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7-O-Methyl-luteone was metabolized in a buffer solution by resting cells of Botrytis cinerea which is known as a fungus detoxifying prenylated isoflavones into further oxygenated metabolites, and we could isolate an unstable epoxy-intermediate. The epoxy-intermediate was easily cyclized under acidic conditions to yield the corresponding isoflavone with a hydroxychroman part structure (= dihydropyrano-isoflavone). The optically active (dextrorotatory) dihydropyrano-isoflavone metabolite was derivatized into the [R]-a-methoxy-a-trifluoromethyl- phenylacetic acid ester and its absolute configuration [S] was unambiguously elucidated by the modified Mosher’s method.

zeitschrift für naturforschung c

7-O-Methyl-luteone Metabolism in Botrytis cinerea: Identification of the Epoxy-Intermediate and Absolute Configuration of the Pyrano-isoflavone Metabolite