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

Barbara Tóth, Erika Liktor-Busa, Norbert Kúsz, Ádám Szappanos, Attila Mándi, Tibor Kurtán, E. Urbán, J. Hohmann, Fang Rong Chang, Andrea Vasas

Research output: Contribution to journalArticle

11 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)2814-2823
Number of pages10
JournalJournal of Natural Products
Volume79
Issue number11
DOIs
Publication statusPublished - Nov 23 2016

Fingerprint

Phenanthrenes
Methicillin
Methicillin-Resistant Staphylococcus aureus
Citrobacter freundii
Enterobacter cloacae
Acinetobacter baumannii
Methylene Chloride
Klebsiella pneumoniae
Biological Products
Dimers
Pseudomonas aeruginosa
Escherichia coli
High Pressure Liquid Chromatography
juncusol

ASJC Scopus subject areas

  • Analytical Chemistry
  • Molecular Medicine
  • Pharmacology
  • Pharmaceutical Science
  • Drug Discovery
  • Complementary and alternative medicine
  • Organic Chemistry

Cite this

Tóth, B., Liktor-Busa, E., Kúsz, N., Szappanos, Á., Mándi, A., Kurtán, T., ... Vasas, A. (2016). Phenanthrenes from Juncus inflexus with Antimicrobial Activity against Methicillin-Resistant Staphylococcus aureus. Journal of Natural Products, 79(11), 2814-2823. https://doi.org/10.1021/acs.jnatprod.6b00581

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, E.; Hohmann, J.; Chang, Fang Rong; Vasas, Andrea.

In: Journal of Natural Products, Vol. 79, No. 11, 23.11.2016, p. 2814-2823.

Research output: Contribution to journalArticle

Tóth, B, Liktor-Busa, E, Kúsz, N, Szappanos, Á, Mándi, A, Kurtán, T, Urbán, E, Hohmann, J, Chang, FR & Vasas, A 2016, 'Phenanthrenes from Juncus inflexus with Antimicrobial Activity against Methicillin-Resistant Staphylococcus aureus', Journal of Natural Products, vol. 79, no. 11, pp. 2814-2823. https://doi.org/10.1021/acs.jnatprod.6b00581
Tóth, Barbara ; Liktor-Busa, Erika ; Kúsz, Norbert ; Szappanos, Ádám ; Mándi, Attila ; Kurtán, Tibor ; Urbán, E. ; Hohmann, J. ; Chang, Fang Rong ; Vasas, Andrea. / Phenanthrenes from Juncus inflexus with Antimicrobial Activity against Methicillin-Resistant Staphylococcus aureus. In: Journal of Natural Products. 2016 ; Vol. 79, No. 11. pp. 2814-2823.
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