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.

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.

Fluid Mosaic Model

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.

Transport Pathways Through Cell

Membranes

Lipids
Lipids are
Biomolecules that contain fatty acids or a steroid
nucleus.
Soluble in organic solvents 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.

Structures of Lipids

Fatty Acids

10

Fatty Acids
Fatty acids
Are long-chain
carboxylic acids.
Typically contain 12-18
carbon atoms.
Are insoluble in water.
Can be saturated or
unsaturated.

11

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
12

Saturated Fatty Acids

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.

13

Some Saturated Fatty Acids

14

Unsaturated Fatty Acids

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

15

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

16

Unsaturated Fatty Acids

17

Comparing Melting Points of

Some Fatty Acids

18

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
19

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
20

Structure and Polarity of A

Glycerophospholipid

21

Lecithin and Cephalin

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

22

Waxes
Waxes are
Esters of saturated fatty acids and long-chain alcohols.
Coatings that prevent loss of water by leaves of plants.
TABLE 17.2

23

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.

24

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

25

Formation of a Triacylglycerol
glycerol

three fatty acids

O

triacylglycerol

CH2

OH

HO C
O

(CH2)14CH3

CH

OH

HO C
O

(CH2)14CH3

HO C

(CH2)14CH3 CH2 O C

CH2

OH

O
(CH2)14CH3

O
CH O C

(CH2)14CH3

+ 3H2O

O
CH2 O C

(CH2)14CH3
26

Olive Oil
Olive oil
Contains a high
percentage of oleic
acid, which is a
monounsaturated fatty
acid with one cis
double bond.

27

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.

28

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.

29

Diagram of Triacylglycerol with

Unsaturated Fatty Acids

Unsaturated fatty acid

chains have kinks that
do not allow close
packing.
30

Saturated and Unsaturated Fatty

Acids In Fats and Oils

31

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.

32

Hydrogenation
O
CH2

(CH2)5CH CH(CH2)7CH3

O
CH

CH2

Ni

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

+ 3HO
2

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

(CH2)14CH3

O
glyceryl tripalmitoleate
(tripalmitolean)

CH

CH2

C (CH2)14CH3
O
C

(CH2)14CH3

glyceryl tripalmitate
(tripalmitin)

33

Hydrolysis
In hydrolysis,
Triacylglycerols split into glycerol and three fatty acids.
An acid or enzyme catalyst is required.
O

CH2

CH

CH2

C
O

(CH2)14CH3

C (CH2)14CH3
H2O
+3
O
C

(CH2)14CH3

H+
CH2 OH
CH

OH

CH2

OH

+3

HO C

(CH2)14CH3

34

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.

35

Saponification
O
CH2 O C

(CH2)14CH3

O
CH O C

(CH2)14CH3

O
CH2 O C

(CH2)14CH3

+ 3NaOH

CH2 OH
CH OH

+ 3
CH2 OH

O
Na+ -O C

(CH2)14CH3

soap
36

Sphingolipids

37

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

38

Sphingosine
Sphingosine is a long-chain unsaturated amino alcohol.
CH3(CH2)12 CH=CHCHOH

CHNH2

CH2OH
sphingosine
39

Sphingolipids
In sphingomyelin, a sphingolipid found in nerve cells
There is an amide bond between a fatty acid and
sphingosine, an 18-carbon alcohol.

40

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

41

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

42

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.

43

Gangliosides
GM2 is a ganglioside
That accumulates in Tay-Sachs disease.

44

Lipid Diseases (Lipidoses)

In many lipid diseases, the deficiency of an enzyme
causes the accumulation of glycolipids.
TABLE 17.3

45

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
46

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.

47

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

48

Some Omega-6 and Omega-3

Fatty Acids

49

Steroids: Cholesterol, Bile Salts,

and Steroid Hormones
CH3
CH3
CH3

CH3
CH3

HO

50

Steroid Nucleus
A steroid nucleus consists of
3 cyclohexane rings.

1 cyclopentane ring.
No fatty acids.

steroid nucleus

51

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
52

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
53

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

TABLE 17.4

54

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.

55

Bile Salts
glycine, an amino acid

cholic acid, a bile acid

CH3

OH
CH3

O
C

CH2
N
H

Polar region

CH3

HO

COO- Na+

OH

Nonpolar region

sodium glycocholate, a bile salt

56

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

57

Types of Lipoproteins
Lipoproteins
Differ in density, composition, and function.
Include low-density lipoprotein (LDLs) and high-density
lipoprotein (HDLs).
TABLE 17.5

58

Transport of Lipoproteins in
the Body

59

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.

60

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.

61

Adrenal Corticosteroids

62

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.

63