title: Flavonoids and other compounds from Ouratea ferruginea (Ochnaceae) as anticancer and chemopreventive agents.
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, (1)H- and (13)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-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.
authors: Programa de Pós-Graduação em Química, ICE-Universidade Federal Rural do Rio de Janeiro, 23890-000, Seropédica, RJ, Brazil. qcf036@hotmail.com
authors: Queli C
authors: QC
authors: Fidelis
authors: Rosane N
authors: RN
authors: Castro
authors: Giselle M S P
authors: GM
authors: Guilhon
authors: Silvane T
authors: ST
authors: Rodrigues
authors: Cristiane M C
authors: CM
authors: de Salles
authors: João B
authors: JB
authors: de Salles
authors: Mario G
authors: MG
authors: de Carvalho
mesh_terms: D015660:7-Alkoxycoumarin O-Dealkylase / Q000378:metabolism; D000818:Animals; D000970:Antineoplastic Agents / Q000737:chemistry / Q000494:pharmacology*; D055162:Biocatalysis / Q000187:drug effects; D018890:Chemoprevention; D003577:Cytochrome P-450 Enzyme System / Q000378:metabolism; D005419:Flavonoids / Q000737:chemistry / Q000494:pharmacology*; D005982:Glutathione Transferase / Q000378:metabolism; D008297:Male; D043842:Ochnaceae / Q000737:chemistry; D051381:Rats; D017208:Rats, Wistar
chemical_list: D000970:Antineoplastic Agents; D005419:Flavonoids; D003577:Cytochrome P-450 Enzyme System; D015660:7-Alkoxycoumarin O-Dealkylase; D005982:Glutathione Transferase