title: Synthesis and evaluation of bibenzyl glycosides as potent tyrosinase inhibitors.
abstract: Bibenzyl glycosides 1-6 were synthesized from 2,4-dihydoxybenzaldehyde and xylose, glucose, cellobiose or maltose. The key steps in the synthesis were the Wittig reaction and trichloroacetimidate glycosylation. Tests for tyrosinase inhibitory activity showed that all were significantly active, indicating that they are unique hydrophilic tyrosinase inhibitors. Bibenzyl xyloside 2 is a particularly potent inhibitor (IC(50) = 0.43 μM, 17 times higher than that of kojic acid). These results suggest that the hydrophilic cavity of tyrosinase might accommodate the bulky carbohydrate on the bibenzyl scaffold.
authors.affiliation: Department of Applied Biochemistry, Faculty of Agriculture, Utsunomiya University, Utsunomiya, Tochigi 321-0943, Japan.
authors.forename: Reiko
authors.initials: R
authors.lastname: Tajima
authors.forename: Hiromi
authors.initials: H
authors.lastname: Oozeki
authors.forename: Seiichi
authors.initials: S
authors.lastname: Muraoka
authors.forename: Saori
authors.initials: S
authors.lastname: Tanaka
authors.forename: Yukari
authors.initials: Y
authors.lastname: Motegi
authors.forename: Hiroyuki
authors.initials: H
authors.lastname: Nihei
authors.forename: Yoichi
authors.initials: Y
authors.lastname: Yamada
authors.forename: Noriyoshi
authors.initials: N
authors.lastname: Masuoka
authors.forename: Ken-ichi
authors.initials: K
authors.lastname: Nihei
mesh_terms: D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D020128:Inhibitory Concentration 50; D014442:Monophenol Monooxygenase / Q000037:antagonists & inhibitors*
chemical_list: D004791:Enzyme Inhibitors; D006027:Glycosides; D014442:Monophenol Monooxygenase