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      Quorum Sensing Inhibitory and Antifouling Activities of New Bromotyrosine Metabolites from the Polynesian Sponge Pseudoceratina n. sp.

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          Abstract

          Four new brominated tyrosine metabolites, aplyzanzines C–F ( 14), were isolated from the French Polynesian sponge Pseudoceratina n. sp., along with the two known 2-aminoimidazolic derivatives, purealidin A ( 5) and 6, previously isolated, respectively, from the sponges Psammaplysilla purpurea and Verongula sp. Their structures were assigned based on the interpretation of their NMR and HRMS data. The compounds exhibited quorum sensing inhibition (QSi) and antifouling activities against several strains of bacteria and microalgae. To our knowledge, the QSi activity of this type of bromotyrosine metabolite is described here for the first time.

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          Quorum sensing inhibitors: an overview.

          Excessive and indiscriminate use of antibiotics to treat bacterial infections has lead to the emergence of multiple drug resistant strains. Most infectious diseases are caused by bacteria which proliferate within quorum sensing (QS) mediated biofilms. Efforts to disrupt biofilms have enabled the identification of bioactive molecules produced by prokaryotes and eukaryotes. These molecules act primarily by quenching the QS system. The phenomenon is also termed as quorum quenching (QQ). In addition, synthetic compounds have also been found to be effective in QQ. This review focuses primarily on natural and synthetic quorum sensing inhibitors (QSIs) with the potential for treating bacterial infections. It has been opined that the most versatile prokaryotes to produce QSI are likely to be those, which are generally regarded as safe. Among the eukaryotes, certain legumes and traditional medicinal plants are likely to act as QSIs. Such findings are likely to lead to efficient treatments with much lower doses of drugs especially antibiotics than required at present. Copyright © 2012 Elsevier Inc. All rights reserved.
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            Cross-species induction of luminescence in the quorum-sensing bacterium Vibrio harveyi.

            Different species of bacteria were tested for production of extracellular autoinducer-like activities that could stimulate the expression of the luminescence genes in Vibrio harveyi. Several species of bacteria, including the pathogens Vibrio cholerae and Vibrio parahaemolyticus, were found to produce such activities. Possible physiological roles for the two V. harveyi detection-response systems and their joint regulation are discussed.
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              Three parallel quorum-sensing systems regulate gene expression in Vibrio harveyi.

              In a process called quorum sensing, bacteria communicate using extracellular signal molecules termed autoinducers. Two parallel quorum-sensing systems have been identified in the marine bacterium Vibrio harveyi. System 1 consists of the LuxM-dependent autoinducer HAI-1 and the HAI-1 sensor, LuxN. System 2 consists of the LuxS-dependent autoinducer AI-2 and the AI-2 detector, LuxPQ. The related bacterium, Vibrio cholerae, a human pathogen, possesses System 2 (LuxS, AI-2, and LuxPQ) but does not have obvious homologues of V. harveyi System 1. Rather, System 1 of V. cholerae is made up of the CqsA-dependent autoinducer CAI-1 and a sensor called CqsS. Using a V. cholerae CAI-1 reporter strain we show that many other marine bacteria, including V. harveyi, produce CAI-1 activity. Genetic analysis of V. harveyi reveals cqsA and cqsS, and phenotypic analysis of V. harveyi cqsA and cqsS mutants shows that these functions comprise a third V. harveyi quorum-sensing system that acts in parallel to Systems 1 and 2. Together these communication systems act as a three-way coincidence detector in the regulation of a variety of genes, including those responsible for bioluminescence, type III secretion, and metalloprotease production.
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                Author and article information

                Journal
                Mar Drugs
                Mar Drugs
                marinedrugs
                Marine Drugs
                MDPI
                1660-3397
                21 May 2020
                May 2020
                : 18
                : 5
                : 272
                Affiliations
                [1 ]IRD, Univ de la Polynésie française, Ifremer, ILM, EIO, F-98713 Papeete, French Polynesia; florent.tintillier@ 123456gmail.com (F.T.); Cecile.Debitus@ 123456ird.fr (C.D.)
                [2 ]CNRS, Institut de Chimie des Substances Naturelles, Université Paris-Saclay, 91190 Gif-sur-Yvette, France; Celine.Moriou@ 123456cnrs.fr (C.M.); Ali.ALMOURABIt@ 123456cnrs.fr (A.A.-M.)
                [3 ]IRD, Univ Brest, CNRS, Ifremer, LEMAR, F-29280 Plouzane, France; marilyne.fauchon@ 123456univ-brest.fr (M.F.); claire.hellio@ 123456univ-brest.fr (C.H.)
                [4 ]Ifremer, IRD, ILM, Univ de la Polynésie française, EIO, F-98719 Taravao, French Polynesia; Denis.Saulnier@ 123456ifremer.fr
                [5 ]Queensland Museum, PO Box 3300, South Brisbane BC 4101, Queensland, Australia; merrick.ekins@ 123456qm.qld.gov.au (M.E.); john.hooper@ 123456qm.qld.gov.au (J.N.A.H.)
                Author notes
                [* ]Correspondence: sylvain.petek@ 123456ird.fr ; Tel.: +33-298-498-651
                Author information
                https://orcid.org/0000-0001-7920-0467
                https://orcid.org/0000-0003-2988-5183
                https://orcid.org/0000-0002-4825-462X
                https://orcid.org/0000-0003-1722-5954
                Article
                marinedrugs-18-00272
                10.3390/md18050272
                7281015
                32455754
                7646ff59-3c5e-4145-b7eb-a14d34a2c82b
                © 2020 by the authors.

                Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license ( http://creativecommons.org/licenses/by/4.0/).

                History
                : 03 April 2020
                : 19 May 2020
                Categories
                Article

                Pharmacology & Pharmaceutical medicine
                sponge,pseudoceratina,quorum sensing inhibitory activity,antifouling,verongiida,bromotyrosine

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