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Molecules 2015, 20(9), 17093-17108;

Antibacterial and Anti-Quorum Sensing Molecular Composition Derived from Quercus cortex (Oak bark) Extract

Microbiological Department, Orenburg State University, 13 Pobedy Avenue, Orenburg 460018, Russia
Author to whom correspondence should be addressed.
Academic Editor: Thomas J. Schmidt
Received: 16 June 2015 / Revised: 26 August 2015 / Accepted: 7 September 2015 / Published: 17 September 2015
(This article belongs to the Section Natural Products Chemistry)
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Quercus cortex (Oak bark) has been used in European folk medicine since medieval times for treatment of diarrhea, stomatitis, pharyngitis and skin inflammations. Its antimicrobial activity is a well-known therapeutic property of oak bark, and its novel anti-quorum sensing (QS) ability has also been described recently. In this study, we examined the bioactive compounds of Quercus cortex extract and compared their direct antibacterial and regulatory anti-QS effects against Chromobacterium violaceum CV026 in a biotest. Evaluation of the original Quercus cortex extract showed weak antibacterial and prominent anti-QS activities that were retained and completely restored when the samples were dried and re-hydrated. The one-step liquid chromatography result indicated that the anti-QS activity might be determined by hydrophobic compounds; however, the subsequent reverse phase high performance liquid chromatography led to dissipation and loss of the activity. The gas chromatography–mass spectrometry gave excellent resolution between a majority of the compounds. Based on this result, 10 of the 35 identified small molecules were selected for further screening. The subsequent investigation indicated several compounds determined both the antibacterial and anti-QS activities of the Quercus cortex extract. Direct antibacterial activity was shown for 1,2,3-benzenetriol and 4-propyl-1,3-benzenediol, while sub-inhibitory concentrations of these compounds led to anti-QS effects. Five compounds: 4-(3-hydroxy-1-propenyl)-2-methoxy-phenol; 3,4,5-trimethoxyphenol; 4-hydroxy-3-methoxybenzaldehyde; 7-hydroxy-6-methoxy-2H-1-benzopyran-2-one and 2H-1-benzopyran-2-one were characterized as QS inhibitors independent of any effect on bacterial growth. Biologically relevant concentrations of each single component showed weak activity only while reconstruction of the small molecule composition derived from the Quercus cortex extract provided comparable complementary activity against C. violaceum CV026 in the biotest as the crude extract. View Full-Text
Keywords: plant-derived molecules; antimicrobials; quorum sensing; Quercus cortex; Chromobacterium violaceum plant-derived molecules; antimicrobials; quorum sensing; Quercus cortex; Chromobacterium violaceum

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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Deryabin, D.G.; Tolmacheva, A.A. Antibacterial and Anti-Quorum Sensing Molecular Composition Derived from Quercus cortex (Oak bark) Extract. Molecules 2015, 20, 17093-17108.

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