The response of filamentous fungus Rhizopus nigricans to flavonoids.

The saprophytic fungus Rhizopus nigricans constitutes a serious problem when thriving on gathered crops. The identification of any compounds, especially natural ones, that inhibit fungal growth, may therefore be important. During its life cycle, Rhizopus nigricans encounters many compounds, among them the flavonoids, plant secondary metabolites that are involved in plant defense against pathogenic microorganisms. Although not being a plant pathogen, Rhizopus nigricans may interact with these compounds in the same way as plant pathogens--in response to the fungitoxic effect of flavonoids the fungi transform them into less toxic metabolites. We have studied the interaction of R. nigricans with some flavonoids. Inhibition of hyphal spreading (from 3% to 100%) was observed by 300 μM flavones, flavanones and isoflavones, irrespective of their basic structure, oxidized or reduced C-ring, and orientation of the B-ring. However, a hydrophobic A-ring was important for the toxicity. R. nigricans transformed some of the flavonoids into glucosylated products. Recognition of substrates for glucosylating enzyme(s) did not correlate with their fungitoxic effect but depended exclusively on the presence of a free -OH group in the flavonoid A-ring and of a hydrophobic B-ring. Although the fungus produced glucosyltransferase constitutively, an additional amount of the enzyme was induced by the substrate flavonoid. Moreover, effective detoxification was shown to require the presence of glucose.