title: Lactones with methylcyclohexane systems obtained by chemical and microbiological methods and their antimicrobial activity.
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.
authors.affiliation: Department of Chemistry, University of Environmental and Life Sciences, Norwida 25, Wrocław 50-375, Poland. magrab@onet.pl.
authors.forename: Małgorzata
authors.initials: M
authors.lastname: Grabarczyk
authors.affiliation: Department of Chemistry, University of Environmental and Life Sciences, Norwida 25, Wrocław 50-375, Poland. katarzyna.winska@up.wroc.pl.
authors.forename: Katarzyna
authors.initials: K
authors.lastname: Wińska
authors.affiliation: Department of Chemistry, University of Environmental and Life Sciences, Norwida 25, Wrocław 50-375, Poland. wanda_m19@o2.pl.
authors.forename: Wanda
authors.initials: W
authors.lastname: Mączka
authors.affiliation: Department of Chemistry, University of Environmental and Life Sciences, Norwida 25, Wrocław 50-375, Poland. anna.zolnierczyk@up.wroc.pl.
authors.forename: Anna K
authors.initials: AK
authors.lastname: Żołnierczyk
authors.affiliation: Department of Biotechnology and Food Microbiology, University of Environmental and Life Sciences, Chełmońskiego 37/41, Wrocław 51-630, Poland. barbara.zarowska@up.wroc.pl.
authors.forename: Barbara
authors.initials: B
authors.lastname: Żarowska
authors.affiliation: Department of Chemistry, University of Environmental and Life Sciences, Norwida 25, Wrocław 50-375, Poland. miroslaw.aniol@up.wroc.pl.
authors.forename: Mirosław
authors.initials: M
authors.lastname: Anioł
mesh_terms: D000890:Anti-Infective Agents / Q000737:chemistry / Q000494:pharmacology; D001419:Bacteria / Q000254:growth & development*; D003510:Cyclohexanes / Q000737:chemistry*; D005658:Fungi / Q000254:growth & development*; D007783:Lactones / Q000737:chemistry / Q000494:pharmacology
chemical_list: D000890:Anti-Infective Agents; D003510:Cyclohexanes; D007783:Lactones; C521475:methylcyclohexane