Acylated oleanane-type saponins from Ganophyllum giganteum

Five oleanane-type saponins, 3-O-beta-D-glucuronopyranosylzanhic acid 28-O-beta-D-xylopyranosyl-(1 -> 3)-[alpha-L-rhamnopyranosyl-(1 -> 2)]-(4-O-acetyl)-beta-D-fucopyranosyl ester (1), 3-O-beta-D-glucopyranosylzanhic acid 28-O-beta-D-xylopyranosyl-(1 -> 3)-[alpha-L-rhamnopyranosyl-(1 -> 2)]-(4-O-acetyl)-beta-D-fucopyranosyl ester (2), zanhic acid 28-O-beta-D-xylopyranosyl-(1 -> 3)-[alpha-L-rhamnopyranosyl-(1 -> 2)]-(4-O-acetyl)-beta-D-fucopyranosyl ester (3), zanhic acid 28-O-alpha-L-rhamnopyranosyl-(1 -> 2)-4-O-[(3'-hydroxy-2'-methyl-butyroyloxy)3-hydroxy-2-methyl-butyroylo xyl]-beta-D-fucopyranosyl ester (4), medicagenic acid 28-O-alpha-L-rhamnopyranosyl-(1 -> 2)-4-O-[(3'-hydroxy-2'-methyl-butyroyloxy)-3-hydroxy-2-methyl-butyroyl oxy]-beta-D-fucopyranosyl ester (5), were isolated from the root barks of Ganophyllum giganteum. Compounds 4 and 5 possessed an unusual substitution of the C-4 position of the beta-D-fucopyranosyl moiety by a C10 ester group formed by two symmetrical C5 nilic acid. From a chemotaxonomic point of view, their structures are in accordance with the previous saponins isolated from the Doratoxyleae tribe of the Sapindaceae family. Their cytotoxicity and anti-inflammatory activity were also evaluated. (C) 2013 Elsevier Ltd. All rights reserved.