2.50
Hdl Handle:
http://hdl.handle.net/10033/602094
Title:
Effects of Halide Ions on the Carbamidocyclophane Biosynthesis in Nostoc sp. CAVN2.
Authors:
Preisitsch, Michael; Heiden, Stefan E; Beerbaum, Monika; Niedermeyer, Timo H J; Schneefeld, Marie; Herrmann, Jennifer; Kumpfmüller, Jana; Thürmer, Andrea; Neidhardt, Inga; Wiesner, Christoph; Daniel, Rolf; Müller, Rolf ( 0000-0002-1042-5665 ) ; Bange, Franz-Christoph; Schmieder, Peter; Schweder, Thomas; Mundt, Sabine
Abstract:
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.
Affiliation:
Helmholtz-Institute for Pharmaceutical Research Saarland (HIPS),Saarland 9 University, 66123 Saarbrücken, Germany.
Citation:
Effects of Halide Ions on the Carbamidocyclophane Biosynthesis in Nostoc sp. CAVN2. 2016, 14 (1): Mar Drugs
Journal:
Marine drugs
Issue Date:
2016
URI:
http://hdl.handle.net/10033/602094
DOI:
10.3390/md14010021
PubMed ID:
26805858
Type:
Article
Language:
en
ISSN:
1660-3397
Appears in Collections:
publications of the department of microbial natural substances ([HIPS]MINS)

Full metadata record

DC FieldValue Language
dc.contributor.authorPreisitsch, Michaelen
dc.contributor.authorHeiden, Stefan Een
dc.contributor.authorBeerbaum, Monikaen
dc.contributor.authorNiedermeyer, Timo H Jen
dc.contributor.authorSchneefeld, Marieen
dc.contributor.authorHerrmann, Jenniferen
dc.contributor.authorKumpfmüller, Janaen
dc.contributor.authorThürmer, Andreaen
dc.contributor.authorNeidhardt, Ingaen
dc.contributor.authorWiesner, Christophen
dc.contributor.authorDaniel, Rolfen
dc.contributor.authorMüller, Rolfen
dc.contributor.authorBange, Franz-Christophen
dc.contributor.authorSchmieder, Peteren
dc.contributor.authorSchweder, Thomasen
dc.contributor.authorMundt, Sabineen
dc.date.accessioned2016-03-17T15:33:33Zen
dc.date.available2016-03-17T15:33:33Zen
dc.date.issued2016en
dc.identifier.citationEffects of Halide Ions on the Carbamidocyclophane Biosynthesis in Nostoc sp. CAVN2. 2016, 14 (1): Mar Drugsen
dc.identifier.issn1660-3397en
dc.identifier.pmid26805858en
dc.identifier.doi10.3390/md14010021en
dc.identifier.urihttp://hdl.handle.net/10033/602094en
dc.description.abstractIn 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.en
dc.language.isoenen
dc.titleEffects of Halide Ions on the Carbamidocyclophane Biosynthesis in Nostoc sp. CAVN2.en
dc.typeArticleen
dc.contributor.departmentHelmholtz-Institute for Pharmaceutical Research Saarland (HIPS),Saarland 9 University, 66123 Saarbrücken, Germany.en
dc.identifier.journalMarine drugsen

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