Xanthones with neuraminidase inhibitory activity from the seedcases of Garcinia mangostana.
Basic Information
ID: ALA1221336
Journal: Bioorg Med Chem
Title: Xanthones with neuraminidase inhibitory activity from the seedcases of Garcinia mangostana.
Authors: Ryu HW, Curtis-Long MJ, Jung S, Jin YM, Cho JK, Ryu YB, Lee WS, Park KH.
Abstract: This study was designed to gain deeper insights into the molecular properties of natural xanthones as neuraminidase inhibitors. A series of xanthones 1-12 was isolated from the seedcases of Garcinia mangostana and evaluated for bacteria neuraminidase inhibitory activity. Compounds 11 and 12 emerged to be new xanthones (mangostenone F, mangostenone G) which we fully spectroscopically characterized. The IC(50) values of compounds 1-12 were determined to range between 0.27-65.7 microM. The most potent neuraminidase inhibitor 10 which has an IC(50) of 270 nM features a 5,8-diol moiety on the B ring. Interestingly, structure-activity studies reveal that these xanthones show different kinetic inhibition mechanisms depending upon the arrangement of hydroxyl groups in the B ring. Compound 6 possessing a 6,7-diol motif on the B-ring operated under the enzyme isomerization model (k(5)=0.1144 microM(-1) s(-1), k(6)=0.001105 s(-1), and K(i)(app)=7.41 microM), whereas compound 10 possessing a 5,8-diol unit displayed simple reversible slow-binding inhibition (k(3)=0.02294 microM(-1) s(-1), k(4)=0.001025 s(-1), and K(i)(app)=0.04468 microM).
CiteXplore: 20696581
DOI: 10.1016/j.bmc.2010.07.033
Patent ID: ┄