Professional Documents
Culture Documents
Chapter 26
26-1
Lipids
Lipids include:
triglycerides, phospholipids, prostaglandins,
prostacyclins, and fat-soluble vitamins.
cholesterol, steroid hormones, and bile acids.
26-2
Triglycerides
1. NaOH, H2 O
2. HCl, H2 O
CH2OH
HOCH
CH2OH
RCOOH
+
1,2,3-Propanetriol
(Glycerol, glycerin)
R'COOH
R''COOH
Fatty acids
26-3
Fatty Acids
Fatty Acids
Higher
mp
12:0
14:0
16:0
18:0
20:0
Melting Point
(C)
Lauric acid
Myristic acid
Palmitic acid
Stearic acid
Arachidic acid
44
58
63
70
77
Lower
mp
16:1
18:1
18:2
18:3
20:4
Palmitoleic acid
1
Oleic acid
16
Linoleic acid
-5
Linolenic acid
-11
Arachidonic acid -49
26-5
Triglycerides
26-6
Triglycerides
example: a triglyceride derived from one molecule
each of palmitic acid, oleic acid, and stearic acid, the
three most abundant fatty acids in the biological
world.
palmitate (16:0)
O
oleate (18:1)
O CH2OC(CH2) 14CH3
stearate (18:0)
CH3(CH2)7 CH=CH(CH2 )7COCH O
CH2OC(CH2) 16CH3
26-7
Triglycerides
O
RCOCH
O
CH2 OCR
+ 3NaOH
A triglyceride
(a triester of glycerol)
saponification
CH2 OH
CHOH
CH2 OH
1,2,3-Propanetriol
(Glycerol; Glycerin)
O
+
3RCO Na
Sodium soaps
COO Na
26-9
26-10
26-11
26-12
+ +
2+
Ca
A sodium soap
(soluble in water as micelles)
-
2+
2Na
26-13
Synthetic Detergents
26-14
Synthetic Detergents
1. H2 SO4
2. NaOH
SO3 Na
Sodium 4-dodecylbenzenesulfonate
(an anionic detergent)
Prostaglandins
3
4
1
2
COOH
10
11 12
13
14
15
16
17
18
19
20
Prostanoic acid
26-16
Prostaglandins, origin
11 12
14
COOH
15
Arachidonic acid
26-17
Prostaglandins, examples
Among the prostaglandins synthesized biochemically
from arachidonic acid are:
O
PGE2
COOH
HO
HO
PGF2
11
15
HO H
9
COOH
HO
11
15
HO H
26-18
Prostaglandins
HO
9
COOH
HO
11
15
HO CH3
(15S)-15-Methyl-PGF2
26-19
Prostaglandins
The PGE1 analog, misoprostol, is used to prevent the
ulceration associated with the use of aspirin.
O
COOH
PGE 1
15
HO
16
HO H
O
COOCH3
Misoprostol
HO
HO
CH3
15 16
26-20
Eicosanoids
HOOC
9
COOH
O
11
12
13
14
15
OH
Thromboxane A2
(a potent vasoconstrictor)
20
O
H 9
6
7
8
11
14
20
15
13
OH
OH
Prostacyclin
(a platelet aggregation inhibitor)
26-21
Eicosanoids
20
HO
6
COOH
14
L-cysteine
Leukotriene C4 (LTC 4)
(a smooth muscle constrictor)
COOH
N
H
HN
O
COOH
NH2
glycine
L-glutamic acid
26-22
Steroids
26-23
Steroids
The fusion of rings is trans and each atom or group at
a ring junction is axial.
The pattern of atoms or groups along the ring
junctions is nearly always trans-anti-trans-anti-trans.
The steroid system is nearly flat and quite rigid.
Most have have axial methyl groups at C-10 and C-13.
CH3
CH3
26-24
Cholesterol
H3 C
H3 C
H
H
HO
26-25
Androgens
H3 C
H3 C
H
H
OH
H
Testosterone
H3 C
H3 C
H
H
HO
Androsterone
26-26
H3 C
H3 C
Nandrolone decanoate
Methenolone
O
OC(CH2 )8 CH3
CH3
H
H
OH
CH3
Methandrostenolone
H3 C
H3 C
H
H
H3 C
4-Androstene-3,17-dione
(andro)
26-27
26-28
Estrogens
H3 C
H3 C
H
H
H3 C
HO
Testosterone
H3 C
H3 C
H
H
HO
Estrone
OH
H
H
H
Progesterone
H3 C
H3 C
H
H
C=O
H
Androsterone
26-29
Synthetic Estrogens
HO
C CH
H3 C
H
H
O
Norethindrone
26-30
Glucorticoid Hormones
O
H3 C
C=O
OH
H
H
O
Cortisone
CH2 OH
H3 C
HO
H3 C
C=O
OH
H
H
O
Cortisol
26-31
Mineralocorticoid Hormones
Synthesized in the adrenal cortex.
Regulate blood pressure and volume by stimulating
the kidneys to absorb Na+, Cl-, and HCO3-.
CH OH
OH 2
C=O
CH
O
H3 C
H
H
Aldosterone
26-32
Bile Acids
COOH
H
H
HO
H
H
OH
26-33
Biosynthesis of Steroids
26-34
Vitamin E
OH
O
Vitamin E (-Tocopherol)
26-35
Phospholipids
26-36
A phosphatidic acid
Phospholipids
Among the most common of these low-molecularweight alcohols are:
26-38
Phospholipids, an example
A lecithin
26-39
Biological Membranes
26-40
Biological Membranes
Fluid-mosaic model of a biological membrane showing
the lipid bilayer and membrane proteins on the inner
and outer surfaces of the membrane and penetrating
the thickness of the membrane.
26-41
Fat-Soluble Vitamins
26-42
Vitamin A
Occurs only in the animal world.
Found in the plant world in the form of a provitamin in
a group of pigments called carotenes.
26-43
Vitamin A
26-44
26-45
Vitamin D
26-47
Vitamin E
26-48
Vitamin K
26-49