Chapter

5
Lipids ()
1

Figure 05.CO: Lipids

Danny E Hooks/ShutterStock, Inc.

Importance of lipids in nutrition

Fat is an essential nutrient (
).
Fats contribute greatly to the flavor
() and texture () of foods.
Fats are one of macronutrients (
).

What are lipids?

The term lipids applies to a broad range
of organic molecules that dissolve easily
in organic solvents such as alcohol (),
ether (), or acetone (), but are much
less soluble in water. ()
Hydrophobic = water-fearing = lipophilic
= fat-loving ()
Hydrophilic = water loving = lipophobic =
fat fearing ()
4

What Are Lipids?

Hydrophobic ()/
hydrophilic ()
Lipophilic ()/
lipophobic()
Classes of lipids ()
Triglycerides ()
Phospholipids ()
Sterols ()
PhotoDisc

Lipids in foods and in the body

Triglycerides = triacylglycerol (
)
Phospholipids () (2% of dietary
lipids)
Sterols () (a small percentage of
our dietary lipids)

PhotoDisc

PhotoDisc

Typical
structure of
phospholipids.

(lecithin)

PhotoDisc

Structure of a sterol
(), cholesterol (
), and a
cholesteryl ester (
).

PhotoDisc

Cholesterol in the body

1/3 from dietary lipids ()
2/3 from endogenous ()
An important component of cell
membranes
A precursor in the synthesis of sex
hormones, adrenal () hormones
(e.g., cortisol), vitamin D, and bile salts
()
PhotoDisc

10

Figure 05.UN01: A generic fatty acid.

11

Figure 05.UN02: A generic triglyceride.

12

Figure 05.UN03: Fat.

13

Figure 05.F01: Fatty acid structure. The basic structure of a fatty

acid is a carbon chain with a methyl end (CH3) and an acid
(carboxyl) end (COOH).
14

Figure 05.F02: Fatty acid chain lengths. Fatty acids can be

classified by their chain length as short-, medium-, or long-chain
15
fatty acids.

Fatty Acids Are Key Building Blocks

Chain Length
424 carbons

16

Medium-chain fatty acid (6-10 carbons)

Caporic acid (, , )
Caprylic acid (, , )
Capric acid (, , )

PhotoDisc

17

Figure 05.F03: Fatty acid chain lengths and liquidity (). As

the chain length of saturated fatty acids increases, they become
more solid at room temperature.
18

Figure 05.F04: Fatty acid nomenclature (). The carbons are

identified by their locations in the chain.
19

Figure 05.F05: Saturated, monounsaturated, and polyunsaturated

fatty acids. Hydrogens saturate the carbon chain of a saturated
fatty acid.
20

Fatty Acids Are Key Building Blocks

Saturation ()
Saturated ()
All single bonds between carbons

Monounsaturated

One carbon-carbon double bond

Polyunsaturated

More than one carbon-carbon double bond

21

Fatty Acids
Straight hydrocarbon chain terminating
with a carboxylic acid group
Fatty acid nomenclature ()
Delta () system - length, number/ position of
double bonds (e.g. 18:2 9,12)
Double bonds counted from omega (methyl)
end (e.g. 18:2 -6 or 18:2 n-6)

22

The structure of linoleic

acid, showing the two
systems for nomenclature.

23
Fig. 5-2, p. 133

Figure 05.05: Hydrogens saturate the carbon chain of a

saturated fatty acid.

24

Visible lipids vs.

Invisible lipids

Figure 05.UN04: Red meat, onions, and garlic.

iStockphoto/Thinkstock

25

Figure 05.F06: Liquid or solid at room temperature?

Short-chain and unsaturated fatty acids cannot pack
tightly together than long-chain saturated fatty acids.

26

Fatty Acids Are Key Building Blocks

Geometric () and
Positional () Isomers
()
Cis fatty acid ()
Trans fatty acids (
)
Hydrogenation ()
Conjugated linoleic acid
()
27

Fatty Acids Are Key Building Blocks

Types of fatty acids
Cis () and trans ()
Hydrogenation () produces trans
fatty acids ()

28

Figure 05.F07: Cis and trans fatty acids. Fatty acids with the bent
cis form are more common in food than the trans form.
29

Fatty Acids Are Key Building Blocks

Types of fatty acids
Essential fatty acids ()
Linoleic acid () and alphalinolenic acid (-)
Cant be made in the body
Used to make eicosanoids ()

30

-, n-3

, n-6

, n-9
Figure 05.F08: Omega-3, omega-6, and omega-9 fatty acids.
31

Gamma-linolenic acid (GLA) (n-6)

( -)

32

Fatty Acids Are Key Building Blocks

Types of fatty acids

Omega-3
Omega-6
Omega-9

33

Fatty Acids Are Key Building Blocks

Nonessential ()
and Essential ()
Fatty Acids
Elongation ()
Desaturation ()
Nonessential fatty
acids
Essential fatty acids
34

Figure 05.F09: Essential and nonessential fatty acids. Your body

makes some types of fatty acids, but others are essential in your diet.
35

Vitamin F

Figure 05.09: Your body makes some types of fatty acids, but
others are essential in your diet.
36

Alpha-linolenic acid (ALA)

It is named all-cis-9,12,15-octadecatrienoic acid (18:3

(n3)). The first double bond is located at the third
carbon from the n end. Thus, -linolenic acid is a
polyunsaturated n-3 (omega-3) fatty acid. It is an isomer
of -linolenic acid (GLA), a polyunsaturated n-6 (omega6) fatty acid.
37

Gamma-linolenic acid (GLA)

-Linolenic acid (gamma-linolenic acid or GLA,

sometimes called gamoleic acid) is an essential fatty
acid (?) found primarily in vegetable oils. However,
it can be synthesized from linoleic acid (C18:2 n-6).
38

Fatty Acids Are Key Building Blocks

Building Eicosanoids ()
Omega-6 fatty acids
Omega-3 fatty acids

39

Figure 05.UN05: Think about healthy fats.

iStockphoto/Thinkstock

40

essential
nonessential

(+1 double bond)

(+2 C)

(C20:4)

(, )
()

(+1 double bond)

(+2 C)
(+1 double bond)

Table 05.T01: Omega-6 to Eicosanoids

41

Table 05.T02: Omega-3 to Eicosanoids

42

Triglycerides ()
Structure
Glycerol () + 3 fatty acids
()

Functions

Energy source
Energy reserve
Insulation and protection
Carrier of fat-soluble
compounds
Sensory qualities in food
43

Function of Triglycerides
Fat performs a
number of essential
functions in the body.
Fat is also a major
energy source.
When at rest,
muscles prefer to
use fat for fuel.

44

Figure 05.UN07: Some foods, like cupcakes, have a high amount

of fat.
iStockphoto/Thinkstock

45

Figure 05.F10: Forming a triglyceride. Condensation reactions

attach three fatty acids to a glycerol backbone to form a
triglyceride. These reactions release water.

46

Figure 05.F11: Functions of triglycerides. Fat performs a number

of essential functions in the body.
47

Figure 05.UN08: A generic triglyceride

48

Figure 05.UN09: A generic glycerol ()

49

Triglycerides in Food
Sources of omega-3 fatty acids
Soybean (), canola (),
walnut (), flaxseed () oils
Salmon (), tuna (), mackerel
()

Sources of omega-6 fatty acids

Vegetable oils ()
Nuts and seeds ()

Photodisc

50

Figure 05.UN06: Fish contains healthy fats.

iStockphoto/Thinkstock

51

Table 05.T03: Omega-3 Fatty Acids in Selected Foods

Data from U.S. Department of Agriculture, Agricultural Research Service.
USDA National Nutrient Database for Standard Reference, Release 25.
2012. www.ars.usda.gov/ba/bhnrc/ndl. Accessed 1/20/13.

52

Triglycerides In Foods
Commercial Processing of Fats
Hydrolysis ()
Oxidation ()
Hydrogenation ()

53

Figure 05.F12: Fat is a major energy source. When at rest,

muscles prefer to use fat for fuel.
Photodisc

54


1000

Figure 05.F13: Adipose cells store fat. Evolution has selected fat,
rather than glycogen, as its primary energy storage medium.
Photo: Donna Beer Stolz, Ph.D., Center for Biologic Imaging, University of Pittsburgh Medical School.

55

Fat = Storage
Evolution has selected fat, rather than glycogen,
as its primary energy storage medium.
A gram of fat stores more than six times as
much energy as a gram of glycogen.

56

Figure 05.F14: Sites for fat storage differ for men and women.
Whereas men often store excess fat in their abdomens () ,
women tend to store it in their hips ().
57

Micronutrient Carrier
Fat is a
micronutrient carrier.
Fat holds more than
just energy.
It also carries
important nutrients,
such as fat-soluble
vitamins and
carotenoids.
58

Figure 05.F15: Fat is a micronutrient carrier. Fat holds more than

just energy. It also carries important nutrients, such as fat-soluble
vitamins and carotenoids.
59

Figure 05.F16: Fat imparts a rich, sensory quality to food.

Photodisc

60

Figure 05.F17: The diversity of fats. Fats are mixtures of saturated

61
Source: Adapted from Nutrition Today (1996).
and unsaturated fatty acids.

Figure 05.UN10: Oils have become so familiar that we often

forget they are highly processed, highly refined foods.
Bragin Alexey/ShutterStock, Inc.

62

Figure 05.FY01_UN01: Look out for fats on the health store shelf.
63

Phospholipids ()
Structure
Glycerol + 2 fatty acids +
phosphate group

Functions
Component of cell membranes
Lipid transport as part of
lipoproteins
Emulsifiers ()

Food sources
Egg yolks (), liver (),
soybeans (), peanuts ()

64

Figure 05.F18: Phospholipid. A phospholipid is soluble in both oil

and water. This is a useful property for transporting fatty
65
substances in the bodys watery fluids.

Figure 05.F19: Cell membranes are phospholipid bilayers. These

membranes primarily consist of phospholipids.
66

Figure 05.UN11: A generic phospholipid.

67

Figure 05.F20: Phospholipids and emulsification. Phospholipids

form water-soluble packages called micelles that suspend fatsoluble compounds in watery media.
68

Figure 05.UN12: Lecithins () in food products are used to

reduce the separation of ingredients.
Comstock/Thinkstock

69

Figure 05.FY02_UN01: Butter.

Multiart/ShutterStock, Inc.

70

Figure 05.FY02_UN02: Butter spread.

Denise Campione/ShutterStock, Inc.

71

Figure 05.FY02_UN03: Margarine spread.

72

Sterols (): Cholesterol ()

Structure
Functions
Component of cell membranes
Precursor to other substances
Sterol hormones
Vitamin D
Bile acids
Synthesis
Made in the liver
Food sources
Found only in animal foods
73

27 C

Figure 05.F21: Sterols. Sterols are multi-ring structures. Because of

its role in heart disease, cholesterol has become the best known
74
sterol.

()

()

Figure 05.F22: Cholesterol is a precursor of vitamin D and sterol

hormones.

75

Table 05.T04: Cholesterol in Selected Foods

Data from U.S. Department of Agriculture, Agricultural

Research Service. USDA National Nutrient Database for
Standard Reference, Release 25. 2012.
www.ars.usda.gov/ba/bhnrc/ndl. Accessed 1/20/13.

76

Lipid Digestion and Absorption

Mouth and stomach
Minimal digestion of triglycerides

Small intestine
Emulsified by phospholipids
Digested by pancreatic lipase
Absorbed into intestinal cells
Formed into chylomicrons () and
moved into lymphatic system ()

77

Figure 05.F23: Triglyceride digestion. Most triglyceride digestion

takes place in the small intestine.
78

Portal vein

Lacteal

Figure 05.F24A: Digestion and absorption of triglycerides.

Minimal fat digestion takes place in the mouth and stomach.

79

Figure 05.F24B: Digestion and absorption of triglycerides. Bile

salts surround the remaining products of fat digestion.
80

Lipid Digestion and Absorption

Digestibility
Steatorrhea ()

Lipid Absorption
Lipoprotein ()
Chylomicron ()

Digestion and Absorption of Sterols

81

Lipids in the Body

Lipoproteins ()
carry lipids around the
body
Chylomicrons ()
Delivers dietary lipids
from intestines to cells
and liver

82

Lipids in the Body

Very low density lipoproteins (VLDLs,
)
Deliver triglycerides to cells
Intermediate-density lipoproteins (IDLs,
)
Remove some phospholipids
Low-density lipoproteins (LDLs, )
Deliver cholesterol to cells
High-density lipoproteins (HDLs, )
Pick up cholesterol for removal or recycling
83

Figure 05.F25: Lipoprotein sizes and composition. Lipoproteins

become less dense as they increase in size. LDL is about double the
84
size of HDL.

Figure 05.UN13: Chylomicron ().

85

Figure 05.UN14: VLDL.

86

Figure 05.UN15: IDL.

87

Figure 05.UN16: LDL.

88

Figure 05.UN17: HDL.

89

Figure 05.26: Plaque buildup in a coronary artery.

W. Ober/Visuals Unlimited

90

Lipids in the Diet

Recommended intake

Consume at least two weekly servings of oily fish

Balance of calories from fat and carbohydrate
Reduce sat and trans fat intake
Total fat: 2035 percent of calories
Need ~2 percent of calories as essential fatty
acids
Improve balance of omega-3 : omega-6 fatty
acids
91

Figure 05.UN18: You can check your lipid levels through a blood
test.
Monkey Business Images/Dreamstime.com

92

Figure 05.UN19: Consume fish, especially oily fish, at least twice

a week.

iStockphoto/Thinkstock

93

Lipids in the Diet

Essential Fatty Acid Requirements
Omega-6 and Omega-3 Balance
Current Dietary Intakes:
about 33% of calories
from lipids in USA
Role of Fat Replacers
Photodisc

94

Recommended Fat Intake

The Dietary Guidelines
for Americans
recommends a fat
intake of 20 to 35
percent of total
calories.
Saturated fat should
supply no more than
10 percent of our total
calories, or about onethird of our fat calories.
95

Figure 05.F27: Recommended Fat Intake. The Dietary Guidelines

for Americans recommends a maximum fat intake of 20 to 35
percent of total calories.

96

Figure 05.F28: Overview of dietary sources of fatty acids.

Adapted from Cancer smart. Scientific American. 1998;4(3):9.
Photos: (man) Photodisc; (peanuts) Photodisc; (french fries)
Kirsta Mackey/ShutterStock, Inc.; (pecans) Photodisc; (salmon)
John A. Rizzo/Photodisc/Getty Images

97

Lipids in the Diet

Fat substitutes
The Olestra
Controversy: Are Fat
Replacers Safe?
composition
Sucrose + 6 - 8 fatty
acids = ester ()
Indigestible
provides zero kcals
Reduces absorption
of fat-soluble
vitamins

98

Figure 05.F29: Olestras structure. The structure of olestra is

unlike the structure of a triglyceride.
99

Figure 05.FY03_UN01: Regular mayonnaise ()

100

Figure 05.FY03_UN02: Light mayonnaise

101

Table 05.T06: Fat Can Markedly Increase Calories in Food

Data from U.S. Department of Agriculture, Agricultural Research Service.
USDA National Nutrient Database for Standard Reference, Release 25.
2012. www.ars.usda.gov/ba/bhnrc/ndl. Accessed 1/20/13.

102

Figure 05.LT01_UN01: The Nutrition Facts panel shown here shows all
of the lipid-related information you can find on a food label.
103

Lipids and Health

Obesity
High-fat diets promote weight gain

Heart disease
High saturated and trans fat intake raises
LDL cholesterol

Cancer

104

AHA Position on Omega-3 Fatty Acids

The American Heart

Association recommends
eating fish (particularly
fatty fish) at least two
times a week. Fish is a
good source of protein
and doesnt have high
saturated fat that fatty
meat products do.

Fatty fish such as

mackerel, lake trout,
herring, sardines,
albacore tuna, and
salmon are high in two
kinds of omega-3 fatty
acids:
eicosapentaenoic acid
(EPA) and
docosahexaenoic acid
(DHA).
105

A Healthy Balance
An appropriate balance of calories from
fat and carbohydrates can have
multiple health benefits aside from
controlling weight.
These include cholesterol levels,
vitamin intake, etc.

106

Position on Fat Replacers

It is the position of the Academy of Nutrition and
Dietetics that the majority of fat replacers, when
used in moderation by adults, can be safe and
useful adjuncts to lowering the fat content of
foods and may play a role in decreasing total
dietary energy and fat intake.
Moderate use of low-calorie, reduced-fat foods,
combined with low total energy intake, could
potentially promote dietary intake consistent with
the objectives of Healthy People 2010 and the
2010 Dietary Guidelines for Americans.
107

The Womens Health Initiative ()

This study sought to
explore whether a
dietary intervention (
) that reduces
intake of total fat and
increases intakes of
fruits, vegetables, and
grains will reduce the
risk of cardiovascular
disease.

The results found that

the intervention had no
effect on the risk of
coronary heart disease,
stroke, or overall
cardiovascular disease.
Since this study was
initiated, scientific
thinking has evolved to
focus on modifying
intake of specific types
of fat.
108

NCEP Tips for Healthful Eating Out

Choose restaurants that have low-fat,
low-cholesterol menu items.
Dont be afraid to ask for foods that
follow your eating pattern.
Select poultry, fish, or meat that is
broiled, grilled, baked, steamed, or
poached rather than fried ().

109

Diet and Cancer

The evidence linking dietary fat to cancer is
inconclusive. The case looks strong when we
compare cancer rates between countries:
Overall cancer rates are generally higher in
countries with high fat intake, and lower in
countries where people eat less fat. But in
population studies within those countries, the
evidence linking fat to cancer is weaker.

110