ADEK -COOH 2 22 a) IUPAC 4 6 18 b 1 1 c t 9 9
C 4 CH 3 (CH 2 ) 2 COOH 40 6 8 10 12 14 16 18 20 22 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 60 80 100 120 140 160 180 200 220 18 18 22 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- c13-1819 2219 18 18 18 20 20 22 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 18 1 17 2 18 1 16 3 17 2 15 4 16 3 14 5 15 4 13 6 5 14 12 11 7 6 13 7 8 8 9 10 11 12 9 10 - - EPA DHA 1826 1833 1836 2046 2053 2263
c 1 2 - IUPAC 18:3cis-6,cis-9,cis12 18:3-6 n -6 n-6-6 -3 - 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 1 2 3 (a) X 2 3 b 5c OH
(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
g/100g mg/100g g/100g mg/100g 5.3 430 3.7 240 41.9 560 3.4 250 () 1.4 50 3.1 370 () 27.5 55 () 10.3(33.5) 420(1400) 19-22.6-3.8 12 3.0-3.3-34.0 19 0.9-35.2-0.1-5.3 - () 51.9-72.3 150 TLC () () () -- -- - - ( )( )1-
,,, Bligh-Dyer :() 120.8 2 Folch : :() 40203 2 () 2001000l ()50 l 2ml KCl 21 0.9KCL 10ml 2 Folch I. 1. 2. 0.30.5 2l 23 2l 0.9KCL 2 3. 21 1.5l 1.5l 4. 30 10 30 5. 15,000 5 6. 5
7. 0.9KCl 0.5l 8. 2ml 21 9.,. () 10.,, 0.5ml, 15,000 5, 10 11. 12. () 13. 1mg/20l(50mg/ml) 14. 20mg (mg) +(mg) (mg) (mg) TLC TLC TLC 520cm TLC (254nm ) 2
200ml ::80201 200ml 1. 2cm () 1cm 1cm 2 1cm 3cm 2. 20l () 1cm 1cm 1l 3. 4 10l () 2 1 4. 5.
6. 3cm () 7. 8.. 9.,. 10.. 11. (2.5mg/ml) 10l25g. 12. 13. 14. L () Ls RfLs/L TLC Rf () () (cm) RfLs/L
II. 20mg ml MeOH-BuOH III. 1. MeOH-BuOH
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
µ µ µ µ µ µ µ
21 22 21 22 18 20 23 26 18 20 23 26 Cholesterol 12 17 24 25 Cholestenone 19 11 13 16 12 17 24 25 27 19 11 13 16 27 14 15 14 15 1 9 1 2 10 8 cholesterol oxidase 9 2 10 8 3 5 4 6 7 3 5 4 6 7 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
µ µ µ µ µ µ µ µ µ
-FID FID -FID CoA - CoA ACS-ACO -trans CoA CoA NADH ASC-ACO-HDT 0.5 nmol 5-100 nmol Fletcher- O- N-