論文 - 詳細
| RRC ID | 77888 |
|---|---|
| 著者 | Zhang J, Koike R, Yamamoto A, Ukiya M, Fukatsu M, Banno N, Miura M, Motohashi S, Tokuda H, Akihisa T. |
| タイトル | Glycosidic inhibitors of melanogenesis from leaves of Passiflora edulis. |
| ジャーナル | Chem Biodivers |
| 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 EpsteinBarr virus early antigen (EBV-EA) activation induced by 12-O-tetradecanoylphorbol-13-acetate (TPA) in Raji cells. |
| 巻・号 | 10(10) |
| ページ | 1851-65 |
| 公開日 | 2013-10-1 |
| DOI | 10.1002/cbdv.201300181 |
| PMID | 24130028 |
| MeSH | Animals Antigens, Viral / chemistry Antigens, Viral / metabolism Cell Differentiation / drug effects Cell Line, Tumor Cell Survival / drug effects Disaccharides / chemistry* Disaccharides / isolation & purification Disaccharides / pharmacology Flavones / chemistry* Flavones / isolation & purification Flavones / pharmacology Flavonoids / chemistry Gene Expression Regulation / drug effects Glycosides / chemistry* Glycosides / isolation & purification Glycosides / pharmacology Glycosides / toxicity Humans Interferon Type I / genetics Melanins / antagonists & inhibitors Melanins / biosynthesis* Methanol / chemistry Mice Monophenol Monooxygenase / genetics Passiflora / chemistry* Passiflora / metabolism Plant Leaves / chemistry* Plant Leaves / metabolism Pregnancy Proteins / genetics Saponins / chemistry* Saponins / isolation & purification Saponins / pharmacology Stereoisomerism Triterpenes / chemistry alpha-MSH / metabolism |
| IF | 2.039 |
| オルトメトリクス指標 |
オルトメトリクス指標項目
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| 最多言及媒体 | Patent(IFI CLAIMS) |
| 各媒体での言及数の合計 | 3 |
| 過去6か月間でのオルトメトリクス指標の変動値 | 0.0 |
| リソース情報 | |
| ヒト・動物細胞 | B16 melanoma 4A5(RCB0557) |