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Five bioactive triterpene oligoglycosides named escins, Ia, Ib, IIa, IIb, and IIIa were isolated from the seeds of horse chestnut tree, Aesculus hippocastanum L. (Hippocastanaceae). The chemical structures of escins Ia, Ib, IIa, IIb, and IIIa were determine on the basis of chemical and physicochemical evidence, which included selective cleavage of the glucuronide linkage using photochemical reaction and lead tetraacetate decarboxylation reaction. Escins Ia, Ib, IIa, and IIb were found to exhibit an ethanol absorption-inhibitory effect and hypoglycemic activity in the oral glucose tolerance test in rats. Some structure-activity relationships are reported.

Betavulgarosides I, II, III, and IV, oleanolic acid oligoglycosides having an unique acidic substituent, were isolated from the root of Beta vulgaris L. (sugar beet) together with betavulgarosides VI, VII, and VIII. The chemical structures of betavulgarosides I, II, III, IV were identified from chemical and physicochemical evidence. Betavulgarosides II, III, and IV were found to exhibit hypoglycemic activity in an oral glucose tolerance test in rats.