Antitumor Agents, 135. Structure and Stereochemistry of Polacandrin, a New Cytotoxic Triterpene from Polanisia, dodecandra

1 October 1992

journal article
Published by American Chemical Society (ACS) in Journal of Natural Products

Vol. 55 (10) , 1488-1497
https://doi.org/10.1021/np50088a015

Abstract

A new dammarane triterpene, polacandrin [1], has been isolated from Polanisia dodecandra. The structure of 1 was established as 1 beta, 3 alpha, 12 beta, 25-tetrahydroxy-20(S),24(S)-epoxydammarane by chemical and spectroscopic methods, which included the concerted application of a number of 2D nmr techniques that involved 1H-1H COSY, HETCOR, NOESY, and long-range HETCOR. Single-crystal X-ray analysis of polacandrin pentahydrate verified the complete structure and stereochemistry. Polacandrin showed potent cytotoxicities against KB (ED50 = 0.60 microgram/ml), P-388 (ED50 = 0.90 microgram/ml), and RPMI-7951 (ED50 = 0.62 microgram/ml) tumor cells.

Keywords

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