Influence of structure of lactones with the methylcyclohexene and dimethylcyclohexene ring on their biotransformation and antimicrobial activity

Abstract

Abstract The aim of this article is influence of the structure of lactones with the methylcyclohexene and dimethylcyclohexene ring on their biotransformation and antimicrobial activity. This work was based on the general remark that even the smallest change in the structure of a compound can affect its biological properties. The results of the biotransformation of four bicyclic unsaturated lactones with one or two methyl groups in the cyclohexene ring was tested using fifteen fungal strains (Fusarium species, Penicillium species, Absidia species, Cunninghamella japonica, and Pleurotus ostreatus) and five yeast strains (Yarrowia lipolytica, Rhodorula marina, Rhodorula rubra, Candida viswanathii, and Saccharomyces cerevisiae). During these transformations, new epoxylactone and hydroxylactone were obtained. The relationship between the substrate structure and the ability of the microorganisms to transform them were analysed. Only compounds with C–O bond of lactone ring in the equatorial position were transformed by fungus. All presented here lactones were examined also for their antimicrobial activity. It turned out that these compounds exhibited growth inhibition of bacteria and fungi, mainly Bacillus subtilis, Candida albicans, Aspergillus niger, and Penicillium expansum.