Skip to main content
Log in

Vernonia anthelmintica (L.) Willd. trivernolin, 1,3-divernolin and vernolic (Epoxyoleic) acid from the seed oil

  • Technical
  • Published:
Journal of the American Oil Chemists Society

Abstract

The epoxy fatty acid components isolated from the seed oil ofV. anthelmintica, Indian ironweed, where the seed had been allowed to undergo lipolysis after grinding, were trivernolin, 1,3-divernolin, and vernolic acid. By inactivation of the hydrolytic enzyme system present in the seed, oil containing more than 50% trivernolin may be obtained. This species has potentialities as a replacement crop for those now in surplus; its seed contains 20 to 26% of an oil rich in epoxyoleic (vernolic) acid combined as glycerides amounting to 70 to 75%.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. Dodoens, Rembert (Henrie Lyte Translation), “A New Herball, or Historie of Plants”, imprinted at London by N. Newton, p. 40 (1586).

  2. Pena, P., and M. de Lobel, “Stirpium Adversaria Nova”, engraved at London by Thomas Pursoetius, p. 145 (1570).

  3. Turner, W., “A New Herball”, imprinted by Steven Mierdman, London, see “Of Coniza”, not paginated (1551).

  4. Ghosh, J. C., Pharm. J.,121, 54 (1928).

    CAS  Google Scholar 

  5. Linné, C. von, Carolini a Linné Species Plantarum, Holmiae, Laurentii Salvii, ed. 2. Vol. II, 1207 (1763).

    Google Scholar 

  6. Linné, C. von (K. L. Willdenow, ed.), Carolini a Linné Species Plantarum, Beroli, G. C. Nauk, ed. 4, Vol. III, Part 3, 1634 (1804).

  7. Gleason, H. A., Bull. N. Y. Bot. Gard.,4, 144 (1906).

    Google Scholar 

  8. Lindley, J., and T. Moore, “The Treasury, of Botany,” Longmans, Green and Co., London, Part 2, p. 1210 (1866).

    Google Scholar 

  9. Dynock, W., C. J. H. Warden, and D. Hooper, “Pharmacographia Indica,” Vol. 2. Trübner & Co., London, p. 241 (1891).

    Google Scholar 

  10. Kesava-Menon, A., J. Soc. Chem. Ind.,29, 1428 (1910).

    Google Scholar 

  11. Chopra, R. N., “Indigenous Drugs of India,” The Art Press, Calcutta, p. 409 (1933).

    Google Scholar 

  12. Chopra, R. N., N. N. Ghosh, and A. K. Mukerji Indian J. Med. Research,22, 183 (1934).

    CAS  Google Scholar 

  13. Majumdar, D. N., Indian J. Pharm.5, 61 (1943).

    CAS  Google Scholar 

  14. Nadkarni, K. M., “The Indian Materia Medica,” Bombay, p. 883 (1927).

  15. Caius, J. F., and K. S. Mhaskar, Indian J. Med. Res.,11, 353 (1923).

    CAS  Google Scholar 

  16. Kirtikar, K. R., and B. D. Basu, “Indian Medicinal Plants,” Indian Press, Allahabad, Part I, p. 670; Part III, Plate No. 515A (1918); also 2nd ed., p. 1325 (1933).

  17. Bhaduri, K., Proc. Chem. Soc. (London),28, 63 (1912).

    Google Scholar 

  18. Vidyarthi, N. L., Proc. Ind. Sci. Congress, Sect III, 79 (1940).

    Google Scholar 

  19. Vidyarthi, N. L., and M. V. Mallya, J. Indian Chem. Soc.,16, 479 (1939).

    CAS  Google Scholar 

  20. Vidyarthi, N. L., Patna Univ. J.,1, 51 (1945).

    CAS  Google Scholar 

  21. Gunstone, F. D., J. Chem. Soc., 1611 (1954).

  22. Smith, C. R., Jr., K. F. Koch, and I. A. Wolff, JAOCS,36, 219 (1959).

    Article  CAS  Google Scholar 

  23. Morris, L. J., “The Absolute Configuration ofcis-12: 13-Epoxyoleic Acid from Vernonia Oil,” Meeting of the A.O.C.S., St. Louis, Mo., May 1–3, 1961.

  24. Morris, L. J., H. Hayes, and R. T. Holman, JAOCS,38, 316 (1961).

    Article  CAS  Google Scholar 

  25. Earle, F. R., I. A. Wolff, and Q. Jones,Ibid., 37, 254 (1960).

    Article  CAS  Google Scholar 

  26. Van Etten, C. H., R. W. Miller, I. A. Wolff, and Q. Jones, J. Agr. & Food Chem.,9, 79 (1961).

    Article  Google Scholar 

  27. Miwa, T. K., F. R. Earle, G. C. Miwa, and I. A., Wolff. “Biosynthesis of Epoxyoleic Acid in MaturingVernonia anthelmintica Seeds. Dihydroxyoleic Acid—A Precursor,” Meeting of American Chemical Society, St. Louis, Mo., March 21–30, 1961.

  28. Riser, G. R., J. R. Hunter, J. S. Ard, and L. P. Witnauer, JAOCS (to be published).

  29. Bharucha, K. E., and F. D. Gunstone, J. Sci., Food Agr.,7, 606 (1956).

    Article  CAS  Google Scholar 

  30. Chisholm, M. J., and C. Y. Hopkins, Can. J. Chem.,35, 358 (1957).

    Article  CAS  Google Scholar 

  31. Hopkins, C. Y., and M. J. Chisholm, JAOCS,35, 96 (1959).

    Google Scholar 

  32. Hopkins, C. Y., and M. J. Chisholm,Ibid., 37, 682 (1960).

    Article  CAS  Google Scholar 

  33. Smith, C. R., Jr., M. O. Bagby, R. L. Lohmar, C. A. Glass, and I. A. Wolff, J. Org. Chem.,25, 218 (1960).

    Article  CAS  Google Scholar 

  34. Vioque, E., L. J. Morris, and R. T. Holman, JAOCS,38, 489 (1961).

    CAS  Google Scholar 

  35. Hopkins, C. Y., and H. J. Bernstein, Can. J. Chem.,37, 775 (1959).

    Article  CAS  Google Scholar 

  36. Gunstone, F. D., and P. J. Sykes, J. Sci. Food and Agr.,12, 115 (1961).

    Article  CAS  Google Scholar 

  37. Smith, C. R., Jr., K. F. Koch, and I. A. Wolff, Chem. and Ind., 259 (1959).

  38. Morris, L. J., R. T. Holman, and K. Fontell, J. Lipid Res.,2, 68 (1961).

    CAS  Google Scholar 

  39. Swern, D., and G. B. Dickel, J. Am. Chem. Soc.,76, 1957 (1954).

    Article  CAS  Google Scholar 

  40. Pigulevskii, G. V., and I. N. Naidenova, Zhur. Obshehei. Khim.,28, 234 (1958).

    CAS  Google Scholar 

  41. Osbond, J. M., Proc. Chem. Soc., 221 (1960) and 5270 (1961).

  42. Tulloch, A. P., B. M. Craig, and G. A. Ledingham, Can. J. Microbiology,5, 485 (1959).

    Article  CAS  Google Scholar 

  43. Tulloch, A. P., Can. J. Chem.,38, 204 (1940).

    Article  Google Scholar 

  44. Chisholm, M. J., and C. Y. Hopkins, Chem. and Ind., 1154 (1959).

  45. Gunstone, F. D., and L. J. Morris, J. Chem. Soc., 2127 (1959).

  46. Earle, F. R., E. H. Melvin, L. H. Mason, C. H. Van Etten, and I. A. Wolff, JAOCS,36, 304 (1959).

    Article  CAS  Google Scholar 

  47. Morris, L. J., and R. T. Holman, J. Lipid Res.,2, 77 (1961).

    CAS  Google Scholar 

  48. Durbetaki, A. J., Anal. Chem.,28, 2000 (1956).

    Article  CAS  Google Scholar 

  49. Scott, W. E., C. F. Krewson, and R. W. Riemenschneider, “Vernonia anthelmintiea (L.) Willd. Enzyme Activity in the Seed,” Meeting of the A.O.C.S., Chicago, Ill., Oct. 30-Nov. 1, 1961.

  50. Radlove, S. B., R. V. Madrigal, and R. Slutkin, JAOCS,37, 570 (1960).

    Article  CAS  Google Scholar 

  51. Daubert, B. F., and E. S. Lutton, J. Am. Chem. Soc.,69, 1449 (1947).

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Additional information

Eastern Utilization Research and Development Division, Agricultural Research Service, U.S.D.A.

About this article

Cite this article

Krewson, C.F., Ard, J.S. & Riemenschneider, R.W. Vernonia anthelmintica (L.) Willd. trivernolin, 1,3-divernolin and vernolic (Epoxyoleic) acid from the seed oil. J Am Oil Chem Soc 39, 334–340 (1962). https://doi.org/10.1007/BF02638798

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02638798

Keywords

Navigation