BIOKIMIA-9 LIPID

DR. ATRA ROMEIDA

KOMPETENSI
DASAR

Setelah mpelajari
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dapat memahami
Copyright 2007 by Pearson Education, Inc.
Publishing as Benjamin Cummings mengenai Lipid
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Lipid : Lemak, Minyak, Lilin
Lipid adalah :
Biomolekul yang mengandung asam lemak atau
mempunyai inti steroid.
Berasal dari kata Yunani LIPOS artinya lemak (fat)

SIFAT FISIKA :
Larut dalam pelarut organik (misal. eter, aseton,
kloroform, benzena) tapi tidak larut dalam air
Dapat diekstrak dari sel-sel menggunakan pelarut
organik (alkohol panas, eter atau pelarut lemak
lainnya )
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Jenis-jenis Lipid
Jenis lipid yang mengandung asam lemak adalah :
Lilin
Lemak dan Minyak (triacylglycerols).
Glycerophospholipids.
Prostaglandins.

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 Penggolongan :
Menurut Bloor:
Lipid sederhana (ester lemak dg berbagai alkohol, misal:
lemak/gliserida dan lilin/waxes)
(1) Lipid gabungan (ester asam lemak yg punya gugus
tambahan, misal: fosfolipid, serebrosida)
(2) Derivat lipid (senyawa yg dihasilkan proses hidrolisa lipid,
misal: asam lemak, gliserol, sterol)

Berdasarkan sifat kimia :

(1) Lipid yg dapat disabunkan/dapat dihidrolisis dg basa
(2) Contoh : lemak
(3) Lipid yg tidak dapat disabunkan contoh : steroid 4
 LEMAK JENUH VS TIDAK JENUH

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
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LEMAK JENUH Rantai tunggal

Copyright 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings

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LEMAK TAK JENUH

Unsaturated fatty acids

Punya rantai rangkap C=C
Typically contain cis double bonds.

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Contoh Lemak tak jenuh

Copyright 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings

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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.

C 11
C 13 C 15

Copyright 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings 9

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)7COOH
6

In fish oils are mostly omega-3 with the

first C=C at C3.
linolenic acid
CH3CH2(CH=CHCH2)3(CH2)6COOH
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Copyright 2007 by Pearson Education, Inc. 10
Publishing as Benjamin Cummings
Some Omega-6 and Omega-3
Fatty Acids

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Learning Check 10

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
CH3CH2CH2CH2CH2CH2CH2CH2CH2COOH

B. monounsaturated omega-3
CH3CH2CH=CHCH2CH2CH2CH2CH2COOH

C. monounsaturated omega-6
CH3CH2CH2CH2CH2CH=CHCH2CH2COOH
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Waxes, Fats, and Oils

Copyright 2007 by Pearson Education, Inc.

Publishing as Benjamin Cummings

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Lilin/Lignin
Adalah :
Esters asam lemak jenuh dan rantai alkohol panjang.
Membungkus (Coatings) yang berguna untuk
mencegah kehilangan air dari permukaan daun.

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Copyright 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings
Fats and Oils: Triacylglycerols

Lemak (Fats) dan minyak (oils)

adalah :
disebut juga triacylglycerols.
Esters dari glycerol.
Dihasilkan dengan cara
esterification.
Terbentuk ketika gugus
hydroxyl dari glycerol bereaksi
dengan gugus carboxyl dari
asam lemak (fatty acids).
Copyright 2007 by Pearson Education, Inc.
Publishing as Benjamin Cummings
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 Triacylglycerols

In a triacylglycerol,
Glycerol forms ester bonds with three fatty acids.

Copyright 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings

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 Pembentukan Triacylglycerol
glycerol + three fatty acids triacylglycerol

O
CH2 OH HO C (CH2)14CH3
O
CH OH + HO C (CH2)14CH3
O O
CH2 OH HO C (CH2)14CH3 CH2 O C (CH2)14CH3
O
CH O C (CH2)14CH3 + 3H2O

O
CH2 O C (CH2)14CH3
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Learning Check 11

What are the fatty acids in the following triacylglycerol?

O
CH2 O C (CH2)16CH3
O
CH O C (CH2)7CH CH(CH2)7CH3
O
CH2 O C (CH2)12CH3

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Solution

O
CH2 O C (CH2)16CH3 Stearic acid
O
CH O C (CH2)7CH CH(CH2)7CH3 Oleic acid
O
CH2 O C (CH2)12CH3 Myristic acid

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Chemical Properties of
Triacylglycerols

Copyright 2007 by Pearson Education, Inc.

Publishing as Benjamin Cummings

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Perangkat KimiaTriacylglycerols

Reaksi kimia triacylglycerols sama dengan alkenes

dan esters.
Dalam hydrogenasi , ikatan rangkap dalam lemak
tak jenuh bereaksi dengan H2 pada katalisis in Ni
atau Pt.
Dalam hydrolysis, ikatan-katan ester dioisahkan
oleh air dan diubah menjadi bentuk asam (acid),
basa (base), atau enzim (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.

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Copyright 2007 by Pearson Education, Inc Publishing as Benjamin Cummings

Hydrogenation
O
CH2 O C (CH2)5CH CH(CH2)7CH3
O Ni
CH O C (CH2)5CH CH(CH2)7CH3 + 3H2
O O
CH2 O C (CH2)5CH CH(CH2)7CH3 CH2 O C (CH2)14CH3
O
glyceryl tripalmitoleate CH O C (CH2)14CH3
(tripalmitolean) O
CH2 O C (CH2)14CH3
glyceryl tripalmitate
(tripalmitin) 24
Learning Check 12
What product(s) is obtained from the complete
hydrogenation of glyceryl trioleate?

1. Glycerol and 3 oleic acids

2. Glyceryltristearate
3. Glycerol and 3 stearic acids

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Solution

What product(s) is obtained from the complete

hydrogenation of glyceryl trioleate?

2. Glyceryltristearate

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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
H H
Trans have bulky groups on opposite sides of C=C.
CH3 (CH2)5 H

C=C trans
H (CH2)7 COOH

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Hydrolysis
In hydrolysis,
Triacylglycerols split into glycerol and three fatty acids.
An acid or enzyme catalyst is required.
O
CH2 O C (CH2)14CH3
O
H+
CH O C (CH2)14CH3 +3H2O
O
CH2 O C (CH2)14CH3 CH2 OH
O
CH OH + 3 HO C (CH2)14CH3

CH2 OH
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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 fatty
acids).
With KOH gives softer soaps.

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Saponification
O
CH2 O C (CH2)14CH3
O
CH O C (CH2)14CH3 + 3NaOH

O CH2 OH
CH2 O C (CH2)14CH3

CH OH O
+ 3 Na+ -O C (CH2)14CH3
CH2 OH soap
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Learning Check 13

What products are obtained from the complete

hydrolysis of glyceryl trioleate?
1. Glycerol and 3 oleic acids
2. Glyceryl tristearate
3. Glycerol and 3 stearic acids

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Solution
What products are obtained from the complete
hydrolysis of glyceryl trioleate?
1. Glycerol and 3 oleic acids

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Learning Check 14
Write the product of the following reaction.

O
CH2 O C (CH2)5CH CH(CH2)7CH3
O
Ni
CH O C (CH2)5CH CH(CH2)7CH3 + 3 H2
O
CH2 O C (CH2)5CH CH(CH2)7CH3

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Solution

O
CH2 O C (CH2)14CH3
O
CH O C (CH2)14CH3
O
CH2 O C (CH2)14CH3

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 Lipid Kompleks

Lipid yg tdp di alam bergabung dg senyawa lain (protein

atau KH)
Lipid (trigliserida, fosfolipid/kolesterol) + protein =
LIPOPROTEIN (dlm plasma darah)
Lipid + KH = LIPOPOLISAKARIDA (terbentuk dalam
dinding sel beberapa jenis bakteri)
Fosfolipid

Disebut juga FOSFATIDAT : gliserida yg mengandung

fosfor dalam bentuk ester asam fosfat
FOSFOGLISERIDA
Termasuk derivat asam fosfatidat (kolin, etanolamina,
serin, inositol, fosfatidilkolin/lesitin, fosfatidiletanolamina,
fosfatidilserin, fosfatidilinositol)
Terdapat dalam sel tumbuhan (kedelai), hewan dan
manusia (telur, otak, hati, ginjal, pankreas, paru-paru,
jantung)
Enzim lesitinase dlm cairan bisa ular kobra dpt
menguraikan asam lemak yg terikat pada C nomor 2
LISOLESITIN
HEMOLISIS (proses perusakan sel darah merah)
 Terpen
Tdr molekul isoprena (2-metilbutadiena)
CH3

H2C = C CH = CH2 isoprena

Termasuk sitral, pinen, geraniol, kamfer, karoten, vitamin A, fitol, skualen

Sitral, pinen & geraniol tdp dalam minyak atsiri yang berasal dari tumbuhan
(exp. terpentin & minyak mawar)
Sitronelal dalam minyak sereh
Kamfer dari pohon kamfer (Chinnamomum camphora)
Karoten (pembentuk vitamin A) dari wortel
Vitamin A dari minyak ikan paus
Fitol adalah hasil hidrolisis klorofil
Skualen dari minyak ikan hiu
 PROBLEM

1. Sebutkan apa saja yang termasuk lipida dan atom

penyusunnya
2. Apa perbedaan lipida dari tumbuhan dan hewan
3. Apa yang menjadi fungsi utama lipida dalam
kehidupan
4. Jelaskan dan gambarkan perbedaan lemak jenuh
(saturated) dan lemak tidak jenuh (nonsaturated)
5. Apa itu asam lemak, rumus bangun, dan dua contoh
6. Sabun sebagai senyawa penggabung lemak dan air.
Bagaimana prosesnya dan gambarkan srukturnya
Glycerophospholipids
Glycerophospholipids are
The most abundant lipids in cell membranes.
Composed of glycerol, two fatty acids, phosphate
and an amino alcohol.

Fatty acid

Fatty acid
Glycerol

Amino
PO4
alcohol
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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 alcohols
HOCH2CHCOO
serine 41
Structure and Polarity of A
Glycerophospholipid

Copyright 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings

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 Lecithin and Cephalin
Lecithin and cephalin are glycerophospholipids
Abundant in brain and nerve tissues.
Found in egg yolk, wheat germ, and yeast.

Copyright 2007 by Pearson Education, Inc Publishing as Benjamin Cummings 43

Learning Check 15

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
O

CH2O C (CH2)16 CH3
+
O NH3

CH2O P O CH2CHCOO-

O-
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Solution
Identify the components and type of glycerophospholipid
O

CH2O C (CH2)16 CH3
O 2 stearic acids

CH2O C (CH2)16 CH3
+
O NH3
type = cephalin
CH2O P O CH2CHCOO-
serine
O-
phosphate amino alcohol
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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.

fatty acid

sphingosine

amino
PO4
alcohol 48
Sphingosine

Sphingosine is a long-chain unsaturated amino alcohol.

CH3(CH2)12 CH=CHCHOH

CHNH2

CH2OH

sphingosine
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 Sphingolipids
In sphingomyelin, a sphingolipid found in nerve cells
There is an amide bond between a fatty acid and
sphingosine, an 18-carbon alcohol.

Copyright 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings 50

Glycosphingolipids
Glycosphingolipids
contain
monosaccharides
bonded to the OH
of sphingosine by a
glycosidic bond.

Copyright 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings

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Glycosphingolipids and
Cerebrosides
Glycosphingolipids
Are sphingolipids that contain
monosaccharides.
Can be a cerebroside with galactose.

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Copyright 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings
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.

Copyright 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings

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Learning Check 16

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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