Stoker Chapter19 (Lipids) - 2 PDF

Chapter 19
Lipids
Chapter 19
Table of Contents
19.1 Structure and Classification of Lipids

19.2 Types 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
19.15 Saponifiable and Nonsaponifiable lipids
Copyright © Cengage Learning. All rights reserved

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 features that serves as the basis for defining
such compounds.
• Classification: Based on two methods
– Biochemical function
– Saponification (hydrolysis under basic conditions)
Copyright © Cengage Learning. All rights reserved 3

Section 19.1
Classification based on Biochemical Function

• For purposes of simplicity of study lipids are divided into
five categories based on their biochemical function:
– Energy-storage lipids - triacylglycerols
– Membrane lipids - phospholipids, sphingoglycolipids,
and cholesterol
– Emulsification lipids - bile acids
– Chemical messenger lipids - steroid hormones and
eicosanoids)
– Protective-coating lipids - biological waxes
– Transport lipids - lipoproteins

Section 19.1
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)

Section 19.1
Structure
• Lipids exhibit
structural diversity
• Some are esters,
some are amides,
and some are
alcohols (acyclic
and cyclic) and
some are
polycyclic.

Section 19.2
Types of Fatty Acids
Saturated and Unsaturated Fatty Acids

• Carboxylic acids with linear (unbranched) carbon chain - Fatty acids
are naturally occurring monocarboxylic acids
• Even # of Carbon atoms:
– Long chain fatty acids: C12 - C26
– Medium chain fatty acids: C6 - C11
– Short-chain fatty acids: C4 - C5
• Two Types:
– Saturated - all C-C bonds are single bonds
– Unsaturated
• Monounsaturated: one C=C bond
• Polyunsaturated: 2 or more C=C bonds present - up to six double
bonds are present in fatty acids

Section 19.2
Saturated Fatty Acids

• Fatty acid with a carbon chain in which all C-C bonds
are single bonds
• Numbering starts from the end of -COOH group
• Structural notation: it indicates number of C atoms
• Example - Lauric acid has 12 C atoms and no double
bonds so it is (12:0)
O
H 3C (CH) 10 C OH
O
or
C
11 9 7 5 3 1 OH
12 10 8 6 4 2

Section 19.2
Unsaturated Fatty Acids
• A monounsaturated
fatty acid is a fatty
acid with a carbon
chain in which one
carbon–carbon
double bond is
present.
• Different ways of
depicting the
structure

Section 19.2
Polyunsaturated Fatty Acids (PUFAs)

• A polyunsaturated fatty acid is a fatty acid 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.
• Two types of unsaturated fatty acids.
– Omega (ω)-3 fatty acids - An unsaturated fatty acid with its
endmost double bond three carbon atoms away from its methyl
end.
– Omega (ω)-6 fatty acid is an unsaturated fatty acid with its
endmost double bond six carbon atoms away from its methyl
end.

Section 19.2
Selected Unsaturated Fatty Acids of Biological Importance
• Numbering starts from the other end of -COOH

• Structural notation: it indicates number of C atoms
– E.g., 18:2 – 18 carbons, 2 double bonds

Section 19.2
Omega Acids
• Essential Fatty Acids: Must be part of diet
• Nutritionally important Omega-3 and Omega-6 fatty acids
– Linolenic acid – Omega-3
– Linoleic acid – Omega-6
• Linoleic Acid Deficiency:
– Skin redness - becomes irritated
– Infections and dehydration
– Liver abnormalities
– Children need it the most
– Human milk has more than cow’s milk

Section 19.2
American Diet
• Sufficient in omega 6 fatty acids
• Deficient in omega 3 fatty acids
– Fish - good source for omega 3 fatty acids
• High rate of heart disease may be due to imbalance in
omega 3 and 6 fatty acids
– Ideal ratio: Omega 6 : Omega 3 (4 - 10 g: 1g)

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 carboxylic acid polar group

Section 19.3
The Melting Point

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

Section 19.3
Space-Filling Molecules
• The number of bends in a fatty acid chain increase as
the number of double bonds increase
• Less packing occurs
• Melting point is lower
• Tend to be liquids at room temperature

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:
– The most widespread energy storage material -
carbohydrate glycogen
– Present in small amounts
• Major Energy– Storage material is triacylglycerols:
– Triacylglycerols are concentrated primarily in special
cells (adipocytes)
– Adipocytes are nearly filled with triacylglycerols.

Section 19.4
p661
Section 19.4
p663
Section 19.4
Two Types of Triacylglycerols

• Simple Triacylglycerols: Three identical fatty acids are
esterified
– Naturally occurring simple triacylglycerols are rare
• Mixed Triacylglycerols: A triester formed from the
esterification of glycerol with more than one kind of fatty
acid
– In nature mostly mixed triacylglycerols are found and
are different even from the same source depending
on the feed, e.g., corn, peanut and wheat -fed cows
have different triacylglycerols

Section 19.4
Figure 19-5 p661

Section 19.4
Figure 19-6 p662

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

Section 19.4
Figure 19-8 p664

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 for a balanced diet:
– Current recommended amounts are: total fat intake in calories:
• 15% - Monounsaturated fat
• 10% - Polyunsaturated
• <10% - Saturated fats
• Studies also indicate that:
– Saturated fats are considered “bad fats”
– Monounsaturated fats are considered “good fats”
– Trans-monounsaturated fats are considered “bad fats”
– Polyunsaturated fats can be both “good fats” and “bad fats”
• Omega 3 and 6 are important “good fats”

Section 19.5
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
– Nuts also contain valuable antioxidant vitamins, minerals,
and plant fiber protein

Section 19.5
Essential Fatty Acids

• Fatty acids that must be obtained from dietary sources – are not
synthesized within the body
• Two most important essential fatty acids are:
– Linoleic acid (18:2) - omega 6
– Linolenic acid (18:3) - omega 3
• Both are 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
• Deficiencies of above two acids may result in skin redness,
infections and dehydration likely and liver abnormalities may
develop

Section 19.5
Artificial Fat Substitute : Olestra

Section 19.5
Artificial Fat Substitute : Olestra

Section 19.6
Chemical Reactions of Triacylglycerols
Partial Hydrolysis
• Chemical Properties due to two functional groups: esters
and alkenes
– Hydrolysis: Partial hydrolysis of triacylglycerols
– Breaking of 1-2 ester bonds to give rise to mono- or
diacylglycerol and fatty acid(s)
– Carried out by enzymes produced by the pancreas

Section 19.6
Figure 19-10 p671

Section 19.6
Saponification
• Hydrolysis in basic solution: Produce salt of fatty acid
and glycerol
O
H 2 C OH
H2C O C R
O
+ 3NaOH HC OH + 3RCOONa
R C O CH
O
Soap
H2C O C R H 2 C OH

Section 19.6
p672
Section 19.6
Hydrogenation
– Addition of hydrogen across double (=) bond - increases degree
of saturation
O O
H2C O C
H2C O C
O O
HC O C + 2H2
HC O C
O O
H2C O C H2C O C
O il Solid
– Many food products are produced by partial hydrogenation of

oils and fats
– Peanut oil + H2 Peanut Butter
– Vegetable oil + H2 Margarine
Section 19.6
Figure 19-11 p673

Section 19.6
p675
Section 19.6

Section 19.6
Halogenation
– Addition of halogen across double (=) bond -
increases degree of saturation
– a test for unsaturation
– the amount of halogen absorbed by a lipid can be
used as an index of the degree of unsaturation; the
index value is called iodine number , the number of
grams of iodine that will add to 100 g of fat or oil
– the rule is: high I2 number indicates a high degree of
unsaturation

Section 19.6
Oxidation
• Double bonds in triacylglycerols are subject to oxidation with oxygen
in air (an oxidizing agent )-Leads to C=C breakage
• Remember that oxidation of alkenes may result into two short chain
molecules – an aldehydes or a carboxylic acid:
– The aldehydes and/or carboxylic acids so produced often have
objectionable odors - fats and oils are said to be rancid
– To avoid this unwanted oxidation process antioxidants are
added as preservatives, e.g., Vitamin C and vitamin E are good
antioxidant preservatives.

Section 19.6
p673
Section 19.7
Membrane Lipids: Phospholipids
• 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: contains one or more fatty acids, a
phosphate group, a platform molecule (glycerol or
sphingosine) to which the fatty acid(s) and the phosphate
group are attached, and an alcohol that is attached to the
phosphate group.
G
Fatty acid Sphingosine
l
y
c
e
Fatty acid Fatty acid
r
o Phosphate Alcohol Phosphate Alcohol
l

Section 19.7
p676
Section 19.7
Glycerophospholipids
• A glycerophospholipid is a lipid that contains 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 in a
glycerophospholipid are ester linkages
• Glycerophospholipids have four ester linkages as
contrasted to three ester linkages in triacylglycerols.

Section 19.7
p677
Section 19.7
• 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, ethanolamine, or serine - respectively known as
phosphatidylcholines, phosphatidylethanolamines, and
phosphatidylserines.

Section 19.7
p678
Section 19.7
p677
Section 19.7

Section 19.7
Figure 19-13b p679

Section 19.7
• Structurally glycerophospholipids are although similar to
triacylglycerols, 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” – Responsible for the their
differing biochemical functions.
– Triacylglycerols are a non-polar
– Glycerophospholipids are polar.

Section 19.7
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
Sphingosine
Fatty acid
Phosphate Alcohol

Section 19.7
p680
Section 19.7
• Saponifiable lipids
• Sphingophospholipids in which the alcohol esterified to
the phosphate group is choline are called
sphingomyelins.
• Sphingomyelins are found in all cell membranes and are
important structural components of the myelin sheath of
neurons

Section 19.8
Membrane Lipids: Sphingoglycolipids
• Sphingoglycolipids: Contains both a fatty acid and carbohydrate

• Simple sphingoglycolipids are called cerebrosides: contains a
single monosaccharide unit - either glucose or galactose
– They occur primarily in brain (7% of dry mass)

Section 19.8
Gangliosides
• Complex sphingoglycolipids are called Gangliosides:
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.

Section 19.8
p682
Section 19.9
Membrane Lipids: Cholesterol
Cholesterol-Third major type of membrane lipid

• A steroid is a lipid whose structure is
based on a fused ring system of
three 6 carbon rings and one 5
carbon ring.
• Cholesterol: C27 steroid molecule
• The principal constituent of
gallstones from which it can be
isolated as white crystalline solid;
name derived from this source
(Greek, chole – bile; steros – solid)
• Important in human cell membranes,
nerve tissue and brain tissue
– Important in chemical synthesis
of various hormones and
vitamins essential for life
Section 19.9
Cholesterol in Food
• Liver synthesizes cholesterol: ~ 1g everyday; so it is not

necessary to consume in the form of diet
• Cholesterol synthesis decrease if it is ingested but reduction
is not sufficient: Leads to cardiovascular disease
• Animal Food: Lot of cholesterol
• Plant Food: No cholesterol
• Medical science now considers high blood cholesterol, along
with high blood pressure and smoking, as the major risk
factors for cardiovascular disease (CVD). High blood
cholesterol contributes to atherosclerosis, which is
characterized by the buildup of plaque along the inner walls of
the arteries.

Section 19.9

Section 19.10
Cell Membranes
Cell Membrane (Plasma Membrane)

• Cells are surrounded by plasma membranes:
– 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 bilayer made up of phospholipids
– Bilayer: Nonpolar tails of phospholipids in the middle and polar
heads are on the surface
• 6 - 9 billionths of a meter thick or 6-9 nanometer thick
– The membrane is a liquid like structure due to unsaturation in
lipid tails

Section 19.10
Cell Membranes
Figure 19-17 p685

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 nor allow rotation of fatty acid tails in the vicinity
– Fits between fatty acid chains of the lipid bilayer: Make it rigid
– Cholesterol thus acts a membrane plasticizer

Section 19.10
Cell Membranes
Membrane Proteins
• The membranes also contain proteins:
– Responsible for moving substances such as nutrients and electrolytes
across the membrane
– Receptors for hormones and neurotransmitters
• The membrane proteins and some lipids are further reacted with
carbohydrates molecules:
– Act as markers: process by which different cells recognize each other

Section 19.10
Cell Membranes
Transport Across Cell Membranes:

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

Section 19.10
Cell Membranes
Passive Transport
• Passive transport - a substance moves

across a cell membrane by diffusion
from a region of higher concentration to
a region of lower concentration.
– Only a few types of molecules,
including O2, N2, H2O, urea, and
ethanol, can cross membranes by
passive transport

Section 19.10
Cell Membranes
Facilitated Transport
• Facilitated transport - 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.
– The specific protein carriers or
transporters are involved in the
process

Section 19.10
Cell Membranes
Active Transport
• Active transport - a
substance moves across a
cell membrane, with the aid
of membrane proteins,
against a concentration
gradient with the expenditure
of cellular energy.
– Proteins involved in
active transport are called
“pumps.” The needed
energy is supplied by
molecules such as ATP.
Section 19.11
Emulsification Lipids: Bile Acids
• An emulsifier is a substance that can disperse and

stabilize water-insoluble substances as colloidal
particles in an aqueous solution.
• Bile Acids: Cholesterol derivatives that functions as
emulsifying agents that make dietary lipids soluble in
aqueous environment of the digestive tract:
– Approximately one third of cholesterol produced by
liver is converted to bile acids.
– Action similar to soap in washing

Section 19.11
Bile Acids
• Bile acids are tri- or dihydroxy A large percentage of gallstones, the
cholesterol derivatives causative agent for many “gallbladder
• The carbon 17 side chain of attacks,” are almost pure crystallized
cholesterol has been oxidized to a cholesterol that has precipitated from
carboxylic acid bile solution.
• 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 (Bile acids) secreted by the
liver, stored in the gallbladder, and
released into the small intestine
during digestion

Section 19.11
Figure 19-24 p688

Section 19.12
Messenger Lipids: Steroid Hormones
Hormones
• A hormone is a biochemical substance produced by a ductless
gland that has a messenger function.
• Hormones serve as a means of communication between various
tissues.
– Some hormones are lipids.
• The lipids that play the role of “chemical messengers” include:
– Steroid hormones – derivatives of cholesterol
– Eicosanoids- derivatives of arachidonic acid
• There are two major classes of steroid hormones:
– Sex hormones - control reproduction and secondary sex
characteristics
– Adrenocorticoid hormones – control numerous biochemical
processes in the body

Section 19.12
Sex Hormones
• Classified into three major groups:
– Estrogens - the female sex hormones
– Androgens - the male sex hormones
– Progestins - the pregnancy hormones

Section 19.12

Section 19.12
Adrenocorticoid Hormones
• Produced by the adrenal glands
- small organs located on top of
each kidney
• 28 Different hormones have
been isolated from the adrenal
cortex
• Two types of adrenocorticoid
hormones:
– Mineralocorticoids - control
the balance of Na and K
ions in cells
– Glucocorticoids - control
glucose metabolism and
counteract inflammation

Section 19.13
Messenger Lipids: Eicosanoids
• Eicosanoids are arachidonic acid (20:4) derivatives:

– Have profound physiological effects at extremely low
concentrations.
– Eicosanoids are hormone-like molecules
– Exert their effects in the tissues where they are synthesized.
– Eicosanoids usually have a very short “life.”
• Physiological effects of eicosanoids:
– Inflammatory response
– Production of pain and fever
– Regulation of blood pressure
– Induction of blood clotting
– Control of reproductive functions, such as induction of labor
– Regulation of the sleep/wake cycle

Section 19.13
Figure 19-28 p693

Section 19.13
Principal Types of Eicosanoids
1. Prostoglandins: 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.
Section 19.13
Principal Types of Eicosanoids
2. Thromboxanes: C20-fatty-acid
derivative containing a cyclic ether ring
and oxygen-containing functional
groups
̶ Promote platelet aggregation.
3. Leukotrienes: C20-fatty-acid derivative

containing three conjugated double
bonds and hydroxyl groups
– Promote inflammatory and
hypersensitivity (allergy) responses

Section 19.14
Protective-Coating Lipids: Biological Waxes
• A biological wax: a
monoester of a long-chain
fatty acid and a long-chain
alcohol.
• The fatty acids found in
biological waxes:
– Generally are 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.
Section 19.14
Protective-Coating Lipids: Biological Waxes
Figure 19-29 p695

Section 19.1
Transport Lipids : Lipoproteins

• responsible for the transport of
other lipids in the body; lipids are
only sparingly soluble in water,
and the movement of lipids from
one organ to another through the
blood stream requires a transport
system that operates via plasma
lipoproteins
• lipoprotein particles consist of a
core of hydrophobic molecules
such as triglycerides or
cholesterol esters (cholesterol
esterified to fa’s). The shell around
the core consists of polar lipids
and proteins
Section 19.1
Transport Lipids : Lipoproteins

• Four major classes:
1. Chylomicrons – transport dietary
TAG from the intestine to the liver
and to adipose tissue
2. Very-low-density lipoprotein
(VLDL) – transport TAG synthesized
in the liver to adipose tissue
3. Low-density lipoprotein (LDL) –
transport cholesterol synthesized in
the liver to cells throughout the body
4. High-density lipoprotein (HDL) –
collect excess cholesterol from body
tissues and transport it back to the
liver for degradation to bile acids

Section 15.15
Saponifiable and Nonsaponifiable Lipids
LIPIDS
SAPONIFIABLE NONSAPONIFIABLE
Triacylglycerols Cholesterol
Glycerophospholipids Bile acids,
Sphingophospholipids Steroid hormones
Sphingoglycolipids Eicosanoids
Biological waxes

Section 15.15
• Saponifiable Lipid: A lipid that undergoes hydrolysis

in a basic solution to yield 2 or more small molecules.
• Saponification is possible in molecules that contain
the following linkages (bonds):
̶ Ester
̶ Amide
̶ Glycosidic

Section 15.15
• Saponifiable Lipids and Linkages:

̶ 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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Chapter 19

19.1 Structure and Classification of Lipids

Copyright © Cengage Learning. All rights reserved

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Classification based on Biochemical Function

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Classification Based on Saponification

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Saturated and Unsaturated Fatty Acids

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Saturated Fatty Acids

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Unsaturated Fatty Acids

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Polyunsaturated Fatty Acids (PUFAs)

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Selected Unsaturated Fatty Acids of Biological Importance

• Numbering starts from the other end of -COOH

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• Water solubility: Short chain fatty acids have some

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The Melting Point

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Two Types of Triacylglycerols

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Figure 19-5 p661

Figure 19-6 p662

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Figure 19-8 p664

“Good Fats” Versus “Bad Fats”

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Fat and Fatty Acid Composition of Nuts

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Essential Fatty Acids

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Artificial Fat Substitute : Olestra

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Artificial Fat Substitute : Olestra

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Figure 19-10 p671

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– Many food products are produced by partial hydrogenation of

Figure 19-11 p673

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Figure 19-13b p679

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• Sphingoglycolipids: Contains both a fatty acid and carbohydrate

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