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[PMID]: | 28425165 |
[Au] Autor: | Akihisa T; Yokokawa S; Ogihara E; Matsumoto M; Zhang J; Kikuchi T; Koike K; Abe M |
[Ad] Endereço: | Research Institute for Science & Technology, Tokyo University of Science, 2641 Yamazaki, Noda, Chiba, 278-8510, Japan. |
[Ti] Título: | Melanogenesis-Inhibitory and Cytotoxic Activities of Limonoids, Alkaloids, and Phenolic Compounds from Phellodendron amurense Bark. |
[So] Source: | Chem Biodivers;14(7), 2017 Jul. | [Is] ISSN: | 1612-1880 |
[Cp] País de publicação: | Switzerland |
[La] Idioma: | eng |
[Ab] Resumo: | 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 IC values in the range of 2.6 - 90.0 µm. In particular, compound 5 exhibited strong cytotoxicity against AZ521 (IC 2.6 µm) which was superior to that of the reference cisplatin (IC 9.5 µm). |
[Mh] Termos MeSH primário: |
Antineoplásicos Fitogênicos/isolamento & purificação Phellodendron/química
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[Mh] Termos MeSH secundário: |
Alcaloides/isolamento & purificação Alcaloides/farmacologia Antineoplásicos Fitogênicos/química Antineoplásicos Fitogênicos/farmacologia Carcinogênese Linhagem Celular Tumoral Seres Humanos Concentração Inibidora 50 Limoninas/isolamento & purificação Limoninas/farmacologia Melanoma Experimental/patologia Metanol Fenóis/isolamento & purificação Fenóis/farmacologia Casca de Planta/química Extratos Vegetais
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[Pt] Tipo de publicação: | JOURNAL ARTICLE |
[Nm] Nome de substância:
| 0 (Alkaloids); 0 (Antineoplastic Agents, Phytogenic); 0 (Limonins); 0 (Phenols); 0 (Plant Extracts); Y4S76JWI15 (Methanol) |
[Em] Mês de entrada: | 1709 |
[Cu] Atualização por classe: | 170922 |
[Lr] Data última revisão:
| 170922 |
[Sb] Subgrupo de revista: | IM |
[Da] Data de entrada para processamento: | 170421 |
[St] Status: | MEDLINE |
[do] DOI: | 10.1002/cbdv.201700105 |
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