7,3'-Di-O-methylorobol

Molecules. 2012 Jul 3;17(7):7989-8000.

Flavonoids and other compounds from Ouratea ferruginea (Ochnaceae) as anticancer and chemopreventive agents.[Pubmed: 22759912 ]

METHODS AND RESULTS:
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.
CONCLUSIONS:
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.

J Asian Nat Prod Res. 2002 Mar;4(1):1-5.

A new coumaronochromone from Sophora japonica.[Pubmed: 11991186 ]

METHODS AND RESULTS:
A new coumaronochromone derivative, sophorophenolone (1), along with 13 known compounds, l-maackiain (2), medicagol (3), 7-O-methylpseudobaptigenin (4), pseudobaptigenin (5), 7,3'-Di-O-methylorobol (6), genistein (7), prunetin (8), daidzein (9), formononetin (10), Di-O-methyldaidzein (11), quercetin (12), kaempferol (13) and isorhamnetin (14) were isolated from pericarps of Sophorajaponica L.
CONCLUSIONS:
The structure of compound 1 was established by UV, IR, MS, and one-dimensional and two-dimensional NMR spectroscopy, including DEPT, NOESY, 1H-1H COSY, HMQC, and HMBC experiments.