RRC ID 52193
著者 Akihisa T, Yokokawa S, Ogihara E, Matsumoto M, Zhang J, Kikuchi T, Koike K, Abe M.
タイトル Melanogenesis-Inhibitory and Cytotoxic Activities of Limonoids, Alkaloids, and Phenolic Compounds from Phellodendron amurense Bark.
ジャーナル Chem Biodivers
Abstract Four limonoids, 1 - 4, five alkaloids, 5 - 9, and four phenolic compounds, 10 - 13, were isolated from a MeOH extract of the bark of Phellodendron amurense (Rutaceae). Among these, compound 13 was new, and its structure was established as rel-(1R,2R,3R)-5-hydroxy-3-(4-hydroxy-3-methoxyphenyl)-6-methoxy-1-(methoxycarbonylmethyl)indane-2-carboxylic acid methyl ester (γ-di(methyl ferulate)) based on the spectrometric analysis. Upon evaluation of compounds 1 - 13 against the melanogenesis in the B16 melanoma cells induced with α-melanocyte-stimulating hormone (α-MSH), four compounds, limonin (1), noroxyhydrastinine (6), haplopine (7), and 4-methoxy-1-methylquinolin-2(1H)-one (8), exhibited potent melanogenesis-inhibitory activities with almost no toxicity to the cells. Western blot analysis revealed that compound 6 inhibited melanogenesis, at least in part, by inhibiting the expression of protein levels of tyrosinase, TRP-1, and TRP-2 in α-MSH-stimulated B16 melanoma cells. In addition, when compounds 1 - 13 were evaluated for their cytotoxic activities against leukemia (HL60), lung (A549), duodenum (AZ521), and breast (SK-BR-3) cancer cell lines, five compounds, berberine (5), 8, canthin-6-one (9), α-di-(methyl ferulate) (12), and 13, exhibited cytotoxicities against one or more cancer cell lines with IC50 values in the range of 2.6 - 90.0 μm. In particular, compound 5 exhibited strong cytotoxicity against AZ521 (IC50 2.6 μm) which was superior to that of the reference cisplatin (IC50 9.5 μm).
巻・号 14(7)
公開日 2017-7-1
DOI 10.1002/cbdv.201700105
PMID 28425165
MeSH Alkaloids / isolation & purification Alkaloids / pharmacology Antineoplastic Agents, Phytogenic / chemistry Antineoplastic Agents, Phytogenic / isolation & purification* Antineoplastic Agents, Phytogenic / pharmacology Carcinogenesis Cell Line, Tumor Humans Inhibitory Concentration 50 Limonins / isolation & purification Limonins / pharmacology Melanoma, Experimental / pathology Methanol Phellodendron / chemistry* Phenols / isolation & purification Phenols / pharmacology Plant Bark / chemistry Plant Extracts
IF 2.039
引用数 6
リソース情報
ヒト・動物細胞 HL60(RCB0041) AZ521(RCB2087)