Section 19.

Structure and Classification of Lipids

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 Chapter 19

Chapter Outline

19.1 Structure and classification of lipids

19.2Types of fatty acids
19.3 Physical properties of fatty acids
19.4 Energy-storage lipids: Triacylglycerols
19.5 Dietary considerations and triacylglycerols
19.6 Chemical reactions of triacylglycerols
19.7 Membrane lipids: Phospholipids
19.8 Membrane lipids: Sphingoglycolipids
19.9 Membrane lipids: Cholesterol
19.10 Cell membranes
19.11 Emulsification lipids: Bile acids
19.12 Messenger lipids: Steroid hormones
19.13 Messenger lipids: Eicosanoids
19.14 Protective-coating lipids: Biological waxes
19.15Saponifiable and nonsaponifiable lipids

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 Section 19.1

Structure and Classification of Lipids

Lipids
• Lipid: An organic compound found in living
organisms that is insoluble (or only sparingly
soluble) in water but soluble in non-polar organic
solvents
• Unlike other biomolecules, lipids do not have a
common structural feature that serves as the
basis for defining such compounds
• Classification is based on two methods
– Biochemical function
– Saponification
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 Section 19.1

Structure and Classification of Lipids

Classification based on Biochemical Function

• Divided into five categories based on their
biochemical function:
– Energy-storage lipids (triacylglycerols)
– Membrane lipids (phospholipids, sphingoglycolipids,
and cholesterol)
– Emulsification lipids (bile acids)
– Messenger lipids (steroid hormones and
eicosanoids)
– Protective-coating lipids (biological waxes)

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 Section 19.1

Structure and Classification of Lipids

Classification Based on Saponification

• Saponification reaction - Hydrolysis reaction that
occurs in a basic solution
• Based on saponification reactions, lipids are
divided into two categories:
– Saponifiable lipids (triacylglycerols, phospholipids,
sphingoglycolipids, cholesterol, and biological waxes)
– Nonsaponifiable lipids (bile acids, steroid
hormones, and eicosanoids)

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 Section 19.1

Structure and Classification of Lipids

Structural Diversity of Lipids

• Lipids exhibit structural diversity
• Some are esters, some are amides, and some
are alcohols (acyclic, cyclic, and polycyclic)

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 Section 19.1

Structure and Classification of Lipids

Figure 19.1 - Structural Formula of Types of Lipids

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 Section 19.1

Structure and Classification of Lipids

A lipid is an organic compound found in living

organisms that is:

a.soluble in water and insoluble in nonpolar organic

solvents.
b.soluble in water and soluble in nonpolar organic solvents.
c.insoluble in water and insoluble in nonpolar organic
solvents.
d.insoluble in water and soluble in nonpolar organic
solvents.

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 Section 19.1

Structure and Classification of Lipids

A lipid is an organic compound found in living

organisms that is:

a.soluble in water and insoluble in nonpolar organic

solvents.
b.soluble in water and soluble in nonpolar organic solvents.
c.insoluble in water and insoluble in nonpolar organic
solvents.
d.insoluble in water and soluble in nonpolar organic
solvents.

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 Section 19.2

Types of Fatty Acids

Fatty Acids - An Introduction

• Fatty acids: Naturally occurring monocarboxylic
acids with linear (unbranched) carbon chain
– Have even number of carbon atoms
• Long-chain fatty acids (C12 to C26)
• Medium-chain fatty acids (C8 to C10)
• Short-chain fatty acids (C4 to C6)
• Two types:
– Saturated - All C–C bonds are single bonds
– Unsaturated
• Monounsaturated
• Polyunsaturated Return to TOC

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 Section 19.2

Types of Fatty Acids

Saturated Fatty Acids

• Fatty acids with a carbon chain in which all C–C
bonds are single bonds
• Numbering starts from the end of –COOH
group
• Consider the structural notations for palmitic
acid:

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 Section 19.2

Types of Fatty Acids

Unsaturated Fatty Acids

• Monounsaturated fatty acid: Fatty acid with a
carbon chain in which one carbon–carbon
double bond is present
• There are different ways of depicting the
structure

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 Section 19.2

Types of Fatty Acids

Polyunsaturated Fatty Acids (PUFAs)

• Fatty acids with a carbon chain in which two or
more carbon–carbon double bonds are present
• Up to six double bonds are found in
biochemically important PUFAs

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 Section 19.2

Types of Fatty Acids

Double-Bond Position in Unsaturated Fatty Acids

• Numbering starts from the other end of –COOH
• Structural notation indicates number of C atoms
• Example:
– 18:2 signifies that a fatty acid has 18 carbons with 2
double bonds

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 Section 19.2

Types of Fatty Acids

Types of Unsaturated Fatty Acids

• Omega (ω)-3 fatty acid: Unsaturated fatty acid
with its endmost double bond three carbon
atoms away from its methyl end
• Omega (ω)-6 fatty acid: Unsaturated fatty acid
with its endmost double bond six carbon atoms
away from its methyl end

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 Section 19.2

Types of Fatty Acids

A fatty acid is a naturally occurring _____ acid that

nearly always contains an _____ number of
carbon atoms with a carbon chain that is _____.

a.monocarboxylic; even; branched

b.dicarboxylic; odd; unbranched
c.monocarboxylic; even; unbranched
d.dicarboxylic; even; branched

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 Section 19.2

Types of Fatty Acids

A fatty acid is a naturally occurring _____ acid that

nearly always contains an _____ number of
carbon atoms with a carbon chain that is _____.

a.monocarboxylic; even; branched

b.dicarboxylic; odd; unbranched
c.monocarboxylic; even; unbranched
d.dicarboxylic; even; branched

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 Section 19.2

Types of Fatty Acids

Which of the following statements is true about the

classification of fatty acids?

a.They are classified as saturated, monounsaturated, or

polyunsaturated fatty acids.
b.They are classified as saturated or branched unsaturated
fatty acids.
c.They are classified as saturated or polyunsaturated fatty
acids.
d.None of the above.

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 Section 19.2

Types of Fatty Acids

Which of the following statements is true about the

classification of fatty acids?

a.They are classified as saturated, monounsaturated, or

polyunsaturated fatty acids.
b.They are classified as saturated or branched unsaturated
fatty acids.
c.They are classified as saturated or polyunsaturated fatty
acids.
d.None of the above.

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 Section 19.3

Physical Properties of Fatty Acids

Water Solubility
• Short-chain fatty acids have some solubility,
whereas long-chain fatty acids are insoluble
• Short-chain fatty acids are sparingly soluble
because of the presence of carboxylic group

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 Section 19.3

Physical Properties of Fatty Acids

Melting Point
• Depends upon the
following:
– Length of carbon
chain
– Degree of
unsaturation (number
of double bonds in a
molecule)

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 Section 19.3

Physical Properties of Fatty Acids

• Number of “bends” in
a fatty acid chain
increases as the
number of double
bonds increases
• Less packing occurs
• Melting point is lower
• Tend to be liquid at
room temperature

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 Section 19.3

Physical Properties of Fatty Acids

Which of the following best describe the physical

properties of fatty acids?

a.Melting points of fatty acids are influenced by the carbon

chain length.
b.Melting points of fatty acids are influenced by their
degree of unsaturation.
c.All physical properties of fatty acids are influenced by the
length and degree of unsaturation of their carbon chain.
d.All the above.

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 Section 19.3

Physical Properties of Fatty Acids

Which of the following best describe the physical

properties of fatty acids?

a.Melting points of fatty acids are influenced by the carbon

chain length.
b.Melting points of fatty acids are influenced by their
degree of unsaturation.
c.All physical properties of fatty acids are influenced by the
length and degree of unsaturation of their carbon chain.
d.All the above.

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 Section 19.4

Energy-Storage Lipids: Triacylglycerols

Energy-Storage Materials
• With the notable exception of nerve cells, human
cells store small amounts of energy-providing
materials
– Carbohydrate glycogen - Most widespread energy
storage material present in small amounts
• Major energy-storage material is triacylglycerol
– Concentrated primarily in special cells (adipocytes)
which are nearly filled with triacylglycerols

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 Section 19.4

Energy-Storage Lipids: Triacylglycerols

Two Types of Triacylglycerols

• Simple triacylglycerol: Triester formed from the
esterification if glycerol with three identical fatty
acid molecules
– Naturally occurring simple triacylglycerols are rare
• Mixed triacylglycerol: Triester formed from the
esterification of glycerol with more than one kind
of fatty acid molecule

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 Section 19.4

Energy-Storage Lipids: Triacylglycerols

Fats and Oils

• Fats:
– Predominantly Saturated
– Solids or semisolids at room temperature
– Source: Animals
• Oils:
– Predominantly unsaturated
– Liquids at room temperature
– Sources: Plants and fish oil
• Pure oils and fats are colorless, odorless, and
tasteless
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 Section 19.4

Energy-Storage Lipids: Triacylglycerols

Triacylglycerols are _____ in their ability to store

energy when compared to glycogen, the energy
storing form of glucose in the human body.

a.less efficient
b.more efficient
c.equally efficient
d.insignificant

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 Section 19.4

Energy-Storage Lipids: Triacylglycerols

Triacylglycerols are _____ in their ability to store

energy when compared to glycogen, the energy
storing form of glucose in the human body.

a.less efficient
b.more efficient
c.equally efficient
d.insignificant

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 Section 19.5

Dietary Considerations and Triacylglycerols

Studies Concerning Role of Dietary Factors as a Cause

of Disease
• Nations whose citizens have high dietary intakes
of fats and oils tend to have higher incidences of
heart disease and certain types of cancers
• Typical American diet contains too much fat
– Americans are being asked to reduce their total
dietary fat intake
• Other studies show that risk factors involve more
than simply the total amount of triacylglycerols
consumed

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 Section 19.5

Dietary Considerations and Triacylglycerols

“Good Fats” Versus “Bad Fats”

• Studies indicate that type of dietary fat and
amount of dietary fat are important to determine
body responses to dietary fat
• Current recommended amount for total fat
intake in calories:
– 15% - Monounsaturated fat
– 10% - Polyunsaturated
– <10% - Saturated fats

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 Section 19.5

Dietary Considerations and Triacylglycerols

“Good Fats” Versus “Bad Fats”

• Studies also indicate that:
– Saturated fats are considered “bad fats”
– Monounsaturated fats are considered “good fats”
– Polyunsaturated fats can be both “good fats” and
“bad fats”
• Omega fats are important

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 Section 19.5

Dietary Considerations and Triacylglycerols

Omega-6 and Omega-3 Fatty Acids in American Diet

• American diet is high in omega-6 fatty acids and
deficient in omega-3 fatty acids
– Fish are a good source for omega-3 fatty acids

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 Section 19.5

Dietary Considerations and Triacylglycerols

Essential Fatty Acids

• Fatty acids that must be obtained from dietary
sources because they cannot be synthesized
within the body
• Two most important essential fatty acids are:
– Linoleic acid (18:2) - Omega 6
– Linolenic acid (18:3) - Omega 3
• Needed for proper membrane structure
• Serve as starting materials for the production of
several nutritionally important longer-chain omega-6
and omega-3 fatty acids

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 Section 19.5

Dietary Considerations and Triacylglycerols

Deficiency of Linoleic and Linoleic Acid

• Results in:
– Skin redness
– Infections and dehydration
– Liver abnormalities

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 Section 19.5

Dietary Considerations and Triacylglycerols

Fat and Fatty Acid Composition of Nuts

• Numerous studies now indicate that eating nuts
can have a strong protective effect against
coronary heart disease
– Low amounts of saturated fatty acids
– Also contain valuable antioxidant vitamins, minerals,
and plant fiber protein

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 Section 19.5

Dietary Considerations and Triacylglycerols

Considerable research in the past two decades

has shown that high intake of dietary
triacylglycerols causes diseases such as obesity,
cancer, hypertension, and atherosclerosis. This is
not true for the Inuit people of Greenland because
their diet is high in _____ fatty acids.

a.saturated
b.Omega-3
c.Omega-6
d.Omega-9
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 Section 19.5

Dietary Considerations and Triacylglycerols

Considerable research in the past two decades

has shown that high intake of dietary
triacylglycerols causes diseases such as obesity,
cancer, hypertension, and atherosclerosis. This is
not true for the Inuit people of Greenland because
their diet is high in _____ fatty acids.

a.saturated
b.Omega-3
c.Omega-6
d.Omega-9
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 Section 19.6

Chemical Reactions of Triacylglycerols

Hydrolysis
• Chemical properties of triacylglycerols are
typical of the functional groups esters and
alkenes
• Carried out by enzymes produced by the
pancreas in a stepwise manner
– Breaking of outer fatty acids produces diacylglycerol
and monoacylglycerol
• Complete hydrolysis - When all three fatty acids
are removed
• Partial hydrolysis - When one or more fatty acid
residue remains Return to TOC

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 Section 19.6

Chemical Reactions of Triacylglycerols

Saponification
• Hydrolysis in basic solution
• Products: Fatty acid and glycerol salts

Fat or oil + 3H 2O 
 3 fatty acids + glycerol

3 fatty acids + 3 NaOH 

 3 fatty acid salts + 3 H 2O

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 Section 19.6

Chemical Reactions of Triacylglycerols

Hydrogenation
• Addition of hydrogen across C–C multiple
bonds, which increases degree of saturation
• Many food products are produced by partial
hydrogenation of oils and fats
– Peanut oil  Peanut butter
– Liquid plant oil  Margarine

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 Section 19.6

Chemical Reactions of Triacylglycerols

Oxidation
• Double bonds in triacylglycerols are subject to
oxidation with oxygen (an oxidizing agent)
• Leads to C=C breakage that produces both
aldehyde and carboxylic acid products
– Products often have objectionable odors, and fats
and oils are said to be rancid
• To avoid this unwanted oxidation process,
antioxidants are added as preservatives
– Example: Vitamin C and vitamin E are naturally
occurring antioxidant
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 Section 19.6

Chemical Reactions of Triacylglycerols

What are the important triacylglycerol reactions?

a.Hydrolysis, hydrogenation, and oxidation

b.Hydrogenation, saponification, and hydrolysis
c.Hydrolysis, saponification, hydrogenation, and oxidation
d.Hydrolysis, saponification, oxidation, and
hydrohalogenation

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 Section 19.6

Chemical Reactions of Triacylglycerols

What are the important triacylglycerol reactions?

a.Hydrolysis, hydrogenation, and oxidation

b.Hydrogenation, saponification, and hydrolysis
c.Hydrolysis, saponification, hydrogenation, and oxidation
d.Hydrolysis, saponification, oxidation, and
hydrohalogenation

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 Section 19.6

Chemical Reactions of Triacylglycerols

Partial triacylglycerol hydrolysis occurs during the

process of digestion in the human body, and it
produces a _____ and _____.

a.glycerol; three fatty acids

b.diacylglycerol; two fatty acids
c.monoacylglycerol; one fatty acid
d.monoacylglycerol; two fatty acids

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 Section 19.6

Chemical Reactions of Triacylglycerols

Partial triacylglycerol hydrolysis occurs during the

process of digestion in the human body, and it
produces a _____ and _____.

a.glycerol; three fatty acids

b.diacylglycerol; two fatty acids
c.monoacylglycerol; one fatty acid
d.monoacylglycerol; two fatty acids

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 Section 19.6

Chemical Reactions of Triacylglycerols

Which of the following statements regarding

saponification of triacylglycerols is correct?

a.Saponification is a hydrolysis reaction carried out in an

alkaline (basic) solution.
b.Saponification of animal fats is the process by which
soaps were made in pioneer times.
c.Saponification is a hydrolysis reaction resulting in the
formation of carboxylate ions.
d.All the above.

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 Section 19.6

Chemical Reactions of Triacylglycerols

Which of the following statements regarding

saponification of triacylglycerols is correct?

a.Saponification is a hydrolysis reaction carried out in an

alkaline (basic) solution.
b.Saponification of animal fats is the process by which
soaps were made in pioneer times.
c.Saponification is a hydrolysis reaction resulting in the
formation of carboxylate ions.
d.All the above.

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 Section 19.6

Chemical Reactions of Triacylglycerols

What process is utilized to convert liquid plant oils

into semi-solid materials that, when ingested, play
a role in raising blood cholesterol levels?

a.Halogenation
b.Hydrohalogenation
c.Hydrogenation
d.Hydrolysis

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 Section 19.6

Chemical Reactions of Triacylglycerols

What process is utilized to convert liquid plant oils

into semi-solid materials that, when ingested, play
a role in raising blood cholesterol levels?

a.Halogenation
b.Hydrohalogenation
c.Hydrogenation
d.Hydrolysis

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 Section 19.6

Chemical Reactions of Triacylglycerols

What process results in breaking the carbon–

carbon double bonds producing both short chain
aldehyde and carboxylic acid products causing the
fats and oils to become rancid?

a.Oxidation
b.Hydrolysis
c.Saponification
d.Hydrogenation

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 Section 19.6

Chemical Reactions of Triacylglycerols

What process results in breaking the carbon–

carbon double bonds producing both short chain
aldehyde and carboxylic acid products causing the
fats and oils to become rancid?

a.Oxidation
b.Hydrolysis
c.Saponification
d.Hydrogenation

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 Section 19.7

Membrane Lipids: Phospholipids

An Introduction
• All cells are surrounded by a membrane that
confines their contents
• Up to 80% of the mass of a cell membrane can
be lipid materials dominated by phospholipids
• Phospholipid: Lipid that contains one or more
fatty acids, a phosphate group, a platform
molecule to which the fatty acid(s) and the
phosphate group are attached, and an alcohol
that is attached to the phosphate group

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 Section 19.7

Membrane Lipids: Phospholipids

Types of Phospholipids Based on Platform Molecule

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 Section 19.7

Membrane Lipids: Phospholipids

Glycerophospholipids
• Lipids that contain two fatty acids and a
phosphate group esterified to a glycerol
molecule and an alcohol esterified to the
phosphate group
• All attachments (bonds) between groups are
ester linkages
– Contain four ester linkages when contrasted to three
ester linkages in triacylglycerols

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 Section 19.7

Membrane Lipids: Phospholipids

Glycerophospholipids
• Undergo hydrolysis and saponification reactions
in a manner similar to that for triacylglycerols
• The alcohol attached to the phosphate group in
a glycophospholipid is usually one of three
amino alcohols:
– Choline - Phosphatidylcholines
– Ethanolamine - Phosphatidylethanolamines
– Serine - Phosphatidylserines

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 Section 19.7

Membrane Lipids: Phospholipids

Glycerophospholipids
• Structurally glycerophospholipids are similar to
triacylglycerols, but they have different
biochemical functions
– Triacylglycerols serve as energy-storage molecules
– Glycerophospholipids function as components of cell
membranes
– A major structural difference between the two types of
lipids is that of their “polarity”, which is responsible for
their differing biochemical functions
• Triacylglycerols are a nonpolar
• Glycerophospholipids are polar
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 Section 19.7

Membrane Lipids: Phospholipids

Sphingophospholipids
• Structures based on the 18-carbon
monounsaturated aminodialcohol sphingosine
• Contains one fatty acid and one phosphate
group attached to a sphingosine molecule, and
an alcohol attached to the phosphate group

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 Section 19.7

Membrane Lipids: Phospholipids

Sphingophospholipids
• Participate in hydrolysis and saponification
reaction
• Sphingophospholipids in which the alcohol
esterified to the phosphate group is choline are
called sphingomyelins
– Found in all cell membranes and are important
structural components of the myelin sheath of
neurons

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 Section 19.7

Membrane Lipids: Phospholipids

What is the most abundant type of membrane

lipid?

a.Cholesterol
b.Sphingoglycolipids
c.Phospholipids
d.Eicosanoids

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 Section 19.7

Membrane Lipids: Phospholipids

What is the most abundant type of membrane

lipid?

a.Cholesterol
b.Sphingoglycolipids
c.Phospholipids
d.Eicosanoids

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 Section 19.8

Membrane Lipids: Sphingoglycolipids

Sphingoglycolipids

• Contains both a fatty acid

and a carbohydrate
component attached to a
sphingosine molecule

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 Section 19.8

Membrane Lipids: Sphingoglycolipids

Cerebrosides
• Simplest sphingoglycolipids
• Contain a single monosaccharide unit–either
glucose or galactose
• Occur primarily in brain (7% of dry mass)

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 Section 19.8

Membrane Lipids: Sphingoglycolipids

Gangliosides
• Complex sphingoglycolipids
• Contain a branched chain of up to seven
monosaccharide residues
• Occur in the gray matter of the brain as well as
in the myelin sheath

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 Section 19.8

Membrane Lipids: Sphingoglycolipids

What is the membrane lipid, sphingoglycolipid,

made up of?

• sphingosine; fatty acid; monosaccharide

• sphingosine; fatty acid; oligosaccharide
• sphingosine; glycerol; fatty acid
• Both (a) and (b)

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 Section 19.8

Membrane Lipids: Sphingoglycolipids

What is the membrane lipid, sphingoglycolipid,

made up of?

• sphingosine; fatty acid; monosaccharide

• sphingosine; fatty acid; oligosaccharide
• sphingosine; glycerol; fatty acid
• Both (a) and (b)

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 Section 19.9

Membrane Lipids: Cholesterol

Cholesterol - Third Major Type of Membrane Lipid

• Is a steroid
– Lipid whose structure is based on a fused-ring
system of three 6-membered rings and one 5-
membered ring
• Cholesterol: C27 steroid molecule and
precursor for other steroid-based lipids
– Important in human cell membranes, nerve tissue,
and brain tissue
– Important in chemical synthesis of various hormones
and vitamins essential for life

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 Section 19.9

Membrane Lipids: Cholesterol

Cholesterol in Food
• Liver synthesizes almost 1g of cholesterol
everyday
– Not necessary to consume in the form of diet
• Cholesterol ingestion decreases biosynthetic
cholesterol production
• Animal food contains lots of cholesterol
• Plant food contains negligible amounts of
cholesterol

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 Section 19.9

Membrane Lipids: Cholesterol

The membrane lipid cholesterol is a steroid whose

structure is based on a fused-ring system that
involves _____ six-membered ring(s) and _____
five-membered ring(s).

a.2, 2
b.3, 2
c.3, 1
d.1, 3

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 Section 19.9

Membrane Lipids: Cholesterol

The membrane lipid cholesterol is a steroid whose

structure is based on a fused-ring system that
involves _____ six-membered ring(s) and _____
five-membered ring(s).

a.2, 2
b.3, 2
c.3, 1
d.1, 3

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 Section 19.10

Cell Membranes

Cell Membrane (Plasma Membrane)

• Lipid-based structure that separates aqueous
interior of a cell from the aqueous environment
surrounding the cell
– Up to 80% of plasma membrane is lipid material
• The membranes are lipid bilayers made up of
phospholipids
– Lipid bilayer: Nonpolar tails of phospholipids are in
the middle and polar heads are on the surface
• 6–9 nanometers thick
• Contains at least one unsaturated fatty acid

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 Section 19.10

Cell Membranes

Cholesterol and Cell Membrane

• Cholesterol molecules are also components of
plasma membranes
– Cholesterol helps regulate membrane fluidity–the
fused-ring system does not allow rotation of fatty acid
tails in the vicinity
– Fits between fatty acid chains of the lipid bilayer

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 Section 19.10

Cell Membranes

Membrane Proteins
• Lipid bilayers also contain proteins
– Responsible for moving substances such as nutrients
and electrolytes across the membrane
– Act as receptors that bind hormones and
neurotransmitters
• The membrane proteins and some lipids further
react with carbohydrate molecules
– Act as markers, substances that play roles in
processes by which different cells recognize each
other

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 Section 19.10

Cell Membranes

Figure 19.21 - Proteins as Important Structural

Components of Cell Membranes

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 Section 19.10

Cell Membranes

Transport Across Cell Membranes

• To maintain cellular processes, various types of
molecules are transported across the cell
membranes
• Three types of transport:
– Passive transport
– Facilitated transport
– Active transport

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 Section 19.10

Cell Membranes

Passive Transport
• Process in which a substance moves across a
cell membrane by diffusion from a region of
higher concentration to a region of lower
concentration
– No cellular energy expenditure
– Only a few types of molecules, including O2, N2, urea,
and ethanol, can cross membranes by this process

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 Section 19.10

Cell Membranes

Facilitated Transport
• Process in which a substance moves across a
cell membrane, with the aid of a membrane
protein, from a region of higher concentration to
a region of lower concentration
– No cellular energy expenditure
– Specific protein carriers or transporters are involved
in the process

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 Section 19.10

Cell Membranes

Active Transport
• Process in which a substance moves across a
cell membrane, with the aid of membrane
proteins, against a concentration gradient
– Involves expenditure of cellular energy
• Supplied by ATP molecules
– Proteins involved in active transport are called
“pumps”

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 Section 19.10

Cell Membranes

Which of the following polarity-based descriptions

is correct for the interior of a lipid bilayer?

a.Polar heads
b.Nonpolar heads
c.Nonpolar tails
d.None of the above

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 Section 19.10

Cell Membranes

Which of the following polarity-based descriptions

is correct for the interior of a lipid bilayer?

a.Polar heads
b.Nonpolar heads
c.Nonpolar tails
d.None of the above

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 Section 19.10

Cell Membranes

What type of transport across membranes requires

the expenditure of cellular energy?

a.Passive
b.Facilitated
c.Active
d.Dialysis

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 Section 19.10

Cell Membranes

What type of transport across membranes requires

the expenditure of cellular energy?

a.Passive
b.Facilitated
c.Active
d.Dialysis

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Copyright ©2016 Cengage Learning. All Rights Reserved. 82

 Section 19.11

Emulsification Lipids: Bile Acids

• Emulsifier: Substance that can disperse and

stabilize water-insoluble substances as
colloidal particles in an aqueous solution
• Bile acid: Cholesterol derivative that functions
as an emulsifying agent that makes dietary
lipids soluble in aqueous environment of the
digestive tract
– Approximately one third of cholesterol produced by
liver is converted to bile acids
– Similar to the action of soap in washing process
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 Section 19.11

Emulsification Lipids: Bile Acids

Bile Acids
• Tri- or dihydroxy cholesterol derivatives
• The carbon 17 side chain of cholesterol has
been oxidized to a carboxylic acid
– The oxidized acid side chain is bonded to an amino
acid (either glycine or taurine) through an amide
linkage
• Bile: A fluid containing emulsifying agents
secreted by the liver, stored in the gallbladder,
and released into the small intestine during
digestion
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 Section 19.11

Emulsification Lipids: Bile Acids

What cholesterol derivative(s) function as a lipid-

emulsifying agent in the aqueous environment of
the digestive tract?

a.Cholic acid
b.12-deoxycholic acid
c.7-deoxycholic acid
d.All of these

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Copyright ©2016 Cengage Learning. All Rights Reserved. 85

 Section 19.11

Emulsification Lipids: Bile Acids

What cholesterol derivative(s) function as a lipid-

emulsifying agent in the aqueous environment of
the digestive tract?

a.Cholic acid
b.12-deoxycholic acid
c.7-deoxycholic acid
d.All of these

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Copyright ©2016 Cengage Learning. All Rights Reserved. 86

 Section 19.12

Messenger Lipids: Steroid Hormones

Hormones
• Biochemical substances produced by a ductless
gland that has a messenger function
• Serve as a means of communication between
various tissues
– Some hormones are lipids
• The lipids that play the role of “chemical
messengers” include:
– Steroid hormone - Derivative of cholesterol
– Eicosanoid - Derivative of fatty acids

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 Section 19.12

Messenger Lipids: Steroid Hormones

Hormones
• There are two major classes of steroid
hormones:
– Sex hormones - Control reproduction and secondary
sex characteristics
– Adrenocorticoid hormones - Regulate numerous
biochemical processes in the body

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 Section 19.12

Messenger Lipids: Steroid Hormones

Sex Hormones
• Classified into three major subclasses:
– Estrogens—the female sex hormones
– Androgens—the male sex hormones
– Progestins—the pregnancy hormones

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 Section 19.12

Messenger Lipids: Steroid Hormones

Adrenocorticoid Hormones
• Produced by the adrenal glands
• 28 Different hormones have been isolated from
the adrenal cortex
• Types of adrenocorticoid hormones:
– Mineralocorticoids - Control the balance of Na+ and
K+ ions in cells
– Glucocorticoids - Control glucose metabolism and
counteract inflammation

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 Section 19.12

Messenger Lipids: Steroid Hormones

What are the two large families of lipids that have

messenger functions?

a.Steroid hormones and phospholipids

b.Steroid hormones and eicosanoids
c.Steroid hormones and triacylglycerols
d.Steroid hormones and sphingolipids

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 Section 19.12

Messenger Lipids: Steroid Hormones

What are the two large families of lipids that have

messenger functions?

a.Steroid hormones and phospholipids

b.Steroid hormones and eicosanoids
c.Steroid hormones and triacylglycerols
d.Steroid hormones and sphingolipids

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 Section 19.13

Messenger Lipids: Eicosanoids

Eicosanoids
• Arachidonic acid (20:4) derivatives
• Have profound physiological effects at extremely
low concentrations
• Are hormone-like molecules
• Exert their effects in the tissues where they are
synthesized
• Usually have a very short “life”

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 Section 19.13

Messenger Lipids: Eicosanoids

Physiological Effects of Eicosanoids

• Include mediation of:
1. Inflammatory response
2. Production of pain and fever
3. Regulation of blood pressure
4. Induction of blood clotting
5. Control of reproductive functions, such as induction
of labor
6. Regulation of the sleep/wake cycle

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 Section 19.13

Messenger Lipids: Eicosanoids

Principle Types of Eicosanoids

1. Prostaglandin: C20-fatty-acid derivative

containing cyclopentane ring and oxygen-
containing functional groups
– Involved in:
• Raising body temperature
• Inhibiting the secretion of gastric juices
• Increasing the secretion of a protective mucus layer
into the stomach
• Relaxing and contracting smooth muscle
• Directing water and electrolyte balance
• Intensifying pain and enhancing inflammation
responses Return to TOC

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 Section 19.13

Messenger Lipids: Eicosanoids

Principle Types of Eicosanoids

2. Thromboxane: C20-fatty-acid derivative

containing a cyclic ether ring and oxygen-
containing functional groups
̶ Promote platelet aggregation
3. Leukotriene: C20-fatty-acid derivative containing
three conjugated double bonds and hydroxy
groups
– Promote inflammatory and hypersensitivity (allergy)
responses

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 Section 19.13

Messenger Lipids: Eicosanoids

The physiological effects of eicosanoids include

mediation of:

a.the inflammatory response and the regulation of blood

pressure.
b.the production of pain and fever and the regulation of the
sleep/wake cycle.
c.the induction of blood clotting and the control of the
reproductive functions.
d.all the above.

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 Section 19.13

Messenger Lipids: Eicosanoids

The physiological effects of eicosanoids include

mediation of:

a.the inflammatory response and the regulation of blood

pressure.
b.the production of pain and fever and the regulation of the
sleep/wake cycle.
c.the induction of blood clotting and the control of the
reproductive functions.
d.all the above.

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Copyright ©2016 Cengage Learning. All Rights Reserved. 98

 Section 19.14

Protective-Coating Lipids: Biological Waxes

Biological Wax
• Monoester of a long-chain fatty acid and a long-
chain alcohol
• The fatty acids found in biological waxes:
– Generally saturated fatty acids
– Contain 14 to 36 carbon atoms
• The alcohols found in biological waxes:
– May be saturated or unsaturated
– May contain 16 to 30 carbon atoms

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 Section 19.14

Protective-Coating Lipids: Biological Waxes

What is the chemical makeup of a biological wax?

a.A monoester of a long-chain fatty acid and a short-chain

alcohol
b.A monoester of a short-chain fatty acid and a short-chain
alcohol
c.A monoester of a short-chain fatty acid and a long-chain
alcohol
d.A monoester of a long-chain fatty acid and a long-chain
alcohol

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 Section 19.14

Protective-Coating Lipids: Biological Waxes

What is the chemical makeup of a biological wax?

a.A monoester of a long-chain fatty acid and a short-chain

alcohol
b.A monoester of a short-chain fatty acid and a short-chain
alcohol
c.A monoester of a short-chain fatty acid and a long-chain
alcohol
d.A monoester of a long-chain fatty acid and a long-chain
alcohol

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 Section 19.15

Saponifiable and Nonsaponifiable Lipids

Saponifiable Lipids
• Lipids that undergo hydrolysis in a basic solution
to yield 2 or more small molecules
• Linkage makeup:
– Triacylglycerols—3 ester bonds
– Glycerophospholipids—4 ester bonds
– Sphingophospholipids—1 amide and 2 ester bonds
– Sphingoglycolipids—1 amide, 1 ester, and 1
glycosidic bond
– Biological waxes—1 ester bond

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 Section 19.15

Saponifiable and Nonsaponifiable Lipids

Figure 19.31 - Classification of Lipids

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 Section 19.15

Saponifiable and Nonsaponifiable Lipids

Which of the following is a nonsaponifiable lipid?

a.Sphingophospholipids
b.Triacylglycerols
c.Steroid hormones
d.Glycerophospholipids

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 Section 19.15

Saponifiable and Nonsaponifiable Lipids

Which of the following is a nonsaponifiable lipid?

a.Sphingophospholipids
b.Triacylglycerols
c.Steroid hormones
d.Glycerophospholipids

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Copyright ©2016 Cengage Learning. All Rights Reserved. 105

 Chapter 19

Concept Question 1
Triacylglycerols found in animals are solids and are called
fats; however, those found in plants are liquids and are
called oils. What is the structural difference in the
triacylglycerol animal fats and plant oils?

a.Triacylglycerols in fats are composed of unsaturated fatty acids,

and in oils, they are composed of saturated fatty acids.
b.Triacylglycerols in fats are composed of saturated fatty acids, and
in oils, they are composed of unsaturated fatty acids.
c.Fats are triacylglycerol mixtures that are liquid at room
temperature, and oils are triacylglycerol mixtures that are solid at
room temperature.
d.None of the above. Return to TOC

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 Chapter 19

Concept Question 1
Triacylglycerols found in animals are solids and are called
fats; however, those found in plants are liquids and are
called oils. What is the structural difference in the
triacylglycerol animal fats and plant oils?

a.Triacylglycerols in fats are composed of unsaturated fatty acids,

and in oils, they are composed of saturated fatty acids.
b.Triacylglycerols in fats are composed of saturated fatty acids, and
in oils, they are composed of unsaturated fatty acids.
c.Fats are triacylglycerol mixtures that are liquid at room
temperature, and oils are triacylglycerol mixtures that are solid at
room temperature.
d.None of the above. Return to TOC

Copyright ©2016 Cengage Learning. All Rights Reserved. 107

 Chapter 19

Concept Question 2

As a result of injury or damage to bodily tissue,

inflammation occurs, which is mediated by _____
that belongs to a class of messenger lipids known
as _____.

a.thromboxanes; steroids
b.prostaglandins; steroids
c.thromboxanes; eicosanoids
d.prostaglandins; eicosanoids

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 Chapter 19

Concept Question 2

As a result of injury or damage to bodily tissue,

inflammation occurs, which is mediated by _____
that belongs to a class of messenger lipids known
as _____.

a.thromboxanes; steroids
b.prostaglandins; steroids
c.thromboxanes; eicosanoids
d.prostaglandins; eicosanoids

Return to TOC

Copyright ©2016 Cengage Learning. All Rights Reserved. 109