The triacylglycerols ofVernonia galamensis andCrepis 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. TheVernonia galamensis oil contained 50% trivernoloyl and 21% divernoloyllinoleoyl glycerols along with 20% triacylglycerols with one vernolic and two other fatty acids. TheCrepis 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 theVernonia galamensis oil. Crepenynic acid was found at both glycerol carbon positions but was more abundant at the 2‐position in theCrepis alpina oil.
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Neff et al. (1993) studied this question.