A detailed structural study of the major acidic triterpene saponins from European oak heartwood, Quercus robur L. and Q. petraea Liebl., revealed the presence of 2 alpha,3 beta,19 alpha-trihydroxyolean-12-ene-24,28-dioic acid (1), 2 alpha,3 beta,19 alpha-23-tetrahydroxyolean-12-ene-24,28-dioic acid (2), and their corresponding glycosides, 28-beta-D-glucopyranosyl-2 alpha,3 beta,19 alpha-trihydroxyolean-12-ene-24,28-dioic acid (3), and 28-beta-D-glucopyranosyl-2 alpha,3 beta,19 alpha,23-tetrahydroxyolean-12-ene-24,28-dioic acid (4). Compounds were isolated and purified by successive flash chromatography and semi-preparative HPLC, and structurally determined by NMR and LC-ESI/MS in the negative ion mode. Compounds 2 and 4 have been identified for the first time in Quercus species and are new compounds.
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