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Date of Publication:2012-01-01

Journal:高等学校化学学报

Volume:33

Issue:4

Page Number:744-749

ISSN No.:0251-0790

Abstract:The natural pentacyclic triterpene compound, oleanolic acid, has a series of biological activities, such as antitumor, anti-HIV, hypoglycemic and liver protective activities, but its relatively weak activities and low bioavailability limit its clinical applications. In order to investigate the hypoglycemic activity of oleanolic acid derivaties, sixteen derivatives were synthesized by modification of oleanolic acid at C2, C3 and C28 positions via oxidation, esterification, cyclization, Mannich reaction and so on. Their structures were determined by physicochemical properties, MS and NMR data. Their in vitro inhibitory activities against alpha-glucosidase were tested. The results show that all the tested compounds exhibit alpha-glucosidase inhibitory activities in various degrees at the concentration of 200 mu g/mL. Among then, 3-oxo and 29-ester derivatives (2, 5-7) show lower inhibitory activity than oleanolic acid. The preliminary analysis of structure-activity relationship revealed that the free carboxyl group at C28 was indispensable and hydroxyl or other hydrogen-based donor groups at C3 contributed to increase inhibitory activity.

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