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Molecules 2016, 21(11), 1453; doi:10.3390/molecules21111453

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

1
Department of Chemistry, Wrocław University of Environmental and Life Sciences, Norwida 25, 50-375 Wrocław, Poland
2
Department of Biotechnology and Food Microbiology, Wrocław University of Environmental and Life Sciences, Chełmońskiego 37/41, 51-630 Wrocław, Poland
3
Faculty of Chemistry, Wroclaw University of Technology, Wybrzeze Wyspianskiego 27, 50-370 Wroclaw, Poland
4
Department of Botany and Ecology, University of Zielona Gora, Szafrana 1, 65-516 Zielona Gora, Poland
*
Author to whom correspondence should be addressed.
Academic Editor: Derek J. McPhee
Received: 15 September 2016 / Revised: 23 October 2016 / Accepted: 28 October 2016 / Published: 31 October 2016
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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. View Full-Text
Keywords: lactones; hydrolytic dehalogenation; antimicrobial activity; deterrent activity lactones; hydrolytic dehalogenation; antimicrobial activity; deterrent activity
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Wińska, K.; Grabarczyk, M.; Mączka, W.; Żarowska, B.; Maciejewska, G.; Dancewicz, K.; Gabryś, B.; Szumny, A.; Anioł, M. Biotransformation of Bicyclic Halolactones with a Methyl Group in the Cyclohexane Ring into Hydroxylactones and Their Biological Activity. Molecules 2016, 21, 1453.

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