Syntheses of alpha-arbutin-alpha-glycosides and their inhibitory effects on human tyrosinase.
Alpha-arbutin is a tyrosinase inhibitor. We synthesized alpha-arbutin-alpha-glycosides by the transglycosylation reaction of cyclomaltodextrin glucanotransferase from Bacillus macerans using alpha-arbutin and starch as acceptor and donor molecules, respectively. We isolated and characterized two major products from the reaction mixture. The structural analyses using 13C- and 1H-NMR spectroscopy proved that they were 4-hydroxyphenyl alpha-maltoside (alpha-Ab-alpha-G1) and 4-hydroxyphenyl alpha-maltotrioside (alpha-Ab-alpha-G2). Both alpha-Ab-alpha-G1 and alpha-Ab-alpha-G2 exhibited competitive-type inhibition on human tyrosinase as alpha-arbutin does. Their K(i) values were calculated to be 0.6 mM and 2.8 mM, respectively, which is slightly and significantly higher than that of alpha-arbutin (0.2 mM).
Sugimoto
Kazuhisa
K
Biochemical Research Laboratory, Ezaki Glico Co., Ltd., 4-6-5 Utajima, Nishiyodogawa-ku, Osaka 555-8502, Japan. sugimoto-kazuhisa@glico.co.jp
Nomura
Koji
K
Nishimura
Takahisa
T
Kiso
Taro
T
Sugimoto
Kenji
K
Kuriki
Takashi
T
D001104:Arbutin / Q000096:biosynthesis* / Q000737:chemistry*; D001407:Bacillus / Q000378:metabolism*; D045744:Cell Line, Tumor; D004789:Enzyme Activation; D004795:Enzyme Stability; D006027:Glycosides / Q000096:biosynthesis / Q000737:chemistry; D006801:Humans; D008545:Melanoma / Q000201:enzymology*; D014442:Monophenol Monooxygenase / Q000737:chemistry*; D010455:Peptides / Q000737:chemistry*
D006027:Glycosides; D010455:Peptides; D001104:Arbutin; D014442:Monophenol Monooxygenase