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Lipids

Lipids

Copyright 2007 by Pearson Education, Inc.


Publishing as Benjamin Cummings

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.

Nutritional Uses of Lipids


We already know that lipids are concentrated sources
of energy (9.45 kcal/g)
other functions:
1) provide means whereby fat-soluble nutrients (e.g.,
sterols, vitamins) can be absorbed by the body
2) structural element of cell, subcellular components
3) components of hormones and precursors for
prostaglandin synthesis

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
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1. Fatty Acids

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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
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Fatty Acid Formulas


The formulas for fatty acids are written as
Condensed formulas.
Line-bond formulas.
For example caprylic acid with 8 carbon atoms.
CH3(CH2)6COOH
CH3CH2CH2CH2CH2CH2CH2COOH
O
OH
9

Saturated Fatty Acids (SFA)


Saturated fatty acids have
Single CC bonds.
Molecules that fit closely together
in a regular pattern.
Strong attractions between fatty
acid chains.
High melting points that make
them solids at room temperature.

10
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Some Saturated Fatty Acids

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11

Structure of Fatty Saturated

O
- C - OH
Benzoic acid

O
- C - OH
OH

Slicilic acid

Unsaturated Fatty Acids


Unsaturated fatty acids
Have one or more double C=C bond
Typically contain cis double bonds.

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13

Structure of Unsaturated Acid


Oleic acid (C18: 1)

Properties of Unsaturated Fatty Acids


Unsaturated fatty acids
Have kinks in the fatty
acid chains.
Do not pack closely.
Have few attractions
between chains.
Have low melting points.
Are liquids at room
temperature.

kinks in
chain

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15

Unsaturated Fatty Acids

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16

Unsaturated Fatty Acids

(The double bonds in the fatty acids are cis (hydrogen atoms are on the same
side of the double bonds of the carbon chain)

Oleic acid (18:1) is a monounsaturated fatty acid

O
C H 3(C H 2) 7 C

C (C H 2) 7 C
H

OH

Linoleic acid (18:2) is a polyunsaturated fatty acid (one of the


omega-6 fatty acids since there is a double bond six carbons from the end of the chain)

C H 3(C H 2) 4 C

C CH2 C
H
H

C (C H 2) 7 C
H

OH
C

Comparing Melting Points of Some


Fatty Acids

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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

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Prostaglandins
O

OH

Prostaglandins are powerful hormones in mammalian systems


Prostaglandins were first isolated from the prostate gland (seminal
fluid)
Prostaglandins have a five-membered ring with a 7-carbon side chain
(often ending in a carboyxlic acid group) adjacent to an 8-carbon chain

Prostaglandins in the Body


Prostaglandins are
Produced by injured
tissues.
Involved in pain,
fever, and
inflammation.
Not produced when
anti-inflammatory
drugs such as aspirin
inhibit their synthesis.
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23

Omega-6 and Omega 3- Fatty Acids


Fatty acids
In vegetable oils are mostly omega-6 with
the first C=C at C6.
linoleic acid
CH3(CH2)4CH=CHCH2CH=CH(CH2)7COOH
6

In fish oils are mostly omega-3 with the


first C=C at C3.
linolenic acid
CH3CH2(CH=CHCH2)3(CH2)6COOH
3
24
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Some Omega-6 and Omega-3


Fatty Acids

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

2. Waxes, Fats, and Oils

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.

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29

Jojoba (Simmondsia sinensis)

www.kerfootgroup.co.uk

30

Fats and Oils: Triacylglycerols


Fats and oils are
Also called triacylglycerols.
Esters of glycerol.
Produced by esterification.
Formed when the hydroxyl
groups of glycerol react with the
carboxyl groups of fatty acids.

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31

2b. Triacylglycerols
In a triacylglycerol,
Glycerol forms ester bonds with three fatty acids.

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32

Formation of a Triacylglycerol
glycerol

three fatty acids

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.

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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

Melting Points of Fats and Oils


A triacylglycerol that is a fat
Is solid at room temperature.
Is prevalent in meats, whole milk, butter, and cheese.
A triacylglycerol that is an oil
Is liquid at room temperature.
Is prevalent in plants such as olive and safflower.

37

Oils with Unsaturated Fatty Acids


Oils
Have more unsaturated fats.
Have cis double bonds that cause kinks in the
fatty acid chains.
Cannot pack triacylglycerol molecules as close
together as in fats.
Have lower melting points than saturated fats.
Are liquids at room temperature.

38

Diagram of Triacylglycerol with


Unsaturated Fatty Acids

Unsaturated fatty acid


chains have kinks that
do not allow close
packing.
39
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TYPICAL FATTY ACID


COMPOSITION OF THE PRINCIPAL
VEGETABLE
AND ANIMAL FATS AND OILS IN
THE US
(% of total fatty acids)

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

Mid oleic sunflower oil

65

26

Corn oil
Palm oil

20:1

L
I
N
O
L
E
I
C

32

Coconut oil

47

18

Palm kernel oil

48

16

15

Butterfat

11

27

12

29

Lard

26

14

44

Beef tallow

24

19

43

http://www.iseo.org

10
3

Safflower (Carthamus tinctorius)


http://en.wikipedia.org/wiki/Safflower

Canola, Rapeseed (Brassica napus L.)


diaryofanutritionist.com

burcon.ca

Palm kernel oil

Castor oil (minyak jarak) Ricinus communis


Sesame oil (minyak wijen)
Kapok seed oil (minyak biji randu/kapok)
Rice bran oil (minyak dedak)
Fish oil (minyak ikan)

Komposisi asam lemak dalam minyak wijen:[1]

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

Saturated and Unsaturated Fatty Acids


in Fats and Oils

45
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Chemical Properties of
Triacylglycerols

Copyright 2007 by Pearson Education, Inc.


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46

Chemical Properties of Triacylglycerols


The chemical reactions of triacylglycerols are similar
to those of alkenes and esters.
In hydrogenation, double bonds in unsaturated
fatty acids react with H2 in the presence of a Ni or
Pt catalyst.
In hydrolysis, ester bonds are split by water in the
presence of an acid, a base, or an enzyme.

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
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Hydrogenation
O
CH2

(CH2)5CH CH(CH2)7CH3

Ni

O
CH
CH2

O
O

+ 3H2

C (CH2)5CH CH(CH2)7CH3
O
C

(CH2)5CH CH(CH2)7CH3 CH2

(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

Olestra, a Fat Substitute


Olestra is
Used in foods as an artificial fat.
Sucrose linked by ester bonds to several long-chain
fatty chains.
Not broken down in the intestinal tract.

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52

Cis and Trans Fatty Acids


Unsaturated fatty acids can be
Cis with bulky groups on same side of C=C.
CH3 (CH2)5
(CH2)7 COOH cis
C=C
H

Trans have bulky groups on opposite sides of C=C.


CH3 (CH2)5
H
C=C
H

trans
(CH2)7 COOH
53

Trans Fatty Acids and


Hydrogenation
Trans fatty acids
Are formed during hydrogenation when cis double
bonds are converted to trans double bonds.
In the body behave like saturated fatty acids.
Are estimated to make up 2-4% of our total
Calories.
Are reported in several studies reported to raise
LDL-cholesterol and lower HDL-cholesterol.

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
57

Saponification and Soap


Saponification
Is the reaction of a fat with a strong base.
Splits triacylglycerols into glycerol and the salts of
fatty acids.
Is the process of forming soaps (salts of fatty
acids).
With KOH gives softer soaps.

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

Glycerophospholipids Are Polar


A glycerophospholipid has
Two nonpolar fatty acid chains.
A phosphate group and a polar amino alcohol.
CH3
+
+
HOCH2CH2NCH3
HOCH2CH2NH3

choline
CH3
ethanolamine
+

NH3

HOCH2CHCOO
serine

Amino alcohols
65

Structure and Polarity of A


Glycerophospholipid

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66

Lecithin and Cephalin


Lecithin and cephalin are glycerophospholipids
Abundant in brain and nerve tissues.
Found in egg yolk, wheat germ, and yeast.

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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

CH2O C (CH2)16 CH3


O

CH2O C (CH2)16 CH3


+

O
NH3

CH2O P O CH2CHCOO
O70

Solution
Identify the components and type of glycerophospholipid
O

CH2O C (CH2)16 CH3


O

CH2O C (CH2)16 CH3

2 stearic acids

O
NH3

CH2O P O CH2CHCOO
serine
Ophosphate
amino alcohol

type = cephalin

71

3a. Sphingolipids

72

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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75

3b. Glycosphingolipids
Glycosphingolipids
contain
monosaccharides
bonded to the OH
of sphingosine by a
glycosidic bond.

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76

Glycosphingolipids and
Cerebrosides
Glycosphingolipids
Are sphingolipids that contain
monosaccharides.
Can be a cerebroside with galactose.

77
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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.

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79

Lipid Diseases (Lipidoses)


In many lipid diseases, the deficiency of an enzyme
causes the accumulation of glycolipids.
Table 2.

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80

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

81

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

82

4. Steroids
Steroids: Cholesterol, Bile Salts,
and Steroid Hormones
CH3
CH3
CH3

CH3
CH3

HO
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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

Cholesterol in the Body


Cholesterol in the body
Is obtained from meats,
milk, and eggs.
Is synthesized in the liver.
Is needed for cell
membranes, brain and
nerve tissue, steroid
hormones, and Vitamin D.
Clogs arteries when high
levels form plaque.

A normal, open artery.

An artery clogged by
cholesterol plaque
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86

Cholesterol in Foods
Cholesterol is
Synthesized in
the liver.
Obtained from
foods.
Considered
elevated if
plasma
cholesterol
exceeds 200
mg/dL.

Table 3.

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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

cholic acid, a bile acid


CH3
OH
CH3

O
C

CH2
N
H

COO- Na+

Polar region

CH3

HO

OH

Nonpolar region

sodium glycocholate, a bile salt


91

Lipoproteins
Lipoproteins
Combine lipids with proteins and phospholipids.
Are soluble in water because the surface consists of polar
lipids.

92
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Types of Lipoproteins
Lipoproteins
Differ in density, composition, and function.
Include low-density lipoprotein (LDLs) and highdensity lipoprotein (HDLs).
Table 4.

93
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Transport of Lipoproteins in the Body

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94

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
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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

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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.

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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

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101

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

Fluid Mosaic Model of Cell


Membranes
The lipid bilayer
Contains proteins, carbohydrates, and
cholesterol.
Has unsaturated fatty acids that make cell
membranes fluid-like rather than rigid.
Has proteins and carbohydrates on the surface
that communicate with hormones and
neurotransmitters.

103

Fluid Mosaic Model

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104

Transport Through Cell


Membranes
The transport of substances through cell
Membranes involves
Diffusion (passive transport), which moves
particles from a higher to a lower concentration.
Facilitated transport, which uses protein channels
to increase the rate of diffusion.
Active transport, which moves ions against a
concentration gradient.

105

Transport Pathways Through Cell


Membranes

Copyright 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings

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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

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Solution
The transport of particles across a cell membrane from
high concentration to low concentration is called
2. Diffusion

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References
http://www.kerfootgroup.co.uk/oil-inventory/jojobawax

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