An antifungalisoflavone, wighteone [5, 7, 4'-trihydroxy-6-(3, 3-dimethylallyl) by the former fungus into 2", 3"-dihydro-3"-hydroxywighteone (wighteone hydrate, 4) and by the latter into dihydrofurano-isoflavone (2) as major metabolites. A small quantity of dihydropyrano-isoflavone (3), 2 and 2",3"-dihydrodihydroxywighteone (5) were detected in the metabolic culture of As fiavus as minor metabolites of 1. Both 3 and 5 were isolated as wighteone metabolites in Ba cinerea cultures.
Cultures of Aspergillus flavus and Botrytis cinerea have been found to rapidly convert the fungitoxic isoflavone licoisoflavone A [5,7,2/,4/-tetrahydroxy-3 /-(3,3-dimethylallyl)isoflavone] into products with reduced antifungal activity, as judged from TLCplate bioassays against the growth of Cladosporium herbarum. Both fungi produced the same five metabolites, but often in greatly differing quantities. Using physico-chemical procedures, the metabolites were characterized as a glycol (2^,3^-dihydrodihydroxylicoisoflavone A), two dihydrofurano-isoflavones (one of which was identical with lupinisoflavone D found in Lupinus albus roots) and two hydroxydihydropyranoisoflavones.
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