Experientia

, Volume 46, Issue 3, pp 324–327 | Cite as

Sylvaticin: A new cytotoxic and insecticidal acetogenin fromRollinia sylvatica (Annonaceae)

  • K. J. Mikolajczak
  • R. V. Madrigal
  • J. K. Rupprecht
  • Y. -H. Hui
  • Y. -M. Liu
  • D. L. Smith
  • J. L. McLaughlin
Research Articles

Summary

Sylvaticin (I), a new tetrahydroxy annonaceous acetogenin with nonadjacent tetrahydrofuran rings, has been isolated from the dried fruits ofRollinia sylvatica St. Hil. (Annonaceae). This compound is extremely cytotoxic to human tumor cells and shows promising insect control properties.

Key words

Sylvaticin acetogenin Rollinia sylvatica Annonaceae brine shrimp cytotoxicity insecticidal striped cucumber beetle European corn borer 

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References

  1. 1.
    Jolad, S. D., Hoffmann, J. J., Schram, K. H., Cole, J. R., Tempesta, M. S., Kriek, G. R., and Bates, R. B., J. org. Chem.47 (1982) 151.Google Scholar
  2. 2.
    Jolad, S. D., Hoffmann, J. J., Cole, J. R., Barry III, C. E., Bates, R. B., Linz, G. S., and Konig, W. A., J. nat. Prod.48 (1985) 644.PubMedGoogle Scholar
  3. 3.
    Dabrah, T. T., and Sneden, A. T., Phytochemistry23 (1984) 2013.Google Scholar
  4. 4.
    Dabrah, T. T., and Sneden, A. T., J. nat. Prod.47 (1984) 652.PubMedGoogle Scholar
  5. 5.
    Etse, J. T., and Waterman, P. G., J. nat. Prod.49 (1986) 684.Google Scholar
  6. 6.
    Cortes, D., Rios, J. L., Villar, A., and Valverde, S., Tetrahedron Lett.25 (1984) 3199.Google Scholar
  7. 7.
    Rupprecht, J. K., Chang, C.-J., Cassady, J. M., McLaughlin, J. L., Mikolajczak, K. L., and Weisleder, D., Heterocycles24 (1986) 1197; Mikolajczak, K. L., McLaughlin, J. L., and Rupprecht, J. K., U.S. Patent No. 4, 721, 727 (issued Jan. 26, 1988).Google Scholar
  8. 8.
    McCloud, T. G., Smith, D. L., Chang, C.-J., and Cassady, J. M., Experientia43 (1987) 947.PubMedGoogle Scholar
  9. 9.
    Pettit, G. R., Cragg, G. M., Polonsky, J., Herald, D. L., Goswami, A., Smith, C. R., Moretti, C., Schmidt, J. M., and Weisleder, D., Can. J. Chem.65 (1987) 1433.Google Scholar
  10. 10.
    Alkofahi, A., Rupprecht, J. K., Smith, D. L., Chang, C.-J., and McLaughlin, J. L. Experientia44 (1988) 83.PubMedGoogle Scholar
  11. 11.
    Fujimoto, Y., Eguchi, T., Kakinuma, K., Ikekawa, N., Sahai, M., and Gupta, Y. K., Chem. pharm. Bull.36 (1988) 4802.PubMedGoogle Scholar
  12. 12.
    Pettit, G. R., Riesen, R., Leet, J. E., Polonsky, J., Smith, C. R., Schmidt, J. M., Dufresne, C., Schaufelberger, D., and Moretti, C., Heterocycles28 (1989) 213.Google Scholar
  13. 13.
    Born, L., Lieb, K., Lorentzen, J. P., Moeschler, H., Nonfon, M., Sollner, R., and Wendisch, D., Planta med. (1989) in press.Google Scholar
  14. 14.
    Abreo, M. L., and Sneden, A. T., J. nat. Prod. (1989) in press.Google Scholar
  15. 15.
    Hui, Y.-H., Rupprecht, J. K., Liu, Y.-M., Anderson, J. E., Smith, D. L., Chang, C.-J., and McLaughlin, J. L., J. nat. Prod.52 (1989) 463; McLaughlin, J. L., and Hui, Y.-H., Chemotherapeutically active acetogenins, U.S. Patent, applied for April 11, 1989.PubMedGoogle Scholar
  16. 16.
    Lieb, F., Nonfon, M., Wachendorff-Neumann, U., and Wendisch, D., Planta med. (1989) in press.Google Scholar
  17. 17.
    Alkofahi, A., Rupprecht, J. K., Liu, Y.-M., Chang, C.-J., Smith, D. L., and McLaughlin, J. L., Experientia46 (1990) in press.Google Scholar
  18. 18.
    Hui, H.-Y., Rupprecht, J. K., Anderson, J. E. Liu, Y.-M., Smith, D. L., Chang, C.-J., and McLaughlin, J. L., Tetrahedron, accepted for publication.Google Scholar
  19. 19.
    Meyer, B. N., Ferrigni, N. R., Putnam, J. E., Jacobsen, L. B., Nichols, D. E., and McLaughlin, J. L., Planta med.45 (1982) 31.PubMedGoogle Scholar
  20. 20.
    Reed, D. K., Warthen, J. D., Jr., Uebel, E. C., and Reed, G. L., J. econ. Ent.75 (1982) 1109.Google Scholar
  21. 21.
    Hoye, T. R., and Suhadolnik, J. C., J. Am. chem. Soc.109 (1987) 4402.Google Scholar

Copyright information

© Birkhäuser Verlag 1990

Authors and Affiliations

  • K. J. Mikolajczak
    • 1
  • R. V. Madrigal
    • 1
  • J. K. Rupprecht
    • 2
  • Y. -H. Hui
    • 2
  • Y. -M. Liu
    • 2
  • D. L. Smith
    • 2
  • J. L. McLaughlin
    • 2
  1. 1.Northern Regional Research CenterUSDA-ARSPeoriaUSA
  2. 2.Department of Medicinal Chemistry and Pharmacognosy, School of Pharmacy and Pharmacal SciencesPurdue UniversityWest LafayetteUSA

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