Anti-MRSA-acting carbamidocyclophanes H-L from the Vietnamese cyanobacterium Nostoc sp. CAVN2

M. Preisitsch, K. Harmrolfs, H.T. Pham, S.E. Heiden, A. Füssel, C. Wiesner, A. Pretsch, M. Swiatecka-Hagenbruch, T.H.J. Niedermeyer, R. Müller, S. Mundt

Publikation: Beitrag in FachzeitschriftArtikelBegutachtung

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. © 2015 Japan Antibiotics Research Association.
OriginalspracheEnglisch
Seiten (von - bis)165-177
Seitenumfang13
FachzeitschriftJournal of Antibiotics
Jahrgang68
Ausgabenummer3
DOIs
PublikationsstatusVeröffentlicht - 3 Sep. 2014
Extern publiziertJa

IMC Forschungsschwerpunkte

  • Medical biotechnology

ÖFOS 2012 - Österreichischen Systematik der Wissenschaftszweige

  • 304005 Medizinische Biotechnologie

Fingerprint

Untersuchen Sie die Forschungsthemen von „Anti-MRSA-acting carbamidocyclophanes H-L from the Vietnamese cyanobacterium Nostoc sp. CAVN2“. Zusammen bilden sie einen einzigartigen Fingerprint.

Dieses zitieren