α-Glucosidase inhibitory caged xanthones from the resin of Garcinia hanburyi

Abstract

A yellow resin (gamboge) from Garcinia hanburyi has been widely used as folk medicine due to its antibacterial and antitumor activities. We isolated four a-glucosidase inhibitory compounds from the methanol extract of gamboge. The compounds (1-4) were identified as gambogoic acid (1), moreollic acid (2), gambogic acid (3), and 10-methoxygambogenic acid (4), respectively through spectroscopic data including 2D-NMR and HREIMS. All compounds were examined in the enzyme inhibition assay against a-glucosidase to identify their inhibitory potencies and kinetic behavior. All compounds (1-4) showed enzyme inhibition against a-glucosidase, but the activity was significantly affected by the methoxy group on C-10 of ring A and pentenyl pyran moiety of ring D. For example, compound 1 (IC 50 =41.4 ?M) bearing pyran ring eight times effective that 4 (IC 50 =350.6 ?M) having geranyl group itself. Most active compound was found out to be gambogoic acid (1) which was analyzed most abundant metabolite in gamboge by LC-ESI-MS/MS. In kinetic study, compounds 1 and 2 were proved as noncompetitive inhibitors. ? The Korean Society for Applied Biological Chemistry 2019.