ArticleMarine drugs2016
Effects of Halide Ions on the Carbamidocyclophane Biosynthesis in Nostoc sp. CAVN2.
Article in Marine drugs, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 23 papers.
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Who cites it
23 citing papers in PubMed, 46 citations in OpenAlex.
- Algal bioactive compounds for next-generation biopesticides: a multi-target resource for sustainable pest management.Environmental science and pollution research international · 2026Review
- Halogenation-Guided Chemical Screening Uncovers Cyanobacterin Analogues from the CyanobacteriumJournal of natural products · 2025Article
- Mining for Halogenated Metabolites ofJournal of natural products · 2025Article
- Chemical diversity of cyanobacterial natural products.Natural product reports · 2025Review
- Structural insights into type III polyketide synthase CylI from cylindrocyclophane biosynthesis.Protein science : a publication of the Protein Society · 2024Article
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- Accelerating the discovery of alkyl halide-derived natural products using halide depletion.Nature chemistry · 2024Article
- A Review of the Antimicrobial Properties of Cyanobacterial Natural Products.Molecules (Basel, Switzerland) · 2023Review
- Cyanobacteria: A Promising Source of Antifungal Metabolites.Marine drugs · 2023Review
- New Nostocyclophanes fromMarine drugs · 2023Article
- Genetic and Biochemical Characterization of Halogenation and Drug Transportation Genes Encoded in the Albofungin Biosynthetic Gene Cluster.Applied and environmental microbiology · 2022Article
- Discovery of Anticancer Agents of Diverse Natural Origin.Journal of natural products · 2022Article
- Genome Mining and Evolutionary Analysis Reveal Diverse Type III Polyketide Synthase Pathways in Cyanobacteria.Genome biology and evolution · 2021Article
- Divergent Synthesis of Novel Cylindrocyclophanes that Inhibit Methicillin-Resistant Staphylococcus aureus (MRSA).ChemMedChem · 2020Article
- Chemistry, bioactivity and biosynthesis of cyanobacterial alkylresorcinols.Natural product reports · 2019Review
- Recent Advances in Exploration and Biotechnological Production of Bioactive Compounds in Three Cyanobacterial Genera:Frontiers in chemistry · 2019Review
- Genome Analysis ofMicroorganisms · 2018Article
- Ribocyclophanes A-E, Glycosylated Cyclophanes with Antiproliferative Activity from Two Cultured Terrestrial Cyanobacteria.Journal of natural products · 2018Article
- The impact of culture conditions on growth and metabolomic profiles of freshwater cyanobacteria.Journal of applied phycology · 2018Article
- A new strategy for aromatic ring alkylation in cylindrocyclophane biosynthesis.Nature chemical biology · 2017Article
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Authors and funding
16 authors at 5 institutions in 1 country.
Funding
No grant is acknowledged in the PubMed record.
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.
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