Lipids

Chapter
Chapter 22

DR. LEONARDO C. MEDINA, JR.

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Chapter Outline
1. Lipids: Hydrophobic
Molecules
2. Classification of Lipids
3. Simple Lipids

4. Compound Lipids
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Steroids

Hydrophobic Lipids and

Biology

Lipids: Hydrophobic
Molecules
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 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

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

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.

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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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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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

glycerol
portion

C
O

R'

R"

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 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

glycerol
portion

C
O

R'

R"

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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 (RCOOH) also
provides an equivalent number of carbons.
Waxes are very large molecules with almost no
polar groups.
O

R'

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

fatty acid

hydrophobic
HC

fatty acid

H2C

phosphate + nitrogen base

hydrophilic

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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

fatty acid

hydrophobic
HC

fatty acid

H2C

phosphate

hydrophilic

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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

fatty acid

hydrophobic
HC

fatty acid

H2C

phosphate + choline

hydrophilic

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Phospholipids
Phosphatidyl Ethanolamines (Cephalins) are
glyceryl esters of fatty acids, phosphoric acid, and
ethanolamine (HOCH2CH2NH2).
H2C

fatty acid

hydrophobic
HC

fatty acid

H2C

phosphate + ethanolamine

hydrophilic

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

HC

CH=CH(CH2)12CH3

HC

NH2

H2C

OH

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

HC

CH=CH(CH 2)12CH3
O

HC

H2C

H
N

O-D-glucose or D-galactose

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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

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shell and the water solution core.

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-densitylipoproteins (VLDL).
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A cutaway of VLDL. Note the single-layer shell and the

lipid core.
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The lipid distribution system through the

bloodstream.

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Biological Membranes

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The fluid-mosaic model of a membrane. Note the

hydrophilic exterior and the hydrophobic interior.

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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).
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