The Lipids

MPU 3343 NUTRITION & PUBLIC HEALTH
Chapter 3 The Lipids: Triglycerides, Phospholipids and Sterols
CHAPTER 3 The Lipids: Triglycerides, Phospholipids and Sterols

Introduction
3.1 The Chemist’s View of Fatty Acids and Triglycerides
3.2 The Chemist’s View of Phospholipids and Sterols
3.3 Digestion, Absorption and Transport of Lipids
3.4 Lipids in the Body
3.5 Health Effects and Recommended Intakes of Saturated Fats, Trans Fats and Cholesterol
3.6 Health Effects and Recommended Intakes of Monounsaturated and Polyunsaturated Fats
Highlight 3 High-Fat Foods – Friend or Foe?
For Internal Circulation Only

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CHAPTER 3 The Lipids: Triglycerides, Phospholipids and Sterols
Introduction
- Poor health
~ Too much fat
~ Too little fat
~ Too much of some kinds of fat
- Family of lipids
~ Triglycerides
~ Phospholipids
~ Sterols
- Composition: C, H, O
- Fatty Acids
~ Methyl group – Carbons – Carboxyl Group
3.1 The Chemist’s View of Fatty Acids and Triglycerides

- Energy provided per gram greater than carbohydrates
~ More carbons and hydrogens
- Preview of lipids
~ Triglycerides: glycerol and three fatty acids
~ Fatty acids: even number of carbons
~ Saturated or unsaturated
~ Omega-3 and omega-6 fatty acids
~ 18-carbon polyunsaturated fatty acids
Fatty Acids
- Methyl group at one end
~ Acid group at other end
- Usually even number of carbons
~ 18-carbon fatty acids abundant in food
- The length of the carbon chain
~ Long-chain (12-24): meats and vegetable oil
~ Medium-chain (6-10): dairy
~ Short-chain (<6): dairy
- The number of double bonds
~ Saturated: full of hydrogens
~ Unsaturated: missing hydrogens
~ Mono-unsaturated
~ Poly-unsaturated
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- The location of the double bonds

~ Double bonds
~ Nearest the methyl end of the carbon chain
~ Omega number represents location of the closest double bond from methyl end
~ Omega-3’s closest double bond is three carbons away from methyl end
~ Linolenic acid
~ Monounsaturated fatty acids
~ Omega-9 groups
~ “Reminder”: Cabon always has 4 bonds
~ Characteristics of Solid Fats and Oils
~ Firmness
~ Polyunsaturated fats tend to be liquid at room temperature
~ Saturated fats tend to be solid
~ Length of carbon chain influences degree of firmness
~ Stability
~ Fats spoil when exposed to oxygen
~ Polyunsaturated fats spoil most readily
~ Saturated:
~ Solid
~ More stable against spoilage
~ Unsaturated:
~ Liquid
~ Less stable (spoils quickly)

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Triglycerides
~ Three fatty acids attached to a glycerol backbone
~ Formed via series of condensation reactions
~ Usually contain mixture of fatty acids

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How to Name Fatty Acids

1. Locate the methyl (omega) End.
2. Start counting carbons from this end, including the carbon that is part of the methyl
group. Find the first carbon that is attached to a double bond.
3. Add the word “omega” before this number.
~ In this example, the first carbon attached to double bond is carbon number 3. This
means it will be called omega-3.
Characteristics of Solid Fats and Oils

- Firmness
~ Polyunsaturated fats tend to be liquid at room temperature
~ Saturated fats tend to be solid
~ Length of carbon chain influences degree of firmness
- Stability
~ Fats spoil when exposed to oxygen
~ Polyunsaturated fats spoil most readily
- Hydrogenation
- Trans-Fatty acids

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Hydrogenation Trans-Fatty Acids

- Protects against oxidation
- Makes liquid oils more solid
- Partial hydrogenation most common
- Hydrogenation = Trans-fatty acids
~ Configuration – cis and trans
~ Relatively few natural sources of trans fat
~ Similarity to other types of fat
~ Advantages vs Disadvantages

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3.2 The Chemist’s View of Phospholipids and Sterols
Phospholipids
- Solubility in fat and water
- Lechitin is best-known
- Structure
~ Glycerol backbone
~ Two fatty acids
~ Phosphate group
- Phospholipids in foods
~ Use by food industry as emulsifiers
~ Food sources richest of lecithin are eggs, liver, soybeans, wheat germ
- Roles of phospholipids
~ Part of cell membranes
~ Emulsifies fats
~ Transports fats

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Sterols
- Sterols in food
~ Cholesterol
~ Plant sterols
- Roles of sterols
~ Made in the body
~ Structural component of cell membranes
~ Body compounds made from cholesterol

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3.3 Digestion, Absorption and Transport of Lipids

Lipid Digestion
- Fats are hydrophobic
~ Digestive enzymes are hydrophilic
- Goal of fat digestion
~ Dismantle triglycerides
~ Monoglycerides, fatty acids and glycerol
- Bile: part hydrophobic & part hydrophilic
~ Can emulsify fat for digestion
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- In the mouth
~ Lingual lipase plays role in fat digestion in infants
- In the stomach
~ Strong muscle contractions
~ Gastric lipase
- In the small intestine
~ Cholecystokinin (CCK)
~ Gall bladder releases bile
~ Bile acts as emulsifier
- Pancreatic Lipase
- Hydrolysis
~ Triglycerides and phospholipids
- Bile’s roles and routes
~ Effect on blood cholesterol levels

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Lipid Absorption
- Absorption:
~ Micelles form to move fats into intestinal cells
- Transport:
~ Small fats → directly into bloodstream
~ Glycerol and short- and medium-chain fatty acids
~ Large fats → Lymphatic system
~ Micelles diffuse into intestinal cells
~ Reassembled into triglycerides
~ Packed with proteins into transport vehicles called chylomicrons
~ Bypass liver at first
- Lymphatic system
~ Lymph
~ Formation of chylomicrons

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Lipid Transport
- Lipoproteins: fat carriers / transporters
- Four main types of lipoproteins
~ Chylomicrons
~ Largest and least dense
~ Transport diet-derived lipids
~ Liver removes remnants from blood
~ Very-low-density lipoproteins (VLDL)
~ Made in the liver
~ Proportion of lipids shifts
~ Low-density lipoproteins (LDL)
~ Cell needs
~ Liver regulation
~ High-density lipoproteins (HDL)
~ Remove cholesterol from cells
~ Carry cholesterol to liver for recycling
~ Anti-inflammatory properties
- Health implications

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Lipoproteins
- Differences between the lipoproteins?
~ Removes fat
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~ HDL: good cholesterol

~ Deposit fat
~ LDL: bad cholesterol
~ VLDL
~ Chylomicrons
3.4 Lipids in the Body

Roles of Triglycerides
- Provide the cells with energy
~ Virtually unlimited ability to store fat energy
- Adipose tissue stores body fat
~ Secrets hormones (adipokines)
- Other uses of fat in the body
~ Skin insulation
~ Shock absorption
~ Cell membrane material
~ cell signalling pathways
Essential Fatty Acids

- Must be supplied by the diet
~ Linoleic acid
~ Linolenic acid
- Can be used to make other fatty acids
- Omega-6 and Omega-3 fatty acids
- Linoleic acid and the Omega-6 family
~ Sources: vegetable oils and meats
- Linolenic acid and the Omega-3 family
~ Cannot be made in the body (must be supplied by food)
~ DHA
~ EPA
- Eicosanoids
~ “Hormonelike”
~ Health benefits
- Omega-6 to Omega-3 ratio
~ Suggested ratio range from 4:1 to 10:1
- Fatty acid deficiencies
~ Rare in the United States and Canada
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~ Symptoms
A Preview of Lipid Metabolism

- Storing fat as fat
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~ Adipose cells store fat after meals

~ Lipoprotein lipase
~ Hydrolyses triglycerides
~ Triglycerides reassembled inside adipose cells
- Using fat for energy
~ Fat supplies 60% of energy needs during rest
~ Energy deprivation
~ Fasting: fat and lean protein tissue used for energy
3.5 Health Effects and Recommended Intakes of Saturated Fats, Trans Fats and Cholesterol
Health Effects of Saturated Fats, Trans Fats and Cholesterol
- Current American diet
~ Excessive amounts of solid fats
- Blood lipid profile
- Heart disease
~ Elevated LDL cholesterol a risk factor
~ Saturated fats increase LDL cholesterol, promote blood clotting
~ Dietary choices
~ Saturated fat: increase LDL, leave HDL alone
~ Trans fats: increase LDL, lower HDL
~ Dietary cholesterol
- Cancer
~ Dietary fat and cancer risk
~ Differs for various types of cancer
~ Promotion rather than initiation of cancer
- Obesity
~ Cutting fat from diet reduces kcalories
~ Dietary recommendations
Recommended Intakes of Saturated Fat, Trans Fat and Cholesterol

- Blood lipid profile
~ Total cholesterol < 200 mg/dL
~ Triglycerides < 150 mg/dL
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~ LDL < 100 mg/dL

~ HDL > 60 mg/dL
- DRI and Dietary Guidelines
~ 20-35% of daily energy from fat
~ Less than 10% of daily intake from saturated fat
~ As little trans fat as possible
~ Less than 300 mg cholesterol
- Avoid getting too little fat
~ Recommendation: one teaspoon of fat with every meal
3.6 Health Effects and Recommended Intakes of Monounsaturated and Polyunsaturated Fats
Health Effects of Monounsaturated and Polyunsaturated Fats
- Heart disease
~ Replace saturated fats with unsaturated fats
~ Regular consumption of omega-3 fatty acids
~ Suppresses inflammation
- Cancer
~ By reducing oxidative stress and suppressing inflammation
- Omega-3 supplements
~ Routine supplementation is not recommended. Excessive intakes of omega-3
polyunsaturated fatty acids may lengthen bleeding time, interfere with wound
healing, raise LDL cholesterol, and suppress immune function
~ People with heart disease, however, may benefit from supplements of omega-3
fatty acids

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Recommended Intakes of Monounsaturated and Polyunsaturated Fats

- 20-35% of kcalories from fat
~ Includes essential fatty acids
~ AI have been established
- DRI
~ Linoleic acid: 5-10% of daily energy
~ Linolenic acid: 0.6-1.2% of daily energy
From Guidelines to Groceries

- Fat-soluble vitamins
~ A, D, E and K
- Flavour, texture and palatability
- Protein foods
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~ Selections
- Milk and milk products
~ Selections
- Vegetables, fruits and grains
~ Lowers consumption of various fats in the diet
~ Provides phytochemicals
- Solid fats and oils
~ Fried and baked goods
- Choose wisely
~ Unprocessed foods
- Read food labels
~ Total fat, saturated fat, trans fat and cholesterol
~ Compare products
~ Percent Daily Value versus percent kcalories from fat
- Fat replacers
~ Types
~ Risks

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Highlight 3
High-Fat Foods – Friend or Foe?
Guidelines for Fat Intake

- Limit saturated fat and trans fat intake
~ Moderate kcalories
~ Enough fat for good health
~ Not too much of the harmful fats
- DRI recommendations
~ Compatible with ow rates of disease
High-Fat Foods and Heart Health

- Use olive oil
~ Benefits for heart health
~ Replace saturated fats
- Nibble on nuts
~ LDL cholesterol
~ Fat composition
~ Cautious advice for dietary inclusion
- Feast on fish
~ Omega-3 fatty acids
~ Environmental contaminants
~ Farm raised versus wild
~ Dietary recommendations

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High-Fat Foods and Heart Health

- Limit fatty meats, whole-milk products and tropical oils
- Saturated fat the top dietary determinant of LDL cholesterol
~ Sources of saturated fat in the U.S.
~ Meats
~ Whole milk products
~ Tropical oils
~ Zero saturated fat is not possible
- Limit hydrogenated foods
~ Trans fat
The Mediterranean Diet

- Features of a traditional Mediterranean diet
~ Low in saturated fat
~ Very low in trans fat
~ Rich in monounsaturated and polyunsaturated fat

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~ Rich in complex carbohydrate and fiber

~ Rich in nutrients and phytochemicals
- Benefits for heart disease risk

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Glossary
Chapter 3 The Lipids
No Term / Word Definition / Meaning

Glossary
1 Adipokines (ADD-ih- Proteins synthesized and secreted by adipose cells.
poe-kines)
2 Adipose (ADD-ih- The body's fat tissue; consists of masses of triglyceride-storing cells.
poce) tissue
3 Antioxidants As a food additive, preservatives that delay or prevent rancidity of fats in
foods and other damage to food caused by oxygen.
4 Arachidonic (a- An omega-6 polyunsaturated fatty acid with 20 carbons and four double
RACK-ih-DON-ic) bonds; present in small amounts in meat and other animal products and
acid synthesized in the body from linoleic acid.
5 Artificial fats Zero-energy fat replacers that are chemically synthesized to mimic the
sensory and cooking qualities of naturally occurring fats but are totally
or partially resistant to digestion.
6 Atherosclerosis (ATH- A type of artery disease characterized by plaques (accumulations of
er-oh-scler-OH-sis) lipid-containing material) on the inner walls of the arteries.
7 Blood lipid profile Results of blood tests that reveal a person's total cholesterol,
triglycerides and various lipoproteins.
8 Cardiovascular disease Diseases of the heart and blood vessels throughout the body.
(CVD) Atherosclerosis is the main cause of CVD. When the arteries that carry
blood to the heart muscle become blocked, the heart suffers damage
known as coronary heart disease (CHD).
9 Cholesterol (koh- One of the sterols containing a four-ring carbon structure with a carbon
LESS-ter-ol) side chain.
10 Choline (KOH-leen) A nitrogen-containing compound found in foods and made in the body
from the amino acid methionine. Choline is part of the phospholipid
lecithin and the neurotransmitter acetylcholine.
11 Chylomicrons (kye-lo- The class of lipoproteins that transport lipids from the intestinal cells to
MY-cronz) the rest of the body.
12 Cis On the near side of; refers to a chemical configuration in which the
hydrogen atoms are located on the same side of a double bond.
13 Condensation A chemical reaction in which water is released as two molecules
combine to form one larger product.
14 Conditionally essential A nutrient that is normally nonessential, but must be supplied by the diet
nutrient in special circumstances when the need for it exceeds the body's ability
to produce it.
15 Conjugated linoleic Several fatty acids that have the same chemical formula as linoleic acid
acids (18 carbons, two double bonds) but with different configurations (the
double bonds occur on adjacent carbons).
16 Docosahexaenoic An omega-3 polyunsaturated fatty acid with 22 carbons and six double
(DOE-cossa-HEXA- bonds; present in fatty fish and synthesized in limited amounts in the
ee-NO-ick) acid body from linolenic acid.
(DHA)
17 Eicosanoids (eye- Derivatives of 20-carbon fatty acids; biologically active compounds that
COSS-uh-noyds) help to regulate blood pressure, blood clotting, and other body functions.
They include prostaglandins (PROS-tah-GLAND-ins), thromboxanes
(throm-BOX-ains), and leukotrienes (LOO-ko-TRY-eens).
18 Eicosapentaenoic An omega-3 polyunsaturated fatty acid with 20 carbons and five double
(EYE-cossa-PENTA- bonds; present in fatty fish and synthesized in limited amounts in the
body from linolenic acid.

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ee-NO-ick) acid
(EPA)
19 Emulsifiers Substances with both water-soluble and fat-soluble portions that promote
the mixing of oils and fats in watery solutions.
20 Endogenous (en- From within the body.
DODGE-eh-nus) Endo = within
Gen = arising
21 Essential fatty acids Fatty acids needed by the body but not made by it in amounts sufficient
to meet physiological needs.
22 Exogenous (eks- From outside the body.
ODGE-eh-nus): Exo = outside
23 Fat replacers Ingredients that replace some or all of the functions of fat and may or
may not provide energy.
24 Fats Lipids that are solid at room temperature (77°F or 25°C).
25 Glycerol (GLISS-er- An alcohol composed of a three-carbon chain, which can serve as the
ol) backbone for a triglyceride.
26 HDL (high-density The type of lipoprotein that transports cholesterol back to the liver from
lipoprotein) the cells; composed primarily of protein.
27 Hormone-sensitive An enzyme inside adipose cells that responds to the body's need for fuel
lipase by hydrolyzing triglycerides so that their parts (glycerol and fatty acids)
escape into the general circulation and thus become available to other
cells for fuel. The signals to which this enzyme responds include
epinephrine and glucagon, which oppose insulin.
28 Hydrogenation A chemical process by which hydrogens are added to monounsaturated
(HIGH-dro-jen-AY- or polyunsaturated fatty acids to reduce the number of double bonds,
shun or high-DROJ- making the fats more saturated (solid) and more resistant to oxidation
eh-NAY-shun) (protecting against rancidity). Hydrogenation produces trans-fatty acids.
29 Hydrophilic (high-dro- A term referring to water-loving, or water-soluble, substances.
FIL-ick)
30 Hydrophobic (high- A term referring to water-fearing, or non-water-soluble, substances; also
dro-FOE-bick) known as lipophilic (fat loving).
Hydro = water
Phobia = fear
Lipo = lipid
Phile = love
31 LDL (low-density The type of lipoprotein derived from very-low-density lipoproteins
lipoprotein) (VLDL) as triglycerides are removed and broken down; composed
primarily of cholesterol.
32 Lecithin (LESS-uh- One of the phospholipids. Both nature and the food industry use lecithin
thin) as an emulsifier to combine water-soluble and fat-soluble ingredients
that do not ordinarily mix, such as water and oil.
33 Linoleic acid (lin-oh- An essential fatty acid with 18 carbons and two double bonds.
LAY-ick)
34 Linolenic acid (lin-oh- An essential fatty acid with 18 carbons and three double bonds.
LEN-ick)
35 Lipases Enzymes that hydrolyze lipids. Lingual lipase refers to the fat-digesting
enzyme secreted from the salivary gland at the base of the tongue.
36 Lipids A family of compounds that includes triglycerides, phospholipids and
sterols. Lipids are characterized by their insolubility in water. (Lipids
also include the fat-soluble vitamins).
37 Lipoprotein lipase An enzyme that hydrolyzes triglycerides passing by in the bloodstream
(LPL) and directs their parts into the cells, where they can be metabolized for
energy or reassembled for storage.

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38 Lipoproteins (LIP-oh- Clusters of lipids associated with proteins that serve as transport vehicles
PRO-teenz) for lipids in the lymph and blood.
39 Micelles (MY-cells) Tiny spherical complexes of emulsified fat that arise during digestion;
most contain bile salts and the products of lipid digestion, including fatty
acids, monoglycerides and cholesterol.
40 Monoglycerides Molecules of glycerol with one fatty acid attached. A molecule of
glycerol with two fatty acids attached is a diglyceride.
Mono = one
Di = two
41 Oils Lipids that are liquid at room temperature (77°F or 25°C).
42 Olestra A synthetic fat made from sucrose and fatty acids that provides 0
kcalories per gram; also known as sucrose polyester.
43 Omega The last letter of the Greek alphabet (ω), used by chemists to refer to the
position of the closest double bond to the methyl (CH3) end of a fatty
acid.
44 Omega-3 fatty acid A polyunsaturated fatty acid in which the closest double bond to the
methyl (CH3) end of the carbon chain is three carbons away.
45 Omega-6 fatty acid A polyunsaturated fatty acid in which the closest double bond to the
methyl (CH3) end of the carbon chain is six carbons away.
46 Oxidation (OKS-ee- The process of a substance combining with oxygen; oxidation reactions
day-shun) involve the loss of electrons.
47 Phospholipid (FOS- A compound similar to a triglyceride but having a phosphate group (a
foe-LIP-id) phosphorus-containing salt) and choline (or another nitrogen-containing
compound) in place of one of the fatty acids.
48 Plaque (PLACK) An accumulation of fatty deposits, smooth muscle cells and fibrous
connective tissue that develops in the artery walls in atherosclerosis.
Plaque associated with atherosclerosis is known as atheromatous (ATH-
er-OH-ma-tus) plaque.
49 Sterols (STARE-ols or Compounds containing a four-ring carbon structure with any of a variety
STEER-ols) of side chains attached.
50 Trans On the other side of; refers to a chemical configuration in which the
hydrogen atoms are located on opposite sides of a double bond.
51 Trans-fatty acids Fatty acids with hydrogens on opposite sides of the double bond.
52 Triglycerides (try- The chief form of fat in the diet and the major storage form of fat in the
GLISS-er-rides) body; composed of a molecule of glycerol with three fatty acids
attached; also called triacylglycerols (try-ay-seel-GLISS-er-ols).
Tri = three
Glyceride = of glycerol
53 VLDL (very-low- The type of lipoprotein made primarily by liver cells to transport lipids
density lipoprotein) to various tissues in the body; composed primarily of triglycerides.
Glossary of Fatty Acids Terms
54 Fatty acids Organic compounds composed of a carbon chain with hydrogens
attached and an acid group (COOH) at one end and a methyl group
(CH3) at the other end.
55 Monounsaturated fatty A fatty acid that lacks two hydrogen atoms and has one double bond
acid (MUFA) between carbons—for example, oleic acid. A monounsaturated fat is
composed of triglycerides in which most of the fatty acids are
monounsaturated.
Mono = one
56 Point of unsaturation The double bond of a fatty acid, where hydrogen atoms can easily be
added to the structure.
57 Polyunsaturated fatty A fatty acid that lacks four or more hydrogen atoms and has two or more
acid (PUFA) double bonds between carbons—for example, linoleic acid (two double
bonds) and linolenic acid (three double bonds). A polyunsaturated fat is
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composed of triglycerides in which most of the fatty acids are

polyunsaturated.
Poly = many
58 Saturated fatty acid A fatty acid carrying the maximum possible number of hydrogen
atoms—for example, stearic acid. A saturated fat is composed of
triglycerides in which most of the fatty acids are saturated.
59 Unsaturated fatty acid A fatty acid that lacks hydrogen atoms and has at least one double bond
between carbons (includes monounsaturated and polyunsaturated fatty
acids). An unsaturated fat is composed of triglycerides in which most of
the fatty acids are unsaturated.

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MPU 3343 NUTRITION & PUBLIC HEALTH

Chapter 3 The Lipids: Triglycerides, Phospholipids and Sterols

CHAPTER 3 The Lipids: Triglycerides, Phospholipids and Sterols

For Internal Circulation Only

CHAPTER 3 The Lipids: Triglycerides, Phospholipids and Sterols

3.1 The Chemist’s View of Fatty Acids and Triglycerides

- The location of the double bonds

For Internal Circulation Only

For Internal Circulation Only

How to Name Fatty Acids

Characteristics of Solid Fats and Oils

For Internal Circulation Only

For Internal Circulation Only

For Internal Circulation Only

Hydrogenation Trans-Fatty Acids

For Internal Circulation Only

3.2 The Chemist’s View of Phospholipids and Sterols

For Internal Circulation Only

For Internal Circulation Only

3.3 Digestion, Absorption and Transport of Lipids

For Internal Circulation Only

For Internal Circulation Only

For Internal Circulation Only

For Internal Circulation Only

For Internal Circulation Only

~ HDL: good cholesterol

3.4 Lipids in the Body

Essential Fatty Acids

A Preview of Lipid Metabolism

~ Adipose cells store fat after meals

Recommended Intakes of Saturated Fat, Trans Fat and Cholesterol

~ LDL < 100 mg/dL

For Internal Circulation Only

Recommended Intakes of Monounsaturated and Polyunsaturated Fats

From Guidelines to Groceries

For Internal Circulation Only

For Internal Circulation Only

Guidelines for Fat Intake

High-Fat Foods and Heart Health

For Internal Circulation Only

High-Fat Foods and Heart Health

The Mediterranean Diet

For Internal Circulation Only

~ Rich in complex carbohydrate and fiber

For Internal Circulation Only

For Internal Circulation Only

No Term / Word Definition / Meaning

For Internal Circulation Only

For Internal Circulation Only

composed of triglycerides in which most of the fatty acids are

For Internal Circulation Only

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