Biotransformation of Bicyclic Halolactones with a Methyl Group in the Cyclohexane Ring into Hydroxylactones and Their Biological Activity.
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 andYarrowia 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.
Department of Chemistry, Wrocław University of Environmental and Life Sciences, Norwida 25, 50-375 Wrocław, Poland. katarzyna.winska@up.wroc.pl.
Katarzyna
K
Wińska
Department of Chemistry, Wrocław University of Environmental and Life Sciences, Norwida 25, 50-375 Wrocław, Poland. magrab@onet.pl.
Małgorzata
M
Grabarczyk
Department of Chemistry, Wrocław University of Environmental and Life Sciences, Norwida 25, 50-375 Wrocław, Poland. wanda_m19@o2.pl.
Wanda
W
Mączka
Department of Biotechnology and Food Microbiology, Wrocław University of Environmental and Life Sciences, Chełmońskiego 37/41, 51-630 Wrocław, Poland. barbara.zarowska@up.wroc.pl.
Barbara
B
Żarowska
Faculty of Chemistry, Wroclaw University of Technology, Wybrzeze Wyspianskiego 27, 50-370 Wroclaw, Poland. gabriela.maciejewska@pwr.edu.pl.
Gabriela
G
Maciejewska
Department of Botany and Ecology, University of Zielona Gora, Szafrana 1, 65-516 Zielona Gora, Poland. k.dancewicz@wnb.uz.zgora.pl.
Katarzyna
K
Dancewicz
Department of Botany and Ecology, University of Zielona Gora, Szafrana 1, 65-516 Zielona Gora, Poland. b.gabrys@wnb.uz.zgora.pl.
Beata
B
Gabryś
Department of Chemistry, Wrocław University of Environmental and Life Sciences, Norwida 25, 50-375 Wrocław, Poland. antjasz@o2.pl.
Antoni
A
Szumny
Department of Chemistry, Wrocław University of Environmental and Life Sciences, Norwida 25, 50-375 Wrocław, Poland. miroslaw.aniol@up.wroc.pl.
Mirosław
M
Anioł
D005670:Fusarium / Q000378:metabolism*; D007783:Lactones / Q000138:chemical synthesis / Q000737:chemistry / Q000493:pharmacokinetics / Q000494:pharmacology; D010407:Penicillium / Q000378:metabolism*; D025062:Yarrowia / Q000378:metabolism*
D007783:Lactones
antimicrobial activity; deterrent activity; hydrolytic dehalogenation; lactones