Journal of the American Oil Chemists' Society

, Volume 75, Issue 12, pp 1761–1765 | Cite as

Cyclopropenoic fatty acids in gymnosperms: The seed oil of Welwitschia

Article

Abstract

The seed oil of the gymnosperm Welwitschia mirabilis was found to contain malvalic acid, a cyclopropenoic fatty acid. This is in sharp contrast to most other gymnosperms, which contain Δ5cis-fatty acids as well as the normal set of fatty acids. The importance of this finding in relation to questions of the evolution of the Gymnospermae and Angiospermae, the two main branches of higher plants, is briefly discussed.

Key words

Angiosperms Cimicifuga cyclopropenoic fatty acids Ephedra evolution Gnetum gymnosperms malvalic acid Pseudotsuga Welwitschia 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    Berry, S.K., Cyclopropenoid Fatty Acids in Some Malaysian Edible Seeds and Nuts, J. Food Sci. Technol. (India) 17:224–227 (1980).Google Scholar
  2. 2.
    Vickery, J.R., The Occurrence of Dihydromalvalic Acid in Some Seed Oils, J. Am. Oil Chem. Soc. 58:731–732 (1981).CrossRefGoogle Scholar
  3. 3.
    Mustafa, J., A. Gupta, M.S. Ahmad, Jr., F. Ahmad, and S.M. Osman, Cyclopropenoid Fatty Acids in Gnetum scandens and Sterculia pallens Seed Oils, Ibid.:1191–1192 (1986).CrossRefGoogle Scholar
  4. 4.
    Aitzetmüller, K., Seed Fatty Acids, Chemotaxonomy and Renewable Resources, in Oils-Fats-Lipids 1995: Proceedings of the 21st World Congress of the International Society for Fat Research, The Hague, 1995, P.J. Barnes & Associates, Bridgwater, 1996, pp. 117–120.Google Scholar
  5. 5.
    Takagi, T. and Y. Itabashi, cis-5-Olefinic Unusual Fatty Acids in Seed Lipids of Gymnospermae and Their Distribution in Triacylglycerols, Lipids 17:716–723 (1982).CrossRefGoogle Scholar
  6. 6.
    Vickery, J.R., F.B. Whitfield, G.L. Ford, and B.H. Kennett, The Fatty Acid Composition of Gymnospermae Seed and Leaf Oils, J. Am. Oil Chem. Soc. 61:573–575 (1984).CrossRefGoogle Scholar
  7. 7.
    Wolff, R.L., and C.C. Bayard, Fatty Acid Composition of Some Pine Seed Oils, Ibid.1043–1046 (1995).Google Scholar
  8. 8.
    Doyle, J.A., M.J. Donoghue, and E.A. Zimmer, Integration of Morphological and Ribosomal RNA Data on the Origin of Angiosperms, Ann. Mo. Bot. Gard. 81:419–450 (1994).CrossRefGoogle Scholar
  9. 9.
    Doyle, J.A., and M.J. Donoghue, The Origin of Angiosperms: A Cladistic Approach, in The Origins of Angiosperms and Their Biological Consequences, edited by E.M. Friis, W.G. Chaloner, and P.R. Crane, Cambridge University Press, Cambridge, 1987, p. 17.Google Scholar
  10. 10.
    Doyle, J.A. and M.J. Donoghue, Phylogenies and Angiosperm Diversification, Paleobiology 19:141–167 (1993).Google Scholar
  11. 11.
    Daulatabad, C.D., S.C. Hiremath, and R.F. Ankalgi, Component Fatty Acids of Welwitschia mirabilis, Hook f. Seed Oil, Fette Seifen Anstrichm. 87:171–172 (1985).Google Scholar
  12. 12.
    Aitzetmüller, K., Fatty Acid Patterns of Ranunculaceae Seed Oils: Phylogenetic Relationships, Plant Syst. Evol. [Suppl.] 9:229–240 (1995).Google Scholar
  13. 13.
    Tsevegsüren, N., and K. Aitzetmüller, Unusual Δ5cis-Fatty Acids in Seed Oils of Cimicifuga Species, J. High Resol. Chromatogr. 20:237–241 (1997).CrossRefGoogle Scholar
  14. 14.
    Aitzetmüller, K., Capillary GLC Fatty Acid Fingerprints of Seed Lipids—A Tool in Plant Chemotaxonomy? Ibid.488–490 (1993).CrossRefGoogle Scholar
  15. 15.
    Aitzetmüller, K., and N. Tsevegsüren, Occurrence of γ-Linolenic Acid in Ranunculaceae Seed Oils, J. Plant Physiol. 143:578–580 (1994).Google Scholar
  16. 16.
    Aitzetmüller, K., and N. Tsevegsüren, Seed Fatty Acids, “Front-End”-Desaturases and Chemotaxonomy—A Case Study in the Ranunculaceae, Ibid.538–543 (1994).Google Scholar
  17. 17.
    Aitzetmüller, K., G. Werner, and N. Tsevegsüren, Screening of Seed Lipids for γ-Linolenic Acid: Capillary Gas-Liquid Chromatographic Separation of 18:3 Fatty Acids with Δ5 and Δ6 Double Bonds, Phytochem. Anal. 4:249–255 (1993).CrossRefGoogle Scholar
  18. 18.
    Tsevegsüren, N., and K. Aitzetmüller, γ-Linolenic Acid in Anemone spp. Seed Lipids, Lipids 28:841–846 (1993).CrossRefGoogle Scholar
  19. 19.
    Tsevegsüren, N. and K. Aitzetmüller, γ-Linolenic and Stearidonic Acids in Mongolian Boraginaceae, J. Am. Oil Chem. Soc. 73:1681–1684 (1996).CrossRefGoogle Scholar
  20. 20.
    Tsevegsüren, N., K. Aitzetmüller, and K. Vosmann, Capillary GLC Study of γ-Linolenic Acid in Youngia tenuicaulis (Campositae) Seed Oil, Proc. 19th Inst. Symp. Capillary Chromatogr. Electrophoresis No. 71, pp. 344–345 (1997).Google Scholar
  21. 21.
    Tsevegsüren, N., K. Aitzetmüller, and K. Vosmann, Unusual Fatty Acids in Compositae: γ-Linolenic Acid in Saussurea spp. Seed Oils, J. High Resol. Chromatogr. 20:315–320 (1997).CrossRefGoogle Scholar
  22. 22.
    Fisher, G.S., and W.H. Schuller, Gas Chromatographic Analysis of Cyclopropenoid Acids in Cottonseed Oils, J. Am. Oil Chem. Soc. 58:943–946 (1981).Google Scholar
  23. 23.
    Schneider, E.L., S.P. Loke, and D.T. Hopkins, Gas-Liquid Chromatographic Analysis of Cyclopropenoid Fatty Acids, Ibid.585–590 (1968).Google Scholar
  24. 24.
    Ahmad, M.S., Jr., M.U. Ahmad, S.M. Osman, and J.A. Ballantine, Eriolaena hookeriana Seed Oil: A Rich Source of Malvalic Acid, Chem. Phys. Lipids 25:29–38 (1979).CrossRefGoogle Scholar
  25. 25.
    Eisele, T.A., L.M. Libbey, N.E. Pawlowski, J.E. Nixon, and R.O. Sinnhuber, Mass Spectrometry of the Silver Nitrate Derivatives of Cyclopropenoid Compounds, Ibid.316–326 (1974).PubMedCrossRefGoogle Scholar
  26. 26.
    Badami, R.C., K.B. Patil, Y.V. Subbarao, G.S.R. Sastri, and G.K. Vishvanathrao, Cyclopropenoid Fatty Acids of Sterculia Oils by Gas-Liquid Chromatography, Fette Seifen Anstrichm. 82:317–318 (1980).CrossRefGoogle Scholar
  27. 27.
    Bohannon, M.B., and R. Kleiman, Cyclopropene Fatty Acids of Selected Seed Oils from Bombacaceae, Malvaceae, and Sterculiaceae, Lipids 13:270–273 (1978).PubMedCrossRefGoogle Scholar
  28. 28.
    Vickery, J.R., The Fatty Acid Composition of Seed Oils from Ten Plant Families with Particular Reference to Cyclopropene and Dihydrosterculic Acids, J. Am. Oil Chem. Soc. 57:87–91 (1980).Google Scholar
  29. 29.
    Lie Ken Jie, M.S.F., Carbocyclic and Furanoid Fatty Acids, in Handbook of Chromatography—Lipids, edited by G. Zweig and J. Sherma, CRC Press, Boca Raton, 1984, pp. 277–294.Google Scholar
  30. 30.
    Christie, W.W., Cyclopropane and Cyclopropene Fatty Acids, in Topics in Lipid Chemistry, Vol. 1, edited by F.D. Gunstone, Logos Press Limited, London, 1970, pp. 1–49.Google Scholar
  31. 31.
    Gaydou, E.-M., and A.R.P. Ramanoelina, Cyclopropenoic Fatty Acids of Malvaceae Seed Oils by Gas-Liquid Chromatography, Fette Seifen Anstrichm. 86:82–84 (1984).CrossRefGoogle Scholar
  32. 32.
    Raju, P.K., and R. Reiser, Gas-Liquid Chromatographic Analysis of Cyclopropene Fatty Acids, Lipds 1:10–15 (1966).Google Scholar
  33. 33.
    Gunstone, F.D., J.L. Harwood, and F.B. Padley, The Lipid Handbook, 2nd edn., Chapman & Hall, London, 1994, pp. 13, 51, 64–65.Google Scholar
  34. 34.
    Bianchini, J-P., A. Ralaimanarivo, and E.M. Gaydou, Effects of Heat and Hydrogenation on Cyclopropenoid Fatty Acid Composition of Baobab (Adansonia suarezensis) Seed Oil, J. Food Sci. 48:253–255, 259 (1983).CrossRefGoogle Scholar
  35. 35.
    Andrianaivo-Rafehivola, A.A., J.M. Cao, and E.M. Gaydou, Effects of Fresh and Heated Baobab Seed Oil Feeding on Growth, Food Consumption and Weight of Some Organs in Rats, Rev. Fr. Corps Gras 41:53–59 (1994).Google Scholar
  36. 36.
    Bianchini, J.P., A. Ralaimanarivo, and E.M. Gaydou, Determination of Cyclopropenoic and Cyclopropanoic Fatty Acids in Cottonseed and Kapok Seed Oils by Gas-Liquid Chromatography, Anal Chem. 53:2194–2201 (1981).CrossRefGoogle Scholar
  37. 37.
    Conway, J., W.M.N. Ratnayake, and R.G. Ackman, Hydrazine Reduction in the Gas-Liquid Chromatographic Analysis of the Methyl Esters of Cyclopropenoic Fatty Acids, J. Am. Oil Chem. Soc. 62:1340–1343 (1985).CrossRefGoogle Scholar
  38. 38.
    Ehrendorfer, F., Systematik und Evolution: Spermatophyta, Samenpflanzen, in Lehrbuch der Botanik für Hochschulen (“Strasburger”), 31st edn., G. Fischer, Stuttgart, 1971, p. 715.Google Scholar
  39. 39.
    Krassilov, V.A., The Origin of Angiosperms: New and Old Problems, Trends Ecol. Evol. 6:215–220 (1991).CrossRefGoogle Scholar
  40. 40.
    Donoghue, M.J., and J.A. Doyle, Angiosperm Monophyly (letter), Ibid.407 (1991).CrossRefGoogle Scholar
  41. 41.
    Litchfield, C., Triglyceride Analysis by Consecutive Liquid-Liquid Partition and Gas-Liquid Chromatography. Ephedra nevadensis Seed Fat, Lipids 3:170–177 (1968).CrossRefGoogle Scholar
  42. 42.
    Kleiman, R., G.F. Spencer, F.R. Earle, and I.A. Wolff, Fatty Acid Composition of Ephedra campylopoda Seed Oil, Chem. Ind. 31:1326–1327 (1967).PubMedGoogle Scholar
  43. 43.
    Smith, C.R., Jr., R. Kleiman, and I.A. Wolff, Caltha palustris L. Seed Oil. A Source of Four Fatty Acids with cis-5-Unsaturation, Lipids 3:37–42 (1968).CrossRefGoogle Scholar
  44. 44.
    Aitzetmüller, K., An Unusual Fatty Acid Pattern in Eranthis Seed Oil, Lipids 31:201–205 (1996).PubMedCrossRefGoogle Scholar
  45. 45.
    Kubitzki, K., Gnetatae, in The Families and Genera of Vascular Plants, Vol. I, edited by K. Kubitzki, Springer, Berlin, 1991, pp. 378–391.Google Scholar

Copyright information

© AOCS Press 1998

Authors and Affiliations

  1. 1.Institute for Chemistry and Physics of LipidsBAGKFMünsterGermany

Personalised recommendations