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Molecules 2012, 17(7), 7989-8000; doi:10.3390/molecules17077989

Flavonoids and Other Compounds from Ouratea ferruginea (Ochnaceae) as Anticancer and Chemopreventive Agents

1
Programa de Pós-Graduação em Química, ICE-Universidade Federal Rural do Rio de Janeiro, 23890-000, Seropédica, RJ, Brazil
2
Faculdade de Química, Instituto de Ciências Exatas e Naturais, Universidade Federal do Pará, Av. Augusto Corrêa 01, 66075-110, Belém, PA, Brazil
3
Departamento de Botânica, Embrapa Amazônia Oriental, Tv. Enéas Pinheiro s/n, 66077-530, Belém, PA, Brazil
4
Laboratório de Bioquímica, Centro de Ciências Biológicas e da Saúde, Centro Universitário da Zona Oeste (UEZO), 23070-200, Rio de Janeiro, RJ, Brazil
5
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 / Revised: 20 June 2012 / Accepted: 22 June 2012 / Published: 3 July 2012
(This article belongs to the Section Natural Products)
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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 Ouratea ferruginea; biflavonoids; isoflavones; chemopreventive agents
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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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.

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