Haloperoxidase Mediated Quorum Quenching by Nitzschia cf pellucida: Study of the Metabolization of N-Acyl Homoserine Lactones by a Benthic Diatom
Diatoms are known to produce a variety of halogenated compounds, which were recently shown to have a role in allelopathic interactions between competing species. The production of these compounds is linked to haloperoxidase activity. This research, has shown that this system may also be involved in...
| Main Authors: | , , , , , , , |
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| Format: | Article |
| Language: | English |
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MDPI AG
2014-01-01
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| Series: | Marine Drugs |
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| Online Access: | http://www.mdpi.com/1660-3397/12/1/352 |
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| author | Michail Syrpas Ewout Ruysbergh Lander Blommaert Bart Vanelslander Koen Sabbe Wim Vyverman Norbert De Kimpe Sven Mangelinckx |
| author_facet | Michail Syrpas Ewout Ruysbergh Lander Blommaert Bart Vanelslander Koen Sabbe Wim Vyverman Norbert De Kimpe Sven Mangelinckx |
| author_sort | Michail Syrpas |
| collection | DOAJ |
| description | Diatoms are known to produce a variety of halogenated compounds, which were recently shown to have a role in allelopathic interactions between competing species. The production of these compounds is linked to haloperoxidase activity. This research, has shown that this system may also be involved in diatom-bacteria interactions via the H2O2 dependent inactivation of a type of quorum sensing (QS) molecule, i.e., N-β-ketoacylated homoserine lactones (AHLs), by a natural haloperoxidase system from the benthic diatom Nitzschia cf pellucida. The AHL degradation pathway towards corresponding halogenated derivatives was elucidated via HPLC-MS analysis and the synthesis of a broad series of novel halogenated AHL analogues as reference compounds. Furthermore, their biological activity as quorum sensing modulators was directly compared and evaluated against a series of naturally occurring β-keto-AHLs. It has been demonstrated that the loss of the QS activity results from the final cleavage of the halogenated N-acyl chain of the signal molecules. |
| first_indexed | 2024-04-14T02:25:31Z |
| format | Article |
| id | doaj.art-89ee2905c76b41b7824f9f1182064590 |
| institution | Directory Open Access Journal |
| issn | 1660-3397 |
| language | English |
| last_indexed | 2024-04-14T02:25:31Z |
| publishDate | 2014-01-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Marine Drugs |
| spelling | doaj.art-89ee2905c76b41b7824f9f11820645902022-12-22T02:17:53ZengMDPI AGMarine Drugs1660-33972014-01-0112135236710.3390/md12010352md12010352Haloperoxidase Mediated Quorum Quenching by Nitzschia cf pellucida: Study of the Metabolization of N-Acyl Homoserine Lactones by a Benthic DiatomMichail Syrpas0Ewout Ruysbergh1Lander Blommaert2Bart Vanelslander3Koen Sabbe4Wim Vyverman5Norbert De Kimpe6Sven Mangelinckx7Department of Sustainable Organic Chemistry and Technology, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, Ghent B-9000, BelgiumDepartment of Sustainable Organic Chemistry and Technology, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, Ghent B-9000, BelgiumLaboratory of Protistology and Aquatic Ecology, Department of Biology, Ghent University, Krijgslaan 281-S8, Ghent B-9000, BelgiumLaboratory of Protistology and Aquatic Ecology, Department of Biology, Ghent University, Krijgslaan 281-S8, Ghent B-9000, BelgiumLaboratory of Protistology and Aquatic Ecology, Department of Biology, Ghent University, Krijgslaan 281-S8, Ghent B-9000, BelgiumLaboratory of Protistology and Aquatic Ecology, Department of Biology, Ghent University, Krijgslaan 281-S8, Ghent B-9000, BelgiumDepartment of Sustainable Organic Chemistry and Technology, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, Ghent B-9000, BelgiumDepartment of Sustainable Organic Chemistry and Technology, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, Ghent B-9000, BelgiumDiatoms are known to produce a variety of halogenated compounds, which were recently shown to have a role in allelopathic interactions between competing species. The production of these compounds is linked to haloperoxidase activity. This research, has shown that this system may also be involved in diatom-bacteria interactions via the H2O2 dependent inactivation of a type of quorum sensing (QS) molecule, i.e., N-β-ketoacylated homoserine lactones (AHLs), by a natural haloperoxidase system from the benthic diatom Nitzschia cf pellucida. The AHL degradation pathway towards corresponding halogenated derivatives was elucidated via HPLC-MS analysis and the synthesis of a broad series of novel halogenated AHL analogues as reference compounds. Furthermore, their biological activity as quorum sensing modulators was directly compared and evaluated against a series of naturally occurring β-keto-AHLs. It has been demonstrated that the loss of the QS activity results from the final cleavage of the halogenated N-acyl chain of the signal molecules.http://www.mdpi.com/1660-3397/12/1/352quorum sensinghaloperoxidasedegradation pathwayAHLreference compoundsdiatom-bacteria interactions |
| spellingShingle | Michail Syrpas Ewout Ruysbergh Lander Blommaert Bart Vanelslander Koen Sabbe Wim Vyverman Norbert De Kimpe Sven Mangelinckx Haloperoxidase Mediated Quorum Quenching by Nitzschia cf pellucida: Study of the Metabolization of N-Acyl Homoserine Lactones by a Benthic Diatom Marine Drugs quorum sensing haloperoxidase degradation pathway AHL reference compounds diatom-bacteria interactions |
| title | Haloperoxidase Mediated Quorum Quenching by Nitzschia cf pellucida: Study of the Metabolization of N-Acyl Homoserine Lactones by a Benthic Diatom |
| title_full | Haloperoxidase Mediated Quorum Quenching by Nitzschia cf pellucida: Study of the Metabolization of N-Acyl Homoserine Lactones by a Benthic Diatom |
| title_fullStr | Haloperoxidase Mediated Quorum Quenching by Nitzschia cf pellucida: Study of the Metabolization of N-Acyl Homoserine Lactones by a Benthic Diatom |
| title_full_unstemmed | Haloperoxidase Mediated Quorum Quenching by Nitzschia cf pellucida: Study of the Metabolization of N-Acyl Homoserine Lactones by a Benthic Diatom |
| title_short | Haloperoxidase Mediated Quorum Quenching by Nitzschia cf pellucida: Study of the Metabolization of N-Acyl Homoserine Lactones by a Benthic Diatom |
| title_sort | haloperoxidase mediated quorum quenching by nitzschia cf pellucida study of the metabolization of n acyl homoserine lactones by a benthic diatom |
| topic | quorum sensing haloperoxidase degradation pathway AHL reference compounds diatom-bacteria interactions |
| url | http://www.mdpi.com/1660-3397/12/1/352 |
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