1

2
Five (5) types of lipids:
Energy-storage lipids: triacylglycerols
Membrane lipids: phospholipids
Emulsification lipids: bile
Messenger lipids: steroid hormones
Protective lipids: biological waxes
3
FATTY ACIDS:
Saturated
Unsaturated
GLYCERIDES:
Neutral
Phosphoglycerides
COMPLEX LIPID:
Lipoproteins
Glycolipids
NONGLYCERIDES:
Sphingolipids
Steroid
Waxes
4
Physical properties
of fatty acids
the length and degree of
unsaturation.


Solubility in H
2
O
Chain Length
Melting Point
chain > > solubility < <


unsaturation > > melting point < < as due to
the lack of compact packing as a result of kinks
introduced by the double bonds
melting point > >

5
Some fatty acids and their common names:
14:0 myristic acid; CH
3
(CH
2
)
12
-COOH

16:0 palmitic acid; CH
3
(CH
2
)
14
-COOH

18:0 stearic acid; CH
3
(CH
2
)
16
-COOH

18:1 cisD
9
oleic acid CH
3
(CH
2
)
7
CH=CH(CH
2
)
7
-COOH

Double bonds in fatty
acids usually have the
cis configuration.
Most naturally
occurring fatty acids
have an even number
of carbon atoms.
C
O
O

1
2
3
4

fatty acid with a cis-D
9

double bond
6
7
Waxes
8
ester of fatty acids and

O
C
30
H
61
O C C
15
H
31

O
C
16
H
33
O C C
15
H
31
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
||
R - C - O - R
1



Waxes :
long chain alcohol
9
C-OH
CH
C-OH
H
H
H
H
HO-
glycerol
Monoacylglycerol/monoglyceride
H-O-C-CH
2
C-R
1
O
Diacylglycerol/
diglyceride
R
2
-CH
2
-C-OH
O
H-O-C-CH
2
C-R
3
O
Triacylglycerol = Triglyceride
10
11
Triglycerides
Stored as droplets of
adipose tissue in body
fat.
Fat stored in this cell
12
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
heart disease, cancer.

cis trans
*
13
PYROLYSIS
Hydrogenation: addition of two hydrogen atoms
over a double bond. Some food products are
partially hydrogenated
O O
// //
CH
2
- O - C - R
1
3

CH
2
- O - C - R


O
//
CH - O - C - R
2
O


O //
// CH
2
= CH - C - H
CH
2
- O - C - R
3

D
fatty acids
acrolein
-o
2


14
- COOH
( fatty acid)

- C = C - + O
2
- C - C - - CHO
- C=O
O - O
(Peroxide)
H
2
O
Oxidation
Oxidation: addition of oxygen (ex: air) can
lead to oxidation of the double bonds present
in a fatty acid, which produces carboxylic
acids.
15
Rancidification
O
//
Fat R - CH
2
- CH
2
- C - O - H
O O
// //
R - C - CH
2
- C - O - H R - C - C + CO
2

//
O Keton
Lipase
-Oksidase
+
the decomposition
of fats and other
lipids by
hydrolysis and or
oxidation
16
Glycerol esterified to 2
fatty acids.
Third position is
phosphate
Other end of phosphate
can combine with other
molecules to form various
derivatives
Amphipathic emulsifying
agents
Production of cell
membrane
PHOSPHATE
O H
H
O H
H
H
O H H
O H
H
H
O H
Phosphatidyl
inositol
17
polar
non-polar
"kink" due to
double bond
O P O
O

O
H
2
C
CH
H
2
C
O C R
1
O O C
O
R
2
X
glycerophospholipid

a polar region:
glycerol, carbonyl O
of fatty acids, P
i
, & the
polar head group (X)

non-polar hydrocarbon tails
of fatty acids (R
1
, R
2
).
Each glycerophospholipid / phosphoacylglycerol
includes :
18
phosphatidyl choline = lechitin
Lecithin, a
common food
additive, is a
phospholipid.
Embedded in
cell
membranes.
19
Cell Membrane
20
Sphingolipids
Sphingosine instead of glycerol

Derivatized at ester C1

Fatty acids added at amine

Different types are found in
plasma membrane and myelin
sheaths

21
2
H
2
C
H
C
O H
C H
N C H
C
C H
2
C H
3
H
( )
1 2
sphingosine
Sphingolipids
/ceramide
H
O H
C
R
O
OH
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
group, esterified to the terminal OH
of the sphingosine
P O O
O
H
2
C
H
2
C
N
+
C H
3
H
3
C
C H
3

OH
Sphingomyelin, a ceramide
with a phosphocholine or
phosphethanolamine head
group, is a common constituent
of plasma membranes
Sphingomyelin

Sphingomyelins
are found
abundantly in the
myelin sheath that
surrounds the
nerve fibers
P O O
O
H
2
C
H
2
C
N
+
C H
3
H
3
C
C H
3

O H
O
H
H
H
O H H
O H
C H
2
O H
H
A cerebroside is a
sphingolipid (ceramide) with a
monosaccharide such as
glucose or galactose as polar
head group.
22
Steroid Nucleus
Consists of:
3 cyclohexane rings.
1 cyclopentane ring.
no fatty acids.



steroid nucleus
23
CH
3
CH
3
CH
3
CH
3
HO
CH
3
Cholesterol
is the most abundant steroid in the body.
has methyl CH
3
- groups, alkyl chain, and -
OH attached to the steroid nucleus.
O H
24
-important constituent of cell
membranes
-has a rigid ring system and a
short branched hydrocarbon
tail.



O H
hydrophobic amphipathic.
Keeps the lipids in membrane
from aggregrating: Keeps the
membrane intact as a bilayer
Precursor to Bile Acids:
- Act as detergents to
dissolve dietary fats
- Fats can be broken
better by enzymes
Precursor to steroid hormones that
regulate gene expression
Precursor to Vitamin D
A normal, open artery.
An artery clogged by
cholesterol plaque
25
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.
O H
26


.
The OH group of cholesterol forms hydrogen bonds
with polar phospholipid head groups.
27
Lipoproteins: LDL, HDL, Etc
combine lipids
with proteins &
phospholipids.

are soluble in
water because the
surface consists of
polar lipids.
28
Types of Lipoproteins
differ in density, composition, and function.
include low-density lipoprotein (LDLs) and high-
density lipoprotein (HDLs).
29
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
30
LDL
circulate in the
blood
Build up in arteries;
lead to heart attack
HDL
level 130 mg/dL,
reflects an increased
risk of heart disease
level < 40 mg/dL, is
thought to increase the
risk for heart disease.
cholesterol lipoprotein,
that returns to the liver ;
removes cholesterol out of
the bloodstream;
believed to prevent heart
attacks