2,3-Dehydro-4 alpha-hydroxylongilactone, a novel quassinoid and two known phenyl propanoids from Eurycoma longifolia Jack

A phytochemical study on the root of Eurycoma longifolia Jack afforded a novel 2,3-dehydro-4 alpha-hydroxylongilactone (1) and two known phenyl propanoids, 2,3-dihydroxy-1-(4'-hydroxy-3'-methoxyphenyl)-propan-1-one (2) and scopolin (3), isolated from this plant for the first time. All structures were characterised by spectroscopic analysis (1D and 2D NMR experiments, HRMS, UV, IR and optical rotation) and by comparison with known data. This is the first report of a C-19 quassinoid from the Simaroubaceae family possessing an unsubstituted vinyl function and a C-4 methyl group of beta-configuration in ring A. (C) 2009 Elsevier Ltd. All rights reserved.