Haloperoxidase Mediated Quorum Quenching by Nitzschia cf pellucida: Study of the Metabolization of N-Acyl Homoserine Lactones by a Benthic Diatom |
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| Authors: | Michail Syrpas Ewout Ruysbergh Lander Blommaert Bart Vanelslander Koen Sabbe Wim Vyverman Norbert De Kimpe Sven Mangelinckx |
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| Institution: | 1.Department of Sustainable Organic Chemistry and Technology, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, Ghent B-9000, Belgium; E-Mails: (M.S.); (E.R.); (N.D.K.);2.Laboratory of Protistology and Aquatic Ecology, Department of Biology, Ghent University, Krijgslaan 281-S8, Ghent B-9000, Belgium; E-Mails: (L.B.); (B.V.); (K.S.) |
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| Abstract: | 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. |
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| Keywords: | quorum sensing haloperoxidase degradation pathway AHL reference compounds diatom-bacteria interactions |
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