DEPARTMENT OF BIOCHEMISTRY

SCHOOL OF BASIC MEDICAL SCIENCES

BABCOCK UNIVERSITY, ILISAN REMO

LIPID STRUCTURE AND FUNCTIONS

Presented by:
PROF. SHOKUNBI O.S. &
MRS. UKANGWA N.A.

October 14, 2024

As partly compiled by Pavla Balínová
Lipid Structure and
Function
Definition
 Lipids are diverse group of molecules
grouped together because they are
insoluble in water but soluble in non-
polar solvents.
Common Physical Properties
of Lipids
 Soluble in non-polar organic solvents
 Contain C, H, O
 Sometimes N & P
 Includes fats and oils – mostly triglycerides
 Fat: solid at room temperature
 Oil: liquid at room temperature
 More highly reduced than CHO
 more energy
 Lipids or Glucose for Energy?
H2 H2 H2 H2 H2 H2 H2 H2
H3C C C C C C C C C O
C C C C C C C C C
H2 H2 H2 H2 H2 H2 H2 H2 OH

More reduced state (more H bound to C)

HC O  More potential for oxidation
HO CH
HC OH
HO CH
Less reduced state (more O bound to C)
HO CH  Less potential for oxidation
CH2OH
 Energy from Lipids
 Compared to carbohydrates, fatty acids
contain more hydrogen molecules per unit of
carbon, thus, they are in a more reduced
form
 Carbohydrates are partially oxidized so they
contain less potential energy (H+ and e-) per
unit of carbon
Functions and Properties
 Concentrated source of energy (9 kcal/gm)
 Energy reserve: any excess energy from
carbohydrates, proteins and lipids are stored
as triglycerides in adipose tissues
 Provide insulation to the body from cold
 Maintain body temperature
 Mechanical insulation
 Protects vital organs
Functions and Properties
 Electrical insulation
 Protects nerves, help conduct electro-chemical
impulses (myelin sheath)
 Supply essential fatty acids (EFA)
 Linoleic acid and linolenic acid
 Formation of cell membranes
 Phospholipids, a type of fat necessary for the
synthesis of every cell membrane (also
glycoproteins and glycolipids)
Functions and Properties
 Synthesis of prostaglandins from fatty acids
 Hormone-like compounds that modulates many
body processes
 Immune system, nervous systems, and GI secretions
 Regulatory functions: lower BP, blood clotting, uterine
contractions
 Help transport fat soluble vitamins
 Palatability and aroma
 Flavor and taste for some species!
 The satiety value – help control appetite
 Fullness; fats are digested slower
Classification of Lipids
o Fatty acids (Polymers of CH2 units)-
Saturated and unsaturated fatty acids
o Glycerides-neutral glyceride
(triglycerides) and phosphoglycerides
o Nonglycerides (sphingolipids, steroids,
waxes)
o Complex lipids (lipoproteins)
Physical Traits of Fatty Acids
 Form membranes, micelles, liposomes
 Orient at water:oil interface
 Contain hydrophobic and hydrophilic groups
 Lipid bilayer for membranes

 Micelles formed during digestion

Physical Traits of Fatty Acids
 Unsaturated fatty acids oxidize
spontaneously in presence of oxygen
 Auto-oxidation, peroxidation, rancidity
 Free radicals formed
 Reduce nutritional value of fats
 Antioxidants prevent oxidation
 Vitamins C and E, selenium
Fatty Acid Structure

=O
-H

-H
H - C - ( C )n - C - OH
-H

-H

Carboxyl
group
Methyl Carbon
group group(s)
 Fatty Acids
 With a few exceptions, natural fatty acids:
 Contain an even number of carbon atoms
 Arranged in an unbranched line
 Have a carboxyl group (-COOH) at one end
 Have a methyl group (CH3) at the other end
Fatty Acid Chain Length
 Short chain: 2 to 6 C (volatile fatty acids)
 Medium chain: 8 – 12 C
 Long chain: 14 – 24 C

 As chain length increases, melting point

increases
 Fatty acids synthesized by plants and animals
have an even number of carbons
 Mostly long chain
 16C to 18C fatty acids are most prevalent
Fatty Acid Saturation
 Saturated - no double bonds
 Unsaturated – contain double bonds
 Monounsaturated – one double bond
 Polyunsaturated - >1 double bond
 The double bond is a point of
unsaturation
 As number of double bonds increases,
melting point decreases
Saturated fatty
acid

Unsaturated
fatty acid
Saturated Fats
 All the chemical bonds between the carbon
are single bonds C-C-C-
 No double bonds
 No space for more H atoms; fully “saturated”
 Solid at room temperature
 Butter, shortening, lard, coconut oil, palm oil, and
fully hydrogenated vegetable oils
 Poultry skin, whole milk
Mono-Unsaturated Fatty Acids
 Only one double bond
 Therefore, two H atoms can be added
 Liquid at room temperature
 Olive oil, canola oil, peanut oil
 Other sources: avocado, almonds,
cashews, pecans and sesame seeds (tahini
paste)
Poly-Unsaturated Fatty Acids
 Two or more double bonds
 Include omega-3 and omega-6 fatty acids
(essential fatty acids)
 Linolenic acid: omega 3 fatty acid
 Linoleic acid: omega 6 fatty acid
 Richest sources of poly-unsaturated fatty
acids include:
 Vegetable oils
 Corn, sunflower, safflower, cotton seed oils
Saturation
 Unsaturated fatty acids
 Converted to saturated fatty acids by rumen
microbes
 More susceptible to rancidity
 Oxidation of double bonds produces peroxides and free
radicals, which can cause damage to other compounds
 Antioxidants
 Vitamins E, C
 Carotenoids
 Such as beta-carotene, lycopene
 Selenium
 Review of Fatty Acid
Nomenclature
 Chain length
 Most fatty acids have an equal number of carbons
 Fish oil is rich in odd-numbered FAs
 Double bonds
 Number
 Location from methyl or carboxyl end
 Degree of “saturation”
H H2 H H H2 H2 H2 H2
H3C C C C C C C C C O
C C C C C C C C C
H2 H H H2 H H2 H2 H2 OH
 Fatty-acid Nomenclature
 Named according to
chain length
 C18
H2 H2 H2 H2 H2 H2 H2 H2
H3C C C C C C C C C O
C C C C C C C C C
H2 H2 H2 H2 H2 H2 H2 H2 OH
 Fatty-acid Nomenclature
 Named according to the number of
double bonds
 C18:0

H2 H2 H2 H2 H2 H2 H2 H2
H3C C C C C C C C C O
C C C C C C C C C
H2 H2 H2 H2 H2 H2 H2 H2 OH

Common name:
Stearic acid
 Fatty-acid Nomenclature
 Named according to the number of
double bonds
 C18:1
H2 H2 H2 H H2 H2 H2 H2
H3C C C C C C C C C O
C C C C C C C C C
H2 H2 H2 H2 H H2 H2 H2 OH

Common name:
Oleic acid
 Fatty-acid Nomenclature
 Named according to the number of
double bonds
 C18:2
H2 H2 H H H2 H2 H2 H2
H3C C C C C C C C C O
C C C C C C C C C
H2 H2 H H2 H H2 H2 H2 OH

Common name:
Linoleic acid
 Fatty-acid Nomenclature
 Named according to the number of
double bonds
 C18:3
H H2 H H H2 H2 H2 H2
H3C C C C C C C C C O
C C C C C C C C C
H2 H H H2 H H2 H2 H2 OH

Common name:
Linolenic acid
 Fatty-acid Nomenclature
 Named according to the
location of the first double bond from
the non-carboxyl end (count from the
methyl end)
 Omega system (e.g., omega 3, 3)
 n–system (e.g., n–3)
H H2 H H H2 H2 H2 H2
H3C C C C C C C C C O
C C C C C C C C C
H2 H H H2 H H2 H2 H2 OH
 Fatty-acid Nomenclature
H2 H2 H2 H H2 H2 H2 H2
H3C C C C C C C C C O
C C C C C C C C C
H2 H2 H2 H2 H H2 H2 H2 OH
Omega 9 or n–9 fatty acid

H2 H2 H H H2 H2 H2 H2
H3C C C C C C C C C O
C C C C C C C C C
H2 H2 H H2 H H2 H2 H2 OH
Omega 6 or n–6 fatty acid

H H2 H H H2 H2 H2 H2
H3C C C C C C C C C O
C C C C C C C C C
H2 H H H2 H H2 H2 H2 OH
Omega 3 or n–3 fatty acid
Fatty Acid Synthesis Issues
Ω-3 Ω-6 Ω-9
C-C-C=C-C-C=C-C-C=C-C-C-C-C-C-C-C-COOH

 Animals can synthesize a fatty acid with a

double bond in the omega 9 position but not
at either 3 or 6 positions
 Omega-3 and omega-6 fatty acids must be
derived from diet
 Cold water fish accumulate high levels of
omega 3 fatty acids from their diet
Omega System and
Essential Fatty Acids
 Linoleic acid is an omega-6 fatty acid
 Linolenic and arachidonic acids are
omega-3 fatty acids
 Linoleic and linolenic acids are essential
fatty acids
 Arachidonic acid can be synthesized from
linoleic acid, so not essential
Fatty-acid Nomenclature
 Named according to location of H’s
 Cis or trans fatty acids

Cis-9-octadecenoic acid Trans-9-octadecenoic acid

(Oleic acid) (Elaidic acid)
 Fatty-acid Nomenclature
H2 H2 H2 H H2 H2 H2 O
H3C C C C C C C C C C
C C C C H C C C C OH
H2 H2 H2 H2 H2 H2 H2 H2

H H2 H2 H2 O
C C C C C
C C C C OH
H2 H2 H2 H2
 Isomers
 Geometrical isomers due  Chain branching
to double bond  Straight
 Cis  Synthesized by
 occurs naturally mammals and plants
 bend in acyl chain  Branched
 Trans  Synthesized by bacteria
 Not as common
 Found in hydrogenated
oils
 Results from bacterial
synthesis
 In fats in ruminants!!
 Straight acyl chains
Cis Fatty Acids
 Melting Points
 Affected by chain length
 Longer chain = higher melting temp

Fatty acid: C12:0 C14:0 C16:0 C18:0 C20:0

Melting point: 44°C 58°C 63°C 72°C 77°C

Which fatty acids are liquid at room temperature?

Which fatty acids are solid at room temperature?
Chain Length
 In most fats with a mixture of fatty acids, the
chain length of the majority of fatty acids will
determine the “hardness” of the fat
 <10 carbons = liquid
 Between 10 and 20 carbons = ???
 >20 carbons = solid

Acetic Acid (2 C) Vinegar Liquid

Stearic Acid (18 C) Beef Tallow Solid

Arachidic Acid (20 C) Butter Solid

 Melting Points
 Affected by number of double bonds
 More saturated = higher melting temp

Fatty acid: C18:0 C18:1 C18:2 C18:3

Melting point: 72°C 16°C –5°C –11°C

Which fatty acid is liquid at room temperature?

Which fatty acids are solid at room temperature?
Acids Carbons Double bonds Abbreviation Source
Acetic 2 0 2:0 bacterial metabolism
Propionic 3 0 3:0 bacterial metabolism
Butyric 4 0 4:0 butterfat
Caproic 6 0 6:0 butterfat
Caprylic 8 0 8:0 coconut oil
Capric 10 0 10:0 coconut oil
Lauric 12 0 12:0 coconut oil
Myristic 14 0 14:0 palm kernel oil
Palmitic 16 0 16:0 palm oil
Palmitoleic 16 1 16:1 animal fats
Stearic 18 0 18:0 animal fats
Oleic 18 1 18:1 olive oil
Linoleic 18 2 18:2 grape seed oil
Linolenic 18 3 18:3 flaxseed (linseed) oil
Arachidonic 20 4 20:4 peanut oil, fish oil
Essential Fatty Acids
 Must be in diet
 Tissues can not synthesize
 Linoleic acid (18:2)
 Omega-6-FA
 Linolenic acid (18:3)
 Omega-3-FA
 Arachidonic (20:4)
 Not found in plants!
 Can be synthesized from C18:2 (linoleic acid) in most
mammals (except in cat)
 Essential nutrient in the diet of cats
 Functions of Essential
Fatty Acids
 A component of the phospholipids in
cell membranes
 Precursor for prostaglandins:
arachidonic acid
 Important metabolic regulator
 Contraction of smooth muscle
 Aggregation of platelets
 Inflammation
Arachidonic Acid
 Prostaglandins
 Thrombocyclin
 Prostacyclin
 Leukotrienes
 Neurotransmitters
 Cytochrome P450
 Synthesized in liver
 elongates linoleic acid (C18:2)
Essential Fatty Acids
 Deficiency of essential fatty acid
intakes:
 Growth retardation
 Problems with reproduction
 Skin lesions
 Kidney and liver disorders
Glycerides
 Neutral fats and oils
 Monoacyl glycerols (monoglycerides)
 Diacyl glycerols (diglycerides)
 Diglycerides found in plant leaves
 One fatty acid is replaced by a sugar (galactose)
 Triacyl glycerols (triglycerides)
 Triglycerides found in seeds and
animal adipose tissue
 Triacyl glycerols (triglycerides)
 Lipid storage form
 Where in the body? Adipocytes!!
 Most lipids consumed are triglycerides
Triglycerides
 Most common structure in dietary lipids
 Composed of one glycerol molecule and three fatty
acids connected by an ester bond (bond between an
alcohol and and organic acid)
 Fatty acids may be same or mixed

Fatty Acid

Fatty Acid
Glycerol

Fatty Acid
 Most Common Fatty Acids in Di-
and Triglycerides
Fatty acid Carbon:Double bonds Double bonds
Myristic 14:0
Palmitic 16:0
Palmitoleic 16:1 Cis-9
Stearic 18:0
Oleic 18:1 Cis-9
Linoleic 18:2 Cis-9,12
Linolenic 18:3 Cis-9,12,15
Arachidonic 20:4 Cis-5,8,11,14
Eicosapentaenoic 20:5 Cis-5,8,11,14,17
Docosahexaenoic 22:6 Cis-4,7,10,13,16,19

CH3(CH2)nCOOH
Complex Lipids - Phospholipids
 Two primary types:
 Glycerophosphatides
 Core structure is glycerol
 Part of cell membranes, chylomicrons,
lipoproteins
 Sphingophosphatides
 Core structure is sphingosine
 Part of sphingomyelin
 Phospholipids
 Structure: Glycerol + 2 fatty acids + phosphate group. Example is
phosphatidylcholine (lecithin), which is most common.
 Function: Main structural component of membranes, where they
arrange in bilayers.
Phospholipid bilayer

Hydrophillic heads

Hydrophobic tails
Phospholipids in Water
Phospholipids
 Significant use in feed industry as
emulsifiers
 Lipids form emulsion in water
 Phospholipid sources:
 Liver, egg yolk,
 Soybeans, wheat germ
 Peanuts
 3. Waxes
 Biological waxes are esters of long-chain (C14 to C36)
saturated and unsaturated fatty acids with long-chain
(C16 to C30) alcohols. Example is
triacontanoylpalmitate. Their melting points (60-100
oC)are generally higher than those of triglycerides.

 Functions:
 In plankton, waxes are the chief storage form of
metabolic fuel.
 Lipids that serve as coatings for plant parts and as
animal coverings (beeswax).
Complex Lipids - Glycolipids
 Carbohydrate component in structure
 Cerebrosides & gangliosides
 Medullary sheaths of nerves; white matter
of brain
Derived Lipids
 Prostaglandins
 Synthesized from arachidonic acid
 Several metabolic functions
 Steroids
 Cholesterol, ergosterol, bile acids
 Terpenes
 Made by plants
 Carotenoids, xanthophylls
 Sterols
 Four carbon rings with no fatty acid tails
 Compounds with multi-ring structure

 Insoluble in water
 Present both in plant and animal foods
 Major sterol is cholesterol
 However, cholesterol is found only in animal
products (manufactured in liver)
 High content in organ meats and egg yolk
Common Sterol Compounds

Vitamin D3
(cholecalciferol)
Cholesterol
(a sterol)

Testosterone Stigmasterol
(a steroid hormone) (a phytosterol)
Cholesterol
 Major steroid in animal tissue
 Amphipathic with a polar head group

( -OH group at C3) and a non polar

hydrocarbon body
 Synthesized from acetyl Co A

 Two forms:

Free, esterified (with a long chain fatty acid)

 Melts at 150 C
o

 Insoluble in water but can be extracted from

tissue by chloroform, ether, benzene

 Function of cholesterol
 In plasma membrane
 In lipoproteins

 Precursor of many other steroids:

a) Bile acids (Cholic acid, taurocholic acid)

b) Steroid hormones (male and female

sex hormones, progesterone,
adrenocortcal)
Artheriosclerosis plaques (Voet and Voet, 2011)
 Cholesterol
 Cholesterol is a fat-like substance, found in the blood stream,
bodily organs and nerve fibres (Ikonen, 2008).

 A constituent of cell membranes and the precursor of steroid

hormones and bile salts (Ikonen, 2008).

 It compartmentalize the plasma membrane into functionally

distinct areas involved in protein sorting events in polarized
cells (lipid raft hypothesis) (Brown and London, 1998; Ikonen,
2008).

 It regulates membrane trafficking in both the exocytotic and

endocytotic pathways, cell migration, and a variety of cell
signalling cascades (Simons and Tomri, 2001).
Cholesterol structure (Voet and Voet, 2011)
 Factors influencing individual cholesterol level

 A diet high in saturated fat content

 Heredity
 Type II diabetes,
 In a healthy organism, an intricate balance is maintained

between the biosynthesis, utilization, and transport of

cholesterol, keeping its harmful deposition to a minimum
(Greenfeder, 2009).
COMPLEX LIPIDS

 Lipoproteins.
 low density lipoproteins (LDL-cholesterol)
 high density lipoproteins (HDL-cholesterol)
 very low density lipoproteins (VLDL-cholesterol)
 Intermediate density lipoprotein (IDL)
 Chylomicrons- transport triglycerides from intestine
(Greendfeder, 2009).
Table 1: Compositions of lipoproteins in plasma of humans

Source: Murray et al., 2003