Antimicrobial activity and bioactive profiling of heterocytous cyanobacterial strains using MS/MS-based molecular networking

Saurav, Kumar; Macho, Markéta; Kust, Andreja; Delawská, Kateřina; Hájek, Jan; Hrouzek, Pavel

doi:10.1007/s12223-019-00737-9

Cited by 23 publications

(13 citation statements)

References 43 publications

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“…Crude extracts were prepared following the pre-established protocol [46,89]. Briefly, freeze-dried biomass of collected pond samples (~20 mg) were grinded (with the sea sand) and extracted three times with 75% MeOH in water followed by bath sonication.…”

Section: Crude Extracts Preparation and Hplc-ms/ms Analysismentioning

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: Crude Extracts Preparation and Hplc-ms/ms Analysismentioning

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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“…task=9581427a15b7422d8bd2b3b4b086189e&view=view_all_annotations_DB). To further expand the annotation coverage, we applied DEREPLICATOR, a recently developed dereplication algorithm that enables high-throughput peptide natural products (PNPs) identification from their tandem mass spectra [14][15][16][17]. Interestingly, this tool allows to putatively identify an unknown PNP from its known variants (for example, with a substitution, a modification or an adduct) through the so-called variable dereplication process (as opposed to the strict dereplication when a PNP is described in the database).…”

Section: Ms/ms Analysis and Annotation Of Cyanobacterial Specialized mentioning

confidence: 99%

New Benthic Cyanobacteria from Guadeloupe Mangroves as Producers of Antimicrobials

et al. 2019

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Benthic cyanobacteria strains from Guadeloupe have been investigated for the first time by combining phylogenetic, chemical and biological studies in order to better understand the taxonomic and chemical diversity as well as the biological activities of these cyanobacteria through the effect of their specialized metabolites. Therefore, in addition to the construction of the phylogenetic tree, indicating the presence of 12 potentially new species, an LC-MS/MS data analysis workflow was applied to provide an overview on chemical diversity of 20 cyanobacterial extracts, which was linked to antimicrobial activities evaluation against human pathogenic and ichtyopathogenic environmental strains.

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“…The Brasilonema strain was collected in Costa Rica, as black mat on a bamboo trunk, on March 18, 2010 by Jan Mareš and isolated into culture by Josef Juráň. Strain was grown in Z' medium in glass columns (300 mL) bubbled with air enriched in 1.5% CO 2 at constant temperature and illumination of 28 • C and 50 µmol photon m −2 s −1 [5]. Biomass was harvested by centrifugation (3125× g), stored at −80 • C, and subsequently lyophilized.…”

Section: Cyanobacterial Strain and Culturing Conditionsmentioning

confidence: 99%

“…For 3.5 billion years, cyanobacteria have kept developing new adaptation features and defense mechanisms which allowed them to colonize the earth, shape its atmosphere from anoxic to oxygenic, and ever since to survive in harsh and strongly competitive environments under extreme temperatures, salt stress, high UV-radiation, and pathogen attack [1,2]. One of these survival strategies is the production of a vast variety of secondary metabolites, exhibiting a broad spectrum of biological activities and properties, including peptides, lipopeptides, polyketides, alkaloids, lipids, and terpenoids [3][4][5][6][7]. When growth conditions are advantageous, cyanobacteria proliferate, resulting in overgrown 2 of 12 populations known as cyanobacterial blooms (CBs), which can be harmful for aquatic life as well as for human health because of the toxins they produce [8,9].…”

Section: Introductionmentioning

confidence: 99%

“…These compounds are usually produced by nonribosomal peptide synthetases (NRPS), polyketide synthases (PKS), or NRPS/PKS hybrid enzymes. Recent advancement in the field of genome sequencing and the rise of fast and extremely accurate analytical methods, such as high-performance liquid chromatography connected to high-resolution mass spectrometry (HPLC-HRMS/MS), have accelerated the discovery of novel secondary metabolites e.g., [5,6,15]. The use of molecular networking as a dereplication strategy allows to identify the complexity of variants produced by respective biosynthetic genes, which in turn produce valuable data for pharmaceutical development, since structural variants often have different biological activities [16][17][18].…”

Section: Introductionmentioning

confidence: 99%

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Discovery of Unusual Cyanobacterial Tryptophan-Containing Anabaenopeptins by MS/MS-Based Molecular Networking

et al. 2020

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Heterocytous cyanobacteria are among the most prolific sources of bioactive secondary metabolites, including anabaenopeptins (APTs). A terrestrial filamentous Brasilonema sp. CT11 collected in Costa Rica bamboo forest as a black mat, was studied using a multidisciplinary approach: genome mining and HPLC-HRMS/MS coupled with bioinformatic analyses. Herein, we report the nearly complete genome consisting of 8.79 Mbp with a GC content of 42.4%. Moreover, we report on three novel tryptophan-containing APTs; anabaenopeptin 788 (1), anabaenopeptin 802 (2), and anabaenopeptin 816 (3). Furthermore, the structure of two homologues, i.e., anabaenopeptin 802 (2a) and anabaenopeptin 802 (2b), was determined by spectroscopic analysis (NMR and MS). Both compounds were shown to exert weak to moderate antiproliferative activity against HeLa cell lines. This study also provides the unique and diverse potential of biosynthetic gene clusters and an assessment of the predicted chemical space yet to be discovered from this genus.

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Antimicrobial activity and bioactive profiling of heterocytous cyanobacterial strains using MS/MS-based molecular networking

Cited by 23 publications

References 43 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

New Benthic Cyanobacteria from Guadeloupe Mangroves as Producers of Antimicrobials

Discovery of Unusual Cyanobacterial Tryptophan-Containing Anabaenopeptins by MS/MS-Based Molecular Networking

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