1

Five (5) types of lipids:

Energy-storage lipids: triacylglycerols

Membrane lipids: phospholipids

Emulsification lipids: bile

Messenger lipids: steroid hormones

Protective lipids: biological waxes

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 FATTY ACIDS:
Saturated
Unsaturated
GLYCERIDES:
Neutral
Phosphoglycerides
NONGLYCERIDES:
Sphingolipids
Steroid
Waxes
COMPLEX LIPID:
Lipoproteins
Glycolipids 3
Fatty acids: a component of
many lipids
Monocarboxylic acids.
Different types of fatty acids:
Saturated fatty acid

Unsaturated fatty acid

Monounsaturated fatty acid: exp (20:1).
Polyunsaturated fatty acids: exp (20:3).

Biosynthesized fatty acids are further classified as:

Long-chain: contain 12-26 carbons
Medium-chain: contain 6-10 carbons
Short-chain: contain 4-6 carbons
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 Physical properties
of fatty acids
the length and degree of
unsaturation. Melting Point

chain > > solubility < <

melting point > >

Solubility in H2O

Chain Length

unsaturation > > melting point < < as due to

the lack of compact packing as a result of kinks
introduced by the double bonds
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 F. A. M. P. (0C) Cis D.B.
16:0
16:1 60
1
18:0 63
18:1 16
18:2 -5
18:3 -11
20:0 75
20:4 -50
1 D.B. 2 D.B.
melting
temperature
All unsaturated
fats are oils at room
temperature

0 1 2 3 4 6
D.B.
 Double bonds in fatty O

C
acids usually have the 3 1 O
4 2
cis configuration.
Most naturally
fatty acid with a cis-9
occurring fatty acids double bond
have an even number
of carbon atoms.
Some fatty acids and their common names:
14:0 myristic acid; CH3(CH2)12-COOH

16:0 palmitic acid; CH3(CH2)14-COOH

18:0 stearic acid; CH3(CH2)16-COOH

18:1 cis9 oleic acid CH3(CH2)7CH=CH(CH2)7-COOH

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18:2 cis 9,12 linoleic acid
CH3(CH2)4CH=CHCH2CH=CH(CH2)7-COOH
is used to synthesize arachidonic acid, which regulates blood pressure,
clotting et

18:3 cis 9,12,15 a-linonenic acid

CH3CH2CH=CHCH2CH=CHCH2CH=CH(CH2)7-COOH
is used to synthesize eicosapentaenoic acid (EPA) and docosahexanoic acid
(DHA) which are required for normal brain function and development (an
omega-3)

20:4 cis5,8,11,14 arachidonic acid

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20:5 cis 5,8,11,14,17
eicosapentaenoic acid(an omega-3)
9
Waxes

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Waxes :
ester of fatty acids and long chain alcohol

O
||
R - C - O - R1

Important in fruits:
1. Natural protective layer in fruits, vegetables, etc.
2. Added in some cases for appearance and protection.
Beeswax (myricyl palmitate),Spermaceti (cetyl palmitate)

O O
C30 H61 O C C15 H31 C16 H33 O C C15 H31
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 O
H
O H C-OHH-O-C-CH2C-R1
HO- CH O
R2-CH2-C-OH
H-O-C-CH2C-R3
H C-OH
H
Diacylglycerol/ Monoacylglycerol/monoglyceride
diglyceride
Triacylglycerol
glycerol = Triglyceride
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13
14
Chemical Properties of Triacylglycerols
The chemical reactions of triacylglycerols are similar
to those of alkenes and esters.
Hydrogenation of double bonds in unsaturated fatty
acids by H2 (compare to alkenes).
Hydrolysis of ester bonds by water
in the presence of an acid, a base,
or an enzyme (compare to esters).

TAG :
* energy reservoirs * insulator
* digested in the small intestine by the
enzyme pancreatic lipase
* saponification : formation of soaps

Monoacylglycerols are absorbed through

the intestinal cells, re-converted to TG
and assembled into lipoproteins 15
Triglycerides
Stored as droplets of
adipose tissue in body
fat.

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Fat stored in this cell
 Hydrogenated Fats
Hydrogenation of
vegetable oils
converts some of
unsaturated bonds to
saturated, trans *
conformation.
Trans fatty acids
extend shelf life,
improve margarine,
shortening.
Diet high in trans
fatty acids risks cis trans
heart disease, cancer.
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PYROLYSIS O O
// //
CH2 - O - C - R1 3 CH2 - O - C - R
fatty acids
O
//
CH - O - C - R2 O
O //
-o2
// CH2 = CH - C - H
CH2 - O - C - R3 acrolein

Hydrogenation: addition of two hydrogen atoms

over a double bond. Some food products are
partially hydrogenated
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Oxidation
- COOH
( fatty acid)
H2 O
- C = C - + O2 -C - C - - CHO
- C=O
O - O
(Peroxide)

Oxidation: addition of oxygen (ex: air) can

lead to oxidation of the double bonds present
in a fatty acid, which produces carboxylic
acids.
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Rancidification O
Lipase
//
Fat R - CH2 - CH2 - C - O - H
the decomposition -Oksidase
of fats and other
lipids by
hydrolysis and or
oxidation O O
// //
R - C - CH2 - C - O - H + R - C - C + CO2
//
O Keton

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 Glycerol esterified to 2
fatty acids.
Third position is
phosphate
Other end of phosphate
can combine with other
molecules to form various
derivatives PHOSPHATE
Amphipathic emulsifying H
agents
OH OH
Production of cell
membrane Phosphatidyl H OH
inositol OH H
H H

H OH
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Each glycerophospholipid / phosphoacylglycerol
includes : O

O H2C O C R2
a polar region:
glycerol, carbonyl O R1 C O CH O
of fatty acids, Pi, & the H2C O P O X
polar head group (X)
O
glycerophospholipid
non-polar hydrocarbon tails
of fatty acids (R1, R2).

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 O

O H2 C O C R2

R1 C O CH O CH3

H2 +
H2 C O P O CH CH2 N CH3

-
OH H CH3
OH Phosphatidylcholine/lechitin
OH
Phosphatidic
Phosphatidyl
Phosphatidylinositol acid
H OH
It is a common
OH H membrane lipid
H H

H OH

In addition to being a membrane lipid,

phosphatidylinositol has roles in cell
signaling.

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phosphatidyl choline = lechitin
Lecithin, a
common food
additive, is a
phospholipid.
Embedded in
cell
membranes.

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Cell Membrane

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Phosphatidyl choline with fatty acids
as oleate and palmitate

O
H2C O O (CH2)7 C C (CH2)7 CH3
H H
O HC O (CH2)14 CH3
CH3
+ O P O CH2
N
H3C O
CH3

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 Sphingolipids
Sphingosine instead of glycerol

Derivatized at ester C1

Fatty acids added at amine

Different types are found in

plasma membrane and myelin
sheaths
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The amino group of sphingosine can
form an amide bond with a fatty acid
carboxyl, to yield a ceramide
Ceramides usually include a polar head
Sphingomyelins group, esterified to the terminal OH
are found of the sphingosine
abundantly in the CHCH O
3 2OH
myelin sheath that H2 HO2
OH +
surrounds the H3 C N
H
C C O P O
nerve fibers OH H OH OH
CH3 OH
H H
Sphingomyelin, a ceramide H C
H
CH
H OH 2 C
with a phosphocholine or
A cerebroside is a head
phosphethanolamine H2N CH
sphingolipid
group, (ceramide)
is a common with a
constituent
OH
monosaccharide
of plasma membranessuch as O C CH
glucose or galactose as polar
head group. Sphingomyelin
Sphingolipids
R (CH 2 )12
/ceramide
sphingosine 28
CH 3
Steroid Nucleus

Consists of:
3 cyclohexane rings.
1 cyclopentane ring.
no fatty acids.

steroid nucleus

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Cholesterol
is the most abundant steroid in the body.
has methyl CH3- groups, alkyl chain, and
-OH attached to the steroid nucleus.

CH3 CH3
CH3
CH3
CH3

HO

HO

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 Precursor to Vitamin D
-important constituent of cell
membranes
-has a rigid ring system and a
short branched hydrocarbon
tail.

Precursor to Bile Acids:

- Act as detergents to
dissolve HO
dietary fats
- Fats can be broken amphipathic. hydrophobic
better by enzymes
Keeps the lipids in membrane Precursor to steroid hormones
from aggregrating: Keeps the that regulate gene expression
membrane intact as a bilayer

An artery clogged by
A normal, open artery. 31
cholesterol plaque
 HO

Cholesterol inserts into bilayer membranes with its hydroxyl group

oriented toward the aqueous phase & its hydrophobic
ring system adjacent to fatty acid chains of phospholipids.

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.
The OH group of cholesterol forms hydrogen bonds with
polar phospholipid head groups. 33
 eukaryotic cell membrane fluidity

High temperature Low temperatur

increase membrane fluidity decrease membrane fluidity

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Lipoproteins: LDL, HDL, Etc

combine lipids
with proteins &
phospholipids.
are soluble in
water because the
surface consists of
polar lipids.

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Types of Lipoproteins
differ in density, composition, and function.
include low-density lipoprotein (LDLs) and high-
density lipoprotein (HDLs).

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Transport of Lipoproteins in the Body

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 Good vs Bad Cholesterol
Related to lipoproteins (protein + lipid
complexes)
Dietary excess fat is packaged into VLDL
Fat cells (adipose cells) take these up convert to
fatty acids
Some VLDL is converted to LDL
LDL is very rich in Cholesterol

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LDL
circulate in the blood
Build up in arteries; lead
to heart attack
level 130 mg/dL,
reflects an increased
risk of heart disease
HDL
cholesterol lipoprotein, that
returns to the liver ; removes
cholesterol out of the
bloodstream;
believed to prevent heart attacks
level < 40 mg/dL, is
thought to increase the
risk for heart disease.
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