CHAPTER 7: Lipids: Structure
and Function
(LECTURE)
Lesson Outline
• Lipids – Overview
• Fatty Acids
• Saponifiable Lipids
• Non-Saponifiable Lipids
Lipids – Overview
• A group of heterogenous biomolecules that are insoluble in water and
soluble in non-polar solvents
• Biological functions:
1. Energy source
2. Insulation of vital organs
3. Covering of nerve fibers
4. Components of cell membrane
5. Chemical messengers (hormones)
Lipids – Overview
Classification of Lipids
Lipids – Overview
Properties of Lipids
• Lipids are oily or greasy nonpolar molecules, stored in the adipose
tissue of the body.
• Lipids are a heterogeneous group of compounds, mainly composed of
hydrocarbon chains.
• Lipids are energy-rich organic molecules, which provide energy for
different life processes.
• Lipids are a class of compounds characterized by their solubility in
nonpolar solvents and insolubility in water.
• Lipids are significant in biological systems as they form a mechanical
barrier dividing a cell from the external environment known as the cell
membrane.
Fatty Acids
• Monocarboxylic acids that contain long, unbranched hydrocarbon
chains, usually 12 to 25 carbons in length
• Smallest fatty acid – butanoic acid (4 carbons)
• Saturated FA – no double bonds
• Monounsaturated FA – has one double bond
• Polyunsaturated FA – has two or more double bonds
Fatty Acids
Fatty Acid Formula
• Condensed and line-bond formula
• Eg. Caprylic acid (C8, saturated)
CH3CH2CH2CH2CH2CH2CH2COOH
CH3―(CH2)6―COOH
octanoic acid (8:0)
Fatty Acids
Fatty Acid Formula
• Eg. Palmitoleic acid (C16, monounsaturated)
CH3CH2CH2CH2CH2CH2CH=CHCH2CH2CH2CH2CH2CH2CH2COOH
CH3(CH2)7CH=CH(CH2)7COOH
cis-9-hexadecenoic acid
16:1(Δ9)
Fatty Acids
Saturated vs. Polyunsaturated Fatty Acids
Fatty Acids
Saturated vs. Polyunsaturated Fatty Acids
Fatty Acids
Saturated vs. Polyunsaturated Fatty Acids
• In unsaturated fatty acids, the stereochemistry at the double bond is
usually cis rather than trans.
• A cis double bond puts a kink/bend in the long-chain hydrocarbon tail,
whereas the shape of a trans fatty acid is like that of a saturated fatty
acid in its fully extended conformation.
• Unsaturated fatty acids have lower melting points than saturated ones.
Plant oils are liquid at room temperature because they have higher
proportions of unsaturated fatty acids than do animal fats, which tend
to be solids.
Fatty Acids
Trans-fat or Trans Fatty Acids
• Unsaturated fatty acids that come from either industrial or natural sources.
More than 278 000 deaths each year globally can be attributed to intake of
industrially produced trans fat. Trans fat clogs arteries, increasing the risk of
heart attacks and deaths.
• Sources:
1. Commercial baked goods, such as cakes, cookies and pies
2. Food shortening
3. Microwave popcorn
4. Frozen pizza
5. Refrigerated dough, such as biscuits and rolls
6. Fried foods, including French fries, doughnuts and fried chicken
7. Nondairy coffee creamer
8. Stick margarine
Fatty Acids
Trans-fat or Trans Fatty Acids
Fatty Acids
Fatty Acids
Essential Fatty Acids
• Fatty acids that mammals
cannot synthesize
• Eg. Omega-3 and Omega-6
fatty acids
• Polyunsaturated fatty acids
• Essential in normal visual
and central nervous system
development
• Omega notation: indicates
the position of the first
double bond starting from
the last carbon
Saponifiable Lipids
• Produce fatty acid salts upon treatment with base
• Glyceryl esters: triglycerides, glycerophospholipids
• Non-glyceryl esters: sphingophospholipids, waxes, glycolipids
Saponifiable Lipids
Triacyglycerols/Triglycerides
• Esters of glycerol and fatty acids
• Found in adipocytes
• Triacylglycerols are major energy reserve and the principal neutral
derivatives of glycerol found in animals. These molecules consist of a
glycerol esterified with three fatty acids.
Saponifiable Lipids
Simple vs. Mixed Triacyglycerols/Triglycerides
Saponifiable Lipids
Fats vs. Oils
• FATS
• TAGs that contain high percentage of saturated fatty acids
• Solid at room temperature
• Usually coming from animal sources
• OILS
• TAGs that contain high percentage of unsaturated fatty acids
• Liquid at room temperature
• Usually coming from plant sources
Saponifiable Lipids
Fats vs. Oils
Saponifiable Lipids
Glycerophospholipids
• Common constituents of cell
membranes
• A triester in which
• First two (2) ―OH groups of glycerol
are esterified with fatty acids (need
not to be identical)
• Third ―OH group esterified with a
phosphate group that is in turn
esterified to an alcohol
Saponifiable Lipids
Glycerophospholipids
• Amphipathic compounds – have hydrophilic heads and hydrophobic
tails
Saponifiable Lipids
Glycerophospholipids
Saponifiable Lipids
Sphingophospholipids
• Derivatives of ceramide (sphingosine + fatty acid)
• Fatty acid is connected with the ―NH3+ group via an amide linkage
• A polar group is usually esterified with the ―OH group on the terminal
carbon
Saponifiable Lipids
Sphingophospholipids
HO CH CH CH2OH O CH2CH2 N(CH3)3
CH NH3 O P O
CH O
(CH2)12
HO CH CH CH2
CH3
CH NH
sphingosine sphingomyelin
CH C O
HO CH CH CH2OH (CH2)12 R
CH NH
CH3
CH C O
(CH2)12 R common constituents of cell membranes
CH3
ceramide
Saponifiable Lipids
Waxes
• Esters formed from fatty
acids and long-chain
monohydric alcohols
• Can be found on:
• Leaf surfaces – prevents
excessive water loss and water
absorption which can lead to
leaf dissolution
• Feathers of birds
• hair
Saponifiable Lipids
Glycolipids
• contain monosaccharides bonded to the ―OH group of ceramide
through a glycosidic bond
• Cerebrosides – glycolipid present in the brain and myelin sheath of the
nerves and the sugar component is either galactose or glucose
• Ganglioside – sugar moiety can be more than one monosaccharides,
disaccharides or trisaccharides
Saponifiable Lipids
Glycolipids
Saponifiable Lipids
Glycolipids
Ganglioside
Non-Saponifiable Lipids
Steroids
• Lipids containing the steroid nucleus which is a fused structure of four
rings
• Cholesterol
• Bile salts
• Hormones
• Vitamin D
Non-Saponifiable Lipids
Steroids – Cholesterol
• Most abundant steroid in the body
• Can be synthesized in the liver and obtained from diet
Non-Saponifiable Lipids
Steroids – Bile Salts
• Synthesized from cholesterol and released by the gall bladder
• Emulsify fats and oils to give a greater surface area for lipid digesting
enzymes
Non-Saponifiable Lipids
Steroids – Steroid Hormones
• Basically organic compounds synthesized in glands and transported by
the bloodstream to various tissues in order to trigger or hinder the
desired process
Non-Saponifiable Lipids
Eicosanoids
• Signaling molecules derived from C20 essential fatty acids
• Act a messengers in the central nervous system
• Prostaglandins
• Thromboxanes
• Leukotrienes
Non-Saponifiable Lipids
Eicosanoids
• Physiological Effects
1. Inflammatory response
2. Production of pain and fever
3. Regulation of blood pressure
4. Induction of blood clotting
5. Control of reproductive functions, such as induction of labor
6. Regulation of the sleep/wake cycle
Non-Saponifiable Lipids
Eicosanoids – Prostaglandins
• a family of compounds that have the 20-carbon skeleton of prostanoic
acid.
• Detected in the seminal fluid, which is produced by the prostate gland
• Prostaglandins are not stored in tissues as such but are synthesized
from membrane-bound 20-carbon PUFA in response to specific
physiological triggers.
• one such polyunsaturated fatty acid is arachidonic acid.
Non-Saponifiable Lipids
Eicosanoids – Prostaglandins
• Involved in:
• Raising body temperature
• Inhibiting the secretion of gastric juices
• Increasing the secretion of a protective mucus layer into the stomach
• Relaxing and contracting smooth muscle
• Directing water and electrolyte balance
• Intensifying pain and enhancing inflammation responses
Non-Saponifiable Lipids
Eicosanoids – Thromboxanes
• also derived from arachidonic acid.
• Promote formation of blood clots
• Thromboxane A2 induces platelet
aggregation and vasoconstriction.
• Aspirin and other NSAIDs inhibit the
synthesis of thromboxanes by
inhibiting the COX (cyclooxygenase)
enzyme.
Non-Saponifiable Lipids
Eicosanoids – COX Enzymes
• The COX (cyclooxygenase) enzyme occurs in two forms:
1. COX-1 catalyzes the normal physiological production of
prostaglandins.
2. COX-2 is responsible for the production of prostaglandins in
inflammation.
• When a tissue is injured or damaged, special inflammatory cells invade the
injured tissue and interact with resident cells, for example, smooth muscle
cells.
• This interaction activates COX-2 and prostaglandins are synthesized.
Non-Saponifiable Lipids
Eicosanoids – COX Enzymes (Inhibition)
• Reversible – Competitive Inhibitors
• Irreversible inactivation – Aspirin
• Non-selective COX Inhibitors – Traditional NSAIDs
• Selective COX-2 Inhibitors – Celecoxib
Non-Saponifiable Lipids
Eicosanoids – COX Enzymes (Inhibition)
• NSAIDS Effects
1. Anti-inflammatory Effect
• reverses vasodilation, edema, tenderness
2. Analgesic Effect
• preventing prostaglandin mediated sensitization of nerve endings
3. Antipyretic Effect
• resets the hypothalamic thermostat by decreasing prostaglandin synthesis
• vasodilation and heat loss
• do not cause hypothermia
Non-Saponifiable Lipids
Eicosanoids – COX Enzymes (Inhibition)
Non-Saponifiable Lipids
Eicosanoids – Leukotrienes
• Signaling lipids for
inflammatory and
hypersensivity responses
• They occur mainly in
leukocytes.
• They produce muscle
contractions, especially in
the lungs and thereby can
cause asthma-like attacks.
They are 100x more potent
than histamine.
• Several recently-developed
anti-asthma drugs inhibit the
synthesis of leukotrienes.
Non-Saponifiable Lipids
Terpenes
• Hydrocarbons or hydrocarbon derivatives constructed from recurring
isoprene units
• Responsible for the scents and tastes of plant products
Non-Saponifiable Lipids
Fat Soluble Vitamins
• a group of vitamins that are absorbed along with fats in the diet and
can be stored in the body's fatty tissue and liver. Because of this
storage capability, they do not need to be consumed as frequently as
water-soluble vitamins. However, consuming them in excess can lead
to toxicity, as the body doesn't easily excrete them.
Non-Saponifiable Lipids
Pheromones
• Chemicals secreted by insects
and animals to transmit
messages to other members
of the species
• Long chain alkenes with
oxygen-containing functional
group
