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Discovery of a Pederin Family Compound in a Nonsymbiotic Bloom-Forming Cyanobacterium

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  • Additional Information
    • Contributors:
      Department of Microbiology; Doctoral Programme in Microbiology and Biotechnology; University Management; Cyanobacteria research; Helsinki Institute of Sustainability Science (HELSUS); Microbial Natural Products; Doctoral Programme in Food Chain and Health
    • Publication Information:
      American Chemical Society
    • Publication Date:
      2021
    • Collection:
      Helsingfors Universitet: HELDA – Helsingin yliopiston digitaalinen arkisto
    • Abstract:
      The pederin family includes a number of bioactive compounds isolated from symbiotic organisms of diverse evolutionary origin. Pederin is linked to beetle-induced dermatitis in humans, and pederin family members possess potent antitumor activity caused by selective inhibition of the eukaryotic ribosome. Their biosynthesis is accomplished by a polyketide/nonribosomal peptide synthetase machinery employing an unusual trans-acyltransferase mechanism. Here, we report a novel pederin type compound, cusperin, from the free-living cyanobacterium Cuspidothrix issatschenkoi (earlier Aphanizomenon). The chemical structure of cusperin is similar to that of nosperin recently isolated from the lichen cyanobiont Nostoc sharing the tehrahydropyran moiety and major part of the linear backbone. However, the cusperin molecule is extended by a glycine residue and lacks one hydroxyl substituent. Pederins were previously thought to be exclusive to symbiotic relationships. However, C. issatschenkoi is a nonsymbiotic planktonic organism and a frequent component of toxic water blooms. Cusperin is devoid of the cytotoxic activity reported for other pederin family members. Hence, our findings raise questions about the role of pederin analogues in cyanobacteria and broaden the knowledge of ecological distribution of this group of polyketides. ; Peer reviewed
    • File Description:
      application/pdf
    • Relation:
      This work was supported by the Czech Science Foundation grant number 14-18067S; the grant of the Faculty of Science, University of South Bohemia GAJU 158/2016/P; Ministry of Education, Youth and Sports of the Czech Republic - National Programme of Sustainability I grant number LO1416 and ALGAMIC project grant number CZ.1.05/2.1.00/19.0392. Access to instruments and other facilities was supported by the Czech research infrastructure for systems biology C4SYS (grant number LM2015055). This work was also supported by the Academy of Finland grant 1273798 to KS. We would like to thank E. Kozlikova-Zapomelova and K. Capkova for isolating and maintaining the strain, T. Galica for help with formatting of Figure 2, ,,and M. Mehrshad for help with sequence annotation.; Kust , A , Mares , J , Jokela , J , Urajova , P , Hajek , J , Saurav , K , Voracova , K , Fewer , D P , Haapaniemi , E , Permi , P , Rehakova , K , Sivonen , K & Hrouzek , P 2018 , ' Discovery of a Pederin Family Compound in a Nonsymbiotic Bloom-Forming Cyanobacterium ' , ACS Chemical Biology , vol. 13 , no. 5 , pp. 1123-1129 . https://doi.org/10.1021/acschembio.7b01048; ORCID: /0000-0003-3978-4845/work/53511808; ORCID: /0000-0001-5096-3575/work/53513768; ORCID: /0000-0002-2904-0458/work/53514110; http://hdl.handle.net/10138/327284; e6caf986-86fc-4910-9010-310f6c75ad2d; 85047646326; 000432900600002
    • Online Access:
      http://hdl.handle.net/10138/327284
    • Rights:
      info:eu-repo/semantics/openAccess ; openAccess
    • Accession Number:
      edsbas.C75B2EA5