Chapter 5

The Lipids: Triglycerides, What if It's All Been a Big Fat

Phospholipids, and Sterols Lie?

Fat Americans sue

fast food firms

I eat all the fat I want but no “starchy

foods” and I lost 10 pounds The Daily News:

I always buy “fat free” foods § High fat

§ Obesity
What is the right approach? § Heart disease
§ Diabetes
Or Is there a right approach?

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 FAT IS AN ESSENTIAL NUTRIENT
IS A “NO FAT”
DIET HEALTHY?

ARE ALL THE LOW FAT AND NO FAT

PRODUCTS REALLY BETTER CHOICES
NUTRITIONALLY?

LIKE CHO, TRIGLYCERIDES ARE

IS IT FATS OR IS IT LIPIDS? COMPOSED OF:
CARBON
LIPIDS: TRIGLYCERIDES HYDROGEN
PHOSPHOLIPIDS
OXYGEN
STEROLS

LIPIDS ARE: HYDROPHOBIC EVERY TRIGLYCERIDE CONTAINS:

LIPOPHILIC ONE GLYCEROL
THREE FATTY ACIDS

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Chemistry of Triglycerides
FATTY ACIDS DETERMINES THE
and Fatty Acids CHARACTERISTICS OF A FAT

Fatty acids contain: SOLID

•  Carbon chain LIQUID
•  Methyl end (CH3)
•  Carboxyl “acid” end Fatty acids that are not joined to another
(COOH) compound, such as glycerol of a triglyceride are
called “free” fatty acids

Eg. Butyric
Caproic, caprilic, capric

CHAIN LENGTH
Saturation
4-24 CARBONS Saturated - solid at room temperature
<6 C SHORT CHAIN - Every carbon atom has as many hydrogen
6-10 C MEDIUM CHAIN atoms bound as possible
12> LONG CHAIN Example: Stearic acid
THE SHORTEST THE MORE LIQUID (LOWER
MELTING POINT), MORE WATER SOLUBLE Unsaturated - liquid at room temperature
(ABSORPTION) - Not all carbons have hydrogen atoms
CARBON ATOMS IDENTIFICATION bound at every possible site
CARBON AT THE ACID END (-COOH) IS THE - Rather, the carbons form “unsaturated”
ALPHA CARBON
double bonds
CARBON AT THE METHYL END (-CH3) IS THE
OMEGA CARBON

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Degree of Unsaturation
POLYUNSATURATED VEGETABLE OILS ARE
Monounsaturated (MUFA) LIQUID AT ROOM TEMPERATURE AND THE
- One unsaturated bond between MORE SATURATED ANIMAL FAT ARE SOLID
two carbons
Example: oleic acid (C18:1) EX BUTTER VS MARGARINE
(OMEGA 9)
Polyunsaturated (PUFA) COCOA BUTTER, COCONUT OIL
- There is more than one
unsaturated bond
Example: linoleic acid (C18:2)
(OMEGA 6 AND 9)

Saturated Fatty Acid Monounsaturated Fatty Acid

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 KEY POINTS
Fatty Acids in Fats and Oils LIPIDS ARE ORGANIC MOLECULES, SOLUBLE IN
ORGANIC SOLVENTS, LESS SOLUBLE IN WATER,
  Olive oil and canola oil (C18:1) INCLUDING TRYGLICERIDES, PHOSPHOLIPIDS AND
STEROLS.
  Vegetable oils - soybean, cottonseed,
FATY ACIDS ARE KEY STRUCTURAL COMPONENTS
safflower, corn, sunflower (C18:2,3)
OF BOTH TRIGLICERIDES AND PHOSPHOLIPIDS
  Tropical
oils - coconut / palm AND ARE SOMETIMES ATTACHED TO
CHOLESTEROL.
(C10:0,C12:0) FATTY ACIDS ARE CARBON CHAINS OF VARIOUS
LENGHTS. FATTY ACIDS WITH NO DOUBLE BONDS
  Fish oils (C20:5, C22:6)
BETWEEN CARBON ATOMS ARE CALLED
  Animal fats - lard /tallow (C16:0, C18:0) SATURATED, WHILE THOSE WITH AT LEAST ONE
DOUBLE BOND ARE CALLED UNSATURATED
FATTY ACIDS

Fatty Acids in Fats and Oils STABILITY

SATURATION INFLUENCES STABILITY

OXIDATION
RANCID
SPOILAGE
PROTECTION:
REFRIGERATED
ANTIOXIDANTS
SATURATION (ADDING HYDROGEN
MOLECULES)=HYDROGENATION

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Processed Fats in Foods
Hydrogenation of fats (adding H+)
a. Makes oils more solid
b. Affects texture
c. Affects stability of fat
- Unsaturated bonds are unstable
d. Produces trans-fatty acids
- Linked to Coronary Heart Disease ?
CIS FATTY ACIDS
HYDROGENS SURROUNDING A DOUBLE BOND
ARE ON THE SAME SIDE OF THE CARBON CHAIN
CAUSING A BEND IN THE CHAIN (MOST
NATURALLY OCCURINF FA)
TRANS FATTY ACIDS
HYDROGENS SURROUNDING A DOUBLE BOND
ARE ON OPPOSITE SIDES OF THE CARBON
CHAIN. THE BENT CARBON CHAIN STRIGHTENS
OUT AND THE FA BECOMES MORE SOLID).
AVANTAGES OF HYDROGENATION
1. PROTECTS AGAINST OXIDATION (SELF LIFE)
2. ALTERS TEXTURE (HYDROGENATED OIL
BECOMES SPREADABLE)
DISADVANTAGES:
1. POLYUNS FATS BECOME MORE SATURATED
2. UNSATURATED MOLECULES AFTER
HYDROGENATION CHANGE SHAPE FROM CIS TO
TRANS
OMEGA-3, -6, AND –9 FATTY ACIDS
THE LOCATION OF THE DOUBLE BOND CLOSEST
TO THE OMEGA (METHYL) END OF THE FA
IDENTIFIES A FATTY ACID’S FAMILY
E.g. OLEIC ACID:OMEGA 9 (DOUBLE BOND AT C 9)
LINOLEIC:OMEGA 6 (DOUBLE BOND AT C 6
AND C9)
ALPHA LINOLENIC: OMEGA 3
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 NONESSENTIAL & ESSENTIAL FA
ESSENTIAL FREE FATTY ACIDS
NONESSENTIAL-THE BODY CAN MAKE THEM
LINOLEIC ACID – PRIMARY MEMBER OF OMEGA-6
E.g. OLEIC FROM STEARIC-DESATURATION
FAMILY
PROCESS
ARACHIDONIC ACID (20:4)
LINOLENIC ACID-PRIMARY MEMBER OF OMEGA-3
ESSENTIALS- THE BODY CANNOT MAKE THEM
FAMILY
E.g. OMEGA-3 (LINOLENIC) AND OMEGA-6
EPA (eicosapentaenoic acid) (20:5)
(LINOLEIC)
DHA (docosahexaenoic acid) (20:6)

EICOSANOIDS (PROSTANOIDS) EICOSANOIDS CAN HAVE OPPOSING

PHYSIOLOGICAL EFFECTS DEPENDING ON
Small proportion of FA are chemical regulators WHETHER THEY ARE DERIVED FROM AN
Signaling molecules or Local Hormones OMEGA 3, 6, 9 FA
Contain 20 or more Carbons
OMEGA-6 LINOLEIC ACID (18:2)
Effects: inflammation processes CONSTRICTING BLOOD VESSELS
blood vessel dilation and constriction PROMOTING BLOOD CLOTTING
blood clotting PROMOTING INFLAMATION

EICOSANOIDS: TROMBOXANES OMEGA-3 ALPHA-LINOLENIC (18:3)

PROSTAGLANDINS DILATING BLOOD VESSELS
LEUKOTRIENES DISCOURAGING BLOOD CLOTTING
REDUCING INFLAMMATION

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 SOURCES OF OMEGA FATTY ACIDS
Hydrogenation
OMEGA 6

LINOLEIC ACID: VEGETABLE OILS, POULTRY FAT

ARACHIDONIC ACID: MEATS OR FROM LINOLEIC

OMEGA-3

LINOLENIC ACID: OILS, NUTS AND SEEDS,

VEGETABLES

EPA AND DHA: HUMAN MILK, SHELFISH AND FISH

Role of triglycerides and

Hydrogenation fatty acids
1. In the body

a. Energy Source
b. Energy Reserve
c. Insulation and Protection

8
 Role of triglycerides and
fatty acids
2. In the diet
a. Carrier of Fat Soluble Compounds
b. Sensory Qualities:provide flavor,
aroma, tenderness to food
c. Slow digestion---> satiety and
fullness
Phospholipids
-Contain both glycerol and FAs
-Are synthesized in the body and not needed in
the diet
-They are diglycerides: 2 FAs +glycerol
and a phosphate group(w/nitrogen component)
-Are hydrophobic and hydrophilic

Lecithin: best-known phospholipid

PHOSPHOLIPIDS SOURCES

EGGS
LIVER
SOYBEANS
WHEAT GERMS
PEANUTS

ACTS AS EMULSIFIERS

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Role of phospholipids
Cell membranes
Lipid transport
Emulsifiers (Lecithins)
STEROLS
DIFFERENT FROM TRYGLICERIDES AND
PHOSPHOLIPIDS
THEY ARE HYDROPHOBIC AND
LIPOPHILIC
MOST STEROLS CONTAIN NO FATTY
ACIDS
THE MOST FAMOUS-CHOLESTEROL-
KEY CONCEPT
PHOSPHOLIPIDS ARE DYGLICERIDES
(GLYCEROL+ 2 FA) WITH A PHOSPHATE/
NITROGEN GROUP. THIS STRUCTURE GIVES
THE PHOSPHOLIPID HYDROPHOBIC AND
HYDROPHILIC REGIONS. PHOSPHOLIPIDS
ARE MAJOR COMPONENTS OF CELL
MEMBRANES, AND ACT AS EMULSIFIERS.
THEY STORE FATTY ACIDS FOR RELEASE
INTO THE CELL.
PHOSPHOLIPIDS ARE NOT NEEDED IN THE
DIET, THE BODY CAN SYNTHESIZE THEM
Sterols (Steroidal compounds)
Chemistry of sterols
Made up of multiple rings
Steroid nucleus
Sterols in foods
Plants and animal foods contain sterols
Cholesterol only found in animal products
- Eggs and organ meats very high sources
(eggs = 250 mg)
Make the distinction between dietary and blood
cholesterol
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Role of Sterols Cholesterol Derived Compounds
1. Bile acids
a. Fat metabolism
b. Polar and non-polar groups
2. Sex hormones
a. Estrogen
b. Testosterone
c. Adrenal hormones
- Corticosteroids
3. Vitamin D
4. Cholesterol

Digestion, Absorption
and Transport

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Digestion Digestion
Mouth Small Intestine
a. Lingual lipase
 Secreted by salivary glands a. Fat entering the small Intestine
(active in infants, little activity in
adults) stimulates release of
cholecystokinin (CCK) causing the
b. Body temperature
gallbladder to release bile into the
Stomach small intestine
Minimum digestion – mixing to expose
fat molecule-attack by gastric lipase

Digestion Bile: An Emulsifier

Small Intestine
b. Emulsification – Bile
▬  Synthesized in the liver
▬  Stored in the gallbladder
▬  Secreted into the common bile duct
▬  Can be reabsorbed
“enterohepatic circulation”
(entero = intestine, hepatic = liver)

Enables fats and water to mix

- Lipases function in a water environment

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 ©2001 Brooks/Cole, a division of Thomson Learning, Inc. Thomson Learning™ is a trademark used herein under license.

©2001 Brooks/Cole, a division of Thomson Learning, Inc. Thomson Learning™ is a trademark used herein under license.

©2001 Brooks/Cole, a division of Thomson Learning, Inc. Thomson Learning™ is a trademark used herein under license.

Absorption

Small molecules:
- Glycerol, Short- and Medium-chain Fatty
Acids
  Diffusedirectly into intestinal cells and
absorbed into blood

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Absorption
Larger molecules:
- Monoglycerides, Long-chain fatty acids
 Bile assists in micelle formation which
are transported into intestinal cells
- Micelle: emulsified fat droplets surrounded by
bile
 Glycerides and fatty acids re-form
triglycerides in intestinal cells
 Chylomicron are then formed:
- from triglycerides, protein and cholesterol
Transport
II.  Very low density lipoprotein (VLDL)
  Lipoprotein made primarily by liver
  Consists mostly of triglycerides
- also of protein and cholesterol
  Transports lipids to various tissues
in the body
VLDL remnant becomes low density lipoprotein
Transport
I.  Chylomicron
  A water soluble transport vehicle for
dietary fatty acids
  Synthesized in the intestinal cell
  Transports fat to cells
Chylomicron remnant goes to liver for
destruction
Transport
III.  Low density lipoprotein (LDL)
  Derived from VLDL
  Consists mostly of cholesterol
  Transports contents to all cells
‘bad’ cholesterol
-Associated with high risk of heart attack
Read ‘ Health Implications’ - Page 143 in text
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Transport Lipoprotein
IV. High density lipoprotein (HDL)

  Transports cholesterol away from

cells to liver

‘good’ cholesterol

Lipoprotein Composition Function of Lipids

1. Energy
a. Lipids circulate in the blood and
provide energy for cells
b. Supplies ~60% of energy need
during rest
- Requires oxygen and some CHO

2. Insulation
a. Lipids serve as an insulator

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Function of Lipids
3. Transport
a. Transport of fat soluble vitamins
4. Building materials
a. Cell membranes
b. Cholesterol
- Hormones
- Glucocorticoids
c. Bioactive compounds
- Prostaglandins
- Thromboxanes
Fat Cell (Adipose Cell)
Fat storage
1.  Body efficiently converts dietary fat to
storage fat
2.  Unlimited capacity to synthesize and
store fats
a. Excess CHO can be converted into fat
b. Excess protein can be converted into fat
3. Fats are stored in adipose tissue
4. One pound of fat equals ~3500 kcal
Adipose cells
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 Adipocyte Health Effects of Lipids
Coronary Heart Disease (CHD)
1.  Positive association with saturated fat
- Some saturated fats raise LDL

2.  Positive association with # LDL

3.  Negative association with MUFA
- Monounsaturated fats raise HDL

Lipids and CHD

4. Negative association with PUFA
- Omega-3 fatty acids (fish oils)
  decrease cholesterol
  reduce blood clotting
  reduce blood pressure?
5.  Positive association with trans-fatty
acids
  Formed in the hydrogenation of
vegetable oils (margarine)

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 Recommended Fat Intake
  20-35% or < of total kcal intake
(average American intake = 38-42%)
  10% or < of total kcals from saturated
  300 mg or < of cholesterol
  Increase PUFA (omega-3 especially)
  Increase MUFA

Recommended Fat Intake

HEALTH EFFECTS OF LIPIDS

20-35% 10% SATURATED CARDIOVASCULAR DISEASE-ATHEROSCLEROSIS

10% MONOUNSAT RISKS
10% POLYUNSAT SATURATED FATS
TRANS-FATS
DAILY VALUE
2000 KCAL x 0.3 = 600 KCAL/DAY FROM FAT BENEFITS
MONOUNSATURATED FATS
600 X 1/9 KCAL = 65 G /DAY OMEGA-3 POLYUNSATURATED FATS
REDUCING RISK

LIFESTYLE FACTORS
DIETARY FACTORS

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 DIETARY FACTORS
LIFESTYLE FATORS
Ø CHOOSE FOODS LOW IN SATURATED FATS
SMOKING Ø CHOOSE FOODS LOW IN TOTAL FATS
Ø CHOOSE FOODS HIGH IN STARCH AND FIBER
Ø CHOOSE FODS LOW IN CHOLESTEROL
ATTAIN DESIRABLE WEIGHT
§ CHOLESTEROL AND BEYOND (INCREASE HDL)
INCREASE PHYSICAL ACTIVITY § ANTIOXIDANTS
§ DIETARY OMEGA 3 FATTY ACIDS
§ SOLUBLE FIBER-BILE
§ THE FRENCH PARADOX
§ THE MEDITERANIAN DIET – OLIVE OIL

The Problems With Olestra

HEALTH EFFECT OF FATS 1. Olestra rapidly depletes blood levels of many
valuable fat-soluble substances, including
carotenoids
CANCER 2. Supplementing olestra with selected vitamins will
not solve all of olestra's nutrient-depletion problems.

3. Olestra causes gastrointestinal disturbances,

OBESITY which are sometimes severe, including diarrhea,
fecal urgency, and more frequent and looser bowel
movements.
4. Olestra sometimes causes underwear staining
associated with "anal leakage."
5. Data are lacking on the health effects of olestra on
potentially vulnerable segments of the population.

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