Induction of steroidal hydroxylase activity by plant defence compounds in the filamentous fungus Cochliobolus lunatus

We investigated the hypothesis that the endogenous role of the commercially important inducible steroid hydroxylase cytochrome P450s of fungi was in defense against plant toxophores/secondary metabolites. Two plant defense compounds, the aglycones tomatidine and solanidine, the steroidal glycoalkaloid alpha-tomatine and the triterpene saponin beta-escin were tested as inducers of 11beta/14alpha-steroid hydroxylase in the filamentous fungus Cochliobolus lunatus. The extracts of saponins from the roots of Primula veris and green oat leaves were also tested as inducers of 11beta/14alpha-hydroxylation activity in progesterone biotransformation with the same fungus. Induction of steroid hydroxylase and inhibition of activity in some cases support our hypothesis that their endogenous function is in biochemical defence against secondary metabolites. 4-Pregnene-3,11,20-trione was added as a substrate for biotransformation with C. lunatus. We isolated from culture broth 14alpha-hydroxy-4-pregnene-3,11,20-trione, and the hitherto unreported compounds, 7alpha,14alpha-dihydroxy-4-pregnene-3,11,20-trione and 7alpha-hydroxy-pregna-4,8(14)-diene-3,11,20-trione.