Biotransformation of Bicyclic Halolactones with a Methyl Group in the Cyclohexane Ring into Hydroxylactones and Their Biological Activity

Molecules

Barbara Żarowska¹  Beata Gabryś²  Katarzyna Dancewicz²  Małgorzata Grabarczyk³  Katarzyna Wińska³  Mirosław Anioł³  Antoni Szumny³  Wanda Mączka³  Gabriela Maciejewska⁴ 

[1] Department of Biotechnology and Food Microbiology, Wrocław University of Environmental and Life Sciences, Chełmońskiego 37/41, 51-630 Wrocław, Poland;Department of Botany and Ecology, University of Zielona Gora, Szafrana 1, 65-516 Zielona Gora, Poland;Department of Chemistry, Wrocław University of Environmental and Life Sciences, Norwida 25, 50-375 Wrocław, Poland;Faculty of Chemistry, Wroclaw University of Technology, Wybrzeze Wyspianskiego 27, 50-370 Wroclaw, Poland;

关键词: lactones;    hydrolytic dehalogenation;    antimicrobial activity;    deterrent activity;   

DOI  :  10.3390/molecules21111453

来源: DOAJ

【 摘 要 】

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.

【 授权许可】

Unknown