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Appl. Sci. 2017, 7(1), 12; doi:10.3390/app7010012

Biotransformation of Lactones with Methylcyclohexane Ring and Their Biological Activity

1
Department of Chemistry, Wroclaw University of Environmental and Life Sciences, Norwida 25, Wrocław 50-375, Poland
2
Department of Biotechnology and Food Microbiology, Wroclaw University of Environmental and Life Sciences, Chełmońskiego 37/41, Wrocław 51-630, Poland
3
Faculty of Chemistry, Wrocław University of Technology, Wybrzeże Wyspiańskiego 27, Wrocław 50-370, Poland
4
Department of Botany and Ecology, University of Zielona Gora, Szafrana 1, Zielona Gora 65-516, Poland
*
Author to whom correspondence should be addressed.
Academic Editor: Miguel Yus Astiz
Received: 14 November 2016 / Revised: 12 December 2016 / Accepted: 19 December 2016 / Published: 24 December 2016
(This article belongs to the Section Chemistry)
View Full-Text   |   Download PDF [2747 KB, uploaded 24 December 2016]   |  

Abstract

The aim of the study was to obtain biological active compounds during biotransformation. Three bicyclic halolactones with methylcyclohexane ring (2-chloro-4-methyl-9-oxabicyclo-[4.3.0]nonan-8-one, 2-bromo-4-methyl-9-oxabicyclo[4.3.0]nona- -8-one and 2-iodo-4-methyl-9-oxabicyclo[4.3.0]nonan-8-one) obtained from the corresponding γ,δ-unsaturated acid were subjected to a screening biotransformation using 22 fungal strains. Two of these strains (Cunninghamella japonica AM472 and Fusarium culmorum AM10) were able to transform halolactones into 2-hydroxy-4-methyl-9-oxabicyclo[4.3.0]nonan-8-one by hydrolytic dehalogenation with good yield. The biotransformation product was structurally different from its synthetically prepared analog. All halolactones and hydroxylactones were tested for their biological activity. The chlorolactone inhibited growth of Staphylococcus aureus (max ΔOD = 0), Escherichia coli (max ΔOD = 0.3) and Candida albicans (max ΔOD = 0) strains. Bromolactone caused inhibition of growth of Staphylococcus aureus (max ΔOD = 0) and Fusarium linii (max ΔOD = 0) strains. Iodolactone limited growth of Staphylococcus aureus (max ΔOD = 0), Escherichia coli (max ΔOD = 0.25), Candida albicans (max ΔOD = 0.45) and Pseudomonas fluorescens (max ΔOD = 0.42) strains. Hydroxylactone caused inhibition of growth of Staphylococcus aureus (max ΔOD = 0.36) and Pseudomonas fluorescens (max ΔOD = 0.39) strains only. The test performed on aphids Myzus persicae (Sulz.) showed that chloro- and bromolactone exhibited deterrent activity after 24 h (ID = 0.5 and 0.4, respectively), while hydroxylactone was a weak attractant (ID = −0.3). View Full-Text
Keywords: lactones; hydrolytic dehalogenation; antimicrobial activity; deterrent activity lactones; hydrolytic dehalogenation; antimicrobial activity; deterrent activity
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Wińska, K.; Grabarczyk, M.; Mączka, W.; Żarowska, B.; Maciejewska, G.; Dancewicz, K.; Gabryś, B.; Anioł, M. Biotransformation of Lactones with Methylcyclohexane Ring and Their Biological Activity. Appl. Sci. 2017, 7, 12.

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