Inhibitory effects of arbutin-β-glycosides synthesized from enzymatic transglycosylation for melanogenesis
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To develop a new skin whitening agent, arbutin-β-glycosides were synthesized and evaluated for their melanogenesis inhibitory activities. Three active compounds were synthesized via the transglycosylation reaction of Thermotoga neapolitana β-glucosidase and purified by recycling preparative HPLC. As compared with arbutin (IC50 = 6 mM), the IC50 values of these compounds were 8, 10, and 5 mM for β-d-glucopyranosyl-(1→6)-arbutin, β-d-glucopyranosyl-(1→4)-arbutin, and β-d-glucopyranosyl-(1→3)-arbutin, respectively. β-d-Glucosyl-(1→3)-arbutin also exerted the most profound inhibitory effects on melanin synthesis in B16F10 melanoma cells. Melanin synthesis was inhibited to a significant degree at 5 mM, at which concentration the melanin content was reduced to below 70% of that observed in the untreated cells. Consequently, β-d-glucopyranosyl-(1→3)-arbutin is a more effective depigmentation agent and is also less cytotoxic than the known melanogenesis inhibitor, arbutin.
KeywordsArbutin Arbutin-β-glycosides Melanoma cell Transglycosylation Tyrosinase
This study was supported, in part, by the Marine and Extreme Genome Research Center Program, Ministry of Marine Affairs and Fisheries, and by the New University for Regional Innovation, Ministry of Education and Human Resources Development, Republic of Korea.