1Heng Savoeun/2008 1

2

cMNgeCIg

Heng Savoeun/2008 2

1- CIv³m:UelKul

1- GamINUGasuIt ‘Amino Acid)

2- RbUetGuIn ‘Protein)

3- kabUGuIRdat ‘Carbohydrate)

4- lIBIt (Lipid )

5- nuyekøGuicGasuIt ‘Nucleic Acid)

2- Gg;suIm (Enzyme)

3- vItamIn ‘Vitamin)

3Heng Savoeun/2008 3

4

niymn&y

• lIBItKWCasarZatuEdlrlaykñúgZaturMlaysrIrag<

ó chloroform(CHCl3) GaestUn Gakul ebnsuIn‘benzene’

nigeGETr EtminrlaykñúgTwk

⇒ lk¡N;Biessrbs´vaKWkarbeg,ItCaRKab´xøaj´lÁit>enAkñúgmCÄdðanTwk

⇒ muxgarrbs´lIBItkñúgPavrs´ KWeZVICaGaharbMrugEdlpþlzamBlx¬s´

nigCasarZatud*sMxan´sMrab´ekasika

Heng Savoeun/2008 4

5

cMENkfñak;lIBIt

Õ tamTMrg´KImI lIBItRtUv:nEckCa2Rkum KW

→lIBItsaMjúaM

→ lIBItgay

Heng Savoeun/2008 5

- GasuItxøaj´‘fatty acid’

- RTIGasuIlKøIesru¨l‘triacylglycerol)

6

GasuItxøaj´‘fatty acid’

• GasuItxøaj´;

Ù GasuItxøaj´Eq¸t (Saturated fatty acids)

Ù GasuItxøaj´minEq¸t (Unsaturated fatty acid)

• - GasuItxøaj´mU"NUminEq¸t (Monounsaturated fatty acids)

• - GasuItxøaj´bU"lIminEq¸t (Polyunsaturated fatty acids )

Heng Savoeun/2008 6

7

GasuItxøaj;Eq ¥t

• GasuItxøaj´Eq¸tKWCaGasuItsrIrag<EdlmanGatUmkabUnCaExSEvgnigKμanExñg

CH3-(CH2)n-COOH GatUmkabUnticCag14 nig

eRcInCag20manedaykMr

Heng Savoeun/2008 7

8

TMrg;GasuItxøaj;Eq¥t

Heng Savoeun/2008 8

• GasuItxøaj´PaKeRcInmanGatUmkabUnCacMnYnKU

eRJHZmμtaGasuItxøaj´ekIteLIgedaysarRbtikmμ

sMeyaKbUkGatUmkabUnmþgBIr

GasuItxøaj´manknÞúyCa

ExSGuIRdUkabUnEdlP¢ab´

eTAnwgkabuksuIl

9Heng Savoeun/2008 9

GasuItxøaj;minEq¥t

• mansm¬&nÆBIrCan´mYyrWeRcInkñúgmUelKul . Ésm¬&nÆbICan´kñúgGasuItxøaj´ KWkMrman

10

stearate KWCa

GasuItxøaj´EqÁt

TMrg;suItxøaj;;minEq¥tEdlmankabUn18

oleate nig linolenate KWCaGasuItxøaj´minEqÁt

Heng Savoeun/2008 10

• GasuItxøaj´EqÁt rwg

• GasuItxøaj´minEqÁt rav

11

Cis nig trans isomers

• sm¬&nÆBIrCan´enAkñúgmU¨elKulGasuItxøaj´ GacmanlTÆPaB KW cis nig trans

isomers . bu¨Enþ TMrg´ trans kRm

Heng Savoeun/2008 11

12Heng Savoeun/2008 12

- TMrg'KImI linolenic acid (18:3Δ9c,12c,15c)

- GñkKImI; rab´BI carbonyl carbon (blue numbering)

- GñksrIr; rab´BI n (ω) carbon (red numbering)

karehAeQμaH

13

GuksuItkm μÉkÉg nigkareLIgxa

Auto-oxidation and rancidity

► kareLIgxa

• GasuItxøaj´kñúgsItuNØPaBbnÞb´ rgnUvbNþrKImI EdlehAza GuksuItkmμÉkÉg

• GasuItxøaj´ RtUvbMEbkeTACa - GuIRdUkabUn‘ hydrocarbons) • - extUn ( ketones)• - GaedGuIt (aldehydes)• - eGbuksuIt ( epoxides) • - Gal´kul( alcohols)

• Heavy metals present at low levels in fats and oils promote auto-oxidation. Fats and oils often are treated with chelating agents such as citric acid.

Heng Savoeun/2008 13

14

Mechanisms of Oxidation

• •+•• +

RH R HR O2 ROO

• + + •ROO R1H ROOH R1

• •+

+ +• •

RO R ROR• •+

• •+

R R RR

ROO ROO ROOR O2

ROO R ROOR

A. epþIm - karbeg,Itra¨DIkal´ alkyl esrI

B. dal - Rbtikmμbnþénra¨DIkal´ peroxy

C. bJ©b´ - karbeg,ItplitplKμanra¨DIkal´

15

General Mechanisms of Autoxidation

14 13 12 11 10 9

- H

CH2 CH CH CH2 CH CH CH2 R(CH2)3CH3

INITIATION

12 11 10 9

•

+ O2

(C H2)4C H3 C H C H C H C H C H2 RC H

•

12 11 10 9

+ H •

(CH2)4CH3 CH CH CH CH CH2 RCH

O

OPROPAGATION

•

16

12 11 10

HYDROPEROXIDE DECOMPOSION - OH

CH CH CH CH CH CH2 R(CH2)4CH3

O

O

H

•

•

12 11 10 9(C H

2)4

C H3 C H C H C H C H C H

2RC H

O

+ HTERMINATION

•

(PENTANE)

•

C H 3 (C H 2)3 C H 2

C H 3 (C H 2)3 C H 3

OC

HC H C H C H C H C H 2 R+ 12 11 10 9

17

Peroxide Decomposition

OH+

•

•

• +

or

R CO

H R1+ •

•+

R' OH ROH•• +

+

R'

R'H+

+ •

R C R1

H

OOH

R C R1

H

O

R C R1

O

R'H

R C R1

H

OH

R1 C H1

O

R

R'

18

RTIGasuIlKøIesru:l (triacylglycerol)

• xøaj´ nigeRbgekIteLIgBIRTIGasuIlKøIesrul ‘ehAza triglycerides)

• RTIGasuIlKøIesrul púSMeLIgBIGasuItxøaj´ nigKøIesrul

glycerol triacylglycerol

Heng Savoeun/2008 18

19

karbegáItxøaj;

karsMeyaKRTIesþrIn BIKøIesrul nigesþrIcGasuIt

20

eRbgqa nigxøaj;

• RTIGasuIlKøIesru¨lEdlcMeJHsItuNØPaBkñúgbnÞb´enArwgehAzaxøaj´

ehIyebIvarav ehAzaeRbgqa

• eRbgmanGasuItxøaj´minEqÁt‘oleic acid sMbUréRkElg’ nigPaKeRcIn

manenAkñúgruk¡Cati dUcCa eRbgsENþk eRbglá

• xøaj´stV‘animal fat’ RtUv:nbeg,IteLIgBIRTIKøIesrItEdlmanGasuIt

xøaj´EqÁt nigcMnYnGatUmkabUnKt´KUr

• eRbgRtI‘fish oils’manpleZ[bx¬s´énGasuItxøaj´minEqÁteRcIn

Heng Savoeun/2008 20

21

xøaj; nigfamBl

• RTIGasuIlKøIesrul KWCazamBlbMrugkñúgxøÜnstV EdlRtUv:nsnSMTukeday

KμanmUelKulTwkkñúgCalikaxøaj´

• Calikaxøaj´sæitenARsTab´xageRkaménEs|k PaKeRcInRtg´k|aleJH

• cMeJHbursmanxøaj´cMnYn21PaKryénTMgn´ ÉRsþIman26PaKry

• brimaNxøaj´enH GaceGaymnusSenAraMuér:n2-3ExedayGt´Gahar

• cMENkKøIkUEsnkñúgxøÜneyIgvijGacp<t´p<g´zamBl:nmindl´1ézáeT

- xøaj´ 9 kcal/g

- RbUetGuInç kabUGuIRdat, 4 kcal/g

Heng Savoeun/2008 21

22

karbMEbkGaharxøaj;

• edaysarkarminrlaykñúgTwkenH Rbdab´rMlayGaharminGacRsUbyk

xøaj´edayRtg´>:neLIy

• vaRtUveZVIRbtikmμbMEbkCamuneRkamGMeBIénGg´suIm lipase rbs´rslMEBg

kñúgeJHev[ntUcedaybg,eTACaKøIesrul nigGasuItxøaj´

• plitplénGuIRdUlIs RtUvRsUbedayRsTab´eJHev[ntUc ehIybnÞab´mk

vak*RtUvpSMeLIgvij rYcRtUv:ndwknaMedayRbUetGuIneTAkñúgQam nigpþl´

eGayCalikaxøaj´

• GasuItxøaj´RtUvbJ¢ÚneTAekasikadéTeT[tEdlvaTTYlrgnUvRbtikmμ

GuIRdUlIs nigGuksuItkmμ rhUtdl´køayCaTwknigósμ&nkabUnic

Heng Savoeun/2008 22

23

sabU‘ (Soap)

P 511 Ch 17

24

mU:elKulsabU‘(Soap Molecule)

25

etIsabU‘rMlayxøaj;dUcemþcHow soap dissolves grease

Fig 17.2

26

lIBItsaMjúaM ‘complex Lipid’

1- KøIesrU:pUsVrlIBIt (glycerophospholipid)

2- sphingolipids

3- esþrU:GuIt (steroids)

Heng Savoeun/2008 26

27

1- KøIesrU:pUsVrlIBIt (glycerophospholipid)

• glycerol 3-phosphate cg

sm¬&nÆeGEsÞenARtg´TItaMg C1

nigC2 CamYybg<MúGasuIlén

GasuItxøaj´

• cMENkpUsVatGaccgsm¬&nÆ

eGEsÞCamYynwgsmasZatu

epSgeT[t dUcCaGal´kulcMnYn 4

KW ethanolamine, choline,

L-serine nig inositol

Heng Savoeun/2008 27

• Phosphatidateman glycerol 3-phosphate nigbg<MúGasuIlBIr

• phosphatidate KWCaTMrg´gayrbs´KøIesrU¨pUsVrlIBIt

• phosphatidatemank|albU¨ElnigknÞúyminbU¨El

28

phosphatidyl choline

•CYnkalRtUv:neKehAza lecithin

•CamUelKul amphiphileEdlman

knÞúyCa hydrophobic nig

k|alCa hydrophilic

Heng Savoeun/2008 28

29

phospatidyl ethanolamine

• Ca cephalin

• CamU¨elKul amphiphile

EdlmanknÞúyCa hydrophobic

nigk|alCa hydrophilic

Heng Savoeun/2008 29

30

phosphatidyl serine

• CamU¨elKul amphiphile

EdlmanknÞúy hydrophobic

nigk|al hydrophilic

Heng Savoeun/2008 30

31

KøIesrU:pUsVrlIBIt

• phosphatidic acid manvtþman tictYcNas´kñúgPñasCIv;

• KøIesrUpUsVrlIBItEdlmanvtþmankñúgPñasCIv;KWk|alrbs´vaman alcohol

Heng Savoeun/2008 31

Inositol

32

2- sphingolipids

• sphingolipids man sphingosine CMnYsKøIesru¨l

• CaTUeTA sphingolipids rgRbtikmμemtabUlIsyWtCag phospholipids ehIyeZVI

eGayTMrg´ekasikamanesærPaBCag

• man sphingolipids cMnYn3EdlRtUvsMeyaKecjBI N-acyl-fatty acid

derivatives of sphingosine (RsLay sphingosine KW ceramide);

• Sphingomyelins

• Cerebrosides

• Gangliosides

Heng Savoeun/2008 32

33

2-1- Sphingomyelins

Heng Savoeun/2008 33

Ù sphingomyelin éneRsam myelin

minRtUv:nrgemtabUlIseTkñúgxøÜnmnusS

Ù sphingomyelin manvtþmany¨ageRcIn

enAkñúgCalikaRbsaT

34

2-2- Cerebrosides

Heng Savoeun/2008 34

• cerebrosidesrW glycosphingolipids

ó galacto-cerebrosides nig gluco-

cerebrosides• cerebroside manvtþmany"ageRcIn

kñúgCalikaRbsaT

• KøIkUlIBIt KWCalIBItsaMjaMmYyEdlmantYnaTIy¨agsMxan´kñúg

sarJg<kay

ó1 CaGñkTTYlxusRtUveTAelIlk¡N;énmuxgarBiessenA

elIPñasekasikaQamRkhm

ó2 Ca receptor sMrab´karcgsm¬&nÆénvIrusnigPñasekasika

35Heng Savoeun/2008 35

2-3- Gangliosides

ó1 CaGñkTTYlxusRtUveTAelI

lk¡N;énmuxgarBiessenA

elIPñasekasikaQamRkhm

ó2 Ca receptor sMrab´GrmUn

36

3- esþrU:GuIt (steroids)

• esþrUGuIt rlaykñúgZaturMlaylIBIt

• vaRtUv:ncat´za lIBIt edaysarcriklk¡N;énPaBrlayrbs´va Rsed[g

• esþrUGuItTaMgGs´manrgVg´ cyclo-pentano phenanthrene Edl mankabUn17

CamUldðanRKw;énTMrg´rbs´va

Heng Savoeun/2008 36

37

kUelesþru:l ‘cholesterol’

• kUelesþru¨l KWCaesþrU¨GuIt

• kñúgznikstV kUelesþrulCasarZatuepþIménBBYk steroid hormone

dUcCa androgen nig estrogen man«TÆiBlelIkarvivDÄ nigmuxgarePT

Heng Savoeun/2008 37