Antimicrobial activity of new bicyclic lactones with three or four methyl groups obtained both synthetically and biosynthetically
Ten new derivatives of isophorone were obtained through a five-step synthesis. Among the products were several unsaturated, bicyclic lactones with three or four methyl groups. These lactones were used as the substrates for biotransformation mediated by selected fungal strains (Fusarium species, Sync...
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| Format: | Article |
| Language: | English |
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Elsevier
2018-03-01
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| Series: | Journal of Saudi Chemical Society |
| Subjects: | |
| Online Access: | http://www.sciencedirect.com/science/article/pii/S1319610316300217 |
| _version_ | 1818355684057546752 |
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| author | Katarzyna Wińska Małgorzata Grabarczyk Wanda Mączka Barbara Żarowska Gabriela Maciejewska Mirosław Anioł |
| author_facet | Katarzyna Wińska Małgorzata Grabarczyk Wanda Mączka Barbara Żarowska Gabriela Maciejewska Mirosław Anioł |
| author_sort | Katarzyna Wińska |
| collection | DOAJ |
| description | Ten new derivatives of isophorone were obtained through a five-step synthesis. Among the products were several unsaturated, bicyclic lactones with three or four methyl groups. These lactones were used as the substrates for biotransformation mediated by selected fungal strains (Fusarium species, Syncephalastrum racemosum, Cunninghamella japonica, Penicillium species, Absidia species, and Pleurotus ostreatus). Four new hydroxylactones were obtained as a result of biotransformation. Because the unsaturated lactone with four methyl groups was a diastereoisomeric mixture, a structural analysis was conducted. The hydroxylactones were also included in this analysis. Both the unsaturated lactones and hydroxylactones were examined for their antimicrobial activity. It was found that some of these compounds exhibited growth inhibition against pathogenic strains of bacteria (Staphylococcus aureus, Pseudomonas fluorescens), yeasts (Candida albicans) and filamentous fungi (Alternaria sp., Penicillium sp.). All obtained compounds were also subjected to scent analysis. |
| first_indexed | 2024-12-13T19:45:13Z |
| format | Article |
| id | doaj.art-5c309e60c69545e79f3b25e3048b46f2 |
| institution | Directory Open Access Journal |
| issn | 1319-6103 |
| language | English |
| last_indexed | 2024-12-13T19:45:13Z |
| publishDate | 2018-03-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Journal of Saudi Chemical Society |
| spelling | doaj.art-5c309e60c69545e79f3b25e3048b46f22022-12-21T23:33:34ZengElsevierJournal of Saudi Chemical Society1319-61032018-03-0122336337110.1016/j.jscs.2016.04.004Antimicrobial activity of new bicyclic lactones with three or four methyl groups obtained both synthetically and biosyntheticallyKatarzyna Wińska0Małgorzata Grabarczyk1Wanda Mączka2Barbara Żarowska3Gabriela Maciejewska4Mirosław Anioł5Department of Chemistry, Wroclaw University of Environmental and Life Sciences, Norwida 25, 50-375 Wrocław, PolandDepartment of Chemistry, Wroclaw University of Environmental and Life Sciences, Norwida 25, 50-375 Wrocław, PolandDepartment of Chemistry, Wroclaw University of Environmental and Life Sciences, Norwida 25, 50-375 Wrocław, PolandDepartment of Biotechnology and Food Microbiology, Wroclaw University of Environmental and Life Sciences, Chełmońskiego 37/41, 51-630 Wrocław, PolandFaculty of Chemistry, Wrocław University of Technology, Wybrzeże Wyspiańskiego 27, 50-370 Wrocław, PolandDepartment of Chemistry, Wroclaw University of Environmental and Life Sciences, Norwida 25, 50-375 Wrocław, PolandTen new derivatives of isophorone were obtained through a five-step synthesis. Among the products were several unsaturated, bicyclic lactones with three or four methyl groups. These lactones were used as the substrates for biotransformation mediated by selected fungal strains (Fusarium species, Syncephalastrum racemosum, Cunninghamella japonica, Penicillium species, Absidia species, and Pleurotus ostreatus). Four new hydroxylactones were obtained as a result of biotransformation. Because the unsaturated lactone with four methyl groups was a diastereoisomeric mixture, a structural analysis was conducted. The hydroxylactones were also included in this analysis. Both the unsaturated lactones and hydroxylactones were examined for their antimicrobial activity. It was found that some of these compounds exhibited growth inhibition against pathogenic strains of bacteria (Staphylococcus aureus, Pseudomonas fluorescens), yeasts (Candida albicans) and filamentous fungi (Alternaria sp., Penicillium sp.). All obtained compounds were also subjected to scent analysis.http://www.sciencedirect.com/science/article/pii/S1319610316300217Unsaturated lactonesBiotransformationHydroxylationAntimicrobial activityOdour |
| spellingShingle | Katarzyna Wińska Małgorzata Grabarczyk Wanda Mączka Barbara Żarowska Gabriela Maciejewska Mirosław Anioł Antimicrobial activity of new bicyclic lactones with three or four methyl groups obtained both synthetically and biosynthetically Journal of Saudi Chemical Society Unsaturated lactones Biotransformation Hydroxylation Antimicrobial activity Odour |
| title | Antimicrobial activity of new bicyclic lactones with three or four methyl groups obtained both synthetically and biosynthetically |
| title_full | Antimicrobial activity of new bicyclic lactones with three or four methyl groups obtained both synthetically and biosynthetically |
| title_fullStr | Antimicrobial activity of new bicyclic lactones with three or four methyl groups obtained both synthetically and biosynthetically |
| title_full_unstemmed | Antimicrobial activity of new bicyclic lactones with three or four methyl groups obtained both synthetically and biosynthetically |
| title_short | Antimicrobial activity of new bicyclic lactones with three or four methyl groups obtained both synthetically and biosynthetically |
| title_sort | antimicrobial activity of new bicyclic lactones with three or four methyl groups obtained both synthetically and biosynthetically |
| topic | Unsaturated lactones Biotransformation Hydroxylation Antimicrobial activity Odour |
| url | http://www.sciencedirect.com/science/article/pii/S1319610316300217 |
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