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Unique Biosynthetic Pathway in Bloom-Forming Cyanobacterial Genus Microcystis Jointly Assembles Cytotoxic Aeruginoguanidines and Microguanidines

  • The cyanobacterial genus Microcystis is known to produce an elaborate array of structurally unique and biologically active natural products, including hazardous cyanotoxins. Cytotoxic aeruginoguanidines represent a yet unexplored family of peptides featuring a trisubstituted benzene unit and farnesylated arginine derivatives. In this study, we aimed at assigning these compounds to a biosynthetic gene cluster by utilizing biosynthetic attributes deduced from public genomes of Microcystis and the sporadic distribution of the metabolite in axenic strains of the Pasteur Culture Collection of Cyanobacteria. By integrating genome mining with untargeted metabolomics using liquid chromatography with mass spectrometry, we linked aeruginoguanidine (AGD) to a nonribosomal peptide synthetase gene cluster and coassigned a significantly smaller product to this pathway, microguanidine (MGD), previously only reported from two Microcystis blooms. Further, a new intermediate class of compounds named microguanidine amides was uncovered, thereby furtherThe cyanobacterial genus Microcystis is known to produce an elaborate array of structurally unique and biologically active natural products, including hazardous cyanotoxins. Cytotoxic aeruginoguanidines represent a yet unexplored family of peptides featuring a trisubstituted benzene unit and farnesylated arginine derivatives. In this study, we aimed at assigning these compounds to a biosynthetic gene cluster by utilizing biosynthetic attributes deduced from public genomes of Microcystis and the sporadic distribution of the metabolite in axenic strains of the Pasteur Culture Collection of Cyanobacteria. By integrating genome mining with untargeted metabolomics using liquid chromatography with mass spectrometry, we linked aeruginoguanidine (AGD) to a nonribosomal peptide synthetase gene cluster and coassigned a significantly smaller product to this pathway, microguanidine (MGD), previously only reported from two Microcystis blooms. Further, a new intermediate class of compounds named microguanidine amides was uncovered, thereby further enlarging this compound family. The comparison of structurally divergent AGDs and MGDs reveals an outstanding versatility of this biosynthetic pathway and provides insights into the assembly of the two compound subfamilies. Strikingly, aeruginoguanidines and microguanidines were found to be as widespread as the hepatotoxic microcystins, but the occurrence of both toxin families appeared to be mutually exclusive.zeige mehrzeige weniger

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Metadaten
Verfasserangaben:Claire Pancrace, Keishi Ishida, Enora BriandORCiD, Douglas Gatte PichiORCiD, Annika R. WeizGND, Arthur GuljarmowORCiD, Thibault ScalvenziORCiD, Nathalie Sassoon, Christian HertweckORCiD, Elke DittmannORCiDGND, Muriel GuggerORCiD
DOI:https://doi.org/10.1021/acschembio.8b00918
ISSN:1554-8929
ISSN:1554-8937
Pubmed ID:https://pubmed.ncbi.nlm.nih.gov/30556994
Titel des übergeordneten Werks (Englisch):ACS chemical biology
Verlag:American Chemical Society
Verlagsort:Washington
Publikationstyp:Wissenschaftlicher Artikel
Sprache:Englisch
Datum der Erstveröffentlichung:17.12.2018
Erscheinungsjahr:2018
Datum der Freischaltung:25.05.2021
Band:14
Ausgabe:1
Seitenanzahl:9
Erste Seite:67
Letzte Seite:75
Fördernde Institution:Ile-de-France ARDoC Grant; Institut Pasteur; German Research Foundation (DFG)German Research Foundation (DFG) [Di910/10-1]; DFGGerman Research Foundation (DFG) [SFB 1127]
Organisationseinheiten:Mathematisch-Naturwissenschaftliche Fakultät / Institut für Biochemie und Biologie
DDC-Klassifikation:5 Naturwissenschaften und Mathematik / 57 Biowissenschaften; Biologie / 570 Biowissenschaften; Biologie
Peer Review:Referiert
Publikationsweg:Open Access / Green Open-Access
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