Antimicrobial Activity of Xanthohumol and Its Selected Structural Analogues
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 (Sta...
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| Format: | Article |
| Language: | English |
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MDPI AG
2016-05-01
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| Series: | Molecules |
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| Online Access: | http://www.mdpi.com/1420-3049/21/5/608 |
| _version_ | 1811314281261563904 |
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| author | Monika Stompor Barbara Żarowska |
| author_facet | Monika Stompor Barbara Żarowska |
| author_sort | Monika Stompor |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-04-13T11:10:13Z |
| format | Article |
| id | doaj.art-9630888829cb499b88a3d5feea531e89 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-04-13T11:10:13Z |
| publishDate | 2016-05-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-9630888829cb499b88a3d5feea531e892022-12-22T02:49:10ZengMDPI AGMolecules1420-30492016-05-0121560810.3390/molecules21050608molecules21050608Antimicrobial Activity of Xanthohumol and Its Selected Structural AnaloguesMonika Stompor0Barbara Żarowska1Department of Chemistry, University of Environmental and Life Sciences, Norwida 25, 50-375 Wrocław, PolandDepartment of Biotechnology and Food Microbiology, University of Environmental and Life Sciences, Chełmońskiego 37/41, 51-630 Wrocław, PolandThe 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.http://www.mdpi.com/1420-3049/21/5/608antimicrobial activityxanthohumolchalconaringeninnaringenin4′-methoxychalconesS. aureusNMR-IR-UV spectra |
| spellingShingle | Monika Stompor Barbara Żarowska Antimicrobial Activity of Xanthohumol and Its Selected Structural Analogues Molecules antimicrobial activity xanthohumol chalconaringenin naringenin 4′-methoxychalcones S. aureus NMR-IR-UV spectra |
| title | Antimicrobial Activity of Xanthohumol and Its Selected Structural Analogues |
| title_full | Antimicrobial Activity of Xanthohumol and Its Selected Structural Analogues |
| title_fullStr | Antimicrobial Activity of Xanthohumol and Its Selected Structural Analogues |
| title_full_unstemmed | Antimicrobial Activity of Xanthohumol and Its Selected Structural Analogues |
| title_short | Antimicrobial Activity of Xanthohumol and Its Selected Structural Analogues |
| title_sort | antimicrobial activity of xanthohumol and its selected structural analogues |
| topic | antimicrobial activity xanthohumol chalconaringenin naringenin 4′-methoxychalcones S. aureus NMR-IR-UV spectra |
| url | http://www.mdpi.com/1420-3049/21/5/608 |
| work_keys_str_mv | AT monikastompor antimicrobialactivityofxanthohumolanditsselectedstructuralanalogues AT barbarazarowska antimicrobialactivityofxanthohumolanditsselectedstructuralanalogues |