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

Tóth, Barbara and Liktor-Busa, Erika and Kúsz, Norbert and Szappanos, Ádám and Mándi, Attila and Kurtán, Tibor and Zsoldiné Urbán, Edit and Hohmann, Judit and Vasas, Andrea (2016) Phenanthrenes from Juncus inflexus with Antimicrobial Activity against Methicillin-Resistant Staphylococcus aureus. JOURNAL OF NATURAL PRODUCTS, 79 (11). pp. 2814-2823. ISSN 0163-3864

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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.

Item Type: Article
Subjects: Q Science / természettudomány > QD Chemistry / kémia > QD04 Organic chemistry / szerves kémia
Q Science / természettudomány > QR Microbiology / mikrobiológia
R Medicine / orvostudomány > RS Pharmacy and materia medica / gyógyszerészet, gyógyászati eszközök
SWORD Depositor: MTMT SWORD
Depositing User: MTMT SWORD
Date Deposited: 07 Nov 2017 06:57
Last Modified: 07 Nov 2017 06:57
URI: http://real.mtak.hu/id/eprint/66881

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