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Occurrence of γ-linolenic acid in compositae: A study of Youngia tenuicaulis seed oil

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Lipids

Abstract

Seeds of Youngia tenuicaulis and other species from the plant family Compositae (Asteraceae) were studied for their oil content and fatty acid composition. The seed oil of Y. tenuicaulis growing in Mongolia was found to contain 5.6% γ-linolenic acid (18∶3Δ6cis,9cis,12cis) in addition to common fatty acids. The oil was analyzed using chromatographic [capillary gas-liquid chromatography (GLC), thin-layer chromatography] and spectroscopic (infrared, gas chromatography-mass spectrometry) techniques. Seed oil fatty acids of Saussurea amara (containing γ-linolenic acid) and of Arctium minus (containing 18∶3Δ3trans,9cis,12cis), as well as Δ5cis- and Δ5trans-18∶3 were used as GLC reference substances. The evolution in this plant family of a large number of different 18∶3 acids as well as the corresponding evolution of unusual desaturases should be investigated. On the other hand, the Δ6cis-desaturase required for the biosynthesis of γ-linolenic acid may have evolved independently several times in unrelated families of the plant kingdom.

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Abbreviations

DMOX:

dimethyloxazoline

ECL:

equivalent chain length

FAME:

fatty acid methyl ester

GLC:

gas chromatography

IR:

infrared

γ-Ln:

γ-inolenic acid

TLC:

thin-layer chromatography

References

  1. Grubov, V.I. (1982) Key to the Vascular Plants of Vongolia, pp. 416–417, Nauka, Leningrad.

    Google Scholar 

  2. Morris, L.J., Marshall, M.O., and Hammond, E.W. (1968) The Trans-3-enoic Acids of Aster alpinus and Arctium minus Seed Oils, Lipids 3, 91–95.

    CAS  Google Scholar 

  3. Spencer, G.F., Kleiman, R., Earle, F.R., and Wolff, I.A. (1969) Cis-5-monoenoic Acids of Carlina (Compositae) Seed Oils, Lipids 4, 99–101.

    CAS  Google Scholar 

  4. Powell, R.G., Smith, C.R., Jr., and Wolff, I.A. (1967) Cis-5,cis-9, cis-12-octadecatrienoic and Some Unusual Oxygenated Acids in Xeranthemum annuum Seed Oil, Lipids 2, 172–177.

    CAS  Google Scholar 

  5. Chisholm, M.J., and Hopkins, C.Y. (1966) Kamlolenic Acid and Other Conjugated Fatty Acids in Certain Seed Oils, J. Am. Oil Chem. Soc. 43, 390–392.

    CAS  Google Scholar 

  6. White, G.A., Willingham, B.C., Skrdla, W.H., Massey, J.H., Higgins, J.J., Calhoun, W., Davis, A.W., Dolan, D.D., and Earle, F.R. (1971) Agronomic Evaluation of Prospective New Crop Species, Econ. Bot. 25, 22–43.

    Google Scholar 

  7. Smith, C.R., Jr., (1974) Saussurea candicans Seed Oil—Alternative Source of Crepenynic Acid, Lipids 9, 640–641.

    CAS  Google Scholar 

  8. Gunstone, F.D. (1954) Fatty Acids. Part II. The Nature of the Oxygenated Acid Present in Vernonia anthelmintica (Willd.) Seed Oil, J. Chem. Soc., 1611–1612.

  9. Chisholm, M.J., and Hopkins, C.Y. (1959) The Oxygenated Fatty Acid of Tragopogon porrifolius Seed Oil, Chem. Ind., 1154–1155.

  10. Ansari, M.H., Ahmad, S., Ahmad, F., Ahmad, M., and Osman, S.M. (1987) Co-occurrence of Coronaric and Vernolic-Acids in Compositae Seed Oils, Fat Sci. Technol. 89, 116–118.

    CAS  Google Scholar 

  11. Powell, R.G., Smith, C.R., Jr., and wolff, I.A. (1967) Geometric Configuration and Etherification Reactions of Some Naturally Occurring 9-Hydroxy-10,12- and 13-Hydroxy-9,11-octadecadienoic Acids, J. Org. Chem. 32, 1442–1446.

    Article  CAS  Google Scholar 

  12. Hegnauer, R. (1977) The Chemistry of the Compositae, in The Biology and Chemistry of the Compositae (Heywood, V.H., Harborne, J.B., and Turner, B.L., eds.), Vol. 1, pp. 283–336, Academic Press, London.

    Google Scholar 

  13. Gunstone, F.D. (1980) Natural Oxygenated Acids, in Fats and Oils: Chemistry and Technology (Hamilton, R.J., and Bhati, A. (eds.), pp. 47–58, Applied Science Publishers, London.

    Google Scholar 

  14. Smith, C.R., Jr. (1970) Occurrence of Unusual Fatty Acids in Plants, Progr. Chem. Fats Other Lipids 11, 137–177.

    Article  CAS  Google Scholar 

  15. Badami, R.C., and Patil, K.B. (1981) Structure and Occurrence of Unusual Fatty Acids in Minor Seed Oils, Progr. Lipid. Res. 19, 119–153.

    Article  Google Scholar 

  16. Tsevegsüren, N., Aitzetmüller, K., and Vosmann, K. (1997) Unusual Fatty Acids in Compositae: γ-Linolenic Acid in Saussurea spp. Seed Oils, J. High Resolut. Chromatogr. 20, 315–320.

    Article  Google Scholar 

  17. Horrobin, D.F. (1992) Nutritional and Medical Importance of γ-Linolenic Acid, Progr. Lipid Res. 31, 163–194.

    Article  CAS  Google Scholar 

  18. Gunstone, F.D. (1992) γ-Linolenic Acid—Occurrence and Physical and Chemical Properties, Progr. Lipid Res. 31, 145–161.

    Article  CAS  Google Scholar 

  19. Tsevegsüren, N., and Aitzetmüller, K. (1993) γ-Linolenic Acid in Anemone spp. Seed Lipids, Lipids 28, 841–846.

    Google Scholar 

  20. Aitzetmüller, K., and Werner, G. (1991) Stearidonic Acid (18∶4ω3) in Primula florindae, Phytochemistry 30, 4011–4013.

    Article  Google Scholar 

  21. Aitzetmüller, K., Werner, G., and Tsevegsüren, N. (1993) Screening of Seed Lipids for γ-Linolenic Acid: Capillary Gas-Liquid Chromatographic Separation of 18∶3 Fatty Acids with Δ-5 and Δ-6 Double Bonds, Phytochem. Anal. 4, 249–255.

    Google Scholar 

  22. Tsevegsüren, N., and Aitzetmüller, K. (1997) Unusual Δ5cis-Fatty Acids in Seed Oils of Cimicifuga Species, J. High Resolut. Chromatogr. 20, 237–241.

    Article  Google Scholar 

  23. Aitzetmüller, K. (1993) Capillary GLC Fatty Acid Fingerprints of Seed Lipids—A Tool in Plant Chemotaxonomy? J. High Resolut. Chromatogr. 16, 488–490.

    Article  Google Scholar 

  24. Christie, W.W. (1989) Gas Chromatography and Lipids—A Practical Guide, pp. 89–110, Oily Press, Dundee.

    Google Scholar 

  25. Tsevegsüren, N., and Aitzetmüller, K. (1996) γ-Linolenic and Stearidonic Acids in Mongolian Boraginaceae, J. Am. Oil Chem. Soc. 73, 1681–1684

    Article  Google Scholar 

  26. Zhang, J.Y., Yu, Q.T., Liu, B.N., and Huang, Z.H. (1988) Chemical Modification in Mass Spectrometry IV—2-Alkenyl-4, 4-Dimethyloxazolines as Derivatives for the Double Bond Location of Long-Chain Olefinic Acids, Biomed. Environ. Mass Spectrom. 15, 33–44.

    Article  CAS  Google Scholar 

  27. Yu, Q.T., Liu, B.N., Zhang, J.Y., and Huang, Z.H. (1998) Location of Double Bonds in Fatty Acids of Fish Oil and Rat Testis Lipids. Gas Chromatography-Mass Spectrometry of the Oxazoline Derivatives, Lipids 24, 79–83.

    Google Scholar 

  28. Fay, L., and Richli, U. (1991) Location of Double Bonds in Polyunsaturated Fatty Acids by Gas Chromatography-Mass Spectrometry After 4,4-Dimethyloxazoline Derivatization, J. Chromatogr. 541, 89–98.

    Article  CAS  Google Scholar 

  29. Aitzetmüller, K., and Tsevegsüren, N. (1994) Seed Fatty Acids, “Front-End” Desaturases and Chemotanonomy—A Case Study in the Ranunculaceae, J. Plant Physiol. 143, 538–543.

    Google Scholar 

  30. Aitzetmüller, K. (1995) Fatty Acid Patterns of Ranunculaceae Seed Oils: Phylogenetic Relationships. Plant Syst. Evol. [Suppl.] 9, 229–240.

    Google Scholar 

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Authors and Affiliations

  1. Chemistry Institute, Mongolian Academy of Sciences, Ulaanbaatar 51, Mongolia

    Nanzad Tsevegsüren

  2. Institute for Chemistry and Physics of Lipids, BAGKF, Piusallee 76, D-48147, Münster, Germany

    Kurt Aitzetmüller & Klaus Vosmann

Authors
  1. Nanzad Tsevegsüren
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  2. Kurt Aitzetmüller
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  3. Klaus Vosmann
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Correspondence to Kurt Aitzetmüller.

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Tsevegsüren, N., Aitzetmüller, K. & Vosmann, K. Occurrence of γ-linolenic acid in compositae: A study of Youngia tenuicaulis seed oil. Lipids 34, 525–529 (1999). https://doi.org/10.1007/s11745-999-0394-4

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  • DOI: https://doi.org/10.1007/s11745-999-0394-4

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