Skip to main content
Log in

Structure revision and cytotoxicity of the germacranolide, stizolicin, fromStizolophus balsamitus (Asteraceae)

  • Short Communications
  • Published:
Experientia Aims and scope Submit manuscript

Summary

The structure of the cytotoxic sesquiterpene lactone, stizolicin, reisolated fromStizolophus balsamitus (Centaurea b.) was revised to atrans, trans germacranolide (1) on the basis of simultaneous application of lanthanide shift reagent and NOE in the NMR.

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

Access this article

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

Instant access to the full article PDF.

References

  1. Epigeal portions collected in June 1978 from Karaj, 40 km west of Tehran, Iran, and shade dried.A voucher specimen (No. 86) is on deposit in the herbarium of the Department of Pharmacognosy, University of Tehran, asCentaurea balsamita Lam.

  2. Lee, K.-H., Kimura, T., Haruna, M., McPhail, A. T., and Onan, D. K., Phytochemistry16 (1977) 1068.

    Google Scholar 

  3. Mukhametzhanov, M. N., Scheichenko, V. I., Bankovskii, A. I., and Rybalko, K. S., Khim. Prir. Soedin.6 (1970) 405 (English edn, p. 525),

    Google Scholar 

  4. Mukhametzhanov, M. N., Scheichenko, V. I., Rybalko, K. S., and Pakaln, D. A., Khim. Prir. Soedin.5 (1969) 125 (English edn, p. 108).

    Google Scholar 

  5. Mukhametzhanov, M. N., Shreter, A. I., and Pakaln, D. A., Khim. Prir. Soedin.5 (1969) 590 (English edn, p. 503).

    Google Scholar 

  6. Rybalko, K. S., Konovalova, O. A., Orishchenko, N. D., and Shreter, A. I., Rastit. Resur.12 (1976) 387; CA85, 174252d.

    Google Scholar 

  7. Bean, M. F., Isolation and Structure Elucidation of Antineoplastic Agents from Plants: Helicteres isora and Stizolophus balsamitus, Ph.D. Dissertation, p. 95. Purdue University, West Lafayette, Indiana 1982.

    Google Scholar 

  8. Bovill, M. J., Cox, P. J., Cradwick, P. D., Guy, M. H. P., Sim, G. A., and White, D. N. J., Acta crystallogr. Sect. B. (1976) 3203.

  9. Samek, Z., Coll Czech. chem. Commun. Engl. Edn43 (1978) 3210.

    Google Scholar 

  10. Herz, W., and Wahlberg, I., Phytochemistry12 (1973) 1421.

    Google Scholar 

  11. Stocklin, W., Waddell, T. G., and Geissman, T. A., Tetrahedron26 (1970) 2397.

    Google Scholar 

  12. Quijano, L., Calderon, J. S., Gomez, G. F., and Rios, C. T., Phytochemistry18 (1979) 843.

    Google Scholar 

  13. Shafizadeh, F., and Bhadane, N. R., Phytochemistry12 (1973) 857.

    Google Scholar 

  14. Rybalko, K. S., Mukhametzhanov, M. N., Scheichenko, V. I., and Konovalova, O. A., Khim. Prir. Soedin.12 (1976) 467 (English edn, p. 412).

    Google Scholar 

  15. Mukhametzhanov, M. N., Scheichenko, V. I., Bankovskii, A. I., and Rybalko, K. S., Khim. Prir. Soedin.7 (1971) 405.

    Google Scholar 

  16. Utkin, L. M., and Serebryakova, A. P., Zh. obshch. Khim.34 (1964) 3496.

    Google Scholar 

  17. Kuzovkov, A. D., Massagetov, P. S., and Bogomazova, R. I., Zh. obsch. Khim.23 (1953) 157.

    Google Scholar 

  18. Cassady, J. M., and Suffness, M., in: Anticancer Agents Based on Natural Product Models, p. 201. Academic Press, New York 1980.

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Additional information

The authors acknowledge the use of the Purdue University Biomedical Magnetic Resonance Laboratory (NIH grant No. RR01077). Support of contract No. N01-CM-97296 and Grant No. CA-33326 from the National Cancer Institute, HHS is gratefully acknowledged. This is paper 18 in the series ‘Potential Antitumor Agents’.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Cassady, J.M., Bean, M.F., McLaughlin, J.L. et al. Structure revision and cytotoxicity of the germacranolide, stizolicin, fromStizolophus balsamitus (Asteraceae). Experientia 40, 930–931 (1984). https://doi.org/10.1007/BF01946442

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF01946442

Key words

Navigation