Le_2023_R.Soc.Open.Sci_10_230676

Beta-mangostin is a xanthone commonly found in the genus Garcinia. Unlike alpha-mangostin, to date, there have only been a few studies on the biological activity and derivatization of beta-mangostin. In this study, two novel glycosylated derivatives of beta-mangostin were successfully synthesized via a one-pot enzymatic reaction. These derivatives were characterized as beta-mangostin 6-O-beta-d-glucopyranoside and beta-mangostin 6-O-beta-d-2-deoxyglucopyranoside by TOF ESI/MS and (1)H and (13)C NMR analyses. Beta-mangostin showed cytotoxicity against KB, MCF7, A549 and HepG2 cancer cell lines, with IC(50) values ranging from 15.42 to 21.13 microM. The acetylcholinesterase and alpha-glucosidase inhibitory activities of beta-mangostin were determined with IC(50) values of 2.17 and 27.61 microM, respectively. A strong anti-microbial activity of beta-mangostin against Gram-positive strains (Bacillus subtilis, Lactobacillus fermentum and Staphylococcus aureus) was observed, with IC(50) values of 0.16, 0.18 and 1.24 microg ml(-1), respectively. Beta-mangostin showed weaker activity against Gram-negative strains (Salmonella enterica, Escherichia coli and Pseudomonas aeruginosa) as well as Candida albicans fungus, with IC(50) and MIC values greater than the tested concentration (greater than 32 microg ml(-1)). The new derivatives of beta-mangostin showed weaker activities than those of beta-mangostin, demonstrating the important role of the hydroxyl group at C-6 of beta-mangostin in its bioactivity.