Lecture-

LIPID
 Fatty acids in food:
saturated vs unsaturated

% Fatty
Source Lauric/Myristic Acids
Palmitic Stearic Oleic Linoleic

Beef 5 26-32 20-25 37-43 2-3

Milk 25 12 33 3
Coconut 74 10 2 7
Corn 8-12 3-4 19-24 34-62
Olive 9 2 84 4
Palm 39 4 40 8
Soybean 9 6 20 52
Sunflower 6 1 21 66
Lecture
Lecture15.
15.Lipids
Lipids 33

Lipid
s
Lipids have low solubility in
water;
Lipids are amphipathic (polar and
nonpolar);
Lipids are a principle component
of biological membranes;
highly reduced forms of carbon;
yield large amount of energy
upon oxidation in metabolism;
 Roles of Lipids

Structural elements (phospholipids, cholesterol)

Energy storage (fatty acids, triacylglycerols)
Hormones ( sex hormones e.g. Estrogen, testosteron)
Enzyme cofactors (coenzyme A)
Electron carriers (coenzyme Q, plastpquinone)
Light-absorbing pigments (carotenoids)
Emulsifying agents (bile salts)
Intracellular messengers (phosphatidyl inositol)
 Spontaneously Formed Lipid Structures

Hydrophobic interactions are important

Head Lipid is an amphipathic molecule,
group
but rarely exists as a monomer.
Tail
group

air
water

monolayer Lipid bilayer

Micelle
 What is soap ?

TAG + 3KOH (NaOH) 3RCOO-K+ + glycerol

FA chains can dissolve in oils while charged carboxyl
group dissolves in water;

Forms a mixed micelle which can remove oils;

Soap form precipitates with divalent cations

(reduces efficiency);

Detergent (modified FAs) do not precipitate with

calcium, used as better cleaning agents.
 Lipids and the Structure of the
Plasma Membrane

To minimize interactions of FA chains (non-

poplar), phospholipids aggregates form a bilayer
structure. glycolipid

Polar head
hydrophobic
tail

Integral
protein cholesterol
 Fluid Mosaic Model

S. J. Singer and G. L. Nicolson, 1972

The phospholipid bilayer is a fluid matrix
The bilayer is a two-dimensional solvent
Lipids and proteins can undergo rotational and
lateral movement Peripheral
Proteins

Two classes of proteins:

peripheral proteins (extrinsic proteins) Transmembrane
Domain (integral
integral proteins (intrinsic proteins) Proteins)
 Fatty Acids as Stored Energy

Fatty acids are the bodys principal

form of stored energy
Carbon almost completely reduced
as CH2
Principal sources: dairy products,
meats: Triacylglycerols,
phospholipids, sterol esters
Lecture
Lecture15.
15.Lipids
Lipids 11
11

Triglycerols (triglycerides)
Triglycerols consist of a glycerol esterified with
three fatty acids
If all fatty acid chains are the same, the molecule
is called triacylglycerol (e.g., tristearin)
O
H2C O

O
CH
O

O
H2C
O
Lecture
Lecture15.
15.Lipids
Lipids 12
12

Fatty Acids
Fatty acids = carboxyl group + a long hydrocarbon chain
HO
H2 H2 H2 H2 H2 H2 H2
C C C C C C C C
O C C C C C C C CH3
H2 H2 H H2 H2 H2 H2 OH

OH O

16:0 =Palmitic Acid=Hexadecanoic acid 18:1 =Oleic acid=9-Octadecenoic acid

Saturated fatty acids are single bonds in all carbon-carbon

bonds;
Unstaurated fatty acids contain one or more double bonds in
hydrocarbon chains;
 Fatty acids
(FAs) and nomenclature
Structure

Basic formula: CH3(CH2)nCOOH

Carboxylic acids with hydrocarbon chains of
4-24 carbons
Free FAs are found in trace quantities in cells
FAs are either:
(i) part of a lipid molecule
(ii) complexed to a carrier protein
(e.g. albumin on blood)

Saturated or unsaturated
 Naturally occurring fatty acids

There is a common pattern in the location of

double bonds:

Unsaturated FA: 9, 12, 15

Polyunsaturated FA:

double bonds are never conjugated and are

seperated byCH2 (-CH=CH-CH2-CH=CH-)n

 Naming of fatty acids
C18

10 9
CH3-(CH2)7-CH=CH-CH2-CH2-CH2-CH2-CH2-CH2-CH2-COOH
Cis 9

18:0, stearic acid : octadecanoic acid

18:1 (9), oleic acid : octadecenoic acid

18:2 (9,12), linoleic acid : octadecadienoic acid

18:3 (9,12,15), -linolenic acid : octadecatrienoic acid

Saturate b.
d Unsaturated
Lecture
Lecture15.
15.Lipids
Lipids 17
17

Common Fatty Acids

Saturated fatty acids:
Lauric acid 12:0
Myristic acid 14:0
Palmitic acid 16:0
Stearic acid 18:0
Unsaturated fatty acids:
Palmitoleic acid16:1
Oleic acid 18:1
Linoleic acid 18:2
A-linoleic acid 18:3 (9,12,15)
G-linoleic acid 18:3 (6,9,12)
Lecture
Lecture15.
15.Lipids
Lipids 18
18

Structural Consequences of
Unsaturation

Saturated chains pack tightly and

form more rigid, organized
aggregates (i.e., membranes);
Unsaturated chains bend and pack
in a less ordered way, with greater
potential for motion.
 Waxes

O
- Esters of long chain fatty acids O

(C14-36) with long chain

(C16-30) alcohols
- High melting points (60-100C)
- Energy storage Oleoyl alcohol Stearic acid
(Plankton, )
-Water repellant
(birds and plants)
 Phospholipids

2 Classes of phospholipids (PL)

(i) glycerolphospholipids glycerol backbone
(ii) sphingomyelin spingosine backbone
Glycerolphospholipids
- essential for membrane structure
- most abundant membrane lipids
Sphingolipids
- Component of a certain membrane
- Sphingosine, fatty acid and glycoside
L-Glycerol-3-phosphate,
the backbone of phospholipids
Lecture
Lecture15.
15.Lipids
Lipids 24
24

Examples of
Phosphatides O
H2C O

Phosphatidylcholine
O
CH
O
CH3 O
H3C N (CH2)2 O P O CH2 Fatty acid moiety
CH3 O

Phosphatidylethanolamine
Fatty acid moiety
H3N (CH2)2

Phosphatidylserine
COO Fatty acid moiety
CH H3C O
NH3
Lecture
Lecture15.
15.Lipids
Lipids 25
25

Sphingolipids
Sphingosine forms the backbone of
sphingolipids (rather than glycerol);
Sphingosines are important components
of biological membranes;
Ceramide = sphingosine + fatty acid (via
an amide linkage);
Sphingomyelins = ceramide +
phospholipids (via 1-hydroxyl group)
Glycosphingolipids = ceramide + -
linked sugar at the 1-hydroxyl moiety.
Sphingolipids
Lecture
Lecture15.
15.Lipids
Lipids 27
27

Examples of Sphingolipids
Sphingosine Ceramide O H3C
H2O OH H OH O P O CH2CH2 N CH3
H OH H OH H
C C CH2 C C CH2 H OH H O CH3
H NH C C CH2
H NH3
H H H NH Cholin
O H
R-COOH O Sphingomyelin
R
fatty acid R
Similarities between phosphatidylcholine
and sphingomelin
Lecture
Lecture15.
15.Lipids
Lipids 29
29

Terpenes
Terpenes are a class of lipids from two or
more molecules of 2-methyl-1,2-
butadiene, or isoprene; head

O
tail

Example of a terpene molecule:2-methyl-1,3-butadiene

CHO

all-trans-retinal
All sterols (including cholesterol) and
steroid hormones are terpene-based
molecules
 Cholesterol
Steroids:
(i) cholesterol and sterols of plants and fungi
(ii) steroid hormones
(iii) bile salts

Roles of cholesterol in mammals

(i) structural component of plasma membrane and
modulates membrane fluidity
(ii) precursor of steroid hormones and bile acids

Rarely found in plants, never in bacteria

Lecture
Lecture15.
15.Lipids
Lipids 31
31

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;
Lecture
Lecture15.
15.Lipids
Lipids 32
32

Steroid Examples OH

H3 C C D
C D CH CH3
A B
A CH2
B O
CH2
testosterone
Cyclopentanoperhydrophenanthrene CH2 synthesized in five
CH CH3 steps from cholesterol
CH2 OH

H3C C D
C D
A B
A B
HO
HO
Cholesterol
Estradiol
Cholestero
Steroid hormones carry messages between tissues

Derivates of sterols;

Sex hormones and

hormones from adrenal
cortex;

Play important roles

in gene expression;

Prednisolone and
prednisone are steroid
drug with potent
antiinflammatory
activities.
 Vitamins

Fat soluble: vitamins A,D,E,K

Long chain polyunsaturates hydrocarbons
attached to 1 or 2 benzene rings
Vitamin A (retinol) Vitamin D
formed from precursor in
stored in liver
skin by UV
precursor:carotene
deficiency: night regulates Ca deposition
blindness
deficiency: rickets
 Vitamins E and K and Lipid Quinones are
oxidation-reduction cofactor

Vit E: biological antioxidants;

Vit K: undergoes a cycle of oxidation and reduction;

during the formation of active prothrombin;

Ubiquinone (coenzyme Q) and plastoquitone:

isoprenoids that functionas lipophilic electron carriers
in the oxidation-reduction reactionsthat drive ATP
synthesis in mitochondria and chloroplasts, respectively.
MATA
AIMASHOU