Structural Characterization of Vanchrobactin, a New Catechol Siderophore Produced by the Fish Pathogen Vibrio anguillarum Serotype O2.

Soengas, Raquel G.; Anta, Cristina; Espada, Alfonso; Paz, Vanessa; Ares, Isabel R.; Balado, Miguel; Rodrı́guez, Jaime; Lemos, Manuel L.; Jiménez, Carlos

doi:10.1002/chin.200703203

Cited by 18 publications

(26 citation statements)

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“…In most pathogenic strains of serotype O1, the system is mediated by the 65 kb virulence plasmid pJM1, harbouring genes for the biosynthesis of the siderophore anguibactin and its cognate transport system [20]. In contrast, serotype O2 strains and some plasmidless serotype O1 strains produce a chromosomally encoded siderophore vanchrobactin [21]–[24]. Nevertheless, despite these studies, the exact role and contribution of many of these virulence factors in full V. anguillarum virulence remain still largely unknown, e.g.…”

Section: Introductionmentioning

confidence: 99%

Does Virulence Assessment of Vibrio anguillarum Using Sea Bass (Dicentrarchus labrax) Larvae Correspond with Genotypic and Phenotypic Characterization?

et al. 2013

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BackgroundVibriosis is one of the most ubiquitous fish diseases caused by bacteria belonging to the genus Vibrio such as Vibrio (Listonella) anguillarum. Despite a lot of research efforts, the virulence factors and mechanism of V. anguillarum are still insufficiently known, in part because of the lack of standardized virulence assays.Methodology/Principal FindingsWe investigated and compared the virulence of 15 V. anguillarum strains obtained from different hosts or non-host niches using a standardized gnotobiotic bioassay with European sea bass (Dicentrarchus labrax L.) larvae as model hosts. In addition, to assess potential relationships between virulence and genotypic and phenotypic characteristics, the strains were characterized by random amplified polymorphic DNA (RAPD) and repetitive extragenic palindromic PCR (rep-PCR) analyses, as well as by phenotypic analyses using Biolog’s Phenotype MicroArray™ technology and some virulence factor assays.Conclusions/SignificanceVirulence testing revealed ten virulent and five avirulent strains. While some relation could be established between serotype, genotype and phenotype, no relation was found between virulence and genotypic or phenotypic characteristics, illustrating the complexity of V. anguillarum virulence. Moreover, the standardized gnotobiotic system used in this study has proven its strength as a model to assess and compare the virulence of different V. anguillarum strains in vivo. In this way, the bioassay contributes to the study of mechanisms underlying virulence in V. anguillarum.

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Section: Introductionmentioning

confidence: 99%

Does Virulence Assessment of Vibrio anguillarum Using Sea Bass (Dicentrarchus labrax) Larvae Correspond with Genotypic and Phenotypic Characterization?

et al. 2013

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“…In addition to the cyclic triscatecholate siderophores, a linear (non-cyclized) triscatecholate siderophore, trivanchrobactin, was reported from the marine isolate Vibrio campbelli DS40M4 [18], [19]. Trivanchrobactin is a linear trimeric ester of the previously reported vanchrobactin, 2,3-DHB-D-Arg-L-Ser [20].…”

Section: Introductionmentioning

confidence: 92%

Turnerbactin, a Novel Triscatecholate Siderophore from the Shipworm Endosymbiont Teredinibacter turnerae T7901

et al. 2013

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Shipworms are marine bivalve mollusks (Family Teredinidae) that use wood for shelter and food. They harbor a group of closely related, yet phylogenetically distinct, bacterial endosymbionts in bacteriocytes located in the gills. This endosymbiotic community is believed to support the host's nutrition in multiple ways, through the production of cellulolytic enzymes and the fixation of nitrogen. The genome of the shipworm endosymbiont Teredinibacter turnerae T7901 was recently sequenced and in addition to the potential for cellulolytic enzymes and diazotrophy, the genome also revealed a rich potential for secondary metabolites. With nine distinct biosynthetic gene clusters, nearly 7% of the genome is dedicated to secondary metabolites. Bioinformatic analyses predict that one of the gene clusters is responsible for the production of a catecholate siderophore. Here we describe this gene cluster in detail and present the siderophore product from this cluster. Genes similar to the entCEBA genes of enterobactin biosynthesis involved in the production and activation of dihydroxybenzoic acid (DHB) are present in this cluster, as well as a two-module non-ribosomal peptide synthetase (NRPS). A novel triscatecholate siderophore, turnerbactin, was isolated from the supernatant of iron-limited T. turnerae T7901 cultures. Turnerbactin is a trimer of N-(2,3-DHB)-L-Orn-L-Ser with the three monomeric units linked by Ser ester linkages. A monomer, dimer, dehydrated dimer, and dehydrated trimer of 2,3-DHB-L-Orn-L-Ser were also found in the supernatant. A link between the gene cluster and siderophore product was made by constructing a NRPS mutant, TtAH03. Siderophores could not be detected in cultures of TtAH03 by HPLC analysis and Fe-binding activity of culture supernatant was significantly reduced. Regulation of the pathway by iron is supported by identification of putative Fur box sequences and observation of increased Fe-binding activity under iron restriction. Evidence of a turnerbactin fragment was found in shipworm extracts, suggesting the production of turnerbactin in the symbiosis.

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“…Knock-out of genes involved in anguibactin production attenuated virulence, confirming that anguibactin is a prerequisite for successful host-invasion of this bacterium [129]. In contrast, the catechol vanchrobactin is chromosome-encoded, and interestingly, the coding genes are silenced in anguibactin producing strains [71,130]. Recently, dimeric and trimeric versions of vanchrobactin were isolated from an unidentified Vibrio by Sandy et al (2010) [65].…”

Section: Natural Product Production By Members Of the Vibrionaceaementioning

confidence: 99%

Production of Bioactive Secondary Metabolites by Marine Vibrionaceae

2011

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Bacteria belonging to the Vibrionaceae family are widespread in the marine environment. Today, 128 species of vibrios are known. Several of them are infamous for their pathogenicity or symbiotic relationships. Despite their ability to interact with eukaryotes, the vibrios are greatly underexplored for their ability to produce bioactive secondary metabolites and studies have been limited to only a few species. Most of the compounds isolated from vibrios so far are non-ribosomal peptides or hybrids thereof, with examples of N-containing compounds produced independent of nonribosomal peptide synthetases (NRPS). Though covering a limited chemical space, vibrios produce compounds with attractive biological activities, including antibacterial, anticancer, and antivirulence activities. This review highlights some of the most interesting structures from this group of bacteria. Many compounds found in vibrios have also been isolated from other distantly related bacteria. This cosmopolitan occurrence of metabolites indicates a high incidence of horizontal gene transfer, which raises interesting questions concerning the ecological function of some of these molecules. This account underlines the pending potential for exploring new bacterial sources of bioactive compounds and the challenges related to their investigation.

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Structural Characterization of Vanchrobactin, a New Catechol Siderophore Produced by the Fish Pathogen Vibrio anguillarum Serotype O2.

Cited by 18 publications

References 1 publication

Does Virulence Assessment of Vibrio anguillarum Using Sea Bass (Dicentrarchus labrax) Larvae Correspond with Genotypic and Phenotypic Characterization?

Does Virulence Assessment of Vibrio anguillarum Using Sea Bass (Dicentrarchus labrax) Larvae Correspond with Genotypic and Phenotypic Characterization?

Turnerbactin, a Novel Triscatecholate Siderophore from the Shipworm Endosymbiont Teredinibacter turnerae T7901

Production of Bioactive Secondary Metabolites by Marine Vibrionaceae

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