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Potent inhibitors of ethanol absorption, elatosides A and B, were isolated from the bark of Aralia elata SEEM, through bioassay-guided separation together with elatosides C and D and four known oleanolic acid glucuronide-saponins, spinasaponin A, spinasaponin A 28-O-glucoside, and stipuleanosides R1 and R2. The structures of elatosides A, B, C, and D were determined on the basis of chemical and physicochemical evidence as oleanolic acid 3-O-¿[beta-D-xylopyranosyl (1--&gt;2)] [beta-D-galactopyranosyl (1--&gt;3)]¿-beta-D-glucopyranosiduronic acid, oleanolic acid 3-O-¿[beta-D-galactopyranosyl (1--&gt;2)] [beta-D-galactopyranosyl (1--&gt;3)]¿-beta-D-glucopyranosiduronic acid, and their 28-O-glucopyranosyl esters, respectively. The inhibitory effect of various oleanolic acid 3, 28-O-bisdesmosides, oleanolic acid 3-O-monodesmosides, and oleanolic acid on ethanol absorption was examined and it was found that the 3-O-glucuronide moiety and the 28-carboxyl group in oleanolic acid glucuronide-saponin were required to exert the inhibitory activity.

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Bioactive Saponins and Glycosides. VI. Elatosides A and B, Potent Inhibitors of Ethanol Absorption, from the Bark of Aralia elata SEEM. (Araliaceae): The Structure-Requirement in Oleanolic Acid Glucuronide-Saponins for the Inhibitory Activity.