title: Influence of structure of lactones with the methylcyclohexene and dimethylcyclohexene ring on their biotransformation and antimicrobial activity.
abstract: The aim of this article is influence of the structure of lactones with the methylcyclohexene and dimethylcyclohexene ring on their biotransformation and antimicrobial activity. This work was based on the general remark that even the smallest change in the structure of a compound can affect its biological properties. The results of the biotransformation of four bicyclic unsaturated lactones with one or two methyl groups in the cyclohexene ring was tested using fifteen fungal strains (Fusarium species, Penicillium species, Absidia species, Cunninghamella japonica, and Pleurotus ostreatus) and five yeast strains (Yarrowia lipolytica, Rhodorula marina, Rhodorula rubra, Candida viswanathii, and Saccharomyces cerevisiae). During these transformations, new epoxylactone and hydroxylactone were obtained. The relationship between the substrate structure and the ability of the microorganisms to transform them were analysed. Only compounds with C-O bond of lactone ring in the equatorial position were transformed by fungus. All presented here lactones were examined also for their antimicrobial activity. It turned out that these compounds exhibited growth inhibition of bacteria and fungi, mainly Bacillus subtilis, Candida albicans, Aspergillus niger, and Penicillium expansum.
authors.affiliation: Department of Chemistry, Wrocław University of Environmental and Life Sciences, Norwida 25, 50-375 Wrocław, Poland.
authors.forename: Katarzyna
authors.initials: K
authors.lastname: Wińska
authors.affiliation: Department of Chemistry, Wrocław University of Environmental and Life Sciences, Norwida 25, 50-375 Wrocław, Poland.
authors.forename: Małgorzata
authors.initials: M
authors.lastname: Grabarczyk
authors.affiliation: Department of Chemistry, Wrocław University of Environmental and Life Sciences, Norwida 25, 50-375 Wrocław, Poland.
authors.forename: Wanda
authors.initials: W
authors.lastname: Mączka
authors.affiliation: Department of Biotechnology and Food Microbiology, Wrocław University of Environmental and Life Sciences, Chełmońskiego 37/41, 51-630 Wrocław, Poland.
authors.forename: Barbara
authors.initials: B
authors.lastname: Żarowska
authors.affiliation: Faculty of Chemistry, Wrocław University of Technology, WybrzeżeWyspiańskiego 27, 50-370 Wrocław, Poland.
authors.forename: Gabriela
authors.initials: G
authors.lastname: Maciejewska
authors.affiliation: Department of Chemistry, Wrocław University of Environmental and Life Sciences, Norwida 25, 50-375 Wrocław, Poland.
authors.forename: Mirosław
authors.initials: M
authors.lastname: Anioł
mesh_terms: D001419:Bacteria / Q000187:drug effects* / Q000254:growth & development; D001711:Biotransformation; D053138:Cyclohexenes / Q000138:chemical synthesis / Q000378:metabolism* / Q000494:pharmacology*; D005658:Fungi / Q000187:drug effects* / Q000254:growth & development / Q000378:metabolism*; D007783:Lactones / Q000138:chemical synthesis / Q000378:metabolism* / Q000494:pharmacology*; D008826:Microbial Sensitivity Tests; D050296:Microbial Viability / Q000187:drug effects; D015394:Molecular Structure; D013329:Structure-Activity Relationship; D015003:Yeasts / Q000254:growth & development / Q000378:metabolism*
chemical_list: D053138:Cyclohexenes; D007783:Lactones
keywords: biological activity; epoxylactone; filamentous fungi; hydroxylactone; unsaturated lactones