Skip to main content
SpringerLink
Log in

Sesquiterpene Lactones and Other Constituents from a Cytotoxic Extract of Michelia floribunda

  • Published:
Pharmaceutical Research Aims and scope Submit manuscript

Abstract

The pentane and CHC13 fractions of a crude extract of Michelia floribunda exhibited cytotoxic activity when tested in KB and P388 tumor cell cultures. Repeated chromatography led to the isolation of three cytotoxic sesquiterpene lactones (costunolide, parthenolide, and santamarine) and a cytotoxic isoquinoline alkaloid (liriodenine). Inactive sesquiterpene lactones obtained during the course of this study included dihydroparthenolide and two new glucosides of dihydrotamaulipin A and dihydroreynosin (1 and 2). The structures of these new compounds were determined through interpretation of their spectroscopic data including 2D-NMR spectroscopy. Syringin was also isolated from the extract.

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

REFERENCES

  1. T. Smitinand and K. Larsen (eds.). Flora of Thailand, Vol. II, ASRCT Press, Bangkok, Thailand, 1975, Part 3.

    Google Scholar 

  2. M. L. Dhar, M. M. Dhar, B. N. Dhawan, B. N. Mehrotra, and C. Ray. Indian J. Exp. Biol. 6:232–247 (1968).

    Google Scholar 

  3. D. S. Bhakuni, M. L. Dhar, M. M. Dhar, B. N. Dhawan, B. Gupta, and R. C. Srimali. Indian J. Exp. Biol 9:91–102 (1971).

    Google Scholar 

  4. M. Mokkhasmit, W. Ngarmwathana, K. Sawasdimongkol, and U. Permphiphat. J. Med. Assoc. Thailand 54:490–504 (1971).

    Google Scholar 

  5. J. J. Hoffmann, S. J. Torrance, R. M. Wiedhopf, and J.R. Cole. J. Pharm. Sci. 66:883–884 (1977).

    Google Scholar 

  6. M. Ogura, G. A. Cordell, and N. R. Farnsworth. Phytochemistry 17:957–961 (1978).

    Google Scholar 

  7. B. S. Aswal, D. S. Bhakuni, A. K. Goel, K. Kar, B. N. Mehrotra, and K. C. Mukherjee. Indian J. Exp. Biol. 22:312–332 (1984).

    Google Scholar 

  8. S. K. Talapatra, A. Patra, and B. Talapatra. Tetrahedron 31:1105–1107 (1975).

    Google Scholar 

  9. T. Iida and K. Ito. Phytochemistry 21:701–703 (1982).

    Google Scholar 

  10. S. K. Talapatra, A. Patra, and B. Talapatra. J. Indian Chem. Soc. 55:1152–1160 (1978).

    Google Scholar 

  11. S. J. Wu, D. Y. Kao, D. Y. Lee, and C. C. Yang. Chung Tsao Yao 12:8–10 (1981).

    Google Scholar 

  12. L. F. Zhu, B. Y. Lu, and D. Xu. Chih Wu Hsueh Pao (Botanica Sinica) 24:355–359 (1982).

    Google Scholar 

  13. Z. M. Lin, S. Jin, X. L. Wang, Q. Y. Xing, Q. Z. Chen, X.L. Luo, S. W. Sun, and Y. P. Ma. Hua Hsueh Tung Pao 30–32 (1984).

  14. R. I. Geran, N. H. Greenberg, M. M. MacDonald, A. M. Schumacher, and B. J. Abott. Cancer Chemother. Rep. (Part 3) 3:1–103 (1972).

    Google Scholar 

  15. J. M. Pezzuto, S. K. Antosiak, W. M. Messmer, M. B. Slaytor, and G. R. Honig. Chem.-Biol. Interact. 43:323–339 (1983).

    Google Scholar 

  16. M. Arisawa, J. M. Pezzuto, C. Bevelle, and G. A. Cordell. J. Nat. Prod. 47:453–458 (1984).

    Google Scholar 

  17. S. T. M. Malingre and F. H. L. Van Os. Phytochemistry 17:564 (1978).

    Google Scholar 

  18. W. Herz and N. Kumar. Phytochemistry 20:1339–1341 (1981).

    Google Scholar 

  19. F. Bohlmann, C. Zdero, R. M. King and H. Robinson. Liebigs Ann. Chem. 240–249 (1984).

  20. J. Pearce, J. Gershenzon, and T. J. Mabry. Phytochemistry 25:159–165 (1986).

    Google Scholar 

  21. N. H. Fisher, T. J. Mabry, and H. B. Kagan. Tetrahedron 24:4091–4097 (1968).

    Google Scholar 

  22. S. M. Kupchan, M. A. Eakin, and A. M. Thomas. J. Med.Chem. 14:1147–1152 (1971).

    Google Scholar 

  23. J. A. Marco. Phytochemistry 28:3121–3126 (1989).

    Google Scholar 

  24. D. Warthen, E. L. Gooden, and M. Jacobson. J. Pharm. Sci. 58:637–638 (1969).

    Google Scholar 

  25. J. L. Hartwell and B. J. Abbott. Adv. Pharmacol. Chemother. 7:117–209 (1969).

    Google Scholar 

  26. G. R. Pettit. Biosynthetic Products for Cancer Chemotherapy, Vol. 1, Plenum Press, New York and London, 1977.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Program for Collaborative Research in the Pharmaceutical Sciences, College of Pharmacy, University of Illinois at Chicago, P.O. Box 6998, Chicago, Illinois, 60680

    Ing-On Mondranondra, Chun-tao Che, Agnes M. Rimando, Harry H. S. Fong & Norman R. Farnsworth

  2. Department of Pharmaceutical Botany, Faculty of Pharmaceutical Sciences, Chulalongkorn University, Bangkok, Thailand

    Ing-On Mondranondra & Srunya Vajrodaya

Authors
  1. Ing-On Mondranondra
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Chun-tao Che
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Agnes M. Rimando
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Srunya Vajrodaya
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Harry H. S. Fong
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Norman R. Farnsworth
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

About this article

Cite this article

Mondranondra, IO., Che, Ct., Rimando, A.M. et al. Sesquiterpene Lactones and Other Constituents from a Cytotoxic Extract of Michelia floribunda . Pharm Res 7, 1269–1272 (1990). https://doi.org/10.1023/A:1015937921880

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1023/A:1015937921880

Search

Navigation