Selectively Halogenated Flavonolignans—Preparation and Antibacterial Activity

0566377 - MBÚ 2023 RIV CH eng J - Journal Article
Hurtová, Martina - Káňová, Kristýna - Dobiasová, S. - Holasová, K. - Čáková, D. - Hoang, L. - Biedermann, David - Kuzma, Marek - Cvačka, Josef - Křen, Vladimír - Viktorová, J. - Valentová, Kateřina
Selectively Halogenated Flavonolignans—Preparation and Antibacterial Activity.
International Journal of Molecular Sciences. Roč. 23, č. 23 (2022), č. článku 15121. E-ISSN 1422-0067
R&D Projects: GA MŠMT(CZ) LTC20070; GA ČR GA21-00551S
EU Projects: European Commission(CZ) CA17104
Institutional support: RVO:61388971 ; RVO:61388963
Keywords : bacteria * biological activity * flavonoids * flavonolignans * halogenation * multidrug resistance
OECD category: Medicinal chemistry; Analytical chemistry (UOCHB-X)
Impact factor: 5.6, year: 2022
Method of publishing: Open access
https://www.mdpi.com/1422-0067/23/23/15121

A library of previously unknown halogenated derivatives of flavonolignans (silybins A and B, 2,3-dehydrosilybin, silychristin A, and 2,3-dehydrosilychristin A) was prepared. The effect of halogenation on the biological activity of flavonolignans was investigated. Halogenated derivatives had a significant effect on bacteria. All prepared derivatives inhibited the AI-2 type of bacterial communication (quorum sensing) at concentrations below 10 µM. All prepared compounds also inhibited the adhesion of bacteria (Staphyloccocus aureus and Pseudomonas aeruginosa) to the surface, preventing biofilm formation. These two effects indicate that the halogenated derivatives are promising antibacterial agents. Moreover, these derivatives acted synergistically with antibiotics and reduced the viability of antibiotic-resistant S. aureus. Some flavonolignans were able to reverse the resistant phenotype to a sensitive one, implying that they modulate antibiotic resistance.
Permanent Link: https://hdl.handle.net/11104/0337716