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Arbutin (4-hydroxyphenyl β-D-glucopyranoside) has been used as a cosmetic whitening agent. 4-Hydroxyphenyl α-D-glucopyranoside (α-arbutin) was enzymatically synthesized from hydroquinone and glucose using CGTase with arbutin and starch1 (Sugimoto et al., 2005). Glucosyltransferases (GTFs) are enzymes that synthesize either dextrans or glucans, using sucrose as a substrate. Glucosyltransferases can catalyze the transfer of a sucrose-derived glucose to other carbohydrates, thereby allowing for oligosaccharide synthesis2. Two arbutin glucosides were synthesized via the acceptor reaction of a glucansucrase from Leuconostoc mesenteroides B-1299CB with arbutin and sucrose. The glucosides were purified by Bio-gel P-2 column chromatography and high performance liquid chromatography, and the structures were elucidated as 4-hydroxyphenyl β-isomaltoside (arbutin-G1), 4-hydroxyphenyl β-isomaltotrioside (arbutin-G2), according to the results of 1H, 13C, HSQC, 1H-1H COSY, and HMBC analyses. Arbutin glucoside (4-hydroxyphenyl β-isomaltoside) exhibited slower effects on DPPH radical scavenging and similar effects on tyrosinase inhibition, and increased inhibitory effect on MMP-1 production induced by UVB than arbutin. Arbutin glycoside showed better inhibitory effect than arbutin on MMP-1 production induced by UVB.
1 Syntheses of α-arbutin-α-glycosides and their inhibitory effects on human tyrosinase Journal of Biosciences and Bioengineering (2005) 99:272-276
2 Synthesis and characterization of novel quercetin-α-D-glucopyranosides using glucansucrase from Leuconostoc mesenteroides Enzyme and Microbial Technology (2007) 40: 1124-1129