China Medical University

Chapter 8 ：Lipids and Proteins are Associated in Biological

Membranes
“Biochemistry” by M.K. Campbell and S.O Farrell

2023/11/24

For : Biochemistry in Daily Life

(General education course)
What lipids do in the body?

Electron micrograph of fat

cells. Much of the cell
volume is taken up by lipid
droplets.
 Learning Objectives

Upon the completion of this lecture, you should be

able to：
1. describe the types of lipids and their basic
structures
2. learn how the structure of fatty acids affects their
physical properties
3. describe the components of the membranes and
the associated lipids and proteins
4. learn how the numbers of cholesterol and different
phospholipids affects the membrane fluidity.
 Lecture Outline

Part1：Types of lipids and their physical properties

1-1. Open chain form lipids
1-2. Cyclic form lipids

Part2：Structures of the biological membranes

2-1. Membrane structures
2-2. Lipids in the membrane bilayers
2-3. Proteins in the membranes bilayers
Part1：Types of lipids and their
physical properties
 Types of lipids

• Lipids: a family of biomolecules that are soluble in

organic solvents, but insoluble in water.

• Lipids include:
• Open Chain forms
• Fatty acids, triacylglycerols, waxes,
glycerolphospholipids
• Prostaglandins (pain, inflammations..)
• Lipid-soluble vitamins (derived lipids)
• Cyclic forms
• Cholesterol, steroid hormones and bile salts
Types of lipids

Lipids

Open chain
Cyclic forms
forms

Cholesterol Bile salts Steroid

hormone

Waxes Triacylglycerols Glycerophospholipids

1-1. Open chain form lipids
 Open Chain Forms: Fatty Acids

a end

Fatty acid:
• an unbranched-chain carboxylic acid, most
commonly of 12 - 20 carbons
• usually contain even numbers of carbons.

w end
 Fatty Acids

• Saturated vs. unsaturated fatty acids

• FA that contain C=C, are unsaturated: If contain only C-C bonds, they
are saturated.
• Mono-unsaturated vs. Poly-unsaturated
 Fatty Acids

• Cis vs. trans unsaturated fatty acids : In most unsaturated fatty

acids, the cis isomer predominates; the trans isomer is rare.
• Essential fatty acids: Human do not synthesize sufficient
amounts of polyunsaturated fatty acids like linoleic acid, linolenic
acid and arachidonic acid. They must be obtained from the diet -
- Essential fatty acids.
cis-Oleic acid ;
cis-double
bond -- a kink trans-Oleic acid;
trans double bond
 Fatty Acids: structures & melting points(I)

• Structures and Melting Points of Common Fatty Acids

月桂酸

肉豆蔻酸

棕櫚酸

硬脂酸
Fatty Acids: structures & melting points(II)

M.P.

棕櫚油酸

油酸

亞麻油酸

次亞麻油酸

花生油酸
Types of lipids: triacylglycerols

Lipids

Open chain
Cyclic forms
forms

Cholesterol Bile salts Steroid

hormone

Waxes Triacylglycerols Glycerophospholipids

 Triacylglycerols

• Triacylglycerol: an ester of glycerol with three fatty acids

• Most fats and oils are mixed triacylglycerols that contain 2 or 3
different fatty acids.
• Triacylglycerols are the major form of energy storage for animals.
Chemical Properties of Triacylglycerols

• Hydrogenation: when hydrogen is added to one or more

C=C to form C-C, in the presence of nickel catalyst.
• Would the melting point change after hydrogenation?

Glycerol trioleate Glycerol tristearate

Types of lipids: Phosphoacylglycerols or
glycerophospholipids

Lipids

Open chain
Cyclic forms
forms

Cholesterol Bile salts Steroid

hormone

Waxes Triacylglycerols Glycerophospholipids

 Phosphoacylglycerols or
phospholipids

• Phospho-lipids are the second most abundant group of naturally

occurring lipids, and they are found in plant and animal membranes
 Structure and properties of a
Phosphoacylglycerol

• Phosphoacylglycerols (phospholipids) : all have nonpolar,

hydrophobic tails plus polar, hydrophilic heads--Amphipathic

Polar head

Nonpolar tails
1-2. Cyclic form lipids
 Cyclic Forms: Steroids

• Steroids: a group of lipids that have fused-ring

structure of 3 six-membered rings, and 1 five-
membered ring.
Highly
hydrophobic
 Biochemical connections to daily life

Cholesterol in the body: saturated fats in the diets may

stimulate the production of cholesterol by the liver.

Fig. 15-7 Excess

cholesterol forms
plaque that can block
an artery, resulting in
a heart attack.
(a). A normal artery;
(b). A blocked artery.

Fig. 15-8 Gallstones forms

in the gallbladder when
cholesterol levels are
high.
 Cholesterols and Sex Hormones

• Cholesterols: The steroid of most interest in our discussion

of biological membranes is cholesterol
• Androgens: male sex hormones
• synthesized in the testes
• responsible for the development of male secondary sex
characteristics
• Testosterone
• Estrogens: female sex hormones
• synthesized in the ovaries
• responsible for the development of female secondary sex
characteristics and control of the menstrual cycle
 Part II
Structures of the biological
membranes
2-1. Membrane structures
 Biological Membranes

• Lipid Bilayers:
• The polar surface of
the bilayer contains
charged groups

• The hydrophobic
tails lie in the interior
of the bilayer
2-2. Lipids in the membrane
bilayers
 Lipids in the membrane bilayers

• Both inner and outer

layers of bilayer
contain mixtures of
lipids

• Compositions on
inside and outside of
lipid bilayer can be
different (asymmetric)
• Fluid Mosaic Model
 Lipids in the membrane bilayers

Q: How would the double bonds conformations

of fatty acids affect the membrane property?
• Kink in hydrocarbon chain
• Causes disorder in
packing against other
chains
• This disorder causes
greater fluidity in
membranes with cis-
double bonds when
compared with saturated
FA chains
WHY ?
Lipids in the membrane bilayers
 Cholesterols in the membrane bilayers

• The presence of
cholesterol reduces
membrane fluidity：
• Presence of
cholesterol reduces
fluidity by stabilizing
extended chain
conformations of
hydrocarbon tails of
FA
• Due to hydrophobic
interactions
Biological Membranes and cholesterols

• Plant membranes have a higher percentage of

unsaturated fatty acids than animal membranes
• The presence of cholesterol is characteristic of
animal rather than plant membranes
• Animal membranes are less fluid (more rigid)
than plant membranes (more cholesterol)
• The membranes of prokaryotes, which contain
no appreciable amounts of steroids, are the
most fluid
2-3. Proteins in the membranes
bilayers
 Biological Membranes:
Fluid Mosaic Model

• Fluid: there is lateral motion of components in the

membrane
• proteins, for example, “float” in the membrane
and can move along its plane

• Mosaic:
• the structure is that of a lipid bilayer with proteins,
glycolipids, and steroids such as cholesterol
embedded in it
 Proteins in the membrane bilayers

• Functions:
transport
substances across
membranes; act as
receptor sites, and
sites of enzyme
catalysis
• Peripheral proteins
• bound by
electrostatic
interactions
• Integral proteins
• bound tightly to
the interior of the
membrane
 Summary

• Lipids includes open chain and cyclic forms.

• The numbers of carbons and double bonds
determines the physical properties of the lipids.
• The biological membrane contains lipids and
proteins.
• Structures of phospholipids and number of
cholesterols will affect the fluidity of membranes.
Class activities
 Quiz
1) What type of lipid does not contain fatty acids?

A. Triacylglycerols
B. Glycerophospholipids
C. Waxes
D. Steroid hormones (e.g. androgens)
 Quiz
2) Which of the following lipids is the major energy
storage form?

A. Glycolipids
B. Glycerophospholipids
C. Cholesterols
D. Triacylglycerols
 Quiz
3) Which statement is true about the biological
membranes?

A. The most abundant lipids in the membrane is

triacylglycerol.
B. The lipid polar heads are buried within the
bilayers.
C. Plant membranes have no cholesterols.
D. The lipid bilayer membranes are symmetric.
 Lipid structures and their properties
4) Place in order the following fatty acids, from the
lowest to the highest melting points ? Which one is
more stable at room temperature.

a). CH3-(CH2)16-COOH (stearic acid)

b). CH3-(CH2)4-CH=CH-CH2-CH=CH-(CH2)7-COOH (linoleic acid)
c). CH3-(CH2)7-CH=CH-(CH2)7-COOH (oleic acid)
d). CH3-CH2-CH=CH-CH2-CH=CH-CH2-CH=CH-(CH2)7-COOH
(linolenic acid)

A). abcd B). bdca C). cbda D). dbca

 Lipid structures and their properties
Q: The melting points varies significantly among
different fatty acids. Please list two factors
associated with the fatty acid structures that affect the
melting points of fatty acids?
 Lipid structures and their properties
5) Most oils from vegetables like olive, soybeans or corns
are liquid at room temperature. However, oils from
coconuts (rich in lauric acid) and palm (rich in palmitic
acid) are solid at room temperature. Why?

A. The majority fatty acids in the coconut and palm

oils have double bonds.
B. Those fatty acids have long hydrocarbon chains
(long-chain fatty acids)
C. The majority fatty acids in the coconut and palm
oils are saturated.
 Lipid structures and their properties

6) In food products, the trans isomer form in the lipids

A. is naturally occurring and is the

predominate form of double bonds
B. can be found in the hydrogenated food
C. can be found in oxidized oils
D. generates kinks in the chemical structures
 Why should we eat more salmon?
• 7). Salmon is a good source of omega-3 fatty acid.
Which of these fatty acids is an omega-3 fatty acid?
Explain.

A.

B. C.

D. E.
 BCH in daily life: Saponification
• 8). Hand-made soaps normally made from a
mixture of oils with different ratios. Variations
in the ratio of oils bring out the properties of
that soap. Increasing the ratio of which kind
of oil would produce softer soaps?

A). Saturated fatty acids

B). Unsaturated fatty acids
 Saponification
• When a fat/oil is heated with strong base (e.g. NaOH)
to give a glycerol and the sodium salts of the fatty
acids (soaps).
• When NaOH is used (solid soap)
• When KOH is used (liquid soap)

Glyceryl 3 sodium
tripalmitate glycerol palmitate (soap)

149
 Glycerophospholipid structures
9) Identify each part of the following glycerophospholipid as
a) Glycerol, b). Unsaturated fatty acid, c). Saturated fatty
acid, d). Phosphate group and e). Amino alcohol. Place
them in order (from 1-5).

2 A). abcde
B). acbde
3
1 C). abbde

4 5 D). acced
 Cholesterols in the membrane
10). Where would cholesterol be found if added to a
phospholipid bilayer?
 Membrane Fluidity
11). The plasma membrane must retain a certain level of
fluidity to function. The temperature of cells is colder near
the hooves on reindeer than it is at the reindeer's torso.
Predict how the plasma membrane composition of epithelial
cells near a reindeer’s hooves would differ from
that of cells on the reindeer’s torso. Why?

A. The membrane lipids near the hooves would contain

more unsaturated fatty acids and membrane lipids in the
torso would contain more saturated.
B. The membrane lipids near the hooves would contain
more saturated and membrane lipids in the torso would
contain more unsaturated.
 Membrane Fluidity
12). If you compare the cholesterol compositions of cell
membranes between fish that live in the deep sea and
the tropical fish, which statement is true?

A. The membranes of the cold water fish has more

cholesterol.

B. The membrane of the tropical fish has more

cholesterol.
 Biochemistry in daily life

13). The
arrangements of
molecules could
affects interaction
between
molecules. Can
you explain why
does the cis
double bond A). Stearic B). Oleic
affect the melting acid acid

points of the fatty

acids?
Biochemistry in daily life 14): From the health
point of view, if you have
Below are products produced by the to choose the bread
hydrogenations of vegetable oils. spread as butter
substitute, which one
would you choose? Why?
Shortening
(solid)
A). Tub margarine
B). Stick margarine
C). Shortening

What chemical property

determines the firmness
Vegetable oils Tub (soft) Stick
(liquid) margarine margarine of these three kinds of
(soft and solid) margarines?
 Membrane Fluidity
15. Why is keeping the membrane fluidity important?
(Hint: what do some membrane proteins do when
they function? What do macrophages do when
encountering bacteria?... )

Key: Membrane fluidity is known to affect the function of

biomolecules residing within or associated with the
membrane structure. For example, the binding of some
peripheral proteins is dependent on membrane
fluidity. Lateral diffusion (within the membrane matrix) of
membrane-related enzymes can affect reaction
rates.Consequently, membrane-dependent functions, such as
phagocytosis and cell signalling, can be regulated by the
fluidity of the cell-membrane
 Applications: Membranes in Drug delivery
• Liposome (80-300 nm): artificial stable structures
based on a lipid bilayer that form a spherical vesicle. It
can be self-assembled spontaneously and reversibly
into organized structures under specific conditions, e.g.,
temperature, pH, the polarity of the medium….
• Liposomes is small and can easily fuse with cell
membranes, thus deliver the contents in it into the
cells.
Hydro-
philic

Hydro-
phobic
Applications: Membranes in Drug delivery
Drug delivery by liposomes:
The release of a drug from
liposomes depends on
the liposome composition,
pH, osmotic gradient,
and the surrounding
environment

Easily fused
with membrane
Pharmacological reports (2012) 64: 1020-1037
 Applications: Membrane in Drug delivery
• Q 16: In the target therapy, drug can be specifically
delivered to the local affected area. Liposomes are
considered to be a good candidate for the target therapy
because the membrane surface could be modified by
adding various biomolecules. If you are developing
liposomes carrier for a cancer drug to the brain tumor
area, how would you modify the membrane surface to
make the liposomes specifically deliver to the brain area?
You are welcome express answers in drawings.

• What are the characteristics

of a good drug carrier?