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Molecules 2015, 20(2), 3335-3353; doi:10.3390/molecules20023335

Lactones with Methylcyclohexane Systems Obtained by Chemical and Microbiological Methods and Their Antimicrobial Activity

1
Department of Chemistry, University of Environmental and Life Sciences, Norwida 25, Wrocław 50-375, Poland
2
Department of Biotechnology and Food Microbiology, University of Environmental and Life Sciences, Chełmońskiego 37/41, Wrocław 51-630, Poland
*
Author to whom correspondence should be addressed.
Academic Editor: Jean Jacques Vanden Eynde
Received: 18 December 2014 / Revised: 9 February 2015 / Accepted: 13 February 2015 / Published: 16 February 2015
(This article belongs to the Section Medicinal Chemistry)
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Abstract

Eight new lactones (δ-chloro-, δ-bromo- and δ-iodo-γ-lactones), each with a methylcyclohexane ring, were obtained by chemical means from (4-methylcyclohex-2-en-1-yl) acetic acid or (6-methylcyclohex-2-en-1-yl) acetic acid. Whole cells of ten fungal strains (Fusarium species, Syncephalastrum racemosum and Botrytis cinerea) were tested on their ability to convert these lactones into other products. Some of the tested fungal strains transformed chloro-, bromo- and iodolactone with a methyl group at C-5 into 2-hydroxy-5-methyl-9-oxabicyclo[4.3.0]nonan-8-one during hydrolytic dehalogenation. When the same lactones had the methyl group at C-3, no structural modifications of halolactones were observed. In most cases, the optical purity of the product was low or medium, with the highest rate for chlorolactone (45.4%) and iodolactone (45.2% and 47.6%). All of the obtained compounds were tested with reference to their smell. Seven halolactones and the hydroxylactone obtained via biotransformation of halolactones with 5-methylcyclohexane ring were examined for their antimicrobial activity. These compounds were capable of inhibiting growth of some bacteria, yeasts and fungi. View Full-Text
Keywords: lactones; biotransformations; hydrolytic dehalogenation; Fusarium species; antimicrobial activity lactones; biotransformations; hydrolytic dehalogenation; Fusarium species; antimicrobial 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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MDPI and ACS Style

Grabarczyk, M.; Wińska, K.; Mączka, W.; Żołnierczyk, A.K.; Żarowska, B.; Anioł, M. Lactones with Methylcyclohexane Systems Obtained by Chemical and Microbiological Methods and Their Antimicrobial Activity. Molecules 2015, 20, 3335-3353.

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