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1 ADEK -COOH 2 22 a) IUPAC b 1 1 c t 9 9

2 C 4 CH 3 (CH 2 ) 2 COOH CH 3 (CH 2 ) 4 COOH CH 3 (CH 2 ) 6 COOH CH 3 (CH 2 ) 8 COOH CH 3 (CH 2 ) 10 COOH CH 3 (CH 2 ) 12 COOH CH 3 (CH 2 ) 14 COOH CH 3 (CH 2 ) 16 COOH CH 3 (CH 2 ) 18 COOH CH 3 (CH 2 ) 20 COOH CH 3 (CH 2 ) 7 CH=CH(CH 2 ) 7 COOH CH 3 (CH 2 ) 7 CH=CH(CH 2 ) 7 COOH CH 3 (CH 2 ) 7 CH=CH(CH 2 ) 11 COOH c9- t9- c O O C CH 3 (CH 2 ) 4 (CH=CH-CH 2 ) 2 (CH 2 ) 6 - COOH CH 3 CH 2 (CH=CH-CH 2 ) 3 (CH 2 ) 6 - COOH CH 3 (CH 2 ) 4 (CH=CH-CH 2 ) 3 (CH 2 ) 3 - COOH CH 3 (CH 2 ) 4 (CH=CHCH 2 ) 4 (CH 2 ) 2 - COOH CH 3 CH 2 (CH=CH-CH 2 ) 5 (CH 2 ) 2 - COOH CH 3 CH 2 (CH=CHCH 2 ) 6 CH 2 - COOH O O C c9,c12- c9,c12,c15- c6,c9,c12- c5,c8,c11,c14- c5,c8,c11,c14- c4,c7,c10,c13,c16,c19- O O C EPA DHA

3 c IUPAC 18:3cis-6,cis-9,cis12 18:3-6 n -6 n EPADHA EPA DHA 3(a) OH 3(b) 3(c) OH 4 4(a) sn-1, 2, 3 sn stereospecifically numbered 4(b) OH TG R, R, R TG TG MG DG 4c MG 2 2--sn-TG 1 3 MG MG 13 MG MG 4dDG 1,3--sn- DG 1, 2 2, 3 DG TGDG (a) X 2 3 b 5c OH

4 (a) (b) (c) HO HO O CH 2 OH sn1 H 2 CO CR O O O CH 2 OH CH HO C H sn2 2 O CR RʼC OCH RC OCH O HO CH O CH 2 OH sn3 H 2 CO CR CH 2 OH CH 2 O CR H O O H C O C R Rʼ C O C H O- H 2 C O P X O O O H 2 C O CR RʼC O C H HO CH 2 CH 2 OH O O OH OH H H H 3 C (CH 2 ) 12 C C CH C CH 2 H OH NH OH CR O

5 g/100g mg/100g g/100g mg/100g () () () 10.3(33.5) 420(1400) () TLC () () () ( )( )1-

6 ,,, Bligh-Dyer :() Folch : :() () l ()50 l 2ml KCl KCL 10ml 2 Folch I l 23 2l 0.9KCL l 1.5l ,

7 7. 0.9KCl 0.5l 8. 2ml 21 9.,. () 10.,, 0.5ml, 15,000 5, () 13. 1mg/20l(50mg/ml) mg (mg) +(mg) (mg) (mg) TLC TLC TLC 520cm TLC (254nm ) 2

8 200ml :: ml 1. 2cm () 1cm 1cm 2 1cm 3cm 2. 20l () 1cm 1cm 1l l ()

9 6. 3cm () , (2.5mg/ml) 10l25g L () Ls RfLs/L TLC Rf () () (cm) RfLs/L

10

11 II. 20mg ml MeOH-BuOH III. 1. MeOH-BuOH

12 O O CH 2 -O-C-R1 CH 2 OH CH 3 -O-C-R1 O O alkali CH -O-C-R2 CH OH CH O 3 ONa + CH 3 -O-C-R2 O CH 2 -O-C-R3 CH 2 OH CH 3 -O-C-R3 triacylglycerol glycerol methylesterified fatty acids

13 µ µ µ µ µ µ µ

14 Cholesterol Cholestenone cholesterol oxidase HO O + H 2 O 2 2H 2 O 2 + H 3 C C C NH 2 H 3 C N C O N H 3 C C C N H 3 C N C O N 4-aminoantipyrine OCH 3 OCH 3 + O 2 + H 3 CO N C 2 H 5 CH 2 CH CH 2 SO 3 Na H 3 CO DAOS OH (N-ethyl-N-(2-hydroxy-3-sulfopropyl)- 3,5-dimethoxyaniline, sodium salt) peroxidase N + C 2 H 5 CH 2 CH CH 2 SO 3 Na OH OH - + 3H 2O

15 µ µ µ µ µ µ µ µ µ

16 -FID FID -FID CoA - CoA ACS-ACO -trans CoA CoA NADH ASC-ACO-HDT 0.5 nmol nmol Fletcher- O- N-

17

09_organal2

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