Bromoalterochromides A and A′, Unprecedented Chromopeptides from a Marine Pseudoalteromonas maricaloris Strain KMM 636T†

Speitling, Michael; Smetanina, O. F.; Кузнецова, Т. А.; Laatsch, Hartmut

doi:10.1038/ja.2007.5

Cited by 47 publications

(51 citation statements)

References 4 publications

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“…S4). Still, the epimerization domains are in the correct locations to encode for D-Thr, D-Val, L-Asn, D-Asn, and D-Leu/Ile as previously described (50,51). The polyketide portion of the biosynthetic pathway is missing the enoyl reductase, which one would predict based on the structure of the molecule.…”

Section: Confirming the Gcf-mf Pairing Of The Bromoalterochromides Frommentioning

confidence: 99%

“…This technique allowed us to correlate MFs [e.g., surfactin/lichenysin and viscosin/ white line-inducing principle (WLIP)/massetolide] from 60 strains of bacilli and pseudomonads to their respective GCFs (46)(47)(48)(49). We then applied this same methodology to assign the gene cluster of the membrane-disrupting antimicrobial agent, the bromoalterochromides (50)(51)(52), from a Panamanian octocoralassociated Pseudoalteromonas species.…”

Section: Significancementioning

confidence: 99%

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MS/MS networking guided analysis of molecule and gene cluster families

Nguyen

Moree

et al. 2013

Proc. Natl. Acad. Sci. U.S.A.

229

238

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The ability to correlate the production of specialized metabolites to the genetic capacity of the organism that produces such molecules has become an invaluable tool in aiding the discovery of biotechnologically applicable molecules. Here, we accomplish this task by matching molecular families with gene cluster families, making these correlations to 60 microbes at one time instead of connecting one molecule to one organism at a time, such as how it is traditionally done. We can correlate these families through the use of nanospray desorption electrospray ionization MS/MS, an ambient pressure MS technique, in conjunction with MS/MS networking and peptidogenomics. We matched the molecular families of peptide natural products produced by 42 bacilli and 18 pseudomonads through the generation of amino acid sequence tags from MS/MS data of specific clusters found in the MS/MS network. These sequence tags were then linked to biosynthetic gene clusters in publicly accessible genomes, providing us with the ability to link particular molecules with the genes that produced them. As an example of its use, this approach was applied to two unsequenced Pseudoalteromonas species, leading to the discovery of the gene cluster for a molecular family, the bromoalterochromides, in the previously sequenced strain P. piscicida JCM 20779 T . The approach itself is not limited to 60 related strains, because spectral networking can be readily adopted to look at molecular family-gene cluster families of hundreds or more diverse organisms in one single MS/MS network.MS/MS molecular networking | mass spectrometry | microbial ecology T ens of thousands of sequenced microbial genomes or rough drafts of genomes are available at this time, and this number is predicted to grow into the millions over the next decades. This wealth of sequence data has the potential to be used for the discovery of small bioactive molecules through genome mining (1-6). Genome mining is a process in which small molecules are discovered by predicting what compound will be genetically encoded based on the sequences of biosynthetic gene clusters. However, the process of mining genetically encoded small molecules is not keeping pace with the rate by which genome sequences are being obtained. In general, genome mining is still done one gene cluster at a time and requires many person-years of effort to annotate a single molecule. The time and significant expertise that current genome mining requires also make genome mining very expensive. In light of this extensive effort and cost, alternative approaches to genome mining and annotating specialized metabolites must be developed that not only take advantage of the sequenced resources available and make it efficient to perform genome mining on a more global scale but also enable the molecular analysis of unsequenced organisms. Such methods will then significantly reduce the cost of genome mining by increasing the speed with which molecules are connected to candidate genes and using resources already available. Here, we put fo...

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Section: Confirming the Gcf-mf Pairing Of The Bromoalterochromides Frommentioning

confidence: 99%

Section: Significancementioning

confidence: 99%

MS/MS networking guided analysis of molecule and gene cluster families

Nguyen

Moree

et al. 2013

Proc. Natl. Acad. Sci. U.S.A.

229

238

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“…A lethal effect of P. piscicida on eukaryotic organisms, such as algae and crustaceans, has previously been reported (36). P. piscicida S2049 produces several bromoalterochromides (37), which have inhibitory properties against Bacillus subtilis (38) and a toxic effect on eukaryotic organisms, such as sea urchins (37). The production of bromoalterochromides by S2049 could explain the toxic effect we observed in the tested eukaryotic organisms.…”

Section: Discussionmentioning

confidence: 57%

Toxicity of Bioactive and Probiotic Marine Bacteria and Their Secondary Metabolites in Artemia sp. and Caenorhabditis elegans as Eukaryotic Model Organisms

Neu

Månsson

Gram

et al. 2014

Appl Environ Microbiol

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bWe have previously reported that some strains belonging to the marine Actinobacteria class, the Pseudoalteromonas genus, the Roseobacter clade, and the Photobacteriaceae and Vibrionaceae families produce both antibacterial and antivirulence compounds, and these organisms are interesting from an applied point of view as fish probiotics or as a source of pharmaceutical compounds. The application of either organisms or compounds requires that they do not cause any side effects, such as toxicity in eukaryotic organisms. The purpose of this study was to determine whether these bacteria or their compounds have any toxic side effects in the eukaryotic organisms Artemia sp. and Caenorhabditis elegans. Arthrobacter davidanieli WX-11, Pseudoalteromonas luteoviolacea S4060, P. piscicida S2049, P. rubra S2471, Photobacterium halotolerans S2753, and Vibrio coralliilyticus S2052 were lethal to either or both model eukaryotes. The toxicity of P. luteoviolacea S4060 could be related to the production of the antibacterial compound pentabromopseudilin, while the adverse effect observed in the presence of P. halotolerans S2753 and V. coralliilyticus S2052 could not be explained by the production of holomycin nor andrimid, the respective antibiotic compounds in these organisms. In contrast, the tropodithietic acid (TDA)-producing bacteria Phaeobacter inhibens DSM17395 and Ruegeria mobilis F1926 and TDA itself had no adverse effect on the target organisms. These results reaffirm TDA-producing Roseobacter bacteria as a promising group to be used as probiotics in aquaculture, whereas Actinobacteria, Pseudoalteromonas, Photobacteriaceae, and Vibrionaceae should be used with caution.

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“…A high-M w protein has been identified as an antibacterial compound (48), and an alkaloid (norharman) was identified as a cytotoxic compound (49). P. piscicida also produces brominated peptides (46,47) that have a cytotoxic effect (50). Despite several attempts, we have not been able to purify the antibacterial compound(s).…”

Section: Discussionmentioning

confidence: 99%

Pseudoalteromonas spp. Serve as Initial Bacterial Attractants in Mesocosms of Coastal Waters but Have Subsequent Antifouling Capacity in Mesocosms and when Embedded in Paint

Bernbom

Olsen³

et al. 2013

Appl Environ Microbiol

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The purpose of the present study was to determine if the monoculture antifouling effect of several pigmented pseudoalteromonads was retained in in vitro mesocosm systems using natural coastal seawater and when the bacteria were embedded in paint used on surfaces submerged in coastal waters. Pseudoalteromonas piscicida survived on a steel surface and retained antifouling activity for at least 53 days in sterile seawater, whereas P. tunicata survived and had antifouling activity for only 1 week. However, during the first week, all Pseudoalteromonas strains facilitated rather than prevented bacterial attachment when used to coat stainless steel surfaces and submerged in mesocosms with natural seawater. The bacterial density on surfaces coated with sterile growth medium was 10 5 cells/cm 2 after 7 days, whereas counts on surfaces precoated with Pseudoalteromonas were significantly higher, at 10 6 to 10 8 cells/cm 2 . However, after 53 days, seven of eight Pseudoalteromonas strains had reduced total bacterial adhesion compared to the control. P. piscicida, P. antarctica, and P. ulvae remained on the surface, at levels similar to those in the initial coating, whereas P. tunicata could not be detected. Larger fouling organisms were observed on all plates precoated with Pseudoalteromonas; however, plates coated only with sterile growth medium were dominated by a bacterial biofilm. Suspensions of a P. piscicida strain and a P. tunicata strain were incorporated into ship paints (Hempasil x3 87500 and Hempasil 77500) used on plates that were placed at the Hempel A/S test site in Jyllinge Harbor. For the first 4 months, no differences were observed between control plates and treated plates, but after 5 to 6 months, the control plates were more fouled than the plates with pseudoalteromonad-based paint. Our study demonstrates that no single laboratory assay can predict antifouling effects and that a combination of laboratory and real-life methods must be used to determine the potential antifouling capability of new agents or organisms.

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Bromoalterochromides A and A′, Unprecedented Chromopeptides from a Marine Pseudoalteromonas maricaloris Strain KMM 636T†

Cited by 47 publications

References 4 publications

MS/MS networking guided analysis of molecule and gene cluster families

MS/MS networking guided analysis of molecule and gene cluster families

Toxicity of Bioactive and Probiotic Marine Bacteria and Their Secondary Metabolites in Artemia sp. and Caenorhabditis elegans as Eukaryotic Model Organisms

Pseudoalteromonas spp. Serve as Initial Bacterial Attractants in Mesocosms of Coastal Waters but Have Subsequent Antifouling Capacity in Mesocosms and when Embedded in Paint

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