier, D. R. (2014). Lippincott’s illustrated reviews. USA:
Lippincott Williams & Wilkins.
• Rodwell, V. W., Bender, D. A., Botham, K. M., Kennelly, P. J., &
Weil, P. A. (2018). Harper's illustrated biochemistry. New York,
NY, USA:: McGraw-Hill Education.
• Vasudevan, D. M., Sreekumari, S., & Vaidyanathan, K.
(2019). Textbook of biochemistry for medical students. Jaypee
brothers Medical publishers.