We. Neff et al., HIGH-PERFORMANCE LIQUID-CHROMATOGRAPHY OF THE TRIACYLGLYCEROLS OF VERNONIA-GALAMENSIS AND CREPIS-ALPINA SEED OILS, Journal of the American Oil Chemists' Society, 70(5), 1993, pp. 449-455
The triacylglycerols of Vernonia galamensis and Crepis alpina seed oil
s were characterized because these oils have high concentrations of ve
rnolic (cis-12,13-epoxy-cis-9-octadecenoic) and crepenynic (cis-9-octa
decen-12-ynoic) acids, respectively. The triacylglycerols were separat
ed from other components of crude oils by solid-phase extraction, foll
owed by resolution and quantitation of the individual triacylglycerols
by reversed-phase high-performance liquid chromatography with an acet
onitrile/methylene chloride gradient and flame-ionization detection. I
solated triacylglycerols were characterized by proton and carbon nucle
ar magnetic resonance and by capillary gas chromatography of their fat
ty acid methyl esters. The locations of the fatty acids on the glycero
l moieties in the oils were obtained by lipolysis. The Vernonia galame
nsis oil contained 50% trivernoloyl and 21% divernoloyllinoleoyl glyce
rols along with 20% triacylglycerols with one vernolic and two other f
atty acids. The Crepis alpina oil contained 36% tricrepenynoyl and 33%
dicrepenynoyllinoleoyl glycerols, 17% triacylglycerols with two crepe
nynic and one other fatty acid and 7% triacylglycerols with one crepen
ynic acid and two other fatty acids. Vernolic acid was found at both t
he 1(3)- and 2-glycerol carbons but was more abundant at the 1,(3)-pos
ition in the Vernonia galamensis oil. Crepenynic acid was found at bot
h glycerol carbon positions but was more abundant at the 2-position in
the Crepis alpina oil.