Plasticity and Evolution of Aeruginosin Biosynthesis in Cyanobacteria

Ishida, Keishi; Welker, Martin; Christiansen, Guntram; Cadel-Six, Sabrina; Bouchier, Christiane; Dittmann, Elke; Hertweck, Christian; Marsac, Nicole Tandeau de

doi:10.1128/aem.02258-08

Cited by 100 publications

(128 citation statements)

References 54 publications

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“…Glycosylated aeruginosins described, until recently, exclusively in non-heterocystous cyanobacteria Planctothrix sp. were found in the same mass range as in our samples (Ishida et al, 2009). An antinflammatory peptide with m/z 865 has been previously reported from a number of terrestrial Nostoc strains (Hrouzek et al, 2011; Kapuscik et al, 2013).…”

Section: Discussionsupporting

confidence: 86%

A Genetic and Chemical Perspective on Symbiotic Recruitment of Cyanobacteria of the Genus Nostoc into the Host Plant Blasia pusilla L.

2016

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Liverwort Blasia pusilla L. recruits soil nitrogen-fixing cyanobacteria of genus Nostoc as symbiotic partners. In this work we compared Nostoc community composition inside the plants and in the soil around them from two distant locations in Northern Norway. STRR fingerprinting and 16S rDNA phylogeny reconstruction showed a remarkable local diversity among isolates assigned to several Nostoc clades. An extensive web of negative allelopathic interactions was recorded at an agricultural site, but not at the undisturbed natural site. The cell extracts of the cyanobacteria did not show antimicrobial activities, but four isolates were shown to be cytotoxic to human cells. The secondary metabolite profiles of the isolates were mapped by MALDI-TOF MS, and the most prominent ions were further analyzed by Q-TOF for MS/MS aided identification. Symbiotic isolates produced a great variety of small peptide-like substances, most of which lack any record in the databases. Among identified compounds we found microcystin and nodularin variants toxic to eukaryotic cells. Microcystin producing chemotypes were dominating as symbiotic recruits but not in the free-living community. In addition, we were able to identify several novel aeruginosins and banyaside-like compounds, as well as nostocyclopeptides and nosperin.

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Section: Discussionsupporting

confidence: 86%

A Genetic and Chemical Perspective on Symbiotic Recruitment of Cyanobacteria of the Genus Nostoc into the Host Plant Blasia pusilla L.

2016

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“…Regulation of synthetase genes for microcystins ( Figure 6A), aeruginosins ( Figure 6B) and cyanopeptolins ( Figure 6C) (Kaneko et al, 2007;Ishida et al, 2009) is likely tied to a need for juxtaposition of these gene products to each other for proper synthesis: rearrangements leading to a loss of function likely means the entire cassette would be quickly lost from the genome. In part, this may explain the absence of these capabilities in some isolates: although intact, the genetic cassettes support selection for organisms producing these compounds, allowing the persistence of these capabilities within the genome.…”

Section: Genomic Consequences Of Nutrient Conditionsmentioning

confidence: 99%

Nutrients drive transcriptional changes that maintain metabolic homeostasis but alter genome architecture in Microcystis

Steffen¹,

Dearth²,

Dill³

et al. 2014

The ISME Journal

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The cyanobacterium Microcystis aeruginosa is a globally distributed bloom-forming organism that degrades freshwater systems around the world. Factors that drive its dispersion, diversification and success remain, however, poorly understood. To develop insight into cellular-level responses to nutrient drivers of eutrophication, RNA sequencing was coupled to a comprehensive metabolomics survey of M. aeruginosa sp. NIES 843 grown in various nutrient-reduced conditions. Transcriptomes were generated for cultures grown in nutrient-replete (with nitrate as the nitrogen (N) source), nitrogen-reduced (with nitrate, urea or ammonium acting as the N sources) and phosphate-reduced conditions. Extensive expression differences (up to 696 genes for urea-grown cells) relative to the control treatment were observed, demonstrating that the chemical variant of nitrogen available to cells affected transcriptional activity. Of particular note, a high number of transposase genes (up to 81) were significantly and reproducibly up-regulated relative to the control when grown on urea. Conversely, phosphorus (P) reduction resulted in a significant cessation in transcription of transposase genes, indicating that variation in nutrient chemistry may influence transcription of transposases and may impact the highly mosaic genomic architecture of M. aeruginosa. Corresponding metabolomes showed comparably few differences between treatments, suggesting broad changes to gene transcription are required to maintain metabolic homeostasis under nutrient reduction. The combined observations provide novel and extensive insight into the complex cellular interactions that take place in this important bloom-forming organism during variable nutrient conditions and highlight a potential unknown molecular mechanism that may drive Microcystis blooms and evolution.

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“…152 Cyanobacteria of the genera Microcystis and Planktothrix have been shown to harbor the FDHs AerJ and McnD within aeruginosin and cyanopeptolin biosynthetic gene clusters, respectively, the presence of which corresponds to the production of halogenated congeners such as 32 and 34 . 110,111 While the activity of the two halogenases has not been reconstituted in vitro and physiological substrates have not been experimentally established, chemical logic suggests that the aeruginosin FDH AerJ mono- or di-chlorinates the first building block of the NRPS peptide, the L-tyrosine-derived 4-hydroxyphenyl lactate while it is acylated to the AerA CP domain. Hence, in effect, AerJ could resemble the β -tyrosine chlorinase SgcC3 in its activity (Figure 8B), though halogenation at a different stage of NRPS elongation cannot be presently ruled out.…”

Section: Flavin-dependent Halogenasesmentioning

confidence: 99%

Enzymatic Halogenation and Dehalogenation Reactions: Pervasive and Mechanistically Diverse

et al. 2017

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Naturally produced halogenated compounds are ubiquitous across all domains of life where they perform a multitude of biological functions and adopt a diversity of chemical structures. Accordingly, a diverse collection of enzyme catalysts to install and remove halogens from organic scaffolds has evolved in nature. Accounting for the different chemical properties of the four halogen atoms (fluorine, chlorine, bromine, and iodine) and the diversity and chemical reactivity of their organic substrates, enzymes performing biosynthetic and degradative halogenation chemistry utilize numerous mechanistic strategies involving oxidation, reduction, and substitution. Biosynthetic halogenation reactions range from simple aromatic substitutions to stereoselective C-H functionalizations on remote carbon centers and can initiate the formation of simple to complex ring structures. Dehalogenating enzymes, on the other hand, are best known for removing halogen atoms from man-made organohalogens, yet also function naturally, albeit rarely, in metabolic pathways. This review details the scope and mechanism of nature’s halogenation and dehalogenation enzymatic strategies, highlights gaps in our understanding, and posits where new advances in the field might arise in the near future.

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Plasticity and Evolution of Aeruginosin Biosynthesis in Cyanobacteria

Cited by 100 publications

References 54 publications

A Genetic and Chemical Perspective on Symbiotic Recruitment of Cyanobacteria of the Genus Nostoc into the Host Plant Blasia pusilla L.

A Genetic and Chemical Perspective on Symbiotic Recruitment of Cyanobacteria of the Genus Nostoc into the Host Plant Blasia pusilla L.

Nutrients drive transcriptional changes that maintain metabolic homeostasis but alter genome architecture in Microcystis

Enzymatic Halogenation and Dehalogenation Reactions: Pervasive and Mechanistically Diverse

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