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Flavonoids and Other Compounds from Ouratea ferruginea (Ochnaceae) as Anticancer and Chemopreventive Agents
Programa de Pós-Graduação em Química, ICE-Universidade Federal Rural do Rio de Janeiro, 23890-000, Seropédica, RJ, Brazil
Faculdade de Química, Instituto de Ciências Exatas e Naturais, Universidade Federal do Pará, Av. Augusto Corrêa 01, 66075-110, Belém, PA, Brazil
Departamento de Botânica, Embrapa Amazônia Oriental, Tv. Enéas Pinheiro s/n, 66077-530, Belém, PA, Brazil
Laboratório de Bioquímica, Centro de Ciências Biológicas e da Saúde, Centro Universitário da Zona Oeste (UEZO), 23070-200, Rio de Janeiro, RJ, Brazil
Núcleo de Pesquisa de Produtos Naturais, Bloco H, CCS-UFRJ, Ilha do Fundão, 21941-970, Rio de Janeiro, RJ, Brasil
* Author to whom correspondence should be addressed.
Received: 16 May 2012; in revised form: 20 June 2012 / Accepted: 22 June 2012 / Published: 3 July 2012
Abstract: The chemical study of the extracts from leaves and stems of Ouratea ferruginea allowed the identification of a new isoflavone, 5-hydroxy-7,3′4′5′-tetramethoxyisoflavone, and twenty two known compounds, including friedelin, 3β-friedelinol, lupeone, a mixture of sitosterol, stigmasterol and campesterol, sitosteryl- and stigmasteryl-3-O-b-D-glucopyranosides, 5,4′-dihydroxy-7,5′,3′-trimethoxyisoflavone, 5,4′-dihydroxy-7,3′-di-methoxyisoflavone (7,3′-di-O-methylorobol), 5,7,4′-trihydroxy-3′,5′-dimethoxyisoflavone (piscigenin), 2R,3R-epicatechin, syringic acid, 2,6-dimethoxybenzoquinone, 2,6-dimethoxyhydroquinone, syringic and ferulic aldehyde, a mixture of vanillic acid, 1-hydroxy-2-methoxy-4-(1E-3-hydroxy-1-propenyl)-benzene and 3,5-dimethoxy-4-hydroxy-dihydrocinamaldehyde, besides amenthoflavone and 7-O-methylamenthoflavone (sequoiaflavone) which are considered as chemotaxonomic markers of Ouratea. The structures were identified by IR, 1H- and 13C-NMR and GC-MS, HPLC-MS, besides comparison with literature data. The inhibitory effects of 5,4′-dihydroxy-7,5′,3′-trimethoxyisoflavone, 7,3′-di-O-methylorobol, piscigenin and 7-O-methylamenthoflavone on cytochrome P450-dependent 7-ethoxycoumarin O-deethylase (ECOD) and glutathione S-transferase (GST) were evaluated in vitro. The 5,4′-dihydroxy-7,5′,3′-trimethoxy-isoflavone was the best inhibitor, inhibiting almost 75% of GST activity. Sequoiaflavone was the most potent inhibitor, inhibiting ECOD assay in 75%. These activities allow us to consider both these flavonoids as potential anticancer and chemopreventive agents.
Keywords: Ouratea ferruginea; biflavonoids; isoflavones; chemopreventive agents
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MDPI and ACS Style
Fidelis, Q.C.; Castro, R.N.; Guilhon, G.M.S.P.; Rodrigues, S.T.; de Salles, C.M.C.; de Salles, J.B.; de Carvalho, M.G. Flavonoids and Other Compounds from Ouratea ferruginea (Ochnaceae) as Anticancer and Chemopreventive Agents. Molecules 2012, 17, 7989-8000.
Fidelis QC, Castro RN, Guilhon GMSP, Rodrigues ST, de Salles CMC, de Salles JB, de Carvalho MG. Flavonoids and Other Compounds from Ouratea ferruginea (Ochnaceae) as Anticancer and Chemopreventive Agents. Molecules. 2012; 17(7):7989-8000.
Fidelis, Queli C.; Castro, Rosane N.; Guilhon, Giselle M. S. P.; Rodrigues, Silvane T.; de Salles, Cristiane M. C.; de Salles, João B.; de Carvalho, Mario G. 2012. "Flavonoids and Other Compounds from Ouratea ferruginea (Ochnaceae) as Anticancer and Chemopreventive Agents." Molecules 17, no. 7: 7989-8000.