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Lipids
Chapter 19
Table of Contents
Lipids
Lipid: An organic compound found in living organisms
that is insoluble (or only sparingly soluble) in water but
soluble in non-polar organic solvents.
Unlike other biomolecules, lipids do not have a common
structural features that serves as the basis for defining
such compounds.
Classification: Based on two methods
Biochemical function
Saponification (hydrolysis under basic conditions)
Structure
Lipids exhibit
structural diversity
Some are esters,
some are amides,
and some are
alcohols (acyclic
and cyclic) and
some are
polycyclic.
H 3C (CH) 10 C OH
O
or
C
11 9 7 5 3 1 OH
12 10 8 6 4 2
A monounsaturated
fatty acid is a fatty
acid with a carbon
chain in which one
carbon carbon
double bond is
present.
Different ways of
depicting the
structure
Omega Acids
Essential Fatty Acids: Must be part of diet
Nutritionally important Omega-3 and Omega-6 fatty acids
Linolenic acid Omega-3
Linoleic acid Omega-6
Linoleic Acid Deficiency:
Skin redness - becomes irritated
Infections and dehydration
Liver abnormalities
Children need it the most
Human milk has more than cow s milk
American Diet
Sufficient in omega 6 fatty acids
Deficient in omega 3 fatty acids
Fish - good source for omega 3 fatty acids
High rate of heart disease may be due to imbalance in
omega 3 and 6 fatty acids
Ideal ratio: Omega 6 : Omega 3 (4 - 10 g: 1g)
Space-Filling Molecules
The number of bends in a fatty acid chain increase as
the number of double bonds increase
Less packing occurs
Melting point is lower
Tend to be liquids at room temperature
Energy-Storage Materials
With the notable exception of nerve cells, human cells
store small amounts of energy providing materials:
The most widespread energy storage material -
carbohydrate glycogen
Present in small amounts
Major Energy Storage material is triacylglycerols:
Triacylglycerols are concentrated primarily in special
cells (adipocytes)
Adipocytes are nearly filled with triacylglycerols.
p661
Section 19.4
Energy-Storage Lipids: Triacylglycerols
p663
Section 19.4
Energy-Storage Lipids: Triacylglycerols
Partial Hydrolysis
Chemical Properties due to two functional groups: esters
and alkenes
Hydrolysis: Partial hydrolysis of triacylglycerols
Breaking of 1-2 ester bonds to give rise to mono- or
diacylglycerol and fatty acid(s)
Carried out by enzymes produced by the pancreas
Saponification
Hydrolysis in basic solution: Produce salt of fatty acid
and glycerol
O
H 2C OH
H2C O C R
O
+ 3NaOH HC OH + 3RCOONa
R C O CH
O
Soap
H2C O C R H 2C OH
p672
Section 19.6
Chemical Reactions of Triacylglycerols
Hydrogenation
Addition of hydrogen across double (=) bond - increases degree
of saturation
O
O
H2C O C
H2C O C
O
O
HC O C + 2H2
HC O C
O O
H2C O C H2C O C
Oil Solid
p675
Section 19.6
Chemical Reactions of Triacylglycerols
Halogenation
Addition of halogen across double (=) bond -
increases degree of saturation
a test for unsaturation
the amount of halogen absorbed by a lipid can be
used as an index of the degree of unsaturation; the
index value is called iodine number , the number of
grams of iodine that will add to 100 g of fat or oil
the rule is: high I2 number indicates a high degree of
unsaturation
Oxidation
Double bonds in triacylglycerols are subject to oxidation with oxygen
in air (an oxidizing agent )-Leads to C=C breakage
Remember that oxidation of alkenes may result into two short chain
molecules an aldehydes or a carboxylic acid:
The aldehydes and/or carboxylic acids so produced often have
objectionable odors - fats and oils are said to be rancid
To avoid this unwanted oxidation process antioxidants are
added as preservatives, e.g., Vitamin C and vitamin E are good
antioxidant preservatives.
p673
Section 19.7
Membrane Lipids: Phospholipids
All cells are surrounded by a membrane that confines
their contents.
Up to 80% of the mass of a cell membrane can be lipid
materials -- dominated by phospholipids.
Phospholipid: contains one or more fatty acids, a
phosphate group, a platform molecule (glycerol or
sphingosine) to which the fatty acid(s) and the phosphate
group are attached, and an alcohol that is attached to the
phosphate group.
G
Fatty acid Sphingosine
l
y
c
e
Fatty acid Fatty acid
r
o Phosphate Alcohol Phosphate Alcohol
l
p676
Section 19.7
Membrane Lipids: Phospholipids
Glycerophospholipids
A glycerophospholipid is a lipid that contains two fatty
acids and a phosphate group esterified to a glycerol
molecule and an alcohol esterified to the phosphate
group.
All attachments (bonds) between groups in a
glycerophospholipid are ester linkages
Glycerophospholipids have four ester linkages as
contrasted to three ester linkages in triacylglycerols.
p677
Section 19.7
Membrane Lipids: Phospholipids
Glycerophospholipids
Glycerophospholipids undergo hydrolysis and
saponification reactions in a manner similar to that for
triacylglycerols
The alcohol attached to the phosphate group in a
glycophospholipid is usually one of three amino alcohols:
choline, ethanolamine, or serine - respectively known as
phosphatidylcholines, phosphatidylethanolamines, and
phosphatidylserines.
p678
Section 19.7
Membrane Lipids: Phospholipids
p677
Section 19.7
Membrane Lipids: Phospholipids
Glycerophospholipids
Structurally glycerophospholipids are although similar to
triacylglycerols, they have different biochemical
functions.
Triacylglycerols serve as energy storage molecules
Glycerophospholipids function as components of cell
membranes
A major structural difference between the two types of
lipids is that of their polarity Responsible for the their
differing biochemical functions.
Triacylglycerols are a non-polar
Glycerophospholipids are polar.
Sphingophospholipids
Structures based on the 18-carbon monounsaturated
aminodialcohol sphingosine
Contains one fatty acid and one phosphate group
attached to a sphingosine molecule and an alcohol
attached to the phosphate group
Sphingosine
Fatty acid
Phosphate Alcohol
p680
Section 19.7
Membrane Lipids: Phospholipids
Saponifiable lipids
Sphingophospholipids in which the alcohol esterified to
the phosphate group is choline are called
sphingomyelins.
Sphingomyelins are found in all cell membranes and are
important structural components of the myelin sheath of
neurons
Gangliosides
Complex sphingoglycolipids are called Gangliosides:
contain a branched chain of up to seven
monosaccharide residues.
Occur in the gray matter of the brain as well as in the
myelin sheath.
p682
Section 19.9
Membrane Lipids: Cholesterol
Cholesterol in Food
Passive Transport
Facilitated Transport
Active Transport
Active transport - a
substance moves across a
cell membrane, with the aid
of membrane proteins,
against a concentration
gradient with the expenditure
of cellular energy.
Proteins involved in
active transport are called
pumps. The needed
energy is supplied by
molecules such as ATP.
Copyright © Cengage Learning. All rights reserved 67
Section 19.11
Emulsification Lipids: Bile Acids
Hormones
A hormone is a biochemical substance produced by a ductless
gland that has a messenger function.
Hormones serve as a means of communication between various
tissues.
Some hormones are lipids.
The lipids that play the role of chemical messengers include:
Steroid hormones derivatives of cholesterol
Eicosanoids- derivatives of arachidonic acid
There are two major classes of steroid hormones:
Sex hormones - control reproduction and secondary sex
characteristics
Adrenocorticoid hormones control numerous biochemical
processes in the body
Adrenocorticoid Hormones
Produced by the adrenal glands
- small organs located on top of
each kidney
28 Different hormones have
been isolated from the adrenal
cortex
Two types of adrenocorticoid
hormones:
Mineralocorticoids - control
the balance of Na and K
ions in cells
Glucocorticoids - control
glucose metabolism and
counteract inflammation
2. Thromboxanes: C20-fatty-acid
derivative containing a cyclic ether ring
and oxygen-containing functional
groups
Promote platelet aggregation.
LIPIDS
SAPONIFIABLE NONSAPONIFIABLE
Triacylglycerols Cholesterol
Glycerophospholipids Bile acids,
Sphingophospholipids Steroid hormones
Sphingoglycolipids Eicosanoids
Biological waxes