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Goniothalamicin and annonacin: Bioactive acetogenins fromGoniothalamus giganteus (Annonaceae)

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Using brine shrimp lethality for activity-directed fractionation, goniothalamicin (I), a new tetrahydroxy-mono-tetrahydrofuran fatty acid γ-lactone (acetogenin), has been isolated from ethanolic extracts of the stem bark ofGoniothalamus giganteus Hook. f., Thomas (Annonaceae). This novel compound was found to be cytotoxic and insecticidal and inhibited the formation of crown gall tumors on potato discs. Annonacin (II), the only other reported mono-tetrahydrofuran acetogenin, was also isolated; the previously reported 9ASK (astrocytoma reversal) activity ofII was confirmed, andII is now also found to be weakly active against 3PS murine leukemia.

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References

  1. ElZayat, A. A. E., Ferrigni, N. R., McCloud, T. G., McKenzie, A. T., Byrn, S. R., Cassady, J. M., Chang, C. J., and McLaughlin, J. L., Tetrahedron Lett.26 (1972) 955.

    Article  Google Scholar 

  2. Jewers, K., Davis, J. B., Dougan, J., Manchanda, A. H., Blunden, G., Kyi, A., and Wetchapinan, S., Phytochemistry11 (1972) 2025.

    Article  CAS  Google Scholar 

  3. Talapatra, S. K., Basa, D., Deb, T., Goswami, S., and Talapatra, B., Indian J. Chem.24B (1985) 29.

    CAS  Google Scholar 

  4. Geran, R. I., Greenberg, N. H., MacDonald, M. M., Schumacher, A. M., and Abbott, B. J., Cancer Chemother. Rep.3 (1972) protocols 16 and 13.

  5. Meyer, B. N., Ferrigni, N. R., Putnam, J. E., Jacobsen, L. B., Nichols, D. E., and McLaughlin, J. L., Planta med.45 (1982) 31.

    Article  CAS  PubMed  Google Scholar 

  6. McCloud, T. G., Smith, D. L., Chang, C. J., and Cassidy, J. M., Experientia43 (1987) 947.

    Article  CAS  PubMed  Google Scholar 

  7. Insecticidal testing obtained from Barnard A. Scott of Lilly Research Laboratories, Greenfield, IN.

  8. McLaughlin, J. L., and Ferrigni, N. R., Proceedings of Symposium on Discovery and Development of Naturally Occurring Antitumor Agents, NCI/Frederick Cancer Research Facility, Frederick, Maryland, July 27–29, 1983, p. 912.

  9. Ferrigni, N. R., Putnam, J. E., Anderson, B., Jacobsen, L. B., Nichols, D. E., Moore, D. S., and McLaughlin, J. L., J. nat. Prod.45 (1982) 679.

    Article  CAS  PubMed  Google Scholar 

  10. Shoemaker, R. H., Abbott, B. J., MacDonald, M. M., Mayo, J. G., Venditti, J. M., and Wolpert DeFilippos, M. K., Cancer Treatment Rep.67 (1983) 1.

    Google Scholar 

  11. Tschesche, R., Grimmer, G., and Sechafer, F., Chem. Ber.86 (1953) 1235.

    Article  CAS  Google Scholar 

  12. Rupprecht, J. K., Chang, C. J., Cassady, J. M., McLaughlin, J. L., Mikolajczak, K. L., and Weisleder, D., Heterocycles24 (1986) 1197.

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Department of Medicinal Chemistry and Pharmacognosy, School of Pharmacy and Pharmacal Sciences, Purdue University, 47907, West Lafayette, Indiana, USA

    A. Alkofahi, J. K. Rupprecht, D. L. Smith, Ch. -J. Chang & J. L. McLaughlin

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  1. A. Alkofahi
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  2. J. K. Rupprecht
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  3. D. L. Smith
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  4. Ch. -J. Chang
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  5. J. L. McLaughlin
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Alkofahi, A., Rupprecht, J.K., Smith, D.L. et al. Goniothalamicin and annonacin: Bioactive acetogenins fromGoniothalamus giganteus (Annonaceae). Experientia 44, 83–85 (1988). https://doi.org/10.1007/BF01960258

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