title: Synthesis of quercetin glycosides and their melanogenesis stimulatory activity in B16 melanoma cells.
abstract: 4'-O-β-d-Glucopyranosyl-quercetin-3-O-β-d-glucopyranosyl-(1→4)-β-d-glucopyra-noside (3) was isolated from Helminthostachys zeylanica root extract as a melanogenesis acceleration compound and was synthesized using rutin as the starting material. Related compounds were also synthesized to understand the structure-activity relationships in melanin biosynthesis. Melanogenesis activities of the glycosides were determined by measuring intracellular melanin content in B16 melanoma cells. Among the synthesized quercetin glycosides, quercetin-3-O-β-d-glucopyranoside (1), quercetin-3-O-β-d-glucopyranosyl-(1→4)-β-d-glucopyranoside (2), and 3 showed more potent intracellular melanogenesis acceleration activities than theophyline used as positive control in a dose-dependent manner with no cytotoxic effect.
authors.affiliation: The United Graduate School of Agricultural Science, Gifu University, 1-1 Yanagido, 501-1193 Gifu, Japan.
authors.forename: Kosei
authors.initials: K
authors.lastname: Yamauchi
authors.affiliation: The United Graduate School of Agricultural Science, Gifu University, 1-1 Yanagido, 501-1193 Gifu, Japan. Electronic address: mitunaga@gifu-u.ac.jp.
authors.forename: Tohru
authors.initials: T
authors.lastname: Mitsunaga
authors.affiliation: Department of Chemistry, Faculty of Mathematics and Natural Sciences, Biopharmaca Research Center, Bogor Agricultural University, Jl. Taman Kencana No. 3, Kampus IPB Taman Kencana, Bogor 16151, Indonesia. Electronic address: ime@ipb.ac.id.
authors.forename: Irmanida
authors.initials: I
authors.lastname: Batubara
mesh_terms: D000818:Animals; D002240:Carbohydrate Sequence; D045744:Cell Line, Tumor / Q000187:drug effects / Q000378:metabolism; D002475:Cellobiose / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D060326:Chemistry Techniques, Synthetic; D004305:Dose-Response Relationship, Drug; D029624:Ferns / Q000737:chemistry; D005960:Glucosides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D008543:Melanins / Q000096:biosynthesis; D008546:Melanoma, Experimental / Q000188:drug therapy* / Q000378:metabolism; D051379:Mice; D008969:Molecular Sequence Data; D015394:Molecular Structure; D018517:Plant Roots / Q000737:chemistry; D011794:Quercetin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D013329:Structure-Activity Relationship
chemical_list: C000592628:4'-O-glucopyranosylquercetin-3-O-glucopyranosyl-(1-4)-glucopyranoside; D005960:Glucosides; D008543:Melanins; D002475:Cellobiose; D011794:Quercetin
keywords: B16 melanoma cells; Quercetin glycoside; TRP-1; Tyrosinase