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Lipids
Lipids
Lipids are
Biomolecules that contain fatty acids or a steroid
nucleus.
Soluble in an organic solvents (e.g., ether, benzene,
acetone, chloroform) but not in water.
Named for the Greek word lipos, which means fat.
Extracted from cells using organic solvents.
Types of Lipids
The types of lipids containing fatty acids are
Waxes.
Fats and oils (triacylglycerols).
Glycerophospholipids.
Prostaglandins.
Not steroids, as they do not contain fatty acids.
Lipid Classes
Simple
: FAs esterified with glycerol
Compound
: same as simple, but with other
compounds also attached
Phospholipids : fats containing phosphoric acid and
nitrogen (lecithin)
Glycolipids
: FAs compounded with CHO, but no N
derived lipids : substances from the above derived by
hydrolysis
Sterols
: large molecular with alcohols found in
nature and combined w/FAs (e.g., cholesterol)
5
Structures of Lipids
6
Copyright 2007 by Pearson Education, Inc.
Publishing as Benjamin Cummings
1. Fatty Acids
Fatty Acids
Fatty acids
Are long-chain
carboxylic acids.
Typically contain 12-18
carbon atoms.
Are insoluble in water.
Can be saturated or
unsaturated.
8
Copyright 2007 by Pearson Education, Inc.
Publishing as Benjamin Cummings
10
Copyright 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings
11
O
- C - OH
Benzoic acid
O
- C - OH
OH
Slicilic acid
kinks in
chain
15
16
(The double bonds in the fatty acids are cis (hydrogen atoms are on the same
side of the double bonds of the carbon chain)
O
C H 3(C H 2) 7 C
C (C H 2) 7 C
H
OH
C H 3(C H 2) 4 C
C CH2 C
H
H
C (C H 2) 7 C
H
OH
C
18
Learning Check
Assign the melting points of 17C, 13C, and 69C
to the correct fatty acid. Explain.
stearic acid (18 C) saturated
oleic acid (18 C) one double bond
linoleic acid (18 C) two double bonds
19
Solution
Stearic acid is saturated and would have a higher
melting point than the unsaturated fatty acids.
Because linoleic has two double bonds, it would have
a lower mp than oleic acid, which has one double
bond.
stearic acid mp 69C saturated
oleic acid mp 13C
linoleic acid mp -17C most unsaturated
20
1a. Prostaglandins
Prostaglandins have
20 carbon atoms in their fatty acid chains.
An OH on carbon 11 and 15.
A trans double bond at carbon 13.
C 11
C 13
C 15
21
Prostaglandins
O
OH
23
25
Learning Check
Write a fatty acid with 10 carbon atoms that is:
A. saturated
B. monounsaturated omega-3
C. monounsaturated omega-6
26
Solution
Write a fatty acid with 10 carbon atoms that is:
A. saturated
CH3CH2CH2CH2CH2CH2CH2CH2CH2COOH
B. monounsaturated omega-3
CH3CH2CH=CHCH2CH2CH2CH2CH2COOH
C. monounsaturated omega-6
CH3CH2CH2CH2CH2CH=CHCH2CH2COOH
27
28
2a. Waxes
Waxes are
Esters of saturated fatty acids and long-chain alcohols.
Coatings that prevent loss of water by leaves of plants.
TABLE 1.
www.kerfootgroup.co.uk
30
2b. Triacylglycerols
In a triacylglycerol,
Glycerol forms ester bonds with three fatty acids.
32
Formation of a Triacylglycerol
glycerol
triacylglycerol
O
CH2
OH
HO C
O
(CH2)14CH3
CH
OH +
HO C
O
(CH2)14CH3
CH2
OH
HO C
(CH2)14CH3
O
CH2 O C
(CH2)14CH3
O
CH O C
(CH2)14CH3 + 3H2O
O
CH2 O C
(CH2)14CH3
33
Olive Oil
Olive oil
Contains a high
percentage of oleic
acid, which is a
monounsaturated fatty
acid with one cis
double bond.
34
Learning Check
What are the fatty acids in the following triacylglycerol?
O
CH2
(CH2)16CH3
O
CH
CH2
C (CH2)7CH CH(CH2)7CH3
O
C
(CH2)12CH3
R1= C18
R2= C18 (1) MUFA= mono unsaturated fatty acid
R3= C14
35
Solution
O
CH2
C (CH2)16CH3
Stearic acid
O
CH
CH2
C (CH2)7CH CH(CH2)7CH3
O
C
(CH2)12CH3
Oleic acid
Myristic acid
36
37
38
L
A
U
R
I
C
M
Y
R
I
S
T
I
C
P
A
L
M
I
T
I
C
S
T
E
A
R
I
C
SATURATED
Oil or Fat
12:0
14:0
O
L
E
I
C
G
A
D
O
L
E
I
C
MONOUNSATURATED
16:0
18:0
18:1
11
45
Peanut oil
L
I
N
O
L
E
N
I
C
POLYUNSATURATED
18:2
18:3
28
58
40
10
11
48
Olive oil
13
71
10
Canola oil
62
22
10
Safflower oil
13
78
Sunflower oil
19
68
65
26
Corn oil
Palm oil
20:1
L
I
N
O
L
E
I
C
32
Coconut oil
47
18
48
16
15
Butterfat
11
27
12
29
Lard
26
14
44
Beef tallow
24
19
43
http://www.iseo.org
10
3
burcon.ca
Asam lemak
Asam palmitat
As palmitoleat
Asam stearat
Asam oleat
Asam linoleat
Asam linolenat
Asam eikosenoat
C16:0
C16:1
C18:0
C18:1
C18:2
C18:3
C20:1
minimum
7,0 %
sangat kecil
3,5 %
35,0 %
35,0 %
sangat kecil
sangat kecil
maksimum
12,0 %
0,5 %
6,0 %
50,0 %
50,0 %
1,0 %
1,0 %
44
45
Copyright 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings
Chemical Properties of
Triacylglycerols
46
47
Hydrogenation of Oils
The hydrogenation of oils
Adds hydrogen (H2) to the carbon atoms of double bonds.
Converts double bonds to single bonds.
Increases the melting point.
Produces solids such as margarine and shortening.
48
Copyright 2007 by Pearson Education, Inc Publishing as Benjamin Cummings
Hydrogenation
O
CH2
(CH2)5CH CH(CH2)7CH3
Ni
O
CH
CH2
O
O
+ 3H2
C (CH2)5CH CH(CH2)7CH3
O
C
(CH2)14CH3
O
glyceryl tripalmitoleate
(tripalmitolean)
CH
CH2
C (CH2)14CH3
O
C
(CH2)14CH3
glyceryl tripalmitate
(tripalmitin)
49
Learning Check
What product(s) is obtained from the complete
hydrogenation of glyceryl trioleate?
1. Glycerol and 3 oleic acids
2. Glyceryltristearate
3. Glycerol and 3 stearic acids
50
Solution
What product(s) is obtained from the complete
hydrogenation of glyceryl trioleate?
2. Glyceryltristearate
51
52
trans
(CH2)7 COOH
53
54
Learning Check
(1) True or (2) False
A. There are more unsaturated fats in vegetable oils.
B. Vegetable oils have higher melting points than fats.
C. Hydrogenation of oils converts some cis-double
bonds to trans- double bonds.
D. Animal fats have more saturated fats.
55
Solution
(1) True or (2) False
A. T There are more unsaturated fats in vegetable oils.
B. F Vegetable oils have higher melting points than fats.
C. T Hydrogenation of oils converts some cis-double
bonds to trans- double bonds.
D. T Animal fats have more saturated fats.
56
Hydrolysis
In hydrolysis,
Triacylglycerols split into glycerol and three fatty acids.
An acid or enzyme catalyst is required.
O
CH2
(CH2)14CH3
O
CH
CH2
O
O
C (CH2)14CH3 +3H2O
O
C
(CH2)14CH3
H+
CH2 OH
CH
OH
+ 3 HO C
(CH2)14CH3
CH2 OH
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58
Saponification
O
CH2 O C
(CH2)14CH3
O
CH O C
(CH2)14CH3 + 3NaOH
O
CH2 O C
CH2 OH
(CH2)14CH3
CH OH
+ 3 Na+ -O C (CH2)14CH3
CH2 OH
soap
59
Learning Check
What products are obtained from the complete
hydrolysis of glyceryl trioleate?
1. Glycerol and 3 oleic acids
2. Glyceryl tristearate
3. Glycerol and 3 stearic acids
60
Solution
What products are obtained from the complete
hydrolysis of glyceryl trioleate?
1. Glycerol and 3 oleic acids
61
Learning Check
Write the product of the following reaction.
O
CH2 O C
O
(CH2)5CH CH(CH2)7CH3
CH
C (CH2)5CH CH(CH2)7CH3 + 3 H2
O
CH2
Ni
(CH2)5CH CH(CH2)7CH3
62
Solution
O
CH2
C
O
CH
C (CH2)14CH3
O
CH2
(CH2)14CH3
(CH2)14CH3
63
2c. Glycerophospholipids
Glycerophospholipids are
The most abundant lipids in cell membranes.
Composed of glycerol, two fatty acids, phosphate
and an amino alcohol.
Fatty acid
Glycerol
Fatty acid
PO4
Amino
alcohol
64
choline
CH3
ethanolamine
+
NH3
HOCH2CHCOO
serine
Amino alcohols
65
67
Learning Check
Identify each as a
A. fatty acid
C. amino alcohol
B. triacylglycerol
D. glycerophospholipid
1. glyceryl trioleate
2. cephalin
3. choline
4. palmitic acid
68
Solution
Identify each as a
A. fatty acid
C. amino alcohol
1. glyceryl trioleate
2. cephalin
3. choline
4. palmitic acid
B. triacylglycerol
D. glycerophospholipid
B. triacylglycerol
D. glycerophospholipid
C. amino alcohol
A. fatty acid
69
Learning Check
Identify the components and type of glycerophospholipid
O
O
NH3
CH2O P O CH2CHCOO
O70
Solution
Identify the components and type of glycerophospholipid
O
2 stearic acids
O
NH3
CH2O P O CH2CHCOO
serine
Ophosphate
amino alcohol
type = cephalin
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3a. Sphingolipids
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Sphingolipids
Sphingolipids
Are similar to phospholipids.
Contain sphingosine (a long-chain amino alcohol), a
fatty acid, phosphate, and a small amino alcohol.
Have polar and nonpolar regions.
fatty acid
sphingosine
PO4
amino
alcohol
73
Sphingosine
Sphingosine is a long-chain unsaturated amino alcohol.
CH3(CH2)12 CH=CHCHOH
CHNH2
CH2OH
sphingosine
74
Sphingolipids
In sphingomyelin, a sphingolipid found in nerve cells
There is an amide bond between a fatty acid and
sphingosine, an 18-carbon alcohol.
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3b. Glycosphingolipids
Glycosphingolipids
contain
monosaccharides
bonded to the OH
of sphingosine by a
glycosidic bond.
76
Glycosphingolipids and
Cerebrosides
Glycosphingolipids
Are sphingolipids that contain
monosaccharides.
Can be a cerebroside with galactose.
77
Copyright 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings
Gangliosides
Gangliosides
Are similar to cerebrosides, but contain two or
more monosaccharides.
Are important in neurons.
Act as receptor for hormones and viruses.
Can accumulate and cause genetic diseases.
78
Gangliosides
GM2 is a ganglioside
That accumulates in Tay-Sachs disease.
79
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Learning Check
Identify each as a
1) Fatty acid
2) Triacylglycerol
3) Amino alcohol
4) Glycerophospholipid
5) Glycosphingolipid
A. Glyceryl trioleate
B. Cephalin
C. Choline
D. Galactocerebroside
E. Palmitic acid
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Solution
A. Glyceryl trioleate
B. Cephalin
C. Choline
D. Galactocerebroside
E. Palmitic acid
2) Triacylglycerol
4) Glycerophospholipid
3) Amino alcohol
5) Glycosphingolipid
1) Fatty acid
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4. Steroids
Steroids: Cholesterol, Bile Salts,
and Steroid Hormones
CH3
CH3
CH3
CH3
CH3
HO
Copyright 2007 by Pearson Education, Inc.
Publishing as Benjamin Cummings
83
Steroid Nucleus
A steroid nucleus consists of
3 cyclohexane rings.
1 cyclopentane ring.
No fatty acids.
steroid nucleus
84
Cholesterol
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
85
An artery clogged by
cholesterol plaque
Copyright 2007 by Pearson Education, Inc.
Publishing as Benjamin Cummings
86
Cholesterol in Foods
Cholesterol is
Synthesized in
the liver.
Obtained from
foods.
Considered
elevated if
plasma
cholesterol
exceeds 200
mg/dL.
Table 3.
87
Learning Check
Match the components of the cholesterol molecule with
the following:
___ carbon chain
___hydroxyl group
___ steroid nucleus
___methyl group
D
CH3
CH3
CH3
CH3
CH3
A
C
HO
88
Solution
Match the components of the cholesterol molecule with
the following:
D carbon chain
A hydroxyl group
C steroid nucleus
B methyl group
D
CH3
CH3
CH3
CH3
CH3
A
C
HO
89
Bile Salts
Bile salts
Are synthesized in the liver from cholesterol.
Are stored in the gallbladder.
Are secreted into the small intestine.
Have a polar and a nonpolar region
Mix with fats to break them part.
Emulsify fat particles to provide large surface area.
90
Bile Salts
glycine, an amino acid
O
C
CH2
N
H
COO- Na+
Polar region
CH3
HO
OH
Nonpolar region
Lipoproteins
Lipoproteins
Combine lipids with proteins and phospholipids.
Are soluble in water because the surface consists of polar
lipids.
92
Copyright 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings
Types of Lipoproteins
Lipoproteins
Differ in density, composition, and function.
Include low-density lipoprotein (LDLs) and highdensity lipoprotein (HDLs).
Table 4.
93
Copyright 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings
Steroid Hormones
Steroid hormones
Are chemical
messengers in cells.
Are produced from
cholesterol.
Include sex hormones
such as androgens
(testosterone) in males
and estrogens
(estradiol) in females.
95
Copyright 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings
Adrenal Corticosteroids
Adrenal corticosteroids are steroid hormones that
Are produced by the adrenal glands located on
the top of each kidney.
Include aldosterone, which regulates electrolytes
and water balance by the kidneys.
Include cortisone, a glucocorticoid, which
increases blood glucose level and stimulates the
synthesis of glycogen in the liver.
96
Adrenal Corticosteroids
97
Anabolic Steroids
Anabolic steroids
Are derivatives of testosterone.
Are used illegally to increase muscle mass.
Have side effects including fluid retention, hair growth,
sleep disturbance, and liver damage.
98
Learning Check
Identify each as a
1. fatty acid
2. steroid
3. triacylglycerol
4. phospholipid
5. sphingolipid
A. cholesterol
B. glycerol, 2 fatty acids, phosphate, and choline
C. glyceryl tristearate
D. sphingosine, fatty acid, phosphate, and choline
E. estradiol
F. bile salts
G. lipids in plasma membranes
99
Solution
A.
B.
C.
D.
E.
F.
G.
cholesterol
2 steroid
glycerol, 2 fatty acids, phosphate, and choline
4 phospholipid
glyceryl tristearate
3 triacylglycerol
sphingosine, fatty acid, phosphate, and choline
5 sphingolipid
estradiol 2 steroid
bile salts 2 steroid
lipids in plasma membranes
4 phospholipid, 5 sphingolipid
.
100
Cell Membranes
Cell Membranes
Cell membranes
Separate cellular contents from the external
environment.
Consist of a lipid bilayer made of two rows of
phospholipids.
Have an inner portion made of the nonpolar tails of
phospholipids with the polar heads at the outer
and inner surfaces.
102
103
104
105
106
Learning Check
The transport of particles across a cell membrane from
high concentration to low concentration is called
1. Facilitated transport
2. Diffusion
3. Active transport
107
Solution
The transport of particles across a cell membrane from
high concentration to low concentration is called
2. Diffusion
108
References
http://www.kerfootgroup.co.uk/oil-inventory/jojobawax
109