When incubated for 7hr with a rat liver homogenate, the prenylated isoflavone luteone, 5,7,2/,4-tetrahydroxy-6-(3,3-dimethylallyl)isoflavone (1), was converted to six derivatives, which were isolated and purified by thin-layer chromatography. Using physicochemical procedures, the metabolites were characterized as a dihydrofurano-isoflavone (2), four newisoflavones with variously oxygenated terminal methyl groups (3, 4, 6 and 7), and a coumaronochromone (5). The geometry of the oxygenated side-chain was unambiguously determined by NMRtechniques (^H-NMR, NOEand 13C-NMR). Wehave already reported the transformation of the antifungal isoflavones, luteone (1), 1} wighteone (8)2) and licoisoflavone A (9)3) by Aspergillusflavus and Botrytis cinerea. Luteone (1), one of the major prenylated isoflavones in lupins (Lupinus spp., Leguminosae), was mainly transformed into luteone hydrate (10) or luteone glycol (ll) by A.flavus, while 1 was metabolized to BC-1 [(-)-2], BC-2 (12) and
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