Cytotoxic polyisoprenes and glycosides of long-chain fatty alcohols from Dimocarpus fumatus

The ethanolic extract from the stem bark of Dimocarpus fumatus, showed in vitro cytotoxic activity against KB cells. Fractionation of the extract gave compounds belonging to different classes. The two major components have been identified as a benzoquinone, sargaquinone, and a chromene, sargaol. One sphingolipid, soyacerebroside I, two glycosides of sitosterol, and fatty acids were also identified. Besides these known compounds, two new glycosides of long-chain fatty alcohols have been identified as 1-O-[alpha-L-rhamnopyranosyl-(1 --> 2)-beta-D-glucopyranosyl-(1 --> 3)-alpha-L-rhamnopyranosyl-(1 --> 6)-beta-D-glucopyranosyl]hexadecanol and 1-O-[[alpha-L-arabinopyranosyl-(1 --> 3)]-alpha-L-rhamnopyranosyl-(1 --> 2)-beta-D-glucopyranosyl-(1 --> 3)-alpha-L-rhamnopyranosyl-(1 --> 6)-beta-D-glucopyranosyl] hexadecanol, and a mixture of three new diacylglycerylglucosides has been isolated. These structures were elucidated by analysis of 2D-NMR and mass spectra. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.