Summary
Gigantecin (I), a novel tetrahydroxy-di-tetrahydrofuran fatty acid γ-lactone (acetogenin), was isolated from an ethanolic extract of the stem bark ofGoniothalamus giganteus Hook. f., Thomas (Annonaceae), by means of activity-directed fractionation (brine shrimp lethality test). This new compound is extremely cytotoxic to human tumor cells, inhibits crown gall tumors on potato discs, and is active in an assay designed to detect antimitotic agents (9 ASK).
Similar content being viewed by others
References
Jolad, S. D., Hoffmann, J. J., Schram, K. H., and Cole, J. R., J. org. Chem.47 (1982) 3151.
Rupprecht, J. K., Chang, C.-J., Cassady, J. M., McLaughlin, J. L., Mikolaczak, K. L., and Weisleder, D., Heterocycles24 (1986) 1197.
Mikolaczak, K. L., McLaughlin, J. L., and Rupprecht, J. K., U.S. Patent No. 4,721,727 (issued Jan. 26, 1988).
Alkofahi, A., Rupprecht, J. K., Smith, D. L., Chang, C.-J., and McLaughlin, J. L., Experientia44 (1988) 83.
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.53 (1989) 463.
Geran, R. I., Greenberg, N. H., McDonald, M. M., Schumacher, A. M., and Abbott, J. B., Cancer Chemother. Rep.3 (1972) protocols 16 and 13.
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 (1984) 955.
Meyer, B. M., Ferrigni, N. R., Putnam, J. E., Jacobsen, L. B., Nichols, D. E., and McLaughlin, J. L., Planta med.45 (1982) 31.
Pettit, G. R., Craig, 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.
Born, L., Lieb, F., Lorentzen, J. P., Moeschler, H., Nonfon, M., Sollner, R., and Wendish, D., Planta med. (in press).
Hoye, T. R. and Suhadolnik, J. C., J. Am. chem. Soc.109 (1987) 4402.
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.
Lgarashi, K., Lkeyama, S., Takeuchi, T., and Sugino, Y., Cell Struct. Funct.3 (1978) 103.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Alkofahi, A., Rupprecht, J.K., Liu, Y.M. et al. Gigantecin: A novel antimitotic and cytotoxic acetogenin, with nonadjacent tetrahydrofuran rings, fromGoniothalamus giganteus (Annonaceae). Experientia 46, 539–541 (1990). https://doi.org/10.1007/BF01954260
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/BF01954260