THE STRUCTURES AND STEREOCHEMISTRY OF CYTOTOXIC SESQUITERPENE QUINONES FROM DACTYLOSPONGIA ELEGANS

Article abstract of DOI:10.1016/S0040-4020(01)80012-0

The cytotoxicity of a crude extract from Dactylospongia elegans stimulated a search for the active constituents.The structures and absolute stereochemistry are elucidated for four new, 9, 11, 18, 19, and thirteen previously described compounds, 3, 4, 6a, 7, 8, 10, 12 - 17, 21.These compounds were isolated from collections of D. elegans obtained from three different Indo-Pacific regions, Fiji, Papua New Guinea, and Thailand.This species appears to elaborate a broader range of the mixed biogenesis sesquiterpene-hydroquinone (-quinone) metabolites in comparison to those of other sponges or seaweeds.Three compounds, 4, 9, and 13, were potent (IC₅₀'s were less than 1 μg/ml).The quinone ring appears to be essential for this in vitro activity.