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Mar. Drugs 2014, 12(1), 352-367; doi:10.3390/md12010352
Article

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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1 Department of Sustainable Organic Chemistry and Technology, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, Ghent B-9000, Belgium 2 Laboratory of Protistology and Aquatic Ecology, Department of Biology, Ghent University, Krijgslaan 281-S8, Ghent B-9000, Belgium
* Authors to whom correspondence should be addressed.
Received: 5 November 2013 / Revised: 16 December 2013 / Accepted: 23 December 2013 / Published: 17 January 2014
(This article belongs to the Special Issue Metabolites in Diatoms)
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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.
Keywords: quorum sensing; haloperoxidase; degradation pathway; AHL; reference compounds; diatom-bacteria interactions quorum sensing; haloperoxidase; degradation pathway; AHL; reference compounds; diatom-bacteria interactions
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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Syrpas, M.; Ruysbergh, E.; Blommaert, L.; Vanelslander, B.; Sabbe, K.; Vyverman, W.; De Kimpe, N.; Mangelinckx, S. Haloperoxidase Mediated Quorum Quenching by Nitzschia cf pellucida: Study of the Metabolization of N-Acyl Homoserine Lactones by a Benthic Diatom. Mar. Drugs 2014, 12, 352-367.

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