Inhibitory effects of arbutin-beta-glycosides synthesized from enzymatic transglycosylation for melanogenesis.

To develop a new skin whitening agent, arbutin-beta-glycosides were synthesized and evaluated for their melanogenesis inhibitory activities. Three active compounds were synthesized via the transglycosylation reaction of Thermotoga neapolitana beta-glucosidase and purified by recycling preparative HPLC. As compared with arbutin (IC(50 )= 6 mM), the IC(50 )values of these compounds were 8, 10, and 5 mM for beta-D -glucopyranosyl-(1-->6)-arbutin, beta-D: -glucopyranosyl-(1-->4)-arbutin, and beta-D -glucopyranosyl-(1-->3)-arbutin, respectively.