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Lipids
Lipids
1
Copyright © 2007 by Pearson Education, Inc.
Publishing as Benjamin Cummings
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Lipids
Lipids are Biomolecules that contain fatty acids or a steroid
nucleus.
Soluble in an organic solvents (e.g., ether, benzene,
2
, . Named for the Greek word lipos, which means “fat.” Extracted from cells using organic solvents.
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Nutritional Uses of Lipids We already know that lipids are concentrated sources
of energy (9.45 kcal/g)
other functions:
3
1) provide means whereby fat-soluble nutrients (e.g.,sterols, vitamins) can be absorbed by the body2) structural element of cell, subcellular components
3) components of hormones and precursors for prostaglandin synthesis
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Types of Lipids
The types of lipids containing fatty acids are Waxes. Fats and oils (triacylglycerols). Glycerophospholipids.
4
Prostaglandins. Not steroids, as they do not contain fatty acids.
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Lipid Classes
Simple : FA’s esterified with glycerol Compound : same as simple, but with other
compounds also attached
Phospholipids : fats containing phosphoric acid and
Glycolipids : FA’s compounded with CHO, but no N derived lipids : substances from the above derived by
hydrolysis Sterols : large molecular with alcohols found in
nature and combined w/FA’s (e.g., cholesterol)
5
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1. Fatty Acids
7
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Fatty Acids
Fatty acids Are long-chain
carboxylic acids.
Typically contain 12-18
8
. 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 exam le ca r lic acid with 8 carbon atoms.
9
CH3—(CH2)6—COOH
CH3—CH2—CH2—CH2—CH2—CH2—CH2—COOH
OH
O
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Saturated fatty acids have Single C–C bonds. Molecules that fit closely together
in a regular pattern.
Saturated Fatty Acids (SFA)
10
Strong attractions between fattyacid chains.
High melting points that make
them solids at room temperature.
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Some Saturated Fatty Acids
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Structure of Fatty Saturated
- C - OH
O
Benzoic acid
- C - O HO
OH Slicilic acid
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Unsaturated Fatty Acids
Unsaturated fatty acids Have one or more double C=C bond Typically contain cis double bonds.
13
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Structure of Unsaturated Acid
Oleic acid (C18: 1)
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Properties of Unsaturated Fatty Acids
Unsaturated fatty acids Have “kinks” in the fatty
acid chains.
Do not pack closely.
“kinks” inchain
15
between chains. Have low melting points. Are liquids at room
temperature.
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Unsaturated Fatty Acids
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Unsaturated Fatty Acids(The double bonds in the fatty acids are cis (hydrogen atoms are on the same
side of the double bonds of the carbon chain)
❍ Oleic acid (18:1) is a monounsaturated fatty acid
C H3(C H2)7 C C (C H2)7 C
O
OH
❍ Linoleic acid (18:2) is a polyunsaturated fatty acid (one of theomega-6 fatty acids since there is a double bond six carbons from the end of the chain)
C H3(C H2)4 C
H
C
H
C H2 C
H
C
H
(C H2)7 C
O
OH
H H
C
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Comparing Melting Points of Some
Fatty Acids
18
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Learning Check
Assign the melting points of –17°C, 13°C, and 69°Cto the correct fatty acid. Explain.
stearic acid (18 C) saturated
oleic acid (18 C) one double bond
19
linoleic 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
20
.stearic acid mp 69°C saturatedoleic acid mp 13°Clinoleic acid mp -17°C most unsaturated
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1a. 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.
21
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C 11C 15C 13
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O
O H
Prostaglandins
❍ Prostaglandins are powerful hormones in mammalian systems Prostaglandins were first isolated from the prostate gland (seminal
fluid)❍ Prostaglandins have a five-membered ring with a 7-carbon side chain
(often ending in a carboyxlic acid group) adjacent to an 8-carbon chain
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Prostaglandins in the Body
Prostaglandins are Produced by injured
tissues.
Involved in pain,
23
,inflammation.
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
24
CH3 ─(CH2)4 ─CH=CH─CH2 ─CH=CH─(CH2)7 ─COOH6
In fish oils are mostly omega-3 with the
first C=C at C3.linolenic acidCH3 ─CH2 ─(CH=CH─CH2)3 ─(CH2)6 ─COOH
3
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Some Omega-6 and Omega-3
Fatty Acids
25
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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
27
B. monounsaturated omega-3CH3—CH2—CH=CH—CH2—CH2—CH2—CH2—CH2—COOH
C. monounsaturated omega-6CH3—CH2—CH2—CH2—CH2—CH=CH—CH2—CH2—COOH
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2. Waxes, Fats, and Oils
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2a. Waxes
Waxes are Esters of saturated fatty acids and long-chain alcohols. Coatings that prevent loss of water by leaves of plants.
TABLE 1.
29
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Jojoba (Simmondsia sinensis)
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www.kerfootgroup.co.uk
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Fats and Oils: Triacylglycerols
Fats and oils are Also called triacylglycerols. Esters of glycerol. Produced by esterification.
31
Formed when the hydroxylgroups of glycerol react with thecarboxyl groups of fatty acids.
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In a triacylglycerol, Glycerol forms ester bonds with three fatty acids.
2b. Triacylglycerols
32
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Formation of a Triacylglycerol
glycerol + three fatty acids triacylglycerol
OHCH2
O
O
(CH2)14CH3CHO
33
OHCH2
O
(CH2)14CH3CHO
2 14 3
+ 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
34
acid with one cisdouble bond.
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Learning Check
What are the fatty acids in the following triacylglycerol?
O
(CH2)16CH3COCH
2
35
R1= C18R2= C18 (1) MUFA= mono unsaturated fatty acidR3= C14
(CH2)12CH3
O
C
CH(CH2)7CH3(CH2)7CHC
O
O
CH2
CH
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Solution
Stearic acid
O
O
(CH2)16CH3COCH2
36
Oleic acid
Myristic acid(CH2)12CH3
O
C
CH(CH2)7CH3(CH2)7CHC
O
O
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.
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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.
38
Cannot pack triacylglycerol molecules as closetogether 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
39
Unsaturated fatty acidchains have kinks thatdo not allow closepacking.
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Safflower (Carthamus tinctorius)
Canola, Rapeseed (Brassica napus L.)
diaryofanutritionist.com
burcon.ca
. .
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Palm kernel oil
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Castor oil (minyak jarak) Ricinus communis Sesame oil (minyak wijen) Kapok seed oil (minyak biji randu/kapok)
Rice bran oil (minyak dedak) Fish oil (minyak ikan)
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Komposisi asam lemak dalam minyak wijen:[1]
Asam lemak minimum maksimum
Asam palmitat C16:0 7,0 % 12,0 %
As palmitoleat C16:1 sangat kecil 0,5 %
Asam stearat C18:0 3,5 % 6,0 %
Asam oleat C18:1 35,0 % 50,0 %
44
Asam linoleat C18:2 35,0 % 50,0 %
Asam linolenat C18:3 sangat kecil 1,0 %
Asam eikosenoat C20:1 sangat kecil 1,0 %
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Saturated and Unsaturated Fatty Acids
in Fats and Oils
45
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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.
In hydrogenation, double bonds in unsaturatedfatt acids react with H in the resence of a Ni or
Chemical Properties of Triacylglycerols
47
Pt catalyst.
In hydrolysis, ester bonds are split by water in thepresence of an acid, a base, or an enzyme.
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Hydrogenation of Oils
The hydrogenation 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.
48
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Hydrogenation
Ni
+ 3H2
CH(CH2)7CH3(CH2)5CH
O
C
CH(CH2)7CH3(CH2)5CH
O
C
O
OCH2
CH
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glyceryl tripalmitoleate(tripalmitolean)
glyceryl tripalmitate(tripalmitin)
O
(CH2)14CH3C
O
(CH2)14CH3C
(CH2)14CH3C
O
O
OCH2
CH2
CH
CH(CH2)7CH3(CH2)5CH
O
COCH2
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What product(s) is obtained from the completehydrogenation of glyceryl trioleate?
1. Glycerol and 3 oleic acids
Learning Check
50
2. Glyceryltristearate3. Glycerol and 3 stearic acids
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What product(s) is obtained from the completehydrogenation of glyceryl trioleate?
2. Glyceryltristearate
Solution
51
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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-chain
fatty chains.
52
.
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Cis and Trans Fatty Acids
Unsaturated fatty acids can be Cis with bulky groups on same side of C=C.
CH3 ─ (CH2)5 (CH2)7 ─ COOH cis
C=C
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H H
Trans have bulky groups on opposite sides of C=C.CH3 ─ (CH2)5 H
C=C transH (CH2)7 ─ COOH
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Trans Fatty Acids and
Hydrogenation
Trans fatty acids
Are formed during hydrogenation when cis doublebonds are converted to trans double bonds.
In the body behave like saturated fatty acids.
54
Are estimated to make up 2-4% of our totalCalories.
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.
55
C. Hydrogenation of oils converts some cis-doublebonds 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.
56
. y rogena on o o s conver s some c s- ou ebonds 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.
O
57
OCH2
OCH
O2
OHCH2
OHCH
OHCH2 O
(CH2)14CH3CHO
H2O
O
(CH2)14CH3C
O
(CH2)14CH3C
(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.
58
s e process o orm ng soaps sa s o a yacids).
With KOH gives softer soaps.
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Saponification
O
O
C (CH2)14CH3
CH O
O
C (CH2)14CH3
CH2
+ 3NaOH
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CH2 O
O
C (CH2)14CH3
Na+ -OOC (CH2)14CH33
OH
CH OH
CH2 OH
CH2
+“soap”
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What products are obtained from the completehydrolysis of glyceryl trioleate?1. Glycerol and 3 oleic acids
2. Glyceryl tristearate
Learning Check
60
3. Glycerol and 3 stearic acids
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What products are obtained from the completehydrolysis of glyceryl trioleate?1. Glycerol and 3 oleic acids
Solution
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Learning Check
Write the product of the following reaction.
OCH2 CH(CH ) CH(CH2)5CH
O
C
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O
O
CH2
CH
O
CH(CH2)7CH3(CH2)5CHC
O
C CH(CH2)7CH3(CH2)5CH
H2Ni
+ 3
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Solution
OCH2
O
(CH2)14CH3
O
C
63
O
O
CH2
CH
(CH2)14CH3
O
C
(CH2)14CH3C
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Glycerophospholipids are The most abundant lipids in cell membranes. Composed of glycerol, two fatty acids, phosphate
and an amino alcohol.
2c. Glycerophospholipids
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Glycerol
PO4Amino
alcohol
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
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+ +HO−CH2−CH2−N−CH3 HO−CH2−CH2−NH3
│choline CH3 ethanolamine
+NH3│ Amino alcohols
HO−CH2−CH−COO−serine
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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. triacylglycerolC. amino alcohol D. glycerophospholipid
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1. glyceryl trioleate2. cephalin3. choline4. palmitic acid
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Solution
Identify each as a A. fatty acid B. triacylglycerolC. amino alcohol D. glycerophospholipid
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1. glyceryl trioleate B. triacylglycerol2. cephalin D. glycerophospholipid3. choline C. amino alcohol4. palmitic acid A. fatty acid
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Learning Check
Identify the components and type of glycerophospholipidO║
CH2−O −C −(CH2)16 −CH3
O
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CH2−O −C −(CH2)16 −CH3+
O NH3
║ │CH2−O −P −O − CH2−CH−COO-
│O-
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Solution
Identify the components and type of glycerophospholipidO║
CH2−O −C −(CH2)16 −CH3
O 2 stearic acids
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CH2−O −C −(CH2)16 −CH3+
O NH3║ │ type = cephalin
CH2−O −P −O − CH2−CH−COO-│ serineO-
phosphate amino alcohol
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3a. 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.
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ave po ar an nonpo ar reg ons.
sphingosine
PO4amino
alcohol
fatty acid
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Sphingosine
Sphingosine is a long-chain unsaturated amino alcohol.
CH3−(CH2)12 −CH=CH−CH−OH
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CH−NH2│
CH2−OH
sphingosine
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3b. Glycosphingolipids
Glycosphingolipidscontainmonosaccharidesbonded to the –OH
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glycosidic bond.
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Glycosphingolipids and
Cerebrosides
Glycosphingolipids Are sphingolipids that contain
monosaccharides. 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.
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. 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 enzymecauses the accumulation of glycolipids.
Table 2.
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Learning Check
Identify each as a1) Fatty acid 2) Triacylglycerol3) Amino alcohol 4) Glycerophospholipid
5) Glycosphingolipid
81
. ycery r o ea eB. CephalinC. CholineD. GalactocerebrosideE. Palmitic acid
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Solution
A. Glyceryl trioleate 2) TriacylglycerolB. Cephalin 4) Glycerophospholipid
C. Choline 3) Amino alcohol
82
. a ac ocere ros e ycosp ngo pE. Palmitic acid 1) Fatty acid
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4. Steroids
Steroids: Cholesterol, Bile Salts,
and Steroid Hormones
8383
CH3
CH3CH3
CH3
HO
CH3
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Steroid Nucleus
A steroid nucleus consists of
3 cyclohexane rings.
1 cyclopentane ring.
No fatty acids.
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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.
85
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.
A normal, open artery.
86
s nee e or cemembranes, brain andnerve tissue, steroidhormones, and Vitamin D.
Clogs arteries when highlevels form plaque.
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An artery clogged bycholesterol plaque
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Cholesterol in Foods
Cholesterol is Synthesized in
the liver.
Obtained from
Table 3.
87
. Considered
elevated if plasma
cholesterolexceeds 200mg/dL.
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Learning Check
Match the components of the cholesterol molecule withthe following:
___ carbon chain ___hydroxyl group
88
___ ___
CH3
CH3CH3
CH3
HO
CH3
AC
B
D
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Solution
Match the components of the cholesterol molecule withthe following:D carbon chain A hydroxyl group
C steroid nucleus B methyl group
89
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.
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.
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
COO- Na+CH2
N
O
COH
CH3
CH3
glycine, an amino acidcholic acid, a bile acid
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OHHO
CH3
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).
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Table 4.
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Transport of Lipoproteins in the Body
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Steroid Hormones
Steroid hormones
Are chemical
messengers in cells.
Are produced from
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.
Include sex hormones
such as androgens
(testosterone) in males
and estrogens(estradiol) in females.
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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
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and water balance by the kidneys. Include cortisone, a glucocorticoid, which
increases blood glucose level and stimulates thesynthesis of glycogen in the liver.
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Adrenal Corticosteroids
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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,
slee disturbance and liver dama e.
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Learning Check
Identify each as a1. fatty acid 2. steroid 3. triacylglycerol4. phospholipid 5. sphingolipid
A. cholesterol
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B. glycerol, 2 fatty acids, phosphate, and cholineC. glyceryl tristearateD. sphingosine, fatty acid, phosphate, and choline
E. estradiolF. bile saltsG. lipids in plasma membranes
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Solution
A. cholesterol 2 steroidB. glycerol, 2 fatty acids, phosphate, and choline
4 phospholipidC. glyceryl tristearate 3 triacylglycerol
D. s hin osine fatt acid hos hate and choline
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5 sphingolipidE. estradiol 2 steroidF. bile salts 2 steroidG. lipids in plasma membranes
4 phospholipid, 5 sphingolipid
.
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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
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p osp o p s. 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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Fluid Mosaic Model of Cell
Membranes
The lipid bilayer Contains proteins, carbohydrates, and
cholesterol.
Has unsaturated fatty acids that make cell
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membranes fluid-like rather than rigid. Has proteins and carbohydrates on the surface
that communicate with hormones andneurotransmitters.
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Fluid Mosaic Model
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Publishing as Benjamin Cummings
Transport Through Cell
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Transport Through Cell
Membranes
The transport of substances through cell
Membranes involves
Diffusion (passive transport), which moves
articles from a hi her to a lower concentration.
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Facilitated transport, which uses protein channelsto increase the rate of diffusion.
Active transport, which moves ions against a
concentration gradient.
Transport Pathways Through Cell
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Transport Pathways Through Cell
Membranes
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Learning Check
The transport of particles across a cell membrane fromhigh concentration to low concentration is called
1. Facilitated transport
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2. Diffusion3. Active transport
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Solution
The transport of particles across a cell membrane fromhigh concentration to low concentration is called
2. Diffusion
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References
http://www.kerfootgroup.co.uk/oil-inventory/jojoba-wax
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