Vernolic acid explained

Vernolic acid (leukotoxin B[1] or isoleukotoxin[2]) is a long chain fatty acid that is monounsaturated and contains an epoxide. It is a cis epoxide derived from the C12–C13 alkene of linoleic acid.[3] Vernolic acid was first definitively characterized in 1954[4] and its absolute configuration determined in 1966.[5] It is a major component in vernonia oil, which is produced in abundance by the genera Vernonia and Euphorbia and is a potentially useful biofeedstock.

Occurrence

Vernonia oil is extracted from the seeds of the Vernonia galamensis (ironweed), a plant native to eastern Africa. The seeds contain about 40 to 42% oil of which 73 to 80% is vernolic acid. The best varieties of V. anthelmintica contain about 30% less vernolic acid.

Vernolic acid is not commonly found in plants in significant quantities, but some plants which do contain it are Vernonia, Stokesia, Crepis (from the daisy family), and Euphorbia lagascae and Bernardia pulchella from the Euphorbiaceae.[6]

Potential applications

Vernonia oil has been proposed as a precursor to adhesives, varnishes and paints, and industrial coatings. Its low viscosity recommends its use as a nonvolatile solvent in oil-based paints since it will become incorporated in the dry paint rather than evaporating into the air.[7]

In its application as an epoxy oil,[8] vernonia oil competes with soybean or linseed oil, which supply most of the market for these applications. Its low viscosity makes it more desirable than fully epoxidized linseed or soybean oils. It is comparable to partially epoxidized linseed or soybean oil.[9]

Toxicity

In a variety of mammalian species, vernolic acid is made by the metabolism of linoleic acid by cytochrome P450 epoxygenase enzymes; under these circumstances it is termed leukotoxin because of its toxic effects on leukocytes and other cell types and of its ability to produce multiple organ failure and respiratory distress when injected into rodent animal models of the acute respiratory distress syndrome.[10] [11] [12] These effects appear due to the conversion of vernolic acid to its dihydroxy counterparts. For instance, (12S,13R)-EpOME is converted by soluble epoxide hydrolase (sEH) to (12R,13R)-dihydroxy-9Z-octadecenoic acid due to inversion at C12 carbon atom during hydrolysis. A mixture of this dihydroxy acid with its 12S,13S enantiomer has been termed isoleukotoxin diol.[13] [14] Some studies suggest but have not yet proven that vernolic acid is responsible for or contributes to multiple organ failure, respiratory distress, and certain other cataclysmic diseases in humans (see).

Related compounds

Notes and References

  1. Web site: PubChem Compound Summary for CID 6449780, Vernolic acid. PubChem. National Center for Biotechnology Information. 29 May 2023.
  2. The octadecanoids: an emerging class of lipid mediators . Quaranta A, Revol-Cavalier J, Wheelock CE . December 2022 . Biochem Soc Trans . 50 . 6 . 1569–1582[1575] . 10.1042/BST20210644 . 9788390 . 36454542.
  3. Cytochrome P450-derived Linoleic Acid Metabolites EpOMEs and DiHOMEs: A Review of Recent Studies . December 2020 . Hildreth K, Kodani SD, Hammock BD, Zhao L . The Journal of Nutritional Biochemistry . 86 . article 108484 . 10.1016/j.jnutbio.2020.108484 . 7606796 . 32827665 .
  4. Gunstone FD . 1954. Fatty acids. Part II. The nature of the oxygenated acid present in Vernonia anthelmintica (Willd.) seed oil . Journal of the Chemical Society . 1954 . 1611–1616 . 10.1039/JR9540001611 .
  5. Naturally occurring epoxy acids. IV. The absolute optical configuration of vernolic acid . January 1966 . Morris . L.J. . Wharry . D.M. . Lipids . 1 . 1 . 41–46 . . 10.1007/BF02668123 .
  6. Cahoon EB, Ripp KG, Hall SE, McGonigle B . Transgenic production of epoxy fatty acids by expression of a cytochrome P450 enzyme from Euphorbia lagascae seed . Plant Physiology . 128 . 2 . 615–24 . February 2002 . 11842164 . 148923 . 10.1104/pp.010768 .
  7. Book: Alternative Field Crops Manual . Vernonia . Teynor TM, Putnam DJ, Oplinger ES, Oelke EA, Kelling KA, Doll JD . 2006-09-10 . February 1992 .
  8. Variability in oil and vernolic acid contents in the new Vernonia galamensis collection from East Africa . Mohamed AI, Mebrahtu T, Andebrhan T . 1999 . 272–274 . Janick J . Perspectives on New Crops and New Uses . 2006-09-10 .
  9. Muturi . Patrick . Wang . Danqing . Dirlikov . Stoil . vanc . Epoxidized vegetable oils as reactive diluents I. Comparison of vernonia, epoxidized soybean and epoxidized linseed oils . Progress in Organic Coatings . 25 . 85–94 . 1994 . 10.1016/0300-9440(94)00504-4 .
  10. Linhartová I, Bumba L, Mašín J, Basler M, Osička R, Kamanová J, Procházková K, Adkins I, Hejnová-Holubová J, Sadílková L, Morová J, Sebo P . RTX proteins: a highly diverse family secreted by a common mechanism . FEMS Microbiology Reviews . 34 . 6 . 1076–112 . November 2010 . 20528947 . 3034196 . 10.1111/j.1574-6976.2010.00231.x .
  11. Spector AA, Kim HY . Cytochrome P450 epoxygenase pathway of polyunsaturated fatty acid metabolism . Biochimica et Biophysica Acta (BBA) - Molecular and Cell Biology of Lipids . 1851 . 4 . 356–65 . April 2015 . 25093613 . 4314516 . 10.1016/j.bbalip.2014.07.020 .
  12. 22715155 . 3413237 . 2012 . Edwards . L. M. . Metabolomics reveals increased isoleukotoxin diol (12,13-DHOME) in human plasma after acute Intralipid infusion . The Journal of Lipid Research . 53 . 9 . 1979–86 . Lawler . N. G. . Nikolic . S. B. . Peters . J. M. . Horne . J . Wilson . R . Davies . N. W. . Sharman . J. E. . 10.1194/jlr.P027706 . free .
  13. Greene JF, Newman JW, Williamson KC, Hammock BD . Toxicity of epoxy fatty acids and related compounds to cells expressing human soluble epoxide hydrolase . Chemical Research in Toxicology . 13 . 4 . 217–26 . April 2000 . 10775319 . 10.1021/tx990162c .
  14. Bioactivation of leukotoxins to their toxic diols by epoxide hydrolase . Moghaddam MF, Grant DF, Cheek JM, Greene JF, Williamson KC, Hammock BD . May 1997 . Nature Medicine . 3 . 5 . Nature Publishing Group . 562–566 . 10.1038/nm0597-562 . 7095900 . 9142128 .

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