Antineoplastic agents. 104. Isolation and structure of the Phyllanthus acuminatus Vahl (Euphorbiaceae) glycosides

George R. Pettit, Gordon M. Cragg, Matthew I. Suffness, John Devens Gust, Fred E. Boettner, M. Williams, J. A. Saenz-Renauld, Peter Brown, Jean M. Schmidt, Paul D. Ellis

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Abstract

Three new antineoplastic glycosides, phyllanthostatins 1 (2a), 2 (2c), and 3 (3a), as well as phyllanthoside (2b), have been isolated from the Central American tree Phyllanthus acuminatus Vahl. The phyllanthostatins 1 (2a), 2 (2c), and 3 (3a) and phyllanthoside (2b) structures were completely assigned by detailed analyses of spectral data (principally by 400-MHz NMR) and have been confirmed by X-ray crystallographic analyses of degradation products. In addition to inhibiting growth of the murine P388 lymphocytic leukemia, both phyllanthostatin 1 and phyllanthoside were found to markedly retard progression of the murine B16 melanoma. One of these unique glycosides, phyllanthoside (2b), is in preclinical development at the U.S. National Cancer Institute.

Original languageEnglish
Pages (from-to)4258-4266
Number of pages9
JournalJournal of Organic Chemistry
Volume49
Issue number22
Publication statusPublished - 1984

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Glycosides
Antineoplastic Agents
Nuclear magnetic resonance
Degradation
X rays
phyllanthoside

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Pettit, G. R., Cragg, G. M., Suffness, M. I., Gust, J. D., Boettner, F. E., Williams, M., ... Ellis, P. D. (1984). Antineoplastic agents. 104. Isolation and structure of the Phyllanthus acuminatus Vahl (Euphorbiaceae) glycosides. Journal of Organic Chemistry, 49(22), 4258-4266.

Antineoplastic agents. 104. Isolation and structure of the Phyllanthus acuminatus Vahl (Euphorbiaceae) glycosides. / Pettit, George R.; Cragg, Gordon M.; Suffness, Matthew I.; Gust, John Devens; Boettner, Fred E.; Williams, M.; Saenz-Renauld, J. A.; Brown, Peter; Schmidt, Jean M.; Ellis, Paul D.

In: Journal of Organic Chemistry, Vol. 49, No. 22, 1984, p. 4258-4266.

Research output: Contribution to journalArticle

Pettit, GR, Cragg, GM, Suffness, MI, Gust, JD, Boettner, FE, Williams, M, Saenz-Renauld, JA, Brown, P, Schmidt, JM & Ellis, PD 1984, 'Antineoplastic agents. 104. Isolation and structure of the Phyllanthus acuminatus Vahl (Euphorbiaceae) glycosides', Journal of Organic Chemistry, vol. 49, no. 22, pp. 4258-4266.
Pettit, George R. ; Cragg, Gordon M. ; Suffness, Matthew I. ; Gust, John Devens ; Boettner, Fred E. ; Williams, M. ; Saenz-Renauld, J. A. ; Brown, Peter ; Schmidt, Jean M. ; Ellis, Paul D. / Antineoplastic agents. 104. Isolation and structure of the Phyllanthus acuminatus Vahl (Euphorbiaceae) glycosides. In: Journal of Organic Chemistry. 1984 ; Vol. 49, No. 22. pp. 4258-4266.
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