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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

1
, 1
, 2
, 2
, 2
, 2,* , 1
 and 1,*
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 which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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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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