Biosynthesis of the Phytoalexin Pisatin : Isoflavone Reduction and Further Metabolism of the Product Sophorol by Extracts of Pisum sativum.

NADPH-dependent reduction of 2',7-dihydroxy-4',5'-methylenedioxyisoflavone to the isoflavanone sophorol, a proposed intermediate step in pisatin biosynthesis, was detected in extracts of Pisum sativum. This isoflavone reductase activity was inducible by treatment of pea seedlings with CuCl(2). The timing of induction coincided with that of the 6a-hydroxymaackiain 3-O-methyltransferase, which catalyzes the terminal biosynthetic step. Neither enzyme was light inducible. Further NADPH-dependent metabolism of sophorol by extracts of Cucl(2)-treated seedlings was also observed; three products were radiolabeled when [(3)H]sophorol was the substrate, one of which is tentatively identified as maackiain.