Antineoplastic agents, 120. pancratium littorale

George Pettit; Venkatswamy Gaddamidi; Delbert L. Herald; Sheo Bux Singh; Gordon M. Cragg; Jean M. Schmidt; Fred E. Boettner; M. Williams; Yoneo Sagawa

doi:10.1021/np50048a005

Antineoplastic agents, 120. pancratium littorale

George Pettit, Venkatswamy Gaddamidi, Delbert L. Herald, Sheo Bux Singh, Gordon M. Cragg, Jean M. Schmidt, Fred E. Boettner, M. Williams, Yoneo Sagawa

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

201 Scopus citations

Abstract

The bulbs of Pancratium littorale collected in Hawaii were found to contain a new phenanthridone biosynthetic product designated pancratistatin (4a) that proved to be effective (38-106% life extension at 0.75-12.5 mg/kg dose levels) against the murine P-388 lymphocytic leukemia. Pancratistatin also markedly inhibited (ED₅₀, 0.01 μg/ml) growth of the P-388 in vitro cell line and in vivo murine M-5076 ovary sarcoma (53-84% life extension at 0.38-3.0 mg/kg). An X-ray crystal structure determination of pancratistatin monomethyl ether (4c) and a detailed high resolution (400 MHz) nmr study of pancratistatin and its pentaacetate (4b) completed assignment of structure 4a. Companion antineoplastic constituents of P. littorale were found to be narciclasine (2c) and its 7-deoxy derivative (2a). The structure of 7-deoxynarciclasine (2c) was also confirmed by an X-ray crystallographic analysis.

Original language	English (US)
Pages (from-to)	995-1002
Number of pages	8
Journal	Journal of Natural Products
Volume	49
Issue number	6
DOIs	https://doi.org/10.1021/np50048a005
State	Published - Jan 1 1986

ASJC Scopus subject areas

Analytical Chemistry
Molecular Medicine
Pharmacology
Pharmaceutical Science
Drug Discovery
Complementary and alternative medicine
Organic Chemistry

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title = "Antineoplastic agents, 120. pancratium littorale",

abstract = "The bulbs of Pancratium littorale collected in Hawaii were found to contain a new phenanthridone biosynthetic product designated pancratistatin (4a) that proved to be effective (38-106% life extension at 0.75-12.5 mg/kg dose levels) against the murine P-388 lymphocytic leukemia. Pancratistatin also markedly inhibited (ED50, 0.01 μg/ml) growth of the P-388 in vitro cell line and in vivo murine M-5076 ovary sarcoma (53-84% life extension at 0.38-3.0 mg/kg). An X-ray crystal structure determination of pancratistatin monomethyl ether (4c) and a detailed high resolution (400 MHz) nmr study of pancratistatin and its pentaacetate (4b) completed assignment of structure 4a. Companion antineoplastic constituents of P. littorale were found to be narciclasine (2c) and its 7-deoxy derivative (2a). The structure of 7-deoxynarciclasine (2c) was also confirmed by an X-ray crystallographic analysis.",

author = "George Pettit and Venkatswamy Gaddamidi and Herald, {Delbert L.} and Singh, {Sheo Bux} and Cragg, {Gordon M.} and Schmidt, {Jean M.} and Boettner, {Fred E.} and M. Williams and Yoneo Sagawa",

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AU - Pettit, George

AU - Gaddamidi, Venkatswamy

AU - Herald, Delbert L.

AU - Singh, Sheo Bux

AU - Cragg, Gordon M.

AU - Schmidt, Jean M.

AU - Boettner, Fred E.

AU - Williams, M.

AU - Sagawa, Yoneo

PY - 1986/1/1

Y1 - 1986/1/1

N2 - The bulbs of Pancratium littorale collected in Hawaii were found to contain a new phenanthridone biosynthetic product designated pancratistatin (4a) that proved to be effective (38-106% life extension at 0.75-12.5 mg/kg dose levels) against the murine P-388 lymphocytic leukemia. Pancratistatin also markedly inhibited (ED50, 0.01 μg/ml) growth of the P-388 in vitro cell line and in vivo murine M-5076 ovary sarcoma (53-84% life extension at 0.38-3.0 mg/kg). An X-ray crystal structure determination of pancratistatin monomethyl ether (4c) and a detailed high resolution (400 MHz) nmr study of pancratistatin and its pentaacetate (4b) completed assignment of structure 4a. Companion antineoplastic constituents of P. littorale were found to be narciclasine (2c) and its 7-deoxy derivative (2a). The structure of 7-deoxynarciclasine (2c) was also confirmed by an X-ray crystallographic analysis.

AB - The bulbs of Pancratium littorale collected in Hawaii were found to contain a new phenanthridone biosynthetic product designated pancratistatin (4a) that proved to be effective (38-106% life extension at 0.75-12.5 mg/kg dose levels) against the murine P-388 lymphocytic leukemia. Pancratistatin also markedly inhibited (ED50, 0.01 μg/ml) growth of the P-388 in vitro cell line and in vivo murine M-5076 ovary sarcoma (53-84% life extension at 0.38-3.0 mg/kg). An X-ray crystal structure determination of pancratistatin monomethyl ether (4c) and a detailed high resolution (400 MHz) nmr study of pancratistatin and its pentaacetate (4b) completed assignment of structure 4a. Companion antineoplastic constituents of P. littorale were found to be narciclasine (2c) and its 7-deoxy derivative (2a). The structure of 7-deoxynarciclasine (2c) was also confirmed by an X-ray crystallographic analysis.

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