title: Antimicrobial Activity of Xanthohumol and Its Selected Structural Analogues.
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.
authors.affiliation: Department of Chemistry, University of Environmental and Life Sciences, Norwida 25, 50-375 Wrocław, Poland. monika.stompor@gmail.com.|Centre for Innovative Research in Medical and Natural Sciences, Faculty of Medicine, University of Rzeszów, Warzywna 1a, 35-310 Rzeszów, Poland. monika.stompor@gmail.com.
authors.forename: Monika
authors.initials: M
authors.lastname: Stompor
authors.affiliation: Department of Biotechnology and Food Microbiology, University of Environmental and Life Sciences, Chełmońskiego 37/41, 51-630 Wrocław, Poland. barbara.zarowska@up.wroc.pl.
authors.forename: Barbara
authors.initials: B
authors.lastname: Żarowska
mesh_terms: D000890:Anti-Infective Agents / Q000494:pharmacology*; D005419:Flavonoids / Q000737:chemistry / Q000494:pharmacology*; D005658:Fungi / Q000187:drug effects; D006090:Gram-Negative Bacteria / Q000187:drug effects; D006094:Gram-Positive Bacteria / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D011427:Propiophenones / Q000737:chemistry / Q000494:pharmacology*; D013057:Spectrum Analysis / Q000379:methods
chemical_list: D000890:Anti-Infective Agents; D005419:Flavonoids; D011427:Propiophenones; C104536:xanthohumol
keywords: 4′-methoxychalcones; NMR-IR-UV spectra; S. aureus; antimicrobial activity; chalconaringenin; naringenin; xanthohumol