Advertisement

Pharmaceutisch Weekblad

, Volume 5, Issue 6, pp 281–286 | Cite as

Pyrrolizidine alkaloids, flavonoids and volatile compounds in the genus Eupatorium

Eupatorium cannabinum L., an ancient drug with new perspectives
  • H. Hendriks
  • Th M. Malingré
  • E. T. Elema
Review Articles

Abstract

Within the scope of a study of antitumour compounds in higher plants a survey is given concerning the presence of pyrrolizidine alkaloids, flavonoids and volatile compounds inEupatorium species. Preliminary results of a phytochemical study of these compounds inE. cannabinum are also presented.

From the results of a GC-MS analysis of an alkaloid extract from aerial parts ofE. cannabinum the conclusion can be drawn, that the composition of pyrrolizidine alkaloids is more complicated than reported in literature. This is caused by the fact that different stereoisomers exist. The presence of at least two alkaloids with a molecular weight of 283 (supinine or isomers) and four alkaloids with a molecular weight of 299 (echinatine or isomers) could be shown. In subterranean plant material also other pyrrolizidine alkaloids are present. A great number of flavonoids, also as glycosides, have been shown inEupatorium species, often in low quantities. Rutin, present in manyEupatorium species, could not be detected in subterranean parts ofE. cannabinum.

Relatively little attention has been paid to the analysis of volatile compounds (essential oils) ofEupatorium species. Thymol derivatives are often reported to be present inEupatorium species. Thirty-five compounds could be detected by means of a GC-MS analysis in the essential oil ofE. cannabinum about which no literature data were available.

Keywords

Molecular Weight Internal Medicine Plant Material Flavonoid Alkaloid 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. Ammu, G. (1974) Indian 121 818, 25 May 1974 [via Chem. Abstr. (1975)82, 007558].Google Scholar
  2. Bohlmann, F., J. Jakupovic andW. Vogel (1982)Phytochemistry 21, 1153.Google Scholar
  3. Bohlmann, F., P.K. Manhanta, A. Suwita, A.A. Natu, C. Zdero, W. Dorner, D. Ehlers andM. Grenz (1977a)Phytochemistry 16, 1973.Google Scholar
  4. Bohlmann, F., J. Jakupovic andM. Lonitz (1977b)Chem. Ber. 110, 301.Google Scholar
  5. Cymerman Craig, J., andK.K. Purushothaman (1970)J. Org. Chem. 35, 1721.Google Scholar
  6. Delle Monache, G., B. Botla, F. Delle Monache, G.B. Marino Bettolo andB. Moreno Murillo (1981)Farmaco [Sci.] 36, 960.Google Scholar
  7. Dobberstein, R.H., M. Tin-WA, H.H.S. Fong, F.A. Crane andN.R. Farnsworth (1977)J. Pharm. Sci. 66, 600.Google Scholar
  8. Dominguez, X.A. (1977). In:The Biology and Chemistry of the Compositae. Vol II. (Heywood, V.H., J.B. Harborne andB.L. Turner, Eds.). Academic Press, London-New York-San Francisco, 487.Google Scholar
  9. Ferraro, G.E., V.S. Martino andJ.D. Coussio (1977)Phytochemistry 16, 1618.Google Scholar
  10. Furaya, T., andM. Hikichi (1973)Phytochemistry 12, 225.Google Scholar
  11. Herz, W., S.V. Govindan, I. Russ-Murari andN. Kumar (1979)J. Org. Chem. 44, 2784.Google Scholar
  12. Herz, W., S.V. Govindan, J. Riess Maurer, B. Kreil, H. Wagner, L. Farkas andJ. Strelisky (1980)Phytochemistry 19, 669.Google Scholar
  13. Herz, W., S.V. Govindan andN. Kumar (1981a)Phytochemistry 20, 1343.Google Scholar
  14. Herz, W., P. Kulanthaivel, P.S. Subramanian, C.C.J. Culvenor andJ.A. Edgar (1981b)Experientia 37, 683.Google Scholar
  15. Hoppe, H.A. (1975)Drogenkunde Band I, Angiospermen.8. Auflage. Walter de Gruyter, Berlin-New York.Google Scholar
  16. Huizing, H.J., F. De Boer andT.H.M. Malingré (1980)J. Chromatogr. 195, 412.Google Scholar
  17. Huizing, H.J., andT.H.M. Malingré (1979)J. Chromatogr. 173, 187.Google Scholar
  18. Kokate, C.K., R.E. Rao andK.C. Varma (1971)The Flavour Industry 2, 177.Google Scholar
  19. Kovach, J.S., M.M. Ames, G. Powis, G.C. Moertel, R.G. Hahn andE.T. Creagan (1979)Humans. Cancer Res. 39, 4540.Google Scholar
  20. Kupchan, S.M., J.R. Knox andM.S. Udayamurthy (1965)J. Pharm. Sci. 54, 929.Google Scholar
  21. Kupchan, S.M., S.W. Sigel, R.J. Hemingway, J.R. Knox andM.S. Udayamurthy (1969)Tetrahedron 25, 1603.Google Scholar
  22. Locock, R.A., J.L. Beal andR.W. Doskotoch (1966)Lloydia 29, 201.Google Scholar
  23. Maarse, H. (1971)Samenstelling van de vluchtige olie van Origanum vulgare ssp. vulgare gedurende de ontwikkeling van de plant. Disseration, Groningen.Google Scholar
  24. Malingré, T.H.M. (1971)Pharm. Weekbl. 106, 738.Google Scholar
  25. Miayzawa, M., andH. Kameoka (1977)Yakugaku Zasshi 97, 120.Google Scholar
  26. Neu, R. (1957)Naturwissenschaften 44, 181.Google Scholar
  27. Ngo Le-Van andThi Van Cuong Pham (1979)Phytochemistry 18, 1859.Google Scholar
  28. Pederson, E. (1975)Phytochemistry 14, 2086.Google Scholar
  29. Romeo De Vivar, A., L.A. Cuevas andC. Guerrero (1971)Rev. Latin. Quim. 2, 32.Google Scholar
  30. Suffnes, M., andJ. Douros (1982)Lloydia 45, 1.Google Scholar
  31. Tsuda, Y., andL. Marion (1963)Can. J. Chem. 41, 1919.Google Scholar
  32. Wagner, H., M.A. Iyengar, L. Hörhammer andW. Herz (1972a)Phytochemistry 11, 1504.Google Scholar
  33. Wagner, H., M.A. Iyengar, P. Düll andW. Herz (1972b)Phytochemistry 11, 1506.Google Scholar
  34. Wagner, H., M.A. Iyengar, O. Seligmann, L. Hörhammer andW. Herz (1972c)Phytochemistry 11, 2630.Google Scholar
  35. Zalkov, L.H., L. Gelbaum, M. Ghosal andT.J. Fleischmann (1977)Phytochemistry 16, 1313.Google Scholar

Copyright information

© Royal Dutch Association for Advancement of Pharmacy 1983

Authors and Affiliations

  • H. Hendriks
    • 1
  • Th M. Malingré
    • 1
  • E. T. Elema
    • 1
  1. 1.Laboratory for PharmacognosyState University GroningenAW GroningenThe Netherlands

Personalised recommendations