Structure and antibacterial activity relationship of quercetin and rutin against test and clinical resistant gramm-negative strains of bacteria

Authors

DOI:

https://doi.org/10.14739/2409-2932.2025.2.324663

Keywords:

1,2,4-triazole, disulfides, mild conditions, high selectivity, antimicrobial activity, antioxidant activity

Abstract

Today, antimicrobial resistance is the number one problem worldwide. According to the latest data, it has found that Acinetobacter baumani, Pseudomonas aeruginosa, Klebsiela pneumonia and Enterobacter cloacae are predominant among all isolated resistant pathogens. So, the search of a new antibacterial drug that can deal with antimicrobial resistance is task number one.

Aim. The study aimed to investigate theoretical and practical relationship of structure and antibacterial activity of quercetin and rutin against test Gram-negative strains: Escherichia coli, Pseudomonas aeruginosa, Proteus vulgaris, and clinical resistant strains such as Pseudomonas aeruginosa, Acinetobacter baumannii, Klebsiella pneumoniae, Enterobacter cloacae.

Materials and methods. The research subjects were quercetin and rutin. The theoretical research was carried out using AutoDockTools 1.5.6; antibacterial effects were evaluated by the well method. Clinical strain of P. aeruginosa, A. baumani, K. pneumonia, E. cloacea were taken from tracheal aspirate and bronchoalveolar lavage.

Results. Theoretical studies showed that none of the investigated antimicrobial drugs inhibit all “targets” mechanism of antibacterial action. Rutin revealed high selectivity to DNA-gyrase, dihydrofolate reductase (DHFR), deacetylase, AHS RhI, Diguanylate cyclase, unlike quercetin which revealed low selectivity. Experimental research demonstrated that against P. aeruginosa rutin and quercetin inhibited growth – 17.0 ± 0.4 mm and 18.0 ± 0.4 mm, against P. vulgaris – 14.0 ± 0.5 mm and 16.0 ± 0.5 mm, against E. coli – 16.0 ± 0.5 mm and 20.0 ± 0.4 mm, respectively. Resistant strain of P. aeruginosa, E. cloacea, A. baumani, K. pneumonia were sensitive to the action of rutin – 23.0 ± 0.3 mm, 25.0 ± 0.2 mm, 24.0 ± 0.3 mm, 23.0 ± 0.3 mm, respectively, while to the action of quercetin resistant strain were low sensitive – 12.0 ± 0.6 mm, 14.0 ± 0.5 mm, 12.0 ± 0.6 mm, 12.0 ± 0.6 mm, respectively.

Conclusions. Theoretical studies of “standard” antimicrobial drugs used in infectious disease treatment protocols are not highly selective inhibitors of “target” antibacterial mechanisms of gram-negative bacteria, unlike rutin, which turned out to be a highly selective inhibitor. According to the results of the theoretical study, it was found that the potential antibacterial activity of rutin exceeds the effect of quercetin by two times. This pattern is fully confirmed by in vitro studies, where the antibacterial effect of rutin against resistant strains was also two times higher.

Author Biographies

O. Yu. Maslov, National University of Pharmacy, Kharkiv

PhD, Assistant of the Department of General Chemistry

 

M. A. Komisarenko, National University of Pharmacy, Kharkiv

PhD, Assistant of the Department of Pharmacognosy and Nutriciology

S. V. Ponomarenko, Mechnikov Institute of Microbiology and Immunology of the NAMS of Ukraine, Kharkiv

PhD, Leader researcher of the Laboratory of Biochemistry and Biotechnology

I. D. Andrieieva, Mechnikov Institute of Microbiology and Immunology of the NAMS of Ukraine, Kharkiv

Leader researcher of Laboratory of Biochemistry and Biotechnology

T. P. Osolodchenko, Mechnikov Institute of Microbiology and Immunology of the NAMS of Ukraine, Kharkiv

PhD, Head of the Laboratory of Biochemistry and Biotechnology

S. V. Kolisnyk, National University of Pharmacy, Kharkiv

PhD, DSc, Professor, Head of the Department of General Chemistry

References

Trauner D, Sailer A. Chemoselective synthesis of unsymmetrical disulfides. Synfacts. 2023;19(6):0617. doi: https://doi.org/10.1055/s-0042-1751888

Yadav A, Gond A, Prasad V. Synthesis of symmetrical disulfides by an NIS/PPh3-mediated reductive self-coupling of sulfonyl hydrazides. Synlett. 2024;35:1453-7. doi: https://doi.org/10.1055/s-0041-1738457

Janská P, Knejzlík Z, Perumal AS, Jurok R, Tokárová V, Nicolau DV, et al. Effect of physicochemical parameters on the stability and activity of garlic alliinase and its use for in-situ allicin synthesis. PLoS One. 2021;16(3):e0248878. doi: https://doi.org/10.1371/journal.pone.0248878

Hotsulia AS, Al Khalaf NA, Fedotov SO, Solomennyi AM, Pidlisnyi OV. [Synthesis and properties of 2-(5-methyl-4-(4-methoxy-phenyl)-1,2,4-triazol-3-ylthio) acetamides]. Ukrainian journal of military medicine. 2024;5(2):110-9. Ukrainian. doi: https://doi.org/10.46847/ujmm.2024.2(5)-110

Kucherenko LI, Karpenko YV, Ohloblina MV, Zazharskyi VV, Bilan MV, Kulishenko OM, et al. [Monitoring the properties of 1,2,4-triazole derivatives for the development of original antimicrobial drugs]. Zaporozhye medical journal. 2024;26(6):481-9. Ukrainian. doi: https://doi.org/10.14739/2310-1210.2024.6.309034

Karpenko Y. Absorption of free radicals of new S-derivatives (1,2,4-triazole-3(2H)-yl)methyl)thiopyrimidines. Chemistry Proceedings. 2024;16(1):62. doi: https://doi.org/10.3390/ecsoc-28-20181

Teskey G, Abrahem R, Cao R, Gyurjian K, Islamoglu H, Lucero M, et al. Glutathione as a marker for human disease. Adv Clin Chem. 2018;87:141-59. doi: https://doi.org/10.1016/bs.acc.2018.07.004

Karpenko YV, Panasenko OI, Kulish SM, Domnich AV. Synthesis and acute toxicity of new S-derivatives (1,2,4-triazole-3(2H)-yl)methyl) thiopyrimidines. Current issues in pharmacy and medicine: science and practice. 2023;16(2):158-64. doi: https://doi.org/10.14739/2409-2932.2023.2.274586

Zhou F, He X, Zhou M, Li N, Wang Q, Zhang X, et al. Generation of perthiyl radicals for the synthesis of unsymmetric disulfides. Nat Commun. 2025;16(1):23. doi: https://doi.org/10.1038/s41467-024-55310-x

Abe Y, Nakabayashi T, Tsurugi J. The preparation of N-(alkylthio)- and N-(arylthio)succinimides. Bulletin of the Chemical Society of Japan. 2006;46(6):1898-9. doi: https://doi.org/10.1246/bcsj.46.1898

Hunter R, Caira M, Stellenboom N. Inexpensive, one-pot synthesis of unsymmetrical disulfides using 1-chlorobenzotriazole. J Org Chem. 2006;71(21):8268-71. doi: https://doi.org/10.1021/jo060693n

Downloads

Additional Files

Published

2025-07-04

How to Cite

1.
Maslov OY, Komisarenko MA, Ponomarenko SV, Andrieieva ID, Osolodchenko TP, Kolisnyk SV. Structure and antibacterial activity relationship of quercetin and rutin against test and clinical resistant gramm-negative strains of bacteria. Current issues in pharmacy and medicine: science and practice [Internet]. 2025Jul.4 [cited 2025Jul.6];18(2):138-47. Available from: https://pharmed.zsmu.edu.ua/article/view/324663