title: Glycosidic inhibitors of melanogenesis from leaves of Passiflora edulis.
abstract: A new flavonoid glycoside, chrysin 6-C-β-rutinoside (chrysin α-L-rhamnopyranosyl-(1→6)-C-β-glucopyranoside; 2), and two new triterpene glycosides, (31R)-31-O-methylpassiflorine (7) and (31S)-31-O-methylpassiflorine (8), along with 14 known glycosides, including three flavonoid glycosides, 1, 3, and 4, six triterpene glycosides, 5, 6, and 9-12, three cyano glycosides, 13-15, and two other glycosides, 16 and 17, were isolated from a MeOH extract of the leaves of Passiflora edulis (passion flower; Passifloraceae). The structures of new compounds were elucidated on the basis of extensive spectroscopic analysis and comparison with literature data. Upon evaluation of compounds 1-17 against the melanogenesis in the B16 melanoma cells induced with α-melanocyte-stimulating hormone (α-MSH), three compounds, isoorientin (1), 2, and (6S,9R)-roseoside (17), exhibited inhibitory effects with 37.3-47.2% reduction of melanin content with no, or almost no, toxicity to the cells (90.8-100.2% cell viability) at 100 μM. Western blot analysis showed that compound 2 reduced the protein levels of MITF, TRP-1, and tyrosinase, in a concentration-dependent manner while exerted almost no influence on the level of TRP-2, suggesting that this compound inhibits melanogenesis on the α-MSH-stimulated B16 melanoma cells by, at least in part, inhibiting the expression of MITF, followed by decreasing the expression of TRP-1 and tyrosinase. In addition, compounds 1-17 were evaluated for their inhibitory effects against the EpsteinBarr virus early antigen (EBV-EA) activation induced by 12-O-tetradecanoylphorbol-13-acetate (TPA) in Raji cells.
authors.affiliation: College of Science and Technology, Nihon University, 1-8-14 Kanda Surugadai, Chiyoda-ku, Tokyo 101-8308, Japan.
authors.forename: Jie
authors.initials: J
authors.lastname: Zhang
authors.forename: Ryosuke
authors.initials: R
authors.lastname: Koike
authors.forename: Ayako
authors.initials: A
authors.lastname: Yamamoto
authors.forename: Motohiko
authors.initials: M
authors.lastname: Ukiya
authors.forename: Makoto
authors.initials: M
authors.lastname: Fukatsu
authors.forename: Norihiro
authors.initials: N
authors.lastname: Banno
authors.forename: Motofumi
authors.initials: M
authors.lastname: Miura
authors.forename: Shigeyasu
authors.initials: S
authors.lastname: Motohashi
authors.forename: Harukuni
authors.initials: H
authors.lastname: Tokuda
authors.forename: Toshihiro
authors.initials: T
authors.lastname: Akihisa
mesh_terms: D000818:Animals; D000956:Antigens, Viral / Q000737:chemistry / Q000378:metabolism; D002454:Cell Differentiation / Q000187:drug effects; D045744:Cell Line, Tumor; D002470:Cell Survival / Q000187:drug effects; D004187:Disaccharides / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D047309:Flavones / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D005419:Flavonoids / Q000737:chemistry; D005786:Gene Expression Regulation / Q000187:drug effects; D006027:Glycosides / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology / Q000633:toxicity; D006801:Humans; D007370:Interferon Type I / Q000235:genetics; D008543:Melanins / Q000037:antagonists & inhibitors / Q000096:biosynthesis*; D000432:Methanol / Q000737:chemistry; D051379:Mice; D014442:Monophenol Monooxygenase / Q000235:genetics; D029598:Passiflora / Q000737:chemistry* / Q000378:metabolism; D018515:Plant Leaves / Q000737:chemistry* / Q000378:metabolism; D011257:Pregnancy Proteins / Q000235:genetics; D012503:Saponins / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D013237:Stereoisomerism; D014315:Triterpenes / Q000737:chemistry; D000521:alpha-MSH / Q000378:metabolism
chemical_list: D000956:Antigens, Viral; D004187:Disaccharides; C033305:Epstein-Barr virus early antigen; D047309:Flavones; D005419:Flavonoids; D006027:Glycosides; D007370:Interferon Type I; D008543:Melanins; D011257:Pregnancy Proteins; D012503:Saponins; D014315:Triterpenes; C588289:chrysin 6-C-rutinoside; C020947:interferon tau; D000521:alpha-MSH; D014442:Monophenol Monooxygenase; D000432:Methanol
keywords: Glycosides; Melanogenesis inhibition; Passiflora edulis