Flavonoids and Other Compounds from <em>Ouratea ferruginea </em>(Ochnaceae) as Anticancer and Chemopreventive Agents
The chemical study of the extracts from leaves and stems of <em>Ouratea ferruginea</em> 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 si...
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MDPI AG
2012-07-01
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| author | Queli C. Fidelis Rosane N. Castro Giselle M. S. P. Guilhon Silvane T. Rodrigues Cristiane M. C. de Salles João B. de Salles Mario G. de Carvalho |
| author_facet | Queli C. Fidelis Rosane N. Castro Giselle M. S. P. Guilhon Silvane T. Rodrigues Cristiane M. C. de Salles João B. de Salles Mario G. de Carvalho |
| author_sort | Queli C. Fidelis |
| collection | DOAJ |
| description | The chemical study of the extracts from leaves and stems of <em>Ouratea ferruginea</em> 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-<em>O</em>-b-D-glucopyranosides, 5,4′-dihydroxy-7,5′,3′-trimethoxyisoflavone, 5,4′-dihydroxy-7,3′-di-methoxyisoflavone (7,3′-di-<em>O</em>-methylorobol), 5,7,4′-trihydroxy-3′,5′-dimethoxyisoflavone (piscigenin), 2<em>R</em>,3<em>R</em>-epicatechin, syringic acid, 2,6-dimethoxybenzoquinone, 2,6-dimethoxyhydroquinone, syringic and ferulic aldehyde, a mixture of vanillic acid, 1-hydroxy-2-methoxy-4-(1<em>E</em>-3-hydroxy-1-propenyl)-benzene and 3,5-dimethoxy-4-hydroxy-dihydrocinamaldehyde, besides amenthoflavone and 7-<em>O</em>-methylamenthoflavone (sequoiaflavone) which are considered as chemotaxonomic markers of <em>Ouratea</em>. The structures were identified by IR, <sup>1</sup>H- and <sup>13</sup>C-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-<em>O</em>-methylorobol, piscigenin and 7-<em>O</em>-methylamenthoflavone on cytochrome P450-dependent 7-ethoxycoumarin <em>O</em>-deethylase (ECOD) and glutathione <em>S</em>-transferase (GST) were evaluated <em>in vitro</em>. 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. |
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| spelling | doaj.art-8bfbceeddc994c93bd76176ad4e2b9d82022-12-21T17:13:04ZengMDPI AGMolecules1420-30492012-07-011777989800010.3390/molecules17077989Flavonoids and Other Compounds from <em>Ouratea ferruginea </em>(Ochnaceae) as Anticancer and Chemopreventive AgentsQueli C. FidelisRosane N. CastroGiselle M. S. P. GuilhonSilvane T. RodriguesCristiane M. C. de SallesJoão B. de SallesMario G. de CarvalhoThe chemical study of the extracts from leaves and stems of <em>Ouratea ferruginea</em> 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-<em>O</em>-b-D-glucopyranosides, 5,4′-dihydroxy-7,5′,3′-trimethoxyisoflavone, 5,4′-dihydroxy-7,3′-di-methoxyisoflavone (7,3′-di-<em>O</em>-methylorobol), 5,7,4′-trihydroxy-3′,5′-dimethoxyisoflavone (piscigenin), 2<em>R</em>,3<em>R</em>-epicatechin, syringic acid, 2,6-dimethoxybenzoquinone, 2,6-dimethoxyhydroquinone, syringic and ferulic aldehyde, a mixture of vanillic acid, 1-hydroxy-2-methoxy-4-(1<em>E</em>-3-hydroxy-1-propenyl)-benzene and 3,5-dimethoxy-4-hydroxy-dihydrocinamaldehyde, besides amenthoflavone and 7-<em>O</em>-methylamenthoflavone (sequoiaflavone) which are considered as chemotaxonomic markers of <em>Ouratea</em>. The structures were identified by IR, <sup>1</sup>H- and <sup>13</sup>C-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-<em>O</em>-methylorobol, piscigenin and 7-<em>O</em>-methylamenthoflavone on cytochrome P450-dependent 7-ethoxycoumarin <em>O</em>-deethylase (ECOD) and glutathione <em>S</em>-transferase (GST) were evaluated <em>in vitro</em>. 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.http://www.mdpi.com/1420-3049/17/7/7989<em>Ouratea ferruginea</em>biflavonoidsisoflavoneschemopreventive agents |
| spellingShingle | Queli C. Fidelis Rosane N. Castro Giselle M. S. P. Guilhon Silvane T. Rodrigues Cristiane M. C. de Salles João B. de Salles Mario G. de Carvalho Flavonoids and Other Compounds from <em>Ouratea ferruginea </em>(Ochnaceae) as Anticancer and Chemopreventive Agents Molecules <em>Ouratea ferruginea</em> biflavonoids isoflavones chemopreventive agents |
| title | Flavonoids and Other Compounds from <em>Ouratea ferruginea </em>(Ochnaceae) as Anticancer and Chemopreventive Agents |
| title_full | Flavonoids and Other Compounds from <em>Ouratea ferruginea </em>(Ochnaceae) as Anticancer and Chemopreventive Agents |
| title_fullStr | Flavonoids and Other Compounds from <em>Ouratea ferruginea </em>(Ochnaceae) as Anticancer and Chemopreventive Agents |
| title_full_unstemmed | Flavonoids and Other Compounds from <em>Ouratea ferruginea </em>(Ochnaceae) as Anticancer and Chemopreventive Agents |
| title_short | Flavonoids and Other Compounds from <em>Ouratea ferruginea </em>(Ochnaceae) as Anticancer and Chemopreventive Agents |
| title_sort | flavonoids and other compounds from lt em gt ouratea ferruginea lt em gt ochnaceae as anticancer and chemopreventive agents |
| topic | <em>Ouratea ferruginea</em> biflavonoids isoflavones chemopreventive agents |
| url | http://www.mdpi.com/1420-3049/17/7/7989 |
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