Cylindrofridins A-C, Linear Cylindrocyclophane-Related Alkylresorcinols from the Cyanobacterium Cylindrospermum stagnale

M. Preisitsch, T.H.J. Niedermeyer, S.E. Heiden, I. Neidhardt, J. Kumpfmüller, M. Wurster, K. Harmrolfs, C. Wiesner, H. Enke, R. Müller, S. Mundt

Publikation: Beitrag in FachzeitschriftArtikelBegutachtung

Abstract

A rapid and exhaustive one-step biomass extraction as well as an enrichment and cleanup procedure has been developed for HPLC-UV detection and quantification of closely related [7.7]paracyclophanes and structural derivatives based on a two-phase solvent system. The procedure has been validated using the biomass of the carbamidocyclophane- and cylindrocyclophane-producing cyanobacterium Nostoc sp. CAVN2 and was utilized to perform a screening comprising 102 cyanobacterial strains. As a result, three new cylindrocyclophane-related alkylresorcinols, cylindrofridins A-C (1-3), and known cylindrocyclophanes (4-6) were detected and isolated from Cylindrospermum stagnale PCC 7417. Structures of 1-3 were elucidated by a combination of 1D and 2D NMR experiments, HRMS, and ECD spectroscopy. Cylindrofridin A (1) is the first naturally occurring [7.7]paracyclophane-related monomeric derivative. In contrast, cylindrofridins B (2) and C (3) represent dimers related to 1. Due to chlorination at the alkyl carbon atom in 1-3, the site of [7.7]paracyclophane macrocycle formation, the cylindrofridins represent linearized congeners of the cylindrocyclophanes. Compounds 1-3 were not toxic against nontumorigenic HaCaT cells (IC50 values >25 μM) compared to the respective cylindrocyclophanes, but 1 was the only cylindrofridin showing moderate activity against methicillin-resistant Staphylococcus aureus (MRSA) and Streptococcus pneumoniae with MIC values of 9 and 17 μM, respectively. © 2015 The American Chemical Society and American Society of Pharmacognosy.
OriginalspracheEnglisch
Seiten (von - bis)106-115
Seitenumfang10
FachzeitschriftJournal of Natural Products
Jahrgang79
Ausgabenummer1
DOIs
PublikationsstatusVeröffentlicht - 18 Dez. 2015
Extern publiziertJa

IMC Forschungsschwerpunkte

  • Medical biotechnology

ÖFOS 2012 - Österreichischen Systematik der Wissenschaftszweige

  • 304005 Medizinische Biotechnologie

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