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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 derivatives,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 mug/mL.Among them,3-oxo and 28-ester
   derivatives(2,57) 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-bond donor groups at C3 contributed to increase inhibitory
   activity.

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