Antineoplastic Agents. 104. Isolation and Structure of the Phyllanthus acuminatus Vahl (Euphorbiaceae) Glycosides

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

doi:10.1021/jo00196a029

Antineoplastic Agents. 104. Isolation and Structure of the Phyllanthus acuminatus Vahl (Euphorbiaceae) Glycosides

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

Research output: Contribution to journal › Article › peer-review

58 Scopus citations

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 language	English (US)
Pages (from-to)	4258-4266
Number of pages	9
Journal	Journal of Organic Chemistry
Volume	49
Issue number	22
DOIs	https://doi.org/10.1021/jo00196a029
State	Published - Mar 1984

ASJC Scopus subject areas

Organic Chemistry

Access to Document

10.1021/jo00196a029

Cite this

@article{4df8d2c482894eec86a8834ab0004acf,

title = "Antineoplastic Agents. 104. Isolation and Structure of the Phyllanthus acuminatus Vahl (Euphorbiaceae) Glycosides",

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.",

author = "George Pettit and Cragg, {Gordon M.} and Suffness, {Matthew I.} and Devens Gust and Boettner, {Fred E.} and M. Williams and Saenz-Renauld, {J. A.} and Peter Brown and Schmidt, {Jean M.} and Ellis, {Paul D.}",

year = "1984",

month = mar,

doi = "10.1021/jo00196a029",

language = "English (US)",

volume = "49",

pages = "4258--4266",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "22",

}

TY - JOUR

T1 - Antineoplastic Agents. 104. Isolation and Structure of the Phyllanthus acuminatus Vahl (Euphorbiaceae) Glycosides

AU - Pettit, George

AU - Cragg, Gordon M.

AU - Suffness, Matthew I.

AU - Gust, Devens

AU - Boettner, Fred E.

AU - Williams, M.

AU - Saenz-Renauld, J. A.

AU - Brown, Peter

AU - Schmidt, Jean M.

AU - Ellis, Paul D.

PY - 1984/3

Y1 - 1984/3

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=0021742058&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0021742058&partnerID=8YFLogxK

U2 - 10.1021/jo00196a029

DO - 10.1021/jo00196a029

M3 - Article

AN - SCOPUS:0021742058

SN - 0022-3263

VL - 49

SP - 4258

EP - 4266

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 22

ER -

Antineoplastic Agents. 104. Isolation and Structure of the Phyllanthus acuminatus Vahl (Euphorbiaceae) Glycosides

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this