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Chemical Compound Review

Vernoleate     (Z)-11-[(2S,3R)-3- pentyloxiran-2-yl]undec...

Synonyms: Vernolic acid, CHEBI:27706, LMFA02000282, AC1O6A3X, 12S,13R-EpOME, ...
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Disease relevance of Vernoleate


High impact information on Vernoleate

  • Furthermore, the C12 and C13 positions in vernolic acid are less depleted, consistent with a change in hybridization state from sp(2) to sp(3) [2].
  • However, the C11 position shows a marked relative enrichment in the vernolic acid, implying that it plays a role in the epoxidase but not the desaturase mechanism [2].
  • To clarify the biosynthetic origin of vernolic acid in E. lagascae seed, an expressed sequence tag analysis was conducted [3].
  • We investigated the substrate preferences of acyl CoA:diacylglycerol acyltransferases (DGAT) of two natural high accumulators of vernolic acid, Vernonia galamensis and Stokesia laevis, as compared with a common oilseed crop soybean [4].
  • Intact vernonia oil as the starting material gave a triple-headed cationic amphiphile, containing three vernolic acid derived moieties connected through a glycerol backbone [5].

Biological context of Vernoleate


Associations of Vernoleate with other chemical compounds


Gene context of Vernoleate

  • Regio- and stereoselectivity of cytochrome P-450 and peroxygenase-dependent formation of cis-12,13-epoxy-9(Z)-octadecenoic acid (vernolic acid) in Euphorbia lagascae [8].
  • The effects of electron donors in the yeast expression system were tested but cytochrome b5 and cytochrome b5 reductase genes from Arabidopsis thaliana co-expressed with the epoxygenase had little effect on vernolic acid accumulation in the yeast [9].


  1. Level of accumulation of epoxy fatty acid in Arabidopsis thaliana expressing a linoleic acid delta12-epoxygenase is influenced by the availability of the substrate linoleic acid. Rezzonico, E., Moire, L., Delessert, S., Poirier, Y. Theor. Appl. Genet. (2004) [Pubmed]
  2. Quantitative deuterium isotopic profiling at natural abundance indicates mechanistic differences for delta 12-epoxidase and delta 12-desaturase in Vernonia galamensis. Billault, I., Duan, J.R., Guiet, S., Robins, R.J. J. Biol. Chem. (2005) [Pubmed]
  3. Transgenic production of epoxy fatty acids by expression of a cytochrome P450 enzyme from Euphorbia lagascae seed. Cahoon, E.B., Ripp, K.G., Hall, S.E., McGonigle, B. Plant Physiol. (2002) [Pubmed]
  4. Diacylglycerol acyltransferases from Vernonia and Stokesia prefer substrates with vernolic acid. Yu, K., McCracken, C.T., Li, R., Hildebrand, D.F. Lipids (2006) [Pubmed]
  5. Novel cationic amphiphilic derivatives from vernonia oil: synthesis and self-aggregation into bilayer vesicles, nanoparticles, and DNA complexants. Grinberg, S., Linder, C., Kolot, V., Waner, T., Wiesman, Z., Shaubi, E., Heldman, E. Langmuir : the ACS journal of surfaces and colloids. (2005) [Pubmed]
  6. Fatty acid selectivity of a lipase purified from Vernonia galamensis seed. Ncube, I., Gitlesen, T., Adlercreutz, P., Read, J.S., Mattiasson, B. Biochim. Biophys. Acta (1995) [Pubmed]
  7. Characterization of a Euphorbia lagascae epoxide hydrolase gene that is induced early during germination. Edqvist, J., Farbos, I. Biochem. Soc. Trans. (2000) [Pubmed]
  8. Regio- and stereoselectivity of cytochrome P-450 and peroxygenase-dependent formation of cis-12,13-epoxy-9(Z)-octadecenoic acid (vernolic acid) in Euphorbia lagascae. Blee, E., Ståhl, U., Schuber, F., Stymne, S. Biochem. Biophys. Res. Commun. (1993) [Pubmed]
  9. Expression of a Stokesia laevis epoxygenase gene. Hatanaka, T., Shimizu, R., Hildebrand, D. Phytochemistry (2004) [Pubmed]
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