Lipids

Chapter
Chapter 22

DR. LEONARDO C. MEDINA, JR.

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 Chapter Outline
1. Lipids: Hydrophobic 4. Compound Lipids
Molecules
5 Steroids
2. Classification of Lipids
6 Hydrophobic Lipids and
Biology
3. Simple Lipids

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Lipids: Hydrophobic
Molecules

3
• Lipids are water insoluble, oily, greasy
biochemical compounds that can be
extracted from cells by nonpolar
solvents such as ether, choroform, or
benzene.
• Unlike carbohydrates, lipids share no
common chemical structure.

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Classification
of Lipids

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 Lipid structures vary markedly. The
following classification scheme
recognizes important structural
differences:
1. Simple lipids
2. Compound lipids
3. Steroids
4. Miscellaneous lipids
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Simple Lipids

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 Fatty Acids
• Fatty acids, which form part of most
lipids, are carboxylic acids with long,
hydrophobic carbon chains.
• All the fatty acids listed in Table are
straight-chain compounds with an even
number of carbon atoms.

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9
 Unsaturated Fatty Acids
• Unsaturated fatty acids may be cis or
trans isomers.
• The trans isomer is almost a linear
molecule, while the double bond in the
cis isomer introduces a kink into the
fatty acid structure.

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11
 Eicosanoids
• The biochemicals derived from the fatty
acid arachidonic acid are collectively
termed eicosanoids.
• Prostaglandins are the best known of the
eicosanoid class, which also includes the
leukotrienes, prostacyclins, and
thromboxanes.
• Cell membranes release arachidonic acid in
response to a variety of circumstances,
including infection and allergic reactions.
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 13
Several examples of eicosanoids.
 Drugs and Eicosanoids
• Many drugs control one or more of the
eicosanoids’ physiological effects.
• Non-steroidal anti-inflammatory drugs
(NSAIDs) block the oxidation of
arachidonic acid to form prostaglandins
and thromboxanes.
– e.g. ibuprofen, ketoprofen,

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 Fats and Oils
• Chemically, fats and oils are esters of
glycerol and the higher molar-mass fatty
acids. H
O
H C O C R
O
glycerol H C O C R'
portion O

H C O C R"

H 15
• Fats may be considered to be triesters formed from the
glycerol and three molecules of fatty acids.
• Most of the fatty acids in these esters have 14-18 carbons.
• Because there are three ester groups per glycerol, the
molecules are called triacylglycerols, or triglycerides.
• The three R groups are usually different.
H
O
H C O C R
O
glycerol H C O C R'
portion O

H C O C R"

H 16
 Waxes
• Waxes are esters of high-molar-mass fatty acids
and high-molar-mass alcohols.
• The alcohol (ROH) contributes up to about 30
carbons, and the fatty acid (R’COOH) also
provides an equivalent number of carbons.
• Waxes are very large molecules with almost no
polar groups.
O

R' C O R
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Compound Lipids

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 Phospholipids
• The phospholipids are a group of compounds that yield one
or more fatty acid molecules, a phosphate group, and
usually a nitrogenous base upon hydrolysis.
• A lipid with both hydrophobic and hydrophilic character is
needed to make membranes. Phospholipids are one of the
most important membrane components.
H2C O fatty acid
hydrophobic
HC O fatty acid

H2C O phosphate + nitrogen base

hydrophilic 19
 Phospholipids
• Phosphatidic acids are gylceryl esters of fatty acids
and phosphoric acid.
• The phosphatidic acids are important intermediates
in the synthesis of triacylglycerols and other
phospholipids.
H2C O fatty acid
hydrophobic
HC O fatty acid

H2C O phosphate
hydrophilic 20
 Phospholipids
• Phosphatidyl cholines (lecithins) are glyceryl esters
of fatty acids, phosphoric acid, and choline.
• Phosphatidly cholines are synthesized in the liver
and are present in considerable amounts in nerve
tissue and brain substance.
H2C O fatty acid
hydrophobic
HC O fatty acid

H2C O phosphate + choline

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hydrophilic
 Phospholipids
• Phosphatidyl Ethanolamines (Cephalins) are
glyceryl esters of fatty acids, phosphoric acid, and
ethanolamine (HOCH2CH2NH2).

H2C O fatty acid

hydrophobic
HC O fatty acid

H2C O phosphate + ethanolamine

hydrophilic 22
 Sphingolipids
• Sphingolipids are compounds that, when
hydrolyzed, yield a hydrophilic group (either
phosphate and choline or a carbohydrate), a long-
chain fatty acid (18-26 carbons), and sphingosine
(an unsaturated amino alcohol).
OH

HC CH=CH(CH2)12CH3

HC NH2

H2C OH 23
 Glycolipids
• Sphingolipids that contain a carbohydrate group
are also known as glycolipids.
– cerebrosides and gangliosides
OH

HC CH=CH(CH 2)12CH3
O
H
HC N C R

H2C O-D-glucose or D-galactose 24

Steroids

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 Steroids
• Steroids are compounds that have the
steroid nucleus, which consists of four
fused carbocyclic rings.

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Structure of cholesterol and cholic acid.

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Biosynthetic relationships
between steroids derived
from cholesterol.

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Hydrophobic Lipids
and Biology

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The hydrophobic nature of lipids has
many important biological
consequences.

1. Lipid aggregation that causes

atherosclerosis
2. Lipid aggregation that forms
biological membranes

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1. Lipid molecules will aggregate to
minimize their contact with water.
2. Depending on the general shape of
the lipid molecule, different-shaped
aggregates form.
3. Smaller lipids like fatty acids will
come together to make micelles.

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If the fatty acid is shown as depicted below,
then a micelle can be visualized as….

CH3(CH2)nCOOH

hydrophobic
hydrophilic

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Cutaway of a micelle. Note that the hydrophobic
chains extend to the center of this aggregate.
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More complex lipids such as phospholipids
and sphinglolipids are shaped differently
than fatty acids and will aggregate
differently in water solutions. They form
liposomes……

hydrophilic
hydrophobic

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A cutaway of a single liposome. Note the bilayer
shell and the water solution core. 35
 Atherosclerosis
• Atherosclerosis is a metabolic disease
that leads to deposits of cholesterol and
other lipids on the inner walls of the
arteries.
• Improper transport of cholesterol
through the blood contributes to
atherosclerosis.
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 Atherosclerosis
• Cholesterol (and other lipids) must be
packaged for transport because lipid
aggregates in the aqueous bloodstream.
• The liver packages dietary lipid into
aggregates known as very-low-density-
lipoproteins (VLDL).

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 A cutaway of VLDL. Note the single-layer shell and the
lipid core. 38
The lipid distribution system through the
bloodstream. 39
Biological Membranes

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 The fluid-mosaic model of a membrane. Note the
hydrophilic exterior and the hydrophobic interior. 41
 How proteins aid membrane transport: Molecules or ions
(symbolized by Y or X) can move from high concentration to
low concentration without energy (facilitated diffusion), but
movement in the reverse direction requires energy (active
transport). 42
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