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Lecture 08

Chapter 4 Carbohydrates (conclusion)

Diabetes (diabetes mellitus) is now the 6th leading cause of death in the United States.

Type 1 Diabetes (also known as insulin-dependent diabetes mellitus (IDDM) or

juvenile-onset diabetes mellitus: The pancreas fails to make insulin. Causes include
genetic mutations, virus infections, toxins, or a immune system disorder that destroys
pancreatic Beta cells. It is treated by daily insulin injections.
A persons body destroys its Beta cells

Type 2 Diabetes (also known as noninsulin-dependent diabetes mellitus

(NDDM) or adult-onset diabetes mellitus: Cells stop responding to insulin (cells
have fewer insulin receptors on their membranes). Type 2 diabetes tends to occur
because of chronic obesity. Its as if the cells get tired of hearing Here comes some
more glucose, suck it up!, and to shut out the news, they fail to make insulin
receptors. Type 2 diabetes can often be controlled by maintaining a healthy weight,
or, in a less desirable way, by injection of additional insulin so that the message gets
through via the few insulin receptors remaining.

Glycemic Response, Glycemic Index and Glycemic Load: See the PowerPoint slides
The glycemic response a measure of the extent to which a food raises the blood glucose
concentration and elicits an insulin response
A desireable glycemic response is characterized by slow absorption of the food, a slow rise in
blood glucose levels, and a smooth return of blood glucose levels to normal values
An undesirable glycemic response is characterized by fat absorption of the food, rapid rise in
blood glucose levels, and a hasty decline in blood glucose levels to below-normal
values
The glycemic index is a method of classifying foods according to the potential to raise blood
glucose.
Glycemic effects of foods are particularly important to diabetics
Glycemic index = how fast a carb triggers a rise in circulating blood sugar. A low GI food will
cause a small rise; a high GI food will trigger a dramatic spike. A GI is 70 or more is
high, a GI of 56-69 is medium, 55 or less is low
Glycemic Load (GL) gives a more complete picture. GI doesnt tell you how much carb is in
a serving of a particular food, but GL does
GL = (GI)(available carb content)/100, where available carb content = (total carb minus
fiber) in grabs
A GL of 20 or more is high, 10 or less is low
Watermelon has a high GI, but there arent many carbs in it so its GL is relatively low
Foods having a low GL almost always have a low GI; foods w/ an intermediate or high GL
may have very low or very high GI
By rapidly releasing sugar, high-glycemic foods spur heavy insulin production, affecting long-
term health
Iclicker question: when blood glucose levels fall, the pancreas secretes GLUCAGON, which acts on
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the liver to cause an inc in blood glucose levels
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Chapter 5 - The Lipids: Triglycerides, Phospholipids and Sterols

Lipids: a family of compounds that includes triglycerides (fats and oils), phospholipids, and
sterols.

Lipids are an unusual classification because the classification is not based on some chemical formula
common to all lipids (as C(H2O)n defines carbohydrates); instead:

Lipids substances that are soluble in organic solvents but insoluble in water.

Other names given substances insoluble in water but soluble in organic solvent are:

nonpolar substances, or hydrophobic ("water hating") substances.

Similarly, substances soluble in water but insoluble in organic solvents are called:

polar substances, or hydrophilic ("water-loving") substances

For example, sugars are polar substances/hydrophilic substances because they are soluble in water.

"Oil and water don't mix!"

Fats: a word used to describe the lipids in food or in the body, both of which are composed mostly of
triglycerides. Oils are fats that are liquid at room temperature.

Of the lipids in foods, 95% are triglycerides.

Of the lipids stored in the body, 99% are triglycerides.

Fat Free Mice!

A new snack food for pampered cats?
No, an important experimental animal created by genetic engineering
Sperm + egg ovum (cell division)-embryodifferentiation leads to liver cells, muscle
cells, skin cells, etc
W/ the fat free mice, he could use stem cell research to get rid of fat
No white adipose tissue- no fat to insulate bodies. Ate and drank a shit ton. The mice are
diabetic (3x normal blood glucose and triglyceride levels)

The Chemist's View of Triglycerides and Fatty Acids

Energy content: The energy available from the oxidation of carbon compounds depends on the
number of oxygen and hydrogen atoms in the compound. The more hydrogen a carbon compound
has, the more energy that is available from its oxidation (where oxidation refers to the rxn of the
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substance w/ O2 to form CO2)

Carbon atoms in fat have more hydrogens than carbon atoms in carbohydrates:
So, fat has more energy per gram (9 kcal) than carbohydrate (4 kcal).

Triglycerides: The chief form of fat in the diet and the major storage form of fat in the body.
Triglycerides are composed of:
A molecule of glycerol (CH2OH-CHOH-CH2OH Figure 5-3) with 3 fatty acids attached.
Glycerol is a 3-carbon alcohol. Alcohol are coupounds w/ -OH groups
Acetic acid a simple 2-carbon fatty acid
Fatty acids are molecules made of chains of carbon and hydrogen atoms of the pattern (-
CH2-) with an acid group of the form -COOH attached at one end (Figure 5-1, pp. 134-
136).
Substances composed of just carbon and hyhdrogen atoms are called hydrocarbons; fatty
acids have hydrocarbon tails.Most naturally occurring fatty acids contain an even number of
carbon atoms, and most are in the size range of 12 to 24 carbon atoms (the most common
ones are 18 carbons long).
Palmitic acid is the name given to the fatty acid that is 16 carbons long; stearic acid is
the name of one thats 18 carbons long

The Fatty Acids

Fatty acids are hydrocarbon chains with a acid group (-COOH) at one end and a -CH3 group
(methyl group) at the other end, as in stearic acid, an 18-carbon fatty acid:

H3C-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-COOH

Triglycerides are referred to by chemists as triacylglycerols, b/c they have 3 acyl chains
Triglyceride formation:

Three fatty acids are attached to glycerol, one at a time, to form triglycerides by three
separate dehydration synthesis reactions (condensation reactions) - Figure 5-4
3 fatty acids are attached to glycerol, one at a time, to form triglycerides by 3 separate
dehydration synthesis rxns (condensation).

Degree of saturation in fatty acids

If two carbon atoms form a double bond with each other, the hydrocarbon chain is said to be
unsaturated.

An example would be the fatty acid, oleic acid, which has 18 carbon atoms, two hydrogens
missing, and one double bond (located between carbons 9 and 10, counting from the
carboxyl end):
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H3C-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH=CH-CH2-CH2-CH2-CH2-CH2-CH2-CH2-COOH

Oleic acid is an 18-carbon mono-unsaturated fatty acid, because it has only one (mono)
double bond.

A polyunsaturated fatty acid has more than one double bond and more than 2 hydrogens missing.

Linoleic acid is an 18-carbon fatty acid with 2 double bonds and 4 hydrogens missing.

Linoleic acid is: an 18-carbon fatty acid w/ 2 double bonds and 4 hydrogens missing. Its
double bonds are b/t carbons 9 and 10 and carbons 12 and 13

H3C-CH2-CH2-CH2-CH2-CH=CH-CH2-CH=CH-CH2-CH2-CH2-CH2-CH2-CH2-CH2-COOH

Linoleic acid would be considered an omega-6 fatty acid, since its first double bond is 6
carbons from the omega end.

Similarly, linolenic acid is a polyunsaturated fatty acid with 3 double bonds, at positions 9-10,
12-13, and 15-16:

H3C-CH2-CH=CH-CH2-CH=CH-CH2-CH=CH-CH2-CH2-CH2-CH2-CH2-CH2-CH2-COOH

Linolenic acid is an omega-3 fatty acid, since its first double bonds is 3 carbons from the omega
end.

The polyunsaturated fatty acids, linoleic acid and linolenic acid, are essential fatty acids: Fatty
acids that are needed by the body, but the body cannot make them in sufficient amounts to meet
needs.

Figure 5-2 shows the structures of omega-6 and omega-3 fatty acids.

Fats in foods: Comparison of dietary fats with regard to their fatty acid composition - Figure 5-6.

Saturated fats have more energy (kcal/gram) than unsaturated or polyunsaturated fats
Fats w/ predominantly saturated fatty acids are sold at room temp

Why are unsaturated fats liquid at room temperature?

Because the double bond makes a kink in the hydrocarbon chain, so that the chains in
neighboring fat molecules don't pack together as well, and the molecules move past one
another.

All naturally occurring unsaturated fatty acids have cis-double bonds: the hydrogens are on the
same side of the double bond:
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H H
-C=C-

Chemically formed unsaturated fatty acids may have trans-double bonds: the hydrogens are on
opposite sides of the double bond from one another:

H
-C=C-
H

See Figure 5-8 for cis- and trans-fatty acids.

Processed fat: Saturation makes substances more stable. Unsaturated fats become rancid if they
react with oxygen, and saturation prevents this from happening. Sometimes, substances known as
antioxidants are added to fats to prevent the fat from becoming rancid.
Antioxidants are compounds that protect other compounds from oxidation by being more
readily oxidized themselves. (Antioxidants react readily w/ oxygen.) Vitamin E is an antioxidant

Hydrogenation of fats: Figure 5-7

Hydrogenation (reaction with hydrogen) offers two advantages:

1) it protects against oxidation (which prolongs shelf life)
2) it alters the texture of food
BUTHydrogenation leads to the formation of trans-fatty acids
Trans-fatty acids have been implicated in heart disease.
Margarine is a processed food product composed of hydrogenated fats

Roles of Triglycerides and Fatty Acids

1) The triglycerides provide the body with energy.

2) Stored fat insulates the body against cold

3) Fat acts as a shock absorber for internal organs.

Essential fatty acids are important starting materials for the formation of:

1) Hormone-like substances known as eicosanoids, such as prostaglandin which regulates

smooth muscle contraction

2) The omega-3 substances, DHA (docosahexaenoic acid) and EPA (eicosapentaenoic

acid) which are essential for normal growth and development.
.

Essential fatty acids should make up 3% of the daily energy intake. See Table 5-2.
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