ArticleThe Journal of antibiotics2015
Anti-MRSA-acting carbamidocyclophanes H-L from the Vietnamese cyanobacterium Nostoc sp. CAVN2.
Article in The Journal of antibiotics, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. An erratum has been issued. Cited by 16 papers.
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Who cites it
16 citing papers in PubMed.
- Halogenation-Guided Chemical Screening Uncovers Cyanobacterin Analogues from the CyanobacteriumJournal of natural products · 2025Article
- Chemical diversity of cyanobacterial natural products.Natural product reports · 2025Review
- Classification ofFrontiers in microbiology · 2025Article
- Cyanobacteria: A Promising Source of Antifungal Metabolites.Marine drugs · 2023Review
- Discovery of Anticancer Agents of Diverse Natural Origin.Journal of natural products · 2022Article
- Structural basis for an unprecedented enzymatic alkylation in cylindrocyclophane biosynthesis.eLife · 2022Article
- Revisiting the role of cyanobacteria-derived metabolites as antimicrobial agent: A 21st century perspective.Frontiers in microbiology · 2022Review
- 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
- Natural Products from Cyanobacteria: Focus on Beneficial Activities.Marine drugs · 2019Review
- Recent Advances in Exploration and Biotechnological Production of Bioactive Compounds in Three Cyanobacterial Genera:Frontiers in chemistry · 2019Review
- 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
- Merocyclophanes C and D from the Cultured Freshwater Cyanobacterium Nostoc sp. (UIC 10110).Journal of natural products · 2017Article
- Effects of Halide Ions on the Carbamidocyclophane Biosynthesis in Nostoc sp. CAVN2.Marine drugs · 2016Article
Corrections and comments
- Erratum issued
Authors and funding
11 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
The methanol extract of the Vietnamese freshwater cyanobacterium Nostoc sp. CAVN2 exhibited cytotoxic effects against MCF-7 and 5637 cancer cell lines as well as against nontumorigenic FL and HaCaT cells and was active against methicillin-resistant Staphylococcus aureus (MRSA) and Streptococcus pneumoniae. High-resolution mass spectrometric analysis indicated the presence of over 60 putative cyclophane-like compounds in an antimicrobially active methanol extract fraction. A paracyclophanes-focusing extraction and separation methodology led to the isolation of 5 new carbamidocyclophanes (1-5) and 11 known paracyclophanes (6-16). The structures and their stereochemical configurations were elucidated by a combination of spectrometric and spectroscopic methods including HRMS, 1D and 2D NMR analyses and detailed comparative CD analysis. The newly described monocarbamoylated [7.7]paracyclophanes (1, 2, 4 and 5) differ by a varying degree of chlorination in the side chains. Carbamidocyclophane J (3) is the very first reported carbamidocyclophane bearing a single halogenation in both butyl residues. Based on previous studies a detailed phylogenetic examination of cyclophane-producing cyanobacteria was carried out. The biological evaluation of 1-16 against various clinical pathogens highlighted a remarkable antimicrobial activity against MRSA with MICs of 0.1-1.0 μM, and indicated that the level of antibacterial activity is related to the presence of carbamoyl moieties.
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