Flavonoids and other compounds from Ouratea ferruginea (Ochnaceae) as anticancer and chemopreventive agents.

• Autor(a) principal: FIDELIS, Q. C.
• Data de Publicação: 2012
• Outros Autores: CASTRO, R. N., GUILHON, G. M. S. P., RODRIGUES, S. T., SALLES, C. M. C. de, SALLES, J. B. de, CARVALHO, M. G. de
• Tipo de documento: Artigo
• Idioma: eng
• Título da fonte: Repositório Institucional da EMBRAPA (Repository Open Access to Scientific Information from EMBRAPA - Alice)
• Texto Completo: http://www.alice.cnptia.embrapa.br/alice/handle/doc/1074725
• topic: Biflavonoides; Isoflavonas; Agentes quimiopreventivos

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.