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Phenanthrenes from Juncus inflexus with Antimicrobial Activity against Methicillin-Resistant Staphylococcus aureus

Tóth, Barbara, Liktor-Busa, Erika, Kúsz, Norbert, Szappanos, Ádám, Mándi, Attila, Kurtán, Tibor, Urbán, Edit, Hohmann, Judit, Chang, Fang-Rong, Vasas, Andrea
Journal of natural products 2016 v.79 no.11 pp. 2814-2823
methicillin-resistant Staphylococcus aureus, high performance liquid chromatography, roots, beta-lactamase, methylene chloride, hexane, ethyl acetate, Pseudomonas aeruginosa, Acinetobacter baumannii, methicillin, Escherichia coli, Juncus, minimum inhibitory concentration, Citrobacter freundii, Enterobacter cloacae, chemical structure, antibacterial properties, antibiotic resistance, phenanthrenes, Klebsiella pneumoniae, active ingredients
The present study has focused on an investigation of the antibacterial effects of Juncus inflexus and the isolation and identification of its active compounds. Eleven phenanthrenes were isolated from a methanolic extract of the roots. Four compounds (jinflexins A–D, 1–4) are new natural products, while seven phenanthrenes [juncuenins A (5), B (6), and D (8), juncusol (7), dehydrojuncuenins A (9) and B (11), and dehydrojuncusol (10)] were isolated for the first time from the plant. Jinflexin D (4) is a dimer with an unprecedented heptacyclic ring system. The absolute configurations of the new compounds were determined by TDDFT-ECD calculations, and their enantiomeric purity was checked by chiral HPLC analysis. Extracts of different polarity (n-hexane, dichloromethane, and ethyl acetate) were evaluated for their antimicrobial effects against methicillin-resistant Staphylococcus aureus, extended-spectrum β-lactamase (ESBL)-producing Citrobacter freundii, Escherichia coli, Enterobacter cloacae, Klebsiella pneumoniae, multiresistant Acinetobacter baumannii, and Pseudomonas aeruginosa. The MIC values of the isolated compounds were determined by a microdilution method. Jinflexin B (2), juncusol (7), juncuenin D (8), and dehydrojuncuenin B (11) showed significant activity (MIC value range 12.5–100 μg/mL) against MRSA strains.