title: Dihydroresveratrol cellobioside and xylobioside as effective melanogenesis activators.
abstract: Dihydroresveratrol cellobioside and xylobioside, whose structures were designed based on that of the naturally occurring melanogenesis-controlling agent dihydroresveratrol glucoside, were synthesized via Schmidt glycosylation as the key step. Both analogues stimulated melanogenesis with efficacies comparable to that of 8-methoxypsoralen, a well-known melanogenesis activator. This suggests that diglycosyl modification of the 4'-OH on the dihydroresveratrol skeleton leads to the activation of melanogenesis, both with and without hydroxymethyl groups in the sugar moieties.
authors.affiliation: Department of Applied Biological Chemistry, Faculty of Agriculture, Utsunomiya University, Tochigi 321-0943, Japan.
authors.forename: Chisato
authors.initials: C
authors.lastname: Oode
authors.affiliation: Department of Applied Life Science, United Graduate School of Agricultural Science, Tokyo University of Agriculture and Technology, Tokyo 183-8509, Japan; Nikkol Group Cosmos Technical Center Co., LTD., Tokyo 174-0046, Japan.
authors.forename: Wataru
authors.initials: W
authors.lastname: Shimada
authors.affiliation: Nikkol Group Cosmos Technical Center Co., LTD., Tokyo 174-0046, Japan.
authors.forename: Mariko
authors.initials: M
authors.lastname: Yokota
authors.affiliation: Department of Chemistry, Faculty of Education, Utsunomiya University, Tochigi 321-0943, Japan.
authors.forename: Yoichi
authors.initials: Y
authors.lastname: Yamada
authors.affiliation: Department of Applied Biological Chemistry, Faculty of Agriculture, Utsunomiya University, Tochigi 321-0943, Japan; Department of Applied Life Science, United Graduate School of Agricultural Science, Tokyo University of Agriculture and Technology, Tokyo 183-8509, Japan. Electronic address: nihei98@cc.utsunomiya-u.ac.jp.
authors.forename: Ken-Ichi
authors.initials: KI
authors.lastname: Nihei
mesh_terms: D000818:Animals; D002470:Cell Survival / Q000187:drug effects*; D002475:Cellobiose / Q000737:chemistry*; D004187:Disaccharides / Q000737:chemistry*; D006031:Glycosylation; D008546:Melanoma, Experimental / Q000188:drug therapy / Q000473:pathology*; D051379:Mice; D013267:Stilbenes / Q000737:chemistry / Q000494:pharmacology*; D014407:Tumor Cells, Cultured
chemical_list: D004187:Disaccharides; D013267:Stilbenes; C544754:dihydroresveratrol; D002475:Cellobiose; C004173:xylobiose
keywords: Dihydroresveratrol cellobioside; Dihydroresveratrol xylobioside; Glycosylation; Melanogenesis activator; Melanogenesis inhibitor