title: Rhododendrol glycosides as stereospecific tyrosinase inhibitors.
abstract: Rhododendrol derivatives 3-12 have been synthesized in six steps, including aldol condensation and/or trichloroacetimidate glycosylation as the key reactions. Each derivative showed effective inhibition of tyrosinase-catalyzed oxidation processes. In particular, a series of synthetic derivatives having an R-stereogenic center at C-2 proved to be more potent than their respective epimers. In addition, the glycosylation on the phenylbutanoid scaffold increased the difference in activity between the isomers. This suggests that the sugar moiety plays an important role in eliciting their potent inhibitory activity.
authors.affiliation: Department of Applied Life Science, United Graduate School of Agricultural Science, Tokyo University of Agriculture and Technology, Tokyo 183-8509, Japan.
authors.forename: Takehiro
authors.initials: T
authors.lastname: Iwadate
authors.affiliation: Department of Applied Life Science, United Graduate School of Agricultural Science, Tokyo University of Agriculture and Technology, Tokyo 183-8509, Japan; Department of Applied Biological Chemistry, Faculty of Agriculture, Utsunomiya University, Tochigi 321-0943, Japan. Electronic address: nihei98@cc.utsunomiya-u.ac.jp.
authors.forename: Ken-ichi
authors.initials: K
authors.lastname: Nihei
mesh_terms: D000440:Butanols / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D004305:Dose-Response Relationship, Drug; D004791:Enzyme Inhibitors / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D006027:Glycosides / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D015394:Molecular Structure; D014442:Monophenol Monooxygenase / Q000037:antagonists & inhibitors* / Q000378:metabolism; D013329:Structure-Activity Relationship
chemical_list: D000440:Butanols; D004791:Enzyme Inhibitors; D006027:Glycosides; C115945:rhododendrol; D014442:Monophenol Monooxygenase
keywords: Aldol condensation; Phenylbutanoid; Rhododendrol glycoside; Trichloroacetimidate glycosylation; Tyrosinase inhibitor