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Molecules 2016, 21(5), 608; doi:10.3390/molecules21050608

Antimicrobial Activity of Xanthohumol and Its Selected Structural Analogues

1
Department of Chemistry, University of Environmental and Life Sciences, Norwida 25, 50-375 Wrocław, Poland
2
Centre for Innovative Research in Medical and Natural Sciences, Faculty of Medicine, University of Rzeszów, Warzywna 1a, 35-310 Rzeszów, Poland
3
Department of Biotechnology and Food Microbiology, University of Environmental and Life Sciences, Chełmońskiego 37/41, 51-630 Wrocław, Poland
*
Author to whom correspondence should be addressed.
Academic Editors: Celestino Santos-Buelga and Arturo San Feliciano
Received: 30 March 2016 / Revised: 27 April 2016 / Accepted: 5 May 2016 / Published: 11 May 2016
(This article belongs to the Special Issue Flavonoids: From Structure to Health Issues)
View Full-Text   |   Download PDF [746 KB, uploaded 11 May 2016]   |  

Abstract

The objective of this study was to evaluate the antimicrobial activity of structural analogues of xanthohumol 1, a flavonoid compound found in hops (Humulus lupulus). The agar-diffusion method using filter paper disks was applied. Biological tests performed for selected strains of Gram-positive (Staphylococcus aureus) and Gram-negative (Escherichia coli) bacteria, fungi (Alternaria sp.), and yeasts (Rhodotorula rubra, Candida albicans) revealed that compounds with at least one hydroxyl group—all of them have it at the C-4 position—demonstrated good activity. Our research showed that the strain S. aureus was more sensitive to chalcones than to the isomers in which the heterocyclic ring C is closed (flavanones). The strain R. rubra was moderately sensitive to only one compound: 4-hydroxy-4’-methoxychalcone 8. Loss of the hydroxyl group in the B-ring of 4’-methoxychalcones or its replacement by a halogen atom (−Cl, −Br), nitro group (−NO2), ethoxy group (−OCH2CH3), or aliphatic substituent (−CH3, −CH2CH3) resulted in the loss of antimicrobial activity towards both R. rubra yeast and S. aureus bacteria. Xanthohumol 1, naringenin 5, and chalconaringenin 7 inhibited growth of S. aureus, whereas 4-hydroxy-4′-methoxychalcone 8 was active towards two strains: S. aureus and R. rubra. View Full-Text
Keywords: antimicrobial activity; xanthohumol; chalconaringenin; naringenin; 4′-methoxychalcones; S. aureus; NMR-IR-UV spectra antimicrobial activity; xanthohumol; chalconaringenin; naringenin; 4′-methoxychalcones; S. aureus; NMR-IR-UV spectra
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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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Stompor, M.; Żarowska, B. Antimicrobial Activity of Xanthohumol and Its Selected Structural Analogues. Molecules 2016, 21, 608.

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