Advertisement

Pharmaceutisch Weekblad

, Volume 8, Issue 5, pp 245–251 | Cite as

Eupatorium cannabinum L.

A review emphasizing the sesquiterpene lactones and their biological activity
  • H. J. Woerdenbag
Review Articles

Abstract

A review onEupatorium cannabinum L. is given, including botany, history and constituents. The sesquiterpene lactones are discussed in more detail, covering their biosynthesis, isolation, analysis and biological activity. Special attention is paid to the cytotoxic and antitumour activities of the sesquiterpene lactones.

Key words

Analysis Antineoplastic agents Biosynthesis Botany Chemistry Cytotoxins Eupatorium cannabium Sesquiterpenes 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    Frohne D, Jensen U. Systematik des Pflanzenreichs. Stuttgart - New York: Gustav Fischer Verlag, 1979:218–55.Google Scholar
  2. 2.
    Hooker JD, Jackson BD. Index Kewensis. Vol. 1. Oxford: Clarendon Press, 1960:915–21.Google Scholar
  3. 3.
    King RM, Robinson H.Eupatorium, a composite genus of arcto-tertiary distribution. Taxon 1970;19:769–74.Google Scholar
  4. 4.
    Hegnauer R. Chemotaxonomie der Pflanzen. Band 3. Basle - Stuttgart: Birkhaüser Verlag, 1964:448.Google Scholar
  5. 5.
    Tutin TG, Heywood VH, Burges NA, et al. Flora Europaea. Vol. 4. Cambridge - London - New York- Melbourne: Cambridge University Press, 1976:109.Google Scholar
  6. 6.
    Malingré ThM.Eupatorium cannabinum L., een oud geneeskruid met nieuwe perspectieven. Pharm Weekbl 1971;106;738–44.PubMedGoogle Scholar
  7. 7.
    Linnaeus C. Species Plantarum. Uppsala, 1753:838.Google Scholar
  8. 8.
    Madaus G. Lehrbuch der biologischen Heilmittel. Leipzig: Georg Thieme Verlag, 1938:1310–4.Google Scholar
  9. 9.
    Dodonaeus R. Herbarius oft Cruydt-Boeck. Leyden, 1681:34–5, 941.Google Scholar
  10. 10.
    Hoppe HA. Drogenkunde. Band i. Angiospermen. Berlin - New York: Walter de Gruyter, 1975:482–4.Google Scholar
  11. 11.
    Van Os FHL, ed. Gids voor geneeskrachtige planten. Amsterdam: The Reader's Digest NV, 1979:157.Google Scholar
  12. 12.
    Von Gizycki F.Eupatorium cannabinum L., Wasserdost und Verwandte (III). Pharmazie 1951;6:686–8.PubMedGoogle Scholar
  13. 13.
    Dolejš L, Herout V. On terpenes. CXLV. Constitution of eupatoriopicrin, a germacranolide fromEupatorium cannabinum L. Coll Czechoslov Chem Commun 1962;27:2654–61.Google Scholar
  14. 14.
    Droždž B, Bialek-Grygiel G. Composition of lactone fraction of leaves and inflorescence ofEupatorium cannabinum. Diss Pharm Pharmacol 1971;23:537–40.Google Scholar
  15. 15.
    McPhail AT, Onan KD. Crystal and molecular structure of eupatolide, the major cytotoxic principle fromEupatorium formosanum HAY. J Chem Soc Perkin II 1975: 1798–801.Google Scholar
  16. 16.
    Droždž B, Grabarczyk H, Samek Z, Holub M, Herout V, Šorm F. Sesquiterpene lactones fromEupatorium cannabinum L. Revision of the structure of eupatoriopicrin. Coll Czechoslov Chem Commun 1972;37:1546–54.Google Scholar
  17. 17.
    Bos R, Hendriks H, Bruins AP, Schripsema J, Kloosterman J, Sipma G. The presence of some sesquiterpene lactones inEupatorium cannabinum L. Farm Tijdschr Belg 1984;61:398.Google Scholar
  18. 18.
    Sagareishvili TG, Alaniya MD, Kemertelidze EP. Nonpolar components ofEupatorium cannabinum. Khim Prir Soedan 1981:106–7.Google Scholar
  19. 19.
    Rodriguez E, Towers GHN, Mitchell JC. Biological activities of sesquiterpene lactones (review). Phytochemistry 1976;15:1573–80.CrossRefGoogle Scholar
  20. 20.
    Fischer NH, Olivier EJ, Fischer HD. The biogenesis and chemistry of sesquiterpene lactones. In: Herz W, Grisebach H, Kirby GW, eds. Fortschritte der Chemie organischer Naturstoffe. Band 38. Wien - New York: Springer-Verlag, 1979:47–390.Google Scholar
  21. 21.
    Sutherland MD; Park RJ. Sesquiterpenes and their biogenesis inMyoporum deserti A. Cunn. In: Pridham JB, ed. Terpenoids in plants. London - New York: Academic Press, 1967:148.Google Scholar
  22. 22.
    Bohlmann F, Mahanta PH, Suwita A, et al. Neue Sesquiterpenlactone und andere Inhaltsstoffe aus Vertretern derEupatorium-Gruppe. Phytochemistry 1977;16:1973–81.CrossRefGoogle Scholar
  23. 23.
    Pedersen E. Echinatine and supinine: pyrrolizidine alkaloids fromEupatorium cannabinum. Phytochemistry 1975;14:2086–7.CrossRefGoogle Scholar
  24. 24.
    Hendriks H, Malingré ThM, Elema ET. Pyrrolizidine alkaloids, flavonoids and volatile compounds in the genusEupatorium. Pharm Weekbl [Sci] 1983;5:281–6.Google Scholar
  25. 25.
    Pagani T, Romussi G. Constituents ofEupatorium cannabinum var.syriacum. Farmaco [Prat] 1967;22:771–85.Google Scholar
  26. 26.
    Oswiecimska M, Sendra J.Eupatorium cannabinum L., search for biologically active fraction. Diss Pharm Pharmacol 1972;24:475–83.Google Scholar
  27. 27.
    Hendriks H, Bos R, Bruins AP. Analysis of the essential oil ofEupatorium cannabinum by combined gás chromatography - mass spectrometry using electron impact and negative ion chemical ionization. Planta Med 1985:541–2.Google Scholar
  28. 28.
    Talaptra SK, Bhar DS, Talaptra B. Dammaradienyl acetate and taraxasterol fromEupatorium cannabinum. Mass spectrometric study of dammaradienyl acetate and its derivates. Aust J Chem 1974;27:1137–42.Google Scholar
  29. 29.
    Dominguez XA. Eupatorieae — chemical review. In: Heywood VH, Harborne JB, Turner BL, eds. The biology and chemistry of the Compositae. Vol. II. London - New York - San Francisco: Academic Press, 1977:487–502.Google Scholar
  30. 30.
    Vollmar A. Über immunstimulierende Wirkprinzipien ausEupatorium perfoliatum (L.) andEupatorium cannabinum (L.). München: Universität München, 1984. Dissertation.Google Scholar
  31. 31.
    Sticher O. Plant mono-, di- and sesquiterpenoids with pharmacological or therapeutic activity. In: Wagner H, Wolff P, eds. Proceedings in life sciences. New natural products and plant drugs with pharmacological, biological or therapeutical activity. Berlin - Heidelberg - New York: Springer-Verlag, 1977:137–76.Google Scholar
  32. 32.
    Cordell GA. Recent experimental and clinical data concerning antitumor and cytotoxic agents from plants. In: Wagner H, Wolff P, eds. Proceedings in life sciences. New natural products and plant drugs with pharmacological, biological or therapeutic activity. Berlin - Heidelberg - New York: Springer-Verlag, 1977:54–81.Google Scholar
  33. 33.
    Smith LW, Culvenor CCJ. Plant sources of hepatotoxic pyrrolizidine alkaloids. Lloydia 1981;44:129–52.Google Scholar
  34. 34.
    Kovach JS, Ames MA, Powis G, Moertel CG, Hahn RG, Creagan ET. Toxicity and pharmacokinetics of a pyrrolizidine alkaloid, indicineN-oxide, in humans. Cancer Res 1979;39:4540–5.PubMedGoogle Scholar
  35. 35.
    Hänsel R, Haas R. Pflanzliche Immunstimulanzien und Hyposensibilisierung mit Pflanzenstoffen. In: Hänsel R, Haas R, eds. Therapie mit Phytoparmaka. Berlin - Heidelberg - New York - Tokyo: Springer-Verlag, 1983:256–61.Google Scholar
  36. 36.
    Wagner H, Proksch A, Riess-Maurer I, et al. Immunstimulierend wirkende Polysaccharide (Heteroglykane) aus höheren Pflanzen. Arzneim Forsch/Drug Res 1984;34:659–61.Google Scholar
  37. 37.
    Wagner H. Immunstimulantien aus Pilzen und höheren Pflanzen. In: Ölschläger H, ed. Fortschritte in der Arzneimittelforschung. Stuttgart: Wissenschaftliche Verlagsgesellschaft mbH, 1984:133–48.Google Scholar
  38. 38.
    Wagner H, Proksch A, Vollmar A, Kreuzkamp B, Bauer J.In vitro Phagozytose Stimulierung durch isolierte Pflanzenstoffe gemessen im Phagozytose-Chemolumineszens-(CL)-Modell. Planta Med 1985:139–44.Google Scholar
  39. 39.
    Rogers D, Moss GP, Neidle S. Proposed conventions for describing germacranolide sesquiterpenes. JSC Chem Comm 1972;142–3.Google Scholar
  40. 40.
    Lee KH, Huang HC, Huang ES, Furukawa H. Antitumor agents II: eupatolide, a new cytotoxic principle fromEupatorium formosanum HAY. J Pharm Sci 1972;61:629–31.PubMedGoogle Scholar
  41. 41.
    Kupchan SM, Kelsey JE, Maruyama M, Cassady JM, Hemingway JC, Knox JR. Tumor inhibitors XLI. Structural elucidation of tumor-inhibitory sesquiterpene lactones fromEupatorium rotundifolium. J Org Chem 1969;34:3876–83.CrossRefPubMedGoogle Scholar
  42. 42.
    Kupchan SM, Maruyama M, Hemingway RJ, Hemingway JC, Shibuya S, Fujita T. Structural elucidation of novel tumor inhibitory sesquiterpene lactones fromEupatorium cuneifolium. J Org Chem 1973;38:2189–96.CrossRefPubMedGoogle Scholar
  43. 43.
    Kupchan SM, Fujita T, Maruyama M, Britton RW. The isolation and structural elucidation of eupaserrin and deacetyleupaserrin, new antileukemic sesquiterpene lactones fromEupatorium semiserratum. J Org Chem 1973;38:1260–4.CrossRefPubMedGoogle Scholar
  44. 44.
    Droždž B, Błoszyk E. Selective detection of sesquiterpene lactones by TLC. Planta Med 1978;33:379–84.Google Scholar
  45. 45.
    Ito K, Sakakibara Y, Haruna M. Seven guaianolides fromEupatorium chinense. Phytochemistry 1982;21: 715–20.CrossRefGoogle Scholar
  46. 46.
    Błoszyk E, Geppert B, Droždž B. Quantitative determination of sesquiterpene lactones in plant material by infared spectroscopy. Planta Med 1978;34:79–86.Google Scholar
  47. 47.
    Pyysalo H, Seppä EL, Widen KG. Application of gas chromatography to the analysis of sesquiterpene lactones fromLactarius (Russulaceae) mushrooms. J Chromatogr 1980;190:466–70.CrossRefGoogle Scholar
  48. 48.
    Strack D, Proksch P, Gülz PG. Analysis of sesquiterpene lactones by high performance liquid chromatography. Z Naturforsch 1980;35c:915–8.Google Scholar
  49. 49.
    Marchand B, Behl HM, Rodriguez E. Application of high-performance liquid chromatography for analysis and isolation of sesquiterpene lactones. J Chromatogr 1983;265:97–104.CrossRefGoogle Scholar
  50. 50.
    Spring O, Priester T, Stransky H, Hager A. Sesquiterpene lactones in sunflower seedlings: distribution in the plant and occurrence in genetic varieties as determined by an isocratic HPLC technique. J Plant Physiol 1985; 120:321–9.Google Scholar
  51. 51.
    Hall IH, Lee KH, Starnes CO, et al. Anti-inflammatory activity of sesquiterpene lactones and related compounds. J Pharm Sci 1979;68:537–42.PubMedGoogle Scholar
  52. 52.
    Hall IH, Starnes CO, Lee KH, Waddell TG. Mode of action of sesquiterpene lactones as anti-inflammatory agents. J Pharm Sci 1980;69:537–43.PubMedGoogle Scholar
  53. 53.
    Hall IH, Lee KH, Starnes CO, Muraoka O, Sumida Y, Waddell TG. Antihyperlipidemic activity of sesquiterpene lactones and related compounds. J Pharm Sci 1980;69:694–7.PubMedGoogle Scholar
  54. 54.
    Suffness M, Douros J. Current status of the NCI plant and animal product program. Lloydia 1982;45:1–14.Google Scholar
  55. 55.
    Kupchan SM, Eakin MA, Thomas AM. Tumor inhibitors 69. Structure-cytotoxicity relationships among the sesquiterpene lactones. J Med Chem 1971;14:1147–52.CrossRefPubMedGoogle Scholar
  56. 56.
    Kupchan SM, Ashmore JW, Sneden AT. Structure-activity relationships amongin vivo active germacranolides. J Pharm Sci 1978;67:865–7.PubMedGoogle Scholar
  57. 57.
    Lee KH, Hall IH, Mar EC, et al. Sesquiterpene antitumor agents: inhibitors of cellular metabolism. Science 1977;196:533–6.PubMedGoogle Scholar
  58. 58.
    Arrick BA, Nathan CF, Cohn ZA. Inhibition of glutathione synthesis augments lysis of murine tumor cells by sulfhydryl-reactive antineoplastics. J Clin Invest 1983;71:258–67.PubMedGoogle Scholar
  59. 59.
    Lee KH, Ibuka T, Wu RY, Geissman TA. Structure-antimicrobial activity relationship among the sesquiterpene lactones and related compounds. Phytochemistry 1977;16:1177–81.CrossRefGoogle Scholar
  60. 60.
    Calzada J, Ciccio JF, Echandi G. Antimicrobial activity of the heliangolide chromaenolide and related sesquiterpene lactones. Phytochemistry 1980;19:967–8.CrossRefGoogle Scholar
  61. 61.
    Hładoń B, Droždž B, Grabarczyk H, Bobkiewicz T, Obszewski J. Sesquiterpene lactones. Part XIII. Cytotoxic activity of eupatolide and eupatoriopicrin on human and animal malignant cells in tissue culturein vitro. Pol J Pharmacol Pharm 1975;27:429–38.PubMedGoogle Scholar
  62. 62.
    Hładoń B, Droždž B, Holub M, Bobkiewicz T. Sesquiterpene lactones. Part XVI.In vitro studies on cytotoxic properties of sesquiterpene lactones in tissue cultures of human and animal malignant cells. Arch Immunol Ther Exp (Warsz) 1975;23:845–55.Google Scholar
  63. 63.
    Woerdenbag HJ, Meijer C, Mulder NH, De Vries EGE, Hendriks H, Malingré ThM. Evaluation of thein vitro cytotoxicity of some sesquiterpene lactones on a human lung carcinoma cell line using the Fast Green dye exclusion assay. Planta Med 1986:112–4.Google Scholar
  64. 64.
    Hładoń B, Chodera A. Sesquiterpene lactones XVII. Cytostatic and pharmacological activity. Arch Immunol Ther Exp (Warsz) 1975;23:857–65.Google Scholar
  65. 65.
    Slee PHThJ, Van Oosterom AT, De Bruijn EA. Predictive testing in cancer chemotherapy. I.In vivo. Pharm Weekbl [Sci] 1985;7:93–9.Google Scholar
  66. 66.
    Woerdenbag HJ, Lemstra W, Malingré ThM, Konings AWT. Phytopharmacological investigation of the cytostatic effect of eupatoriopicrin on the Lewis Lung tumor. In: Federation of Medical Scientific Societies, Proceedings of the 27th Dutch Federation Meeting. Groningen: Federation of Medical Scientific Societies, 1986:452.Google Scholar
  67. 67.
    Takahashi T, Eto H, Ichimura T, Murae T. Hiyodorilactones A and B, new tumor inhibitory germacranolides fromEupatorium sachalinense Makino. Chem Lett 1978:1345–8.Google Scholar
  68. 68.
    Herz W, Govindan SV. Eucannabinolide and other constituents ofSchkuhria virgata. Phytochemistry 1980;19:1234–6.CrossRefGoogle Scholar
  69. 69.
    Takahashi T, Ichimura T, Murae T. Hiyodorilactones D, E and F, new cytotoxic sesquiterpene lactones fromEupatorium sachalinense Makino. Chem Pharm Bull 1979;27:2539–43.Google Scholar

Copyright information

© Royal Dutch Association for Advancement of Pharmacy 1986

Authors and Affiliations

  • H. J. Woerdenbag
    • 1
  1. 1.Laboratory of PharmacognosyState University of GroningenAW GroningenThe Netherlands

Personalised recommendations