Transformation of β-damascone to (+)-(S)-4-hydroxy-β-damascone by fungal strains and its evaluation as a potential insecticide against aphids Myzus persicae and lesser mealworm Alphitobius diaperinus Panzer

Abstract

Microbial conversion of β-damascone (1) into 4-hydroxy-β-damascone (2) was studied. The results showed the potential of the tested biocatalysts for the regio- and enantioselective hydroxylation of substrate 1. The highest enantioselectivity was exhibited by strain Mortierella isabellina AM212. β-Damascone (1) was a relatively good deterrent towards Alphitobius diaperinus and it was behaviorally inactive to Myzus persicae. The racemic compound 2 and its (+)-(S)-enantiomer were stronger antifeedants against A. diaperinus than β-damascone (1), in the case of M. persicae only (+)-(S)-(2) exhibited the deterrent properties.