title: Phenylethanoid and phenylpropanoid glycosides with melanogenesis inhibitory activity from the flowers of Narcissus tazetta var. chinensis.
abstract: A methanol extract of the flowers of Narcissus tazetta var. chinensis Roem. (Amaryllidaceae) demonstrated inhibitory effects on melanogenesis in theophylline-stimulated murine B16 melanoma 4A5 cells. From the extract, four new phenylethanoid glycosides, tazettosides A–D (1–4), and a new phenylpropanoid glycoside, tazettoside E (5), were isolated along with 23 known compounds (6–28). Of the isolates, 1 (IC50 = 22.0 μM) and 4 (82.5 μM), 3-methoxy-8,9-methylenedioxy-3,4-dihydrophenanthridine (13, IC50 = 28.5 μM), 5,6-dihydrobicolorine (14, 23.7 μM), tazettine (16, 60.8 μM), benzyl β-D-glucopyranosyl-(1→6)-β-D-glucopyranoside (18, 27.8 μM), 2-(3,4-dimethoxyphenyl)ethyl β-D-glucopyranosyl-(1→6)-β-D-glucopyranoside (21, 74.6 μM), 3-phenylpropyl β-D-glucopyranoside (22, 59.0 μM), and cinnamyl β-D-glucopyranosyl-(1→6)-β-D-glucopyranoside (24, 88.0 μM) showed inhibitory effects without notable cytotoxicity at the effective concentrations.
authors.forename: Toshio
authors.initials: T
authors.lastname: Morikawa
authors.forename: Kiyofumi
authors.initials: K
authors.lastname: Ninomiya
authors.forename: Hiroyuki
authors.initials: H
authors.lastname: Kuramoto
authors.forename: Iyori
authors.initials: I
authors.lastname: Kamei
authors.forename: Masayuki
authors.initials: M
authors.lastname: Yoshikawa
authors.forename: Osamu
authors.initials: O
authors.lastname: Muraoka
mesh_terms: D000818:Animals; D045744:Cell Line, Tumor; D035264:Flowers / Q000737:chemistry; D006027:Glycosides / Q000737:chemistry / Q000494:pharmacology*; D008543:Melanins / Q000096:biosynthesis*; D008546:Melanoma, Experimental / Q000378:metabolism*; D051379:Mice; D014442:Monophenol Monooxygenase / Q000378:metabolism; D031427:Narcissus / Q000737:chemistry*; D010936:Plant Extracts / Q000494:pharmacology*
chemical_list: D006027:Glycosides; D008543:Melanins; D010936:Plant Extracts; D014442:Monophenol Monooxygenase