US EPA

6909257 

Journal Article 

Development of alpha-arbutin: Production at industrial scale and application for a skin-lightening cosmetic ingredient 

Kazuhisha, S; Takahisha, N; Takahashi, K; , 

2007 

GAKUSHIN PUBL CO 

TOKYO 

235-246 

WOS:000253338800001 

We found a new enzyme that efficiently catalyzes transglycosylation reaction toward phenolic hydroxyl groups. The enzyme, hydroquinone glucosylating enzyme, catalyzed alpha-anomer selective glycosylation of hydroquinone, and the yield of the resulting product, 4-hydroxyphenyl-O-alpha-D-glucopyranoside, was high enough to be used for industrial production. Kojic acid, caffeic acid, and many other phenolic compounds were also glycosylated by the reaction of this enzyme. However, alcohols were not glycosylated by the enzyme. The application studies of 4-hydroxyphenyl-O-alpha-D-glucopyranoside, i.e., alpha-arbutin were carried out. alpha-Arbutin strongly inhibited human tyrosinase, and its inhibitory effect on human tyrosinase was much higher than that of its isomer, 4-hydroxyphenyl-O-beta-D-glucopyranoside, i.e., arbutin. We also synthesized some kinds of glycosides of alpha-arbutin and arbutin. The comparison of their inhibitory effects on human tyrosinase indicated that the molecular size and electrostatic potentials around the benzene ring are important for inducing the inhibitory effect of hydroquinone glycosides toward human tyrosinase. We examined the inhibitory effects of alpha-arbutin on melanin biosynthesis. alpha-Arbutin inhibited melanin syntheses of HMV-II cells and human skin model in a dose-dependent manner at noncytotoxic concentrations. These results demonstrate that alpha-arbutin is an effective and safe ingredient for skin-lightening.