The Metabolome of a Cyanobacterial Bloom Visualized by MS/MS-Based Molecular Networking Reveals New Neurotoxic Smenamide Analogs (C, D, and E)

Via, Christopher W.; Glukhov, Evgenia; Costa, Samuel Macedo; Zimba, Paul V.; Moeller, P.; Gerwick, William H.; Bertin, Matthew J.

doi:10.3389/fchem.2018.00316

Cited by 28 publications

(35 citation statements)

References 28 publications

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“…These tools enable to analyse and curate hundreds to thousands of obtained MS/MS data from analytes within the extract which is almost impossible to analyse manually [26]. Recent application of these tools in the field of annotating metabolites from cyanobacterial bloom led to the discovery of various novel compounds as well as unknown analogues [27][28][29][30].…”

Section: Introductionmentioning

confidence: 99%

Insight Into Unprecedented Diversity of Cyanopeptides in Eutrophic Ponds Using a MS/MS Networking Approach

Kust¹,

Řeháková²,

Vrba³

et al. 2020

Preprint

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Man-made shallow fishponds in the Czech Republic have been facing a high eutrophication since 1950s. Anthropogenic eutrophication and feeding of fish have strongly affected the physico-chemical properties of water and its aquatic community composition leading to harmful algal bloom formation. In our current study, we have characterised the phytoplankton community across three hypertrophic ponds to assess the phytoplankton dynamics during the vegetation season. We microscopically identified and quantified 29 cyanobacterial taxa comprised of non-toxigenic and toxigenic species. Further, a detailed cyanopeptides (CNPs) profiling was performed using molecular networking analysis of liquid chromatography tandem mass spectrometry (LC–MS/MS) data coupled with dereplication strategy. This MS networking approach coupled with dereplication on online global natural product social networking (GNPS) web platform led us to putatively identify forty CNPs: fourteen anabaenopeptins, ten microcystins, five cyanopeptolins, six microginins, two cyanobactins, a dipeptide radiosumin, a cyclooctapeptide planktocyclin and epidolastatin12. We have applied the binary logistic regression to estimate the CNPs producer by correlating the GNPS data with the species abundance. Usage of The combination of molecular networking and dereplication on online global natural product social networking (GNPS) web platform has proved as a valuable approach for rapid and simultaneous detection of high number of peptides, and rapidly assessing the risk for harmful bloom.

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Section: Introductionmentioning

confidence: 99%

Insight Into Unprecedented Diversity of Cyanopeptides in Eutrophic Ponds Using a MS/MS Networking Approach

Kust¹,

Řeháková²,

Vrba³

et al. 2020

Preprint

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“…[15][16][17] Extracts and chromatography fractions from environmental collections of bloom material are very complex with respect to metabolite composition making a comprehensive characterization of all metabolites present challenging. 9 MS/MS-based molecular networking provides an approach to aid in chemical space assessments of extracts, and recent workflows have been developed to target geometric isomers and chlorinated metabolites. 11 In the current report, we utilized MS/MS-based molecular networking to capture the halogenated chemical space present in Trichodesmium extracts.…”

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confidence: 99%

Isolation of Isotrichophycin C and Trichophycins G–I from a Collection of Trichodesmium thiebautii

et al. 2020

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The trichophycin family of compounds are chlorinated polyketides first discovered from environmental collections of a bloom-forming Trichodesmium sp. cyanobacterium. In an effort to fully capture the chemical space of this group of metabolites, the utilization of MS/MS-based molecular networking of a Trichodesmium thiebautii extract revealed a metabolome replete with halogenated compounds. Subsequent MS-guided isolation resulted in the characterization of isotrichophycin C and trichophycins G-I (1-4). These new metabolites had intriguing structural variations from those trichophycins previously characterized, which allowed for a comparative study to examine structural features that are associated with toxicity to murine neuroblastoma cells. Additionally, we propose the absolute configuration of the previously characterized trichophycin A (5). Overall, the metabolome of the Trichodesmium bloom is hallmarked by an unprecedented amount of chlorinated molecules, many of which remain to be structurally characterized. 4 and derivatives of 1, 3, and trichophycin A. ECD data of 1 and trichophycin C. EC50 curves of 1-3 and acetylated derivatives, and phylogenetic analysis.

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“…Liquid chromatography mass spectrometry (LC-MS) datasets for marine sponge extracts are starting to be made accessible on metabolome mining tools, such as the Global Natural Products Social (GNPS) Molecular Networking platform, which enables a communitywide effort to curate natural products, dereplicate previously known natural products, and discover novel natural products based on chemical similarity to known natural product structures (Wang et al 2016). Molecular networking was also used to advance the diversity of smenamides, hybrid polyketide-peptide natural products of cyanobacterial origin first described from the sponge Smenospongia aurea (Teta et al 2013;Via et al 2018). Advances in mass spectrometry instrumentation have the potential to transform sponge-derived natural product discovery.…”

Section: Sponge-derived Natural Products Chemistrymentioning

confidence: 99%

Chemical Ecology of Marine Sponges: New Opportunities through “-Omics”

Paul

Freeman

Agarwal

2019

Integrative and Comparative Biology

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The chemical ecology and chemical defenses of sponges have been investigated for decades; consequently, sponges are among the best understood marine organisms in terms of their chemical ecology, from the level of molecules to ecosystems. Thousands of natural products have been isolated and characterized from sponges, and although relatively few of these compounds have been studied for their ecological functions, some are known to serve as chemical defenses against predators, microorganisms, fouling organisms, and other competitors. Sponges are hosts to an exceptional diversity of microorganisms, with almost 40 microbial phyla found in these associations to date. Microbial community composition and abundance are highly variable across host taxa, with a continuum from diverse assemblages of many microbial taxa to those that are dominated by a single microbial group. Microbial communities expand the nutritional repertoire of their hosts by providing access to inorganic and dissolved sources of nutrients. Not only does this continuum of microorganism–sponge associations lead to divergent nutritional characteristics in sponges, these associated microorganisms and symbionts have long been suspected, and are now known, to biosynthesize some of the natural products found in sponges. Modern “omics” tools provide ways to study these sponge–microbe associations that would have been difficult even a decade ago. Metabolomics facilitate comparisons of sponge compounds produced within and among taxa, and metagenomics and metatranscriptomics provide tools to understand the biology of host–microbe associations and the biosynthesis of ecologically relevant natural products. These combinations of ecological, microbiological, metabolomic and genomics tools, and techniques provide unprecedented opportunities to advance sponge biology and chemical ecology across many marine ecosystems.

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The Metabolome of a Cyanobacterial Bloom Visualized by MS/MS-Based Molecular Networking Reveals New Neurotoxic Smenamide Analogs (C, D, and E)

Cited by 28 publications

References 28 publications

Insight Into Unprecedented Diversity of Cyanopeptides in Eutrophic Ponds Using a MS/MS Networking Approach

Insight Into Unprecedented Diversity of Cyanopeptides in Eutrophic Ponds Using a MS/MS Networking Approach

Isolation of Isotrichophycin C and Trichophycins G–I from a Collection of Trichodesmium thiebautii

Chemical Ecology of Marine Sponges: New Opportunities through “-Omics”

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