Antitumor agents, 135. Structure and stereochemistry of polacandrin, a new cytotoxic triterpene from Polanisia dodecandra.
A new dammarane triterpene, polacandrin , 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.
Shi, Q; Chen, K; Fujioka, T; Kashiwada, Y; Chang, JJ; Kozuka, M; Estes, JR; McPhail, AT; McPhail, DR; Lee, KH
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