Abstract

The aim of this study was the chemical synthesis of a series of halo- and unsaturated lactones, as well as their microbial transformation products. Finally some of their biological activities were assessed. Three bicyclic halolactones with a methyl group in the cyclohexane ring were obtained from the corresponding γ,δ-unsaturated ester during a two-step synthesis. These lactones were subjected to screening biotransformation using twenty two fungal strains. These strains were tested on their ability to transform halolactones into new hydroxylactones. Among the six strains able to catalyze hydrolytic dehalogenation, only two (Fusarium equiseti, AM22 and Yarrowia lipolytica, AM71) gave a product in a high yield. Moreover, one strain (Penicillium wermiculatum, AM30) introduced the hydroxy group on the cyclohexane ring without removing the halogen atom. The biological activity of five of the obtained lactones was tested. Some of these compounds exhibited growth inhibition against bacteria, yeasts and fungi and deterrent activity against peach-potato aphid.

Highlights

  • IntroductionChloro-organic compounds are used in many areas

  • Due to their properties, chloro-organic compounds are used in many areas

  • Substrates for biotransformation halolactones 3–5 were obtained during the two-step synthesis

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Summary

Introduction

Chloro-organic compounds are used in many areas They are very often applied as antifungal [1,2], antibacterial [3], antifidant [4,5], cytotoxic, and anticancer agents [6]. They are used as organic solvents, refrigerants and media, dielectrics, pesticides, monomers for the production of plastic materials, and intermediates for organic synthesis [7]. Halogened compounds could be obtained by using the biotransformation method

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