title: Synthesis of dihydroresveratrol glycosides and evaluation of their activity against melanogenesis in B16F0 melanoma cells.
abstract: Dihydroresveratrol glucoside 1 isolated from Camellia oleifera and its xyloside derivative 2 were synthesized for the first time in 5 steps from TBS-protected aldehyde 4. Natural product 1 is a potent melanogenesis inhibitor in B16F0 melanoma cells (approximately 40 fold more potent than kojic acid). In contrast, the synthetic product 2 stimulates melanogenesis, suggesting that a single hydroxymethyl group in the glycoside substituent of dihydroresveratrols is responsible for inhibition or activation of melanogenesis.
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: Yukiko
authors.initials: Y
authors.lastname: Izutsu
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 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 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: K
authors.lastname: Nihei
mesh_terms: D000818:Animals; D045744:Cell Line, Tumor; D004354:Drug Screening Assays, Antitumor; D006027:Glycosides / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008543:Melanins / Q000096:biosynthesis*; D008546:Melanoma, Experimental / Q000378:metabolism* / Q000473:pathology; D051379:Mice; D021241:Spectrometry, Mass, Electrospray Ionization; D013267:Stilbenes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology
chemical_list: D006027:Glycosides; D008543:Melanins; D013267:Stilbenes; C544754:dihydroresveratrol
keywords: Camellia oleifera; Dihydroresveratrol glycoside; Glycosylation; Melanogenesis activator; Melanogenesis inhibitor