15 ch110 lipids timberlake.ppt
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Chapter 15 Lipids
15.1
Lipids
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Lipids
Lipids are
Biomolecules that contain fatty acids or a steroid
nucleus.
Soluble in organic solvents but not in water. Named for the Greek word lipos, which means fat. Extracted from cells using organic solvents.
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Types of Lipids
The types of lipids containing fatty acids are
Waxes.
Fats and oils (triacylglycerols).
Glycerophospholipids.
Prostaglandins.
Not steroids, as they do not contain fatty acids.
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Structures of Lipids
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15.2 Fatty Acids
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Fatty Acids
Fatty acids
Are long-chain
carboxylic acids.
Typically contain 12-18carbon atoms.
Are insoluble in water.
Can be saturated or
unsaturated.
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Fatty Acid Formulas
The formulas for fatty acids are written as
Condensed formulas.
Line-bond formulas.
For example caprylic acid with 8 carbon atoms.
CH3(CH2)6COOH
CH3CH2CH2CH2CH2CH2CH2COOH
OH
O
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Saturated fatty acids have
Single CC bonds. Molecules that fit closely together
in a regular pattern. Strong attractions between fatty
acid chains.
High melting points that make
them solids at room temperature.
Saturated Fatty Acids
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Some Saturated Fatty Acids
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Unsaturated Fatty Acids
Unsaturated fatty acids
Have one or more double C=C bond
Typically contain cis double bonds.
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Properties of Unsaturated Fatty
Acids
Unsaturated fatty acids
Have kinks in the fattyacid chains.
Do not pack closely.
Have few attractionsbetween chains.
Have low melting points.
Are liquids at roomtemperature.
kinks inchain
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Unsaturated Fatty Acids
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Comparing Melting PointsofSome Fatty Acids
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Learning Check
Assign the melting points of17C, 13C, and 69Cto the correct fatty acid. Explain.
stearic acid (18 C) saturated
oleic acid (18 C) one double bondlinoleic acid (18 C) two double bonds
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Solution
Stearic acid is saturated and would have a higher
melting point than the unsaturated fatty acids.
Because linoleic has two double bonds, it would have
a lower mp than oleic acid, which has one double
bond.
stearic acid mp 69C saturated
oleic acid mp 13C
linoleic acid mp -17C most unsaturated
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Prostaglandins
Prostaglandins have
20 carbon atoms in their fatty acid chains.
An OH on carbon 11 and 15.
A trans double bond at carbon 13.
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C 11
C 15C 13
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Prostaglandins in the Body
Prostaglandins are
Produced by injuredtissues.
Involved in pain,fever, andinflammation.
Not produced whenanti-inflammatory
drugs such as aspirininhibit their synthesis.
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Omega-6 and Omega 3- Fatty
Acids
Fatty acids
In vegetable oils are mostly omega-6 with
the first C=C at C6.
linoleic acid
CH3(CH2)4CH=CHCH2CH=CH(CH2)7COOH6
In fish oils are mostly omega-3 with the
first C=C at C3.
linolenic acidCH3CH2(CH=CHCH2)3(CH2)6COOH
3
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Some Omega-6 and Omega-3
Fatty Acids
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Learning Check
Write a fatty acid with 10 carbon atoms that is:
A. saturated
B. monounsaturated omega-3
C. monounsaturated omega-6
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Solution
Write a fatty acid with 10 carbon atoms that is:
A. saturated
CH3
CH2
CH2
CH2
CH2
CH2
CH2
CH2
CH2
COOH
B. monounsaturated omega-3
CH3CH2CH=CHCH2CH2CH2CH2CH2COOH
C. monounsaturated omega-6
CH3CH2CH2CH2CH2CH=CHCH2CH2COOH
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Waxes, Fats, and Oils
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Waxes
Waxes are
Esters of saturated fatty acids and long-chain alcohols.
Coatings that prevent loss of water by leaves of plants.
TABLE 17.2
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Fats and Oils: Triacylglycerols
Fats and oilsare
Also called triacylglycerols.
Esters of glycerol.
Produced by esterification. Formed when the hydroxyl
groups of glycerol react with the
carboxyl groups of fatty acids.
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In a triacylglycerol,
Glycerol forms ester bonds with three fatty acids.
Triacylglycerols
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Formation of a Triacylglycerol
glycerol + three fatty acids triacylglycerol
OHCH2
OH
OHCH2
CHO
(CH2)14CH3CHO
O
(CH2)14CH3CHO
O
(CH2)14CH3CHO
+ 3H2O
O
O
C (CH2)14CH3
CH O
O
C (CH2)14CH3
CH2 O
O
C (CH2)14CH3
CH2
+
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Olive Oil
Olive oil
Contains a high
percentage of oleic
acid, which is a
monounsaturated fatty
acid with one cis
double bond.
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Learning Check
What are the fatty acids in the following triacylglycerol?
(CH2)12CH3
O
C
CH(CH2)7CH3(CH2)7CH
O
C
O
(CH2)16CH3C
O
O
OCH2
CH2
CH
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Solution
Stearic acid
Oleic acid
Myristic acid(CH2)12CH3
O
C
CH(CH2)7CH3(CH2)7CH
O
C
O
(CH2)16CH3C
O
O
OCH2
CH2
CH
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Melting Points of Fats and Oils
A triacylglycerol that is a fat
Is solid at room temperature.
Is prevalent in meats, whole milk, butter, and cheese.
A triacylglycerol that is an oil
Is liquid at room temperature.
Is prevalent in plants such as olive and safflower.
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Oils with Unsaturated Fatty Acids
Oils
Have more unsaturated fats.
Have cis double bonds that cause kinks in the
fatty acid chains. Cannot pack triacylglycerol molecules as close
together as in fats.
Have lower melting points than saturated fats.
Are liquids at room temperature.
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Diagram of Triacylglycerol with
Unsaturated Fatty Acids
Unsaturated fatty acid
chains have kinks that
do not allow close
packing.
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Saturated and Unsaturated Fatty
Acids In Fats and Oils
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Chemical Properties of
Triacylglycerols
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The chemical reactions of triacylglycerols are similar
to those of alkenes and esters.
Inhydrogenation, double bonds in unsaturated
fatty acids react with H2 in the presence of a Ni orPt catalyst.
In hydrolysis, ester bonds are split by water in the
presence of an acid, a base, or an enzyme.
Chemical Properties of
Triacylglycerols
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Hydrogenation of Oils
Thehydrogenation of oils
Adds hydrogen (H2) to the carbon atoms of double bonds.
Converts double bonds to single bonds.
Increases the melting point.
Produces solids such as margarine and shortening.
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Hydrogenation
Ni
+ 3H2
glyceryl tripalmitoleate
(tripalmitolean)
glyceryl tripalmitate
(tripalmitin)
O
(CH2)14CH3C
O
(CH2)14CH3C
O
(CH2)14CH3C
O
O
OCH2
CH2
CH
CH(CH2)7CH3(CH2)5CH O
C
CH(CH2)7CH3(CH2)5CH
O
C
CH(CH2)7CH3(CH2)5CH
O
C
O
O
OCH2
CH2
CH
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What product(s) is obtained from the complete
hydrogenation of glyceryl trioleate?
1. Glycerol and 3 oleic acids2. Glyceryltristearate
3. Glycerol and 3 stearic acids
Learning Check
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What product(s) is obtained from the complete
hydrogenation of glyceryl trioleate?
2. Glyceryltristearate
Solution
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Olestra, A Fat Substitute
Olestra is
Used in foods as an artificial fat.
Sucrose linked by ester bonds to several long-chainfatty chains.
Not broken down in the intestinal tract.
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Cisand TransFatty Acids
Unsaturated fatty acids can be
Cis with bulky groups on same side of C=C.CH3 (CH2)5 (CH2)7COOH cis
C=CH H
Trans have bulky groups on opposite sides of C=C.
CH3 (CH2)5 H
C=C trans
H (CH2)7COOH
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Trans Fatty Acids and
Hydrogenation
Trans fatty acids
Are formed during hydrogenation when cis double
bonds are converted to trans double bonds.
In the body behave like saturated fatty acids. Are estimated to make up 2-4% of our total
Calories.
Are reported in several studies reported to raise
LDL-cholesterol and lower HDL-cholesterol.
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Learning Check
(1) True or (2) False
A. There are more unsaturated fats in vegetable oils.
B. Vegetable oils have higher melting points than fats.C. Hydrogenation of oils converts some cis-double
bonds to trans- double bonds.
D. Animal fats have more saturated fats.
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Solution
(1) True or (2) False
A. T There are more unsaturated fats in vegetable oils.
B. F Vegetable oils have higher melting points than fats.
C. T Hydrogenation of oils converts some cis-double
bonds to trans- double bonds.
D. T Animal fats have more saturated fats.
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Hydrolysis
In hydrolysis,
Triacylglycerols split into glycerol and three fatty acids.
An acid or enzyme catalyst is required.
OCH2
OCH
OCH2
OHCH2
OHCH
OHCH2
O
(CH2)14CH3CHO
H2O
O
(CH2)14CH3C
O
(CH2)14CH3C
O
(CH2)14CH3C
H++3
+ 3
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Saponification and Soap
Saponification
Is the reaction of a fat with a strong base.
Splits triacylglycerols into glycerol and the salts of
fatty acids.
Is the process of forming soaps (salts of fattyacids).
With KOH gives softer soaps.
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Saponification
O
O
C (CH2)14CH3
CH O
O
C (CH2)14
CH3
CH2 O
O
C (CH2)14CH3
CH2
+ 3NaOH
Na+-O
O
C (CH2)14CH33
OH
CH OH
CH2 OH
CH2
+
soap
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What products are obtained from the complete
hydrolysis of glyceryl trioleate?
1. Glycerol and 3 oleic acids
2. Glyceryl tristearate3. Glycerol and 3 stearic acids
Learning Check
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What products are obtained from the complete
hydrolysis of glyceryl trioleate?
1. Glycerol and 3 oleic acids
Solution
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Learning Check
Write the product of the following reaction.
OCH2
O
O
CH2
CH
CH(CH2)7CH3(CH2)5CH
O
CO
CH(CH2)7CH3(CH2)5CHC
O
C CH(CH2)7CH3(CH2)5CH
H2
Ni+ 3
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Solution
O
O
CH2
CH
OCH2
(CH2)14CH3
O
C
O(CH2)14CH3C
(CH2)14CH3
O
C
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Glycerophospholipids are
The most abundant lipids in cell membranes.
Composed of glycerol, two fatty acids, phosphateand an amino alcohol.
Glycerol
PO4Amino
alcohol
Glycerophospholipids
Fatty acid
Fatty acid
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Glycerophospholipids Are Polar
A glycerophospholipid has
Two nonpolar fatty acid chains.
A phosphate group and a polar amino alcohol.
CH3
+ +HOCH2CH2NCH3 HOCH2CH2NH3
choline CH3 ethanolamine
+
NH3
Amino alcoholsHOCH2CHCOO
serine
St t d P l it f A
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Structure and Polarity of A
Glycerophospholipid
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Lecithin and cephalin are glycerophospholipids
Abundant in brain and nerve tissues.
Found in egg yolk, wheat germ, and yeast.
Lecithin and Cephalin
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Learning Check
Identify each as a
A. fatty acid B. triacylglycerol
C. amino alcohol D. glycerophospholipid
1. glyceryl trioleate
2. cephalin
3. choline
4. palmitic acid
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Solution
Identify each as a
A. fatty acid B. triacylglycerol
C. amino alcohol D. glycerophospholipid
1. glyceryl trioleate B. triacylglycerol
2. cephalin D. glycerophospholipid
3. choline C. amino alcohol
4. palmitic acid A. fatty acid
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Learning Check
Identify the components and type of glycerophospholipid
O
CH2O C (CH2)16 CH3
OCH2O C (CH2)16 CH3
+
O NH3
CH2O P O CH2CHCOO-
O-
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Solution
Identify the components and type of glycerophospholipidO
CH2O C (CH2)16 CH3
O 2 stearic acids
CH2O C (CH2)16 CH3
+
O NH3
type = cephalinCH2O P O CH2CHCOO-
serineO-
phosphate amino alcohol
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Sphingolipids
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Sphingolipids
Sphingolipids
Are similar to phospholipids.
Contain sphingosine (a long-chain amino alcohol), a
fatty acid, phosphate, and a small amino alcohol.
Have polar and nonpolar regions.
sphingosine
PO4amino
alcohol
fatty acid
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Sphingosine
Sphingosine is a long-chain unsaturated amino alcohol.
CH3(CH
2)12
CH=CHCHOH
CHNH2
CH2OH
sphingosine
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In sphingomyelin, a sphingolipid found in nerve cells
There is an amide bond between a fatty acid andsphingosine, an 18-carbon alcohol.
Sphingolipids
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Glycosphingolipids
Glycosphingolipids
contain
monosaccharides
bonded to theOHof sphingosine by aglycosidic bond.
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Glycosphingolipids and
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Glycosphingolipids and
Cerebrosides
Glycosphingolipids
Are sphingolipids that containmonosaccharides.
Can be a cerebroside with galactose.
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Gangliosides
Gangliosides Are similar to cerebrosides, but contain two or
more monosaccharides.
Are important in neurons.
Act as receptor for hormones and viruses.
Can accumulate and cause genetic diseases.
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Gangliosides
GM2 is a ganglioside That accumulates in Tay-Sachs disease.
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Lipid Diseases (Lipidoses)
In many lipid diseases, the deficiency of an enzyme
causes the accumulation of glycolipids.
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TABLE 17.3
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Learning Check
Identify each as a
1) Fatty acid 2) Triacylglycerol
3) Amino alcohol 4) Glycerophospholipid
5) Glycosphingolipid
A. Glyceryl trioleate
B. Cephalin
C. Choline
D. Galactocerebroside
E. Palmitic acid
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Solution
A. Glyceryl trioleate 2) Triacylglycerol
B. Cephalin 4) Glycerophospholipid
C. Choline 3) Amino alcohol
D. Galactocerebroside 5) Glycosphingolipid
E. Palmitic acid 1) Fatty acid
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Steroids: Cholesterol, Bile Salts,
and Steroid Hormones
CH3
CH3CH3
CH3
HO
CH3
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Steroid Nucleus
Asteroid nucleus consists of
3 cyclohexane rings.
1 cyclopentane ring.
No fatty acids.
steroid nucleus
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Cholesterol
Cholesterol
Is the most abundant steroid in the body.
Has methyl CH3- groups, alkyl chain, and -OH
attached to the steroid nucleus.
CH3
CH3CH3
CH3
HO
CH3
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Cholesterol in the Body
Cholesterol in the body
Is obtained from meats,
milk, and eggs.
Is synthesized in the liver.
Is needed for cell
membranes, brain and
nerve tissue, steroid
hormones, and Vitamin D.
Clogs arteries when highlevels form plaque.
A normal, open artery.
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An artery clogged by
cholesterol plaque
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Cholesterol in Foods
Cholesterol is
Synthesized inthe liver.
Obtained from
foods. Considered
elevated ifplasma
cholesterolexceeds 200mg/dL.
TABLE 17.4
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Learning Check
Match the components of the cholesterol molecule with
the following:
___ carbon chain ___hydroxyl group
___ steroid nucleus ___methyl group
CH3
CH3CH3
CH3
HO
CH3
AC
B
D
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Solution
Match the components of the cholesterol molecule with
the following:
D carbon chain A hydroxyl group
C steroid nucleus B methyl group
CH3
CH3CH3
CH3
HO
CH3
AC
B
D
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Bile Salts
Bile salts
Are synthesized in the liver from cholesterol.
Are stored in the gallbladder.
Are secreted into the small intestine.
Have a polar and a nonpolar region
Mix with fats to break them part.
Emulsify fat particles to provide large surface area.
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Bile Salts
OH
COO- Na+CH2
H
N
O
COH
CH3
CH3
HO
CH3
glycine, an amino acidcholic acid, a bile acid
sodium glycocholate, a bile salt
Nonpolar region
Polar region
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Lipoproteins
Lipoproteins Combine lipids with proteins and phospholipids. Are soluble in water because the surface consists of
polar lipids.
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Types of Lipoproteins
Lipoproteins
Differ in density, composition, and function.
Include low-density lipoprotein (LDLs) and high-
density lipoprotein (HDLs).
TABLE 17.5
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Transport of Lipoproteins in
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Transport of Lipoproteins in
the Body
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S i
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Steroid Hormones
Steroid hormones
Are chemical
messengers in cells.
Are produced from
cholesterol.
Include sex hormones
such as androgens
(testosterone) in
males and estrogens(estradiol) in females.
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Ad l C i id
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Adrenal Corticosteroids
Adrenal corticosteroids are steroid hormones that
Are produced by the adrenal glands located on
the top of each kidney.
Include aldosterone, which regulates electrolytes
and water balance by the kidneys.
Include cortisone, a glucocorticoid, which
increases blood glucose level and stimulates the
synthesis of glycogen in the liver.
Ad l C i id
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Adrenal Corticosteroids
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A b li St id
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Anabolic Steroids
Anabolic steroids Are derivatives of testosterone.
Are used illegally to increase muscle mass.
Have side effects including fluid retention, hair growth,
sleep disturbance, and liver damage.
Copyright 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings
L i Ch k
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Learning Check
Identify each as a
1. fatty acid 2. steroid 3. triacylglycerol
4. phospholipid 5. sphingolipid
A. cholesterolB. glycerol, 2 fatty acids, phosphate, and choline
C. glyceryl tristearate
D. sphingosine, fatty acid, phosphate, and choline
E. estradiol
F. bile salts
G. lipids in plasma membranes
S l ti
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Solution
A. cholesterol 2 steroidB. glycerol, 2 fatty acids, phosphate, and choline
4 phospholipid
C. glyceryl tristearate 3 triacylglycerol
D. sphingosine, fatty acid, phosphate, and choline5 sphingolipid
E. estradiol 2 steroid
F. bile salts 2 steroid
G. lipids in plasma membranes
4 phospholipid, 5 sphingolipid
.
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Cell Membranes
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Publishing as Benjamin Cummings
C ll M b
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Cell Membranes
Cell membranes
Separate cellular contents from the external
environment.
Consist of a lipid bilayer made of two rows of
phospholipids.
Have an inner portion made of the nonpolar tails of
phospholipids with the polar heads at the outer
and inner surfaces.
Fluid Mosaic Model of Cell
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Membranes
The lipid bilayer
Contains proteins, carbohydrates, and
cholesterol.
Has unsaturated fatty acids that make cellmembranes fluid-like rather than rigid.
Has proteins and carbohydrates on the surface
that communicate with hormones and
neurotransmitters.
Fl id M i M d l
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Fluid Mosaic Model
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Publishing as Benjamin Cummings
Transport Through Cell
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p g
Membranes
The transport of substances through cell
Membranes involves
Diffusion (passive transport), which moves
particles from a higher to a lower concentration. Facilitated transport, which uses protein channels
to increase the rate of diffusion.
Active transport, which moves ions against a
concentration gradient.
Transport Pathways Through Cell
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p y g
Membranes
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Learning Check
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Learning Check
The transport of particles across a cell membrane from
high concentration to low concentration is called
1. Facilitated transport
2. Diffusion
3. Active transport
Solution
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Solution
The transport of particles across a cell membrane from
high concentration to low concentration is called
2. Diffusion