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Open AccessArticle

Effects of Halide Ions on the Carbamidocyclophane Biosynthesis in Nostoc sp. CAVN2

Institute of Pharmacy, Department of Pharmaceutical Biology, Ernst-Moritz-Arndt-University, Friedrich-Ludwig-Jahn-Straße 17, 17489 Greifswald, Germany
Institute of Pharmacy, Department of Pharmaceutical Biotechnology, Ernst-Moritz-Arndt-University, Felix-Hausdorff-Straße 3, 17489 Greifswald, Germany
Leibniz Institute for Molecular Pharmacology (FMP), Robert-Rössle-Straße 10, 13125 Berlin, Germany
Interfaculty Institute of Microbiology and Infection Medicine, Eberhard Karls University, Auf der Morgenstelle 28, 72076 Tübingen, Germany
German Centre for Infection Research (DZIF), Partner Site Tübingen (T.H.J.N.) and Partner Site Hannover-Braunschweig, Germany
Institute for Medical Microbiology and Hospital Epidemiology, Hannover Medical School, Carl-Neuberg-Straße 1, 30625 Hannover, Germany
Helmholtz Institute for Pharmaceutical Research Saarland, Helmholtz Centre for Infection Research, and Department of Pharmaceutical Biotechnology, Saarland University, Campus E8.1, 66123 Saarbrücken, Germany
Leibniz Institute for Natural Product Research and Infection Biology, Hans Knöll Institute (HKI), Department of Biomolecular Chemistry, Beutenbergstraße 11a, 07745 Jena, Germany
Institute of Microbiology and Genetics, Department of Genomic and Applied Microbiology and Göttingen Genomics Laboratory, Georg-August University, Grisebachstraße 8, 37077 Göttingen, Germany
Institute of Technology, Department of Pharmacology, Toxicology and Clinical Pharmacy, Technical University of Braunschweig, Mendelssohnstraße 1, 38106 Braunschweig, Germany
Sealife PHARMA GmbH, Technopark 1/Obj.C/EG, 3430 Tulln, Austria
Author to whom correspondence should be addressed.
Academic Editor: Orazio Taglialatela-Scafati
Mar. Drugs 2016, 14(1), 21;
Received: 15 October 2015 / Revised: 9 December 2015 / Accepted: 21 December 2015 / Published: 20 January 2016
(This article belongs to the Special Issue Compounds from Cyanobacteria)
In this study, the influence of halide ions on [7.7]paracyclophane biosynthesis in the cyanobacterium Nostoc sp. CAVN2 was investigated. In contrast to KI and KF, supplementation of the culture medium with KCl or KBr resulted not only in an increase of growth but also in an up-regulation of carbamidocyclophane production. LC-MS analysis indicated the presence of chlorinated, brominated, but also non-halogenated derivatives. In addition to 22 known cylindrocyclophanes and carbamidocyclophanes, 27 putative congeners have been detected. Nine compounds, carbamidocyclophanes M−U, were isolated, and their structural elucidation by 1D and 2D NMR experiments in combination with HRMS and ECD analysis revealed that they are brominated analogues of chlorinated carbamidocyclophanes. Quantification of the carbamidocyclophanes showed that chloride is the preferably utilized halide, but incorporation is reduced in the presence of bromide. Evaluation of the antibacterial activity of 30 [7.7]paracyclophanes and related derivatives against selected pathogenic Gram-positive and Gram-negative bacteria exhibited remarkable effects especially against methicillin- and vancomycin-resistant staphylococci and Mycobacterium tuberculosis. For deeper insights into the mechanisms of biosynthesis, the carbamidocyclophane biosynthetic gene cluster in Nostoc sp. CAVN2 was studied. The gene putatively coding for the carbamoyltransferase has been identified. Based on bioinformatic analyses, a possible biosynthetic assembly is discussed. View Full-Text
Keywords: Nostoc sp.; carbamidocyclophane; [7.7]paracyclophane; halogen; bromo-analogue; biosynthesis; gene cluster; bioactivity; MRSA; Mycobacterium Nostoc sp.; carbamidocyclophane; [7.7]paracyclophane; halogen; bromo-analogue; biosynthesis; gene cluster; bioactivity; MRSA; Mycobacterium
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Preisitsch, M.; Heiden, S.E.; Beerbaum, M.; Niedermeyer, T.H.J.; Schneefeld, M.; Herrmann, J.; Kumpfmüller, J.; Thürmer, A.; Neidhardt, I.; Wiesner, C.; Daniel, R.; Müller, R.; Bange, F.-C.; Schmieder, P.; Schweder, T.; Mundt, S. Effects of Halide Ions on the Carbamidocyclophane Biosynthesis in Nostoc sp. CAVN2. Mar. Drugs 2016, 14, 21.

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