Lipids

Lipids
• Biological compound soluble in non-polar s
olvent
• Chemically heterogeneous: Simple or Comp
lex
• Simple Lipid: alcohol + one or more fatty aci
ds
• Complex lipid: alcohol + fatty acid + someth
ing else
Classification of Lipids
 Fatty Acids

• Linear Molecules 10-20 carbons in length

• Even number of carbons
• No other functional groups but carboxyl
• Sometimes alkene groups C=C
– Saturated vs. unsaturated
 Water Solubility
• Hydrophobic part of molecule dominates: very insolu
ble in water
• Forms micelles in water
* *
*
*

*
*

*
 saturated Fatty Acids

Fatty Acid # of Carbons # of C=C

lauric 12 0

myristic 14 0

palmitic 16 0

stearic 18 0
 Unsaturated Fatty Acids

Fatty Acid # of Carbons # of C=C

oleic 18 1

linoleic 18 2

linolenic 18 3

arachadonic 20 4
 Properties of Fats and Oils
• Triacylglycerols in natural fats and oils are non
polar, hydrophobic molecules with no ionic c
harges.
• Oil: A mixture of triacylglycerols that is liquid
because it contains a high proportion of unsat
urated fatty acids.
• Fat: A mixture of triacylglycerols that is solid b
ecause it contains a high proportion of saturat
ed fatty acids.
10
 Cis vs Trans Fatty Acids
• Cis fatty acids occur naturally
• Trans fatty acids occur during hydrogenation reaction
s
H H
CC

CH
CH
CHCHCHCH CH
2CH
CH
2 CH
2 CO
2
3 2 2 2 2 2

H
CH
CH
2 CH
2 CH
2 CO
2
CC

CH
CH
CH
CH
CH
CH H
322222
 Triglycerides: Fats and Oils

• Glycerol + 3 Fa
tty Acids
• Connected by
ester bonds
 Triglyceride

OH
CH
2
O
CH
OH
+3 C
HO
OH
CH
2

2O C
CH
O

OC
CH
O

CH
2O C
 Fat or Oil
• Depends on melting point- solid or liquid at room te
mperature
• Depends mostly on degree of unsaturation
• Animal Fats more saturated, plant oils more unsatura
ted
 Dietary Fatty Acids

• Saturated fats associated with Heart Disease

• Promotes higher levels of blood cholesterol
• Animal fats also contain cholesterol, plants have no c
holesterol
 Artificial Fats
• Simpless: micro-particles of proteins
– Smooth cream texture
– Not heat stable
– 1.3 Cal/gram vs. 9 Cal/gram for fats

• Olestra: polymer of sucrose and fatty acids

– Not digestable
– Taste and texture of fats
– Causes loss of fat soluble vitamins and other side effects
 Waxes

• Long chain fatty acid + long chain fatty alcohol

CH
3(CH
)
2
14C
OCH
2(CH
)
2
12CH
3

Myristyl palmitate
Wax Block Diagram
 Phosphoglycerides
• Glycerol, 2 fatty acids, phosphate + another alcohol

Fatty Acid
Glycerol

Fatty Acid

Phosphate alcohol
 O

CH 2 O C (CH 2 )16 -CH 3

O Phosphatidic acid

CH O C (CH 2 )16 -CH 3

O

CH 2 O P OH

OH
Alcohols used in phosphoglycerides
CH
3
+
HOCH
2 CH
2 N CH
3

CH
3

choline

O
NH
2

HOCH
CH
2 C
OHHONH
CH
2CH
2 2

serine ethanolamine
 Phosphatidyl Choline (lecithin)
O
-
CH2 O C (CH
2)16 CH3
O
-
CH O C (CH
2)16 CH3
O CH3

CH2 O P O CH2CH2 N+ CH3

O- CH3

• Lectithin used as emulsifier

• Dipalmitoyl phosphatidyl choline formed as
surfactant in lung cells
Phosphatidyl serine: a cephalin found in cell memran
es

CH2 O C (CH2)16-CH3
O

CH O C (CH2)16-CH3
O

CH2 O P O CH2 CH NH3+

O- COO-
Sphinglipids: Sphingosine + fatty acid + somethin
g else

OH

CH
2 CH
2 CH
2 CH
2 CH2 CH
2 CH CHCH
2
H
C CH
3 2 CH
2 CH
2 CH
2 CH2 CH
2 CH CHOH

NH
2

CH
3 (CH
)12CH
2 CHCH
OH Sphingosine
CH
NH2

CH
OH
 Ceramide: sphingosine + fatty acid

CH
3 (CH
)
2
12CH
CH
CH
OH
O

CH
NH
C(CH
)
2
14CH
3

CH
OH

CH
3 (CH
)12CH
2 CHCH
OH Sphingosine
CH
NH2

CH
OH
Sphingomyelin: sphingosine, fatty acid, phosphate
and choline

Sphingomyelins fou
nd in myelin sheath
around neurons
 Sphingomyelin

Fatty acid

CH
3 (CH
2)12
CHCH
CHOH
O

CH
NHC (CH
2)14CH
3

O CH
3

+
CH
O P O CH
CH
2 2 N CH
3

- CH
O 3

phosphate choline
Lipid Storage Diseases
 Biological Membranes
• Separates cell interior from exterior, or ce
llular organelles from cytoplasml
• About 60% lipid and 40% protein
– Lipid mostly phosphoglyceride, sphingomyel
in and cholesterol
• Found as Lipid Bilayer
Lipid Bilayer
 Steroids
• Non-saponifiable lipids derived from cholester
ol

Steroid Ring System

 Cholesterol
CH
3 CH
3

2)3 CHCH
CH (CH 3

CH
3

HO

Found in Diet (animal fats)

Endogenous synthesized in liver
 Cholesterol
• Essential component of cell membranes
• Used as raw material for sex hormones and ad
renocorticoid hormones
• Used to make bile salts
• High blood levels also associated with heart di
sease, atherosclerosis, arterial plaques
Cholesterol transported as Lipoprotein complex (LDL)
 Lipoproteins classified by Density

• HDL: High-density Lipoprotein

• LDL: Low-density Lipoprotein
• VLDV: Very low-density Lipoprotein
– Triglycerides and cholesterol
• Chylomicron
– Mostly triglycerides
Biological flow of Cholesterol
 Male Sex Hormones
• Testosterone
– Produced by testes
– Male genitals and secondary sex characteristics
– Muscle growth
• Anabolic Steroids (fake testosterone)
– Intended to prevent muscle atrophy
– Used by athletes, widely banned
– Bad side effects
 Female Sex Hormones
• Estrogen(estradiol, estrone) and progersteron
e
– Produced by ovaries
– Reproductive cycle and secondary female characte
ristics
• Mimicked by birth control pills
Classification of Lipids