Anti-infective Natural Products from Cyanobacteria

Niedermeyer, Timo H. J.

doi:10.1055/s-0035-1546055

Cited by 59 publications

(42 citation statements)

References 176 publications

(211 reference statements)

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“…KEYWORDS allelopathy, cellular differentiation, cyanobacteria, natural products, nonribosomal peptide C yanobacteria are one of the most prolific sources of small-molecule natural products featuring potent bioactivities, as well as exhibiting unique structural properties (1)(2)(3). Phylogenomic surveys of cyanobacteria have revealed a large number of orphan biosynthetic gene clusters (BGCs) that await mining and characterization of their products, in particular in late-branching lineages of the cyanobacterial phylum (4,5).…”

Section: Importancementioning

confidence: 99%

High-Density Cultivation of Terrestrial Nostoc Strains Leads to Reprogramming of Secondary Metabolome

Guljamow

Kreische

Ishida

et al. 2017

Appl Environ Microbiol

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Terrestrial symbiotic cyanobacteria of the genus Nostoc exhibit a large potential for the production of bioactive natural products of the nonribosomal peptide, polyketide, and ribosomal peptide classes, and yet most of the biosynthetic gene clusters are silent under conventional cultivation conditions. In the present study, we utilized a high-density cultivation approach recently developed for phototrophic bacteria to rapidly generate biomass of the filamentous bacteria up to a density of 400 g (wet weight)/liter. Unexpectedly, integrated transcriptional and metabolomics studies uncovered a major reprogramming of the secondary metabolome of two Nostoc strains at high culture density and a governing effect of extracellular signals in this process. The holistic approach enabled capturing and structural elucidation of novel variants of anabaenopeptin, including one congener with potent allelopathic activity against a strain isolated from the same habitat. The study provides a snapshot on the role of cell-type-specific expression for the formation of natural products in cyanobacteria.IMPORTANCE Terrestrial filamentous cyanobacteria are a largely untapped source of small-molecule natural products. Exploitation of the phototrophic organisms is hampered by their slow growth and the requirement of photobioreactors. The present study not only demonstrates the suitability of a recently developed two-tier vessel cultivation approach for the rapid generation of biomass of Nostoc strains but also demonstrates a pronounced upregulation of high value natural products at ultrahigh culture densities. The study provides new guidelines for high-throughput screening and exploitation of small-molecule natural products and can facilitate the discovery new bioactive products from terrestrial cyanobacteria.

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Section: Importancementioning

confidence: 99%

High-Density Cultivation of Terrestrial Nostoc Strains Leads to Reprogramming of Secondary Metabolome

Guljamow

Kreische

Ishida

et al. 2017

Appl Environ Microbiol

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“…It is well-known that cyanobacteria release by exudation or cell lysis a variety of organic molecules such as organic acids, carbohydrates, proteins, and lipids (Amemiya et al 1990;Tonietto et al 2014;Kehr and Dittmann 2015), including bioactive compounds (Sivonen and Börner 2008). Indeed, freshwater cyanobacteria are able to produce a variety of secondary metabolites (aeruginosins: Ersmark et al 2008;anabaenopeptins: Itou et al 1999;cyanobactins: Sivonen et al 2010;cyanopeptolins: Bister et al 2004;microginins: Ishida et al 2000;microviridins: Ishitsuka et al 1990) displaying various bioactivities including cytotoxic, antiviral, antimalarial, or allelopathic through the inhibition of vital eukaryotic enzymes (mostly serine proteases; Welker and Von Döhren 2006;Niedermeyer 2015 and references herein). Among them, the microcystins (MC) are the most widely distributed and studied cyanotoxins due to their detrimental impact on a variety of organisms, including humans (Carmichael 1992).…”

Section: Original Researchmentioning

confidence: 99%

Role of bacteria in the production and degradation of Microcystis cyanopeptides

et al. 2016

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The freshwater cyanobacteria, Microcystis sp., commonly form large colonies with bacteria embedded in their mucilage. Positive and negative interactions between Microcystis species and their associated bacteria have been reported. However, the potential role of bacteria in the production and degradation of cyanobacterial secondary metabolites has not been investigated. In this study, a Microcystis‐associated bacterial community was isolated and added to the axenic M. aeruginosa PCC7806 liquid culture. After 3 years of cocultivation, we studied the bacterial genetic diversity adapted to the PCC7806 strain and compared the intra‐ and extracellular concentration of major cyanopeptides produced by the cyanobacterial strain under xenic and axenic conditions. Mass spectrometric analyses showed that the intracellular concentration of peptides was not affected by the presence of bacteria. Interestingly, the produced peptides were detected in the axenic media but could not be found in the xenic media. This investigation revealed that a natural bacterial community, dominated by Alpha‐proteobacteria, was able to degrade a wide panel of structurally varying cyclic cyanopeptides.

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“…Introduction Cyanobacteria are an intriguing source for structurally diverse and biologically active natural products. Especially the genera Microcystis, Nostoc, and Lyngbya or Moorea are chemically well-characterized [1][2][3][4][5][6][7]. Several strains of the family Hapalosiphonaceae produce indole alkaloids [8].…”

Section: Inhibit T Cell Proliferationmentioning

confidence: 99%

Hapalindoles from the Cyanobacterium Hapalosiphon sp. Inhibit T Cell Proliferation

et al. 2019

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Supporting information available online at http://www.thieme-connect.de/products ABSTR AC T Novel immunomodulating agents are currently sought after for the treatment of autoimmune diseases and cancers. In this context, a screening campaign of a collection of 575 cyanobacteria extracts for immunomodulatory effects has been conducted. The screening resulted in several active extracts.Here we report the results of subsequent studies on an extract from the cyanobacterium Hapalosiphon sp. CBT1235. We identified 5 hapalindoles as the compounds responsible for the observed immunomodulatory effect. These indole alkaloids are produced by several strains of the cyanobacterial family Hapalosiphonaceae. They are known for their anti-infective, cytotoxic, and other bioactivities. Modulation of the activity of human immune cells has not yet been described. The immunomodulatory activity of the hapalindoles was characterized in vitro using flow cytometry-based measurements of T cell proliferation after carboxyfluorescein diacetate succinimidyl ester staining, and apoptosis and necrosis induction after annexin V/propidium iodide staining. The most potent compound, hapalindole A, reduced T cell proliferation with an IC 50 of 1.56 µM, while relevant levels of apoptosis were measurable only at 10-fold higher concentrations. Hapalindole A-formamide and hapalindole J-formamide, isolated for the first time from a natural source, had much lower activity than the nonformylated derivatives while, at the same time, being less selective for antiproliferative over apoptotic effects.

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Anti-infective Natural Products from Cyanobacteria

Cited by 59 publications

References 176 publications

High-Density Cultivation of Terrestrial Nostoc Strains Leads to Reprogramming of Secondary Metabolome

High-Density Cultivation of Terrestrial Nostoc Strains Leads to Reprogramming of Secondary Metabolome

Role of bacteria in the production and degradation of Microcystis cyanopeptides

Hapalindoles from the Cyanobacterium Hapalosiphon sp. Inhibit T Cell Proliferation

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