HIGH-PERFORMANCE LIQUID-CHROMATOGRAPHY OF THE TRIACYLGLYCEROLS OF VERNONIA-GALAMENSIS AND CREPIS-ALPINA SEED OILS

被引:20
作者
NEFF, WE
ADLOF, RO
KONISHI, H
WEISLEDER, D
机构
[1] Department of Agriculture, Food Quality and Safety Research, National Center for Agricultural Utilization Research, Agricultural Research Service, U.S., Peoria, 61604, Illinois
关键词
CARBON NMR; CREPENYNIC ACID; EPOXY AND ACETYLENIC MONOACID TRIGLYCERIDES; FLAME-IONIZATION DETECTION; GAS CHROMATOGRAPHY; PROTON NMR; REVERSED-PHASE HIGH-PERFORMANCE LIQUID CHROMATOGRAPHY; STEREOCHEMISTRY; VERNOLIC ACID;
D O I
10.1007/BF02542574
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
The triacylglycerols of Vernonia galamensis and Crepis alpina seed oils were characterized because these oils have high concentrations of vernolic (cis-12,13-epoxy-cis-9-octadecenoic) and crepenynic (cis-9-octadecen-12-ynoic) acids, respectively. The triacylglycerols were separated from other components of crude oils by solid-phase extraction, followed by resolution and quantitation of the individual triacylglycerols by reversed-phase high-performance liquid chromatography with an acetonitrile/methylene chloride gradient and flame-ionization detection. Isolated triacylglycerols were characterized by proton and carbon nuclear magnetic resonance and by capillary gas chromatography of their fatty acid methyl esters. The locations of the fatty acids on the glycerol moieties in the oils were obtained by lipolysis. The Vernonia galamensis oil contained 50% trivernoloyl and 21% divernoloyllinoleoyl glycerols along with 20% triacylglycerols with one vernolic and two other fatty acids. The Crepis alpina oil contained 36% tricrepenynoyl and 33% dicrepenynoyllinoleoyl glycerols, 17% triacylglycerols with two crepenynic and one other fatty acid and 7% triacylglycerols with one crepenynic acid and two other fatty acids. Vernolic acid was found at both the 1(3)- and 2-glycerol carbons but was more abundant at the 1,(3)-position in the Vernonia galamensis oil. Crepenynic acid was found at both glycerol carbon positions but was more abundant at the 2-position in the Crepis alpina oil.
引用
收藏
页码:449 / 455
页数:7
相关论文
共 20 条
[1]   PREPARATION OF DEUTERIUM-LABELED METHYL LINOLEATE AND ITS GEOMETRIC ISOMERS FROM NATURAL SEED OILS [J].
ADLOF, RO ;
RAKOFF, H ;
EMKEN, EA .
JOURNAL OF THE AMERICAN OIL CHEMISTS SOCIETY, 1991, 68 (05) :303-306
[2]   PILOT-PLANT EXTRACTION OF OIL FROM VERNONIA-GALAMENSIS SEED [J].
AYORINDE, FO ;
CARLSON, KD ;
PAVLIK, RP ;
MCVETY, J .
JOURNAL OF THE AMERICAN OIL CHEMISTS SOCIETY, 1990, 67 (08) :512-518
[3]   C-13-NMR OF DOUBLE AND TRIPLE BOND CARBON-ATOMS OF UNSATURATED FATTY-ACID METHYL-ESTERS [J].
BUS, J ;
SIES, I ;
LIEKENJIE, MSF .
CHEMISTRY AND PHYSICS OF LIPIDS, 1977, 18 (01) :130-144
[4]  
BUTTERFIELD R O, 1978, Progress in Lipid Research, V17, P93, DOI 10.1016/0079-6832(78)90006-X
[5]   CHEMICAL EPOXIDATION OF A NATURAL UNSATURATED EPOXY SEED OIL FROM VERNONIA-GALAMENSIS AND A LOOK AT EPOXY OIL MARKETS [J].
CARLSON, KD ;
CHANG, SP .
JOURNAL OF THE AMERICAN OIL CHEMISTS SOCIETY, 1985, 62 (05) :934-939
[6]  
CARLSON KD, 1981, NEW SOURCES FATS OIL, pCH21
[7]  
CHRISTIE WW, 1989, GAS CHROMATOGRAPHY L, P242
[8]  
CHRISTIE WW, 1987, LIPID ANAL, P145
[9]   COMPOSITIONAL VARIATION IN SEED OILS OF CREPIS GENUS [J].
EARLE, FR ;
BARCLAY, AS ;
WOLFF, IA .
LIPIDS, 1966, 1 (05) :325-&
[10]   PMR ANALYSIS OF NON-CONJUGATED ALKENOIC AND ALKYNOIC ACIDS AND ESTERS [J].
FROST, DJ ;
GUNSTONE, FD .
CHEMISTRY AND PHYSICS OF LIPIDS, 1975, 15 (01) :53-85