Cited by 209Cholinesterase and Neurodegenerative DiseasesFlavonoids in Medical ResearchBioactive natural compounds

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Structural aspects of flavonoids as inhibitors of human butyrylcholinesterase

Katalinić, Maja, Rusak, Gordana, Domaćinović Barović, Jelena, Šinko, Goran, Jelić, Dubravko, Antolović, Roberto, Kovarik, Zrinka·2010·European Journal of Medicinal Chemistry

DOI 10.1016/j.ejmech.2009.09.041

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Abstract

Selected flavonoids: galangin, kaempferol, quercetin, myricetin, fisetin, apigenin, luteolin and rutin, reversibly inhibited human butyrylcholinesterase (BChE, EC 3.1.1.8). Inhibition potency of the flavonoids we attributed to their chemical structure, i.e., the number of OH groups and their side on the phenyl ring. The most potent BChE inhibitor among the tested flavonoids was galangin, which showed 12 times higher preference for binding to BChE (7 micromol/L) than to the related enzyme human acetylcholinesterase (AChE, EC 3.1.1.7). Docking study showed that flavonoids bind to the BChE active site by forming multiple hydrogen bonds and pi-pi interactions. The UV-VIS (200-500 nm) absorption spectra of the flavonoid phosphate buffer solution (pH 7.4), with the exception of rutin, revealed time dependant changes indicating precipitation of flavonoids or in the case of myricetin, a change in the chemical structure resulting in a BChE non-inhibiting specie. Selected flavonoids showed no cytotoxic effect on HepG2 and A549 cell lines at concentrations up to 200 micromol/L. Cytotoxicity was observed only for fisetin, apigenin and luteolin in the THP-1 cell line with IC50 of 30, 60 and 70 micromol/L, respectively.

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Rapid colorimetric assay for cellular growth and survival: Application to proliferation and cytotoxicity assays
Mosmann, T. (1983) · Journal of Immunological Methods · doi:10.1016/0022-1759(83)90303-4 · Cited by 56,104
A new and rapid colorimetric determination of acetylcholinesterase activity
Ellman, G. L., Courtney, K. D., Andres, V., & Featherstone, R. M. (1961) · Biochemical Pharmacology · doi:10.1016/0006-2952(61)90145-9 · Cited by 27,221
Pathways towards and Away from Alzheimer’s Disease
Mattson, M. P. (2004) · Nature · doi:10.1038/nature02621 · Cited by 3,052
Neurobiology of butyrylcholinesterase
Darvesh, S., Hopkins, D. A., & Geula, C. (2003) · Nature reviews. Neuroscience · doi:10.1038/nrn1035 · Cited by 896
A critical review of the data related to the safety of quercetin and lack of evidence of in vivo toxicity, including lack of genotoxic/carcinogenic properties
Harwood, M., Danielewska-Nikiel, B., Borzelleca, J. F., Flamm, G., Williams, G. M., & Lines, T. C. (2007) · Food and Chemical Toxicology · doi:10.1016/j.fct.2007.05.015 · Cited by 890
Relative bioavailability of the antioxidant flavonoid quercetin from various foods in man
Hollman, P. C. H., van Trijp, J. M. P., Buysman, M. N. C. P., van der Gaag, M. S., Mengelers, M. J. B., de Vries, J. H. M., & Katan, M. (1997) · FEBS Letters · doi:10.1016/s0014-5793(97)01367-7 · Cited by 782
Flavonoids in Health and Disease
Rice-Evans, C. A., & Packer, L. (2003) · CRC Press eBooks · doi:10.1201/9780367803681 · Cited by 693
Acetylcholinesterase knockouts establish central cholinergic pathways and can use butyrylcholinesterase to hydrolyze acetylcholine
Mesulam, M. M., Guillozet-Bongaarts, A. L., Shaw, P. L., Levey, A. I., Duysen, E. G., & Lockridge, O. (2002) · Neuroscience · doi:10.1016/s0306-4522(01)00613-3 · Cited by 662
Flavonoids and the brain: interactions at the blood–brain barrier and their physiological effects on the central nervous system
Youdim, K. A., Shukitt‐Hale, B., & Joseph, J. A. (2004) · Free Radical Biology and Medicine · doi:10.1016/j.freeradbiomed.2004.08.002 · Cited by 378
THE INHIBITION OF ARGINASE BY AMINO ACIDS
Hunter, A., & Downs, C. E. (1945) · Journal of Biological Chemistry · doi:10.1016/s0021-9258(18)51079-6 · Cited by 324

Show all 23 references

Research works printed but not linked: 6

Rusak, 2002, Food Technol. Biotechnol, 40, 267
Čalić, 2005, Croat. Chem. Acta, 78, 367
Gutzeit, 2005, Croat. Chem. Acta, 78, 337
Kovarik, 1999, Period. Biol., 101, 7
Ngamelue, 2007, Acta Crystallogr., 63, 723
Verbanac, 2005, Croat. Chem. Acta, 78, 133

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Authors: Katalinić, M., Rusak, G., Domaćinović Barović, J., Šinko, G., Jelić, D., Antolović, R., & Kovarik, Z.
Affiliations: Institute for Medical Research and Occupational Health (HR)
University of Zagreb (HR)
GlaxoSmithKline (Croatia) (HR)
University of Rijeka (HR)
Corresponding author: Kovarik, Zrinka
ORCID: Katalinić, Maja
Rusak, Gordana
Šinko, Goran
Antolović, Roberto
Kovarik, Zrinka
Venue: European Journal of Medicinal Chemistry
Publisher: Elsevier BV
Published: 2010-01
Volume: 45
Issue: 1
Pages: 186-192
ISSN: 0223-5234 (ISSN-L)
DOI: 10.1016/j.ejmech.2009.09.041
OpenAlex: W2084585115
Cited by: 206
References: 23
Citations by year: 2026: 14 · 2025: 16 · 2024: 11 · 2023: 16 · 2022: 22 · 2021: 9 · 2020: 16 · 2019: 10 · 2018: 13 · 2017: 15 · 2016: 10 · 2015: 10 · 2014: 15 · 2013: 9 · 2012: 10
FWCI: 5.29
Type: journal article
Language: en
Open access: closed
Licence: www.elsevier.com/tdm/userlicense/1.0/ (tdm)
Locations: European Journal of Medicinal Chemistry (publishedVersion)
PubMed (publishedVersion)
Topics: Health Sciences › Medicine › Pharmacology (medical) › Cholinesterase and Neurodegenerative Diseases
Health Sciences › Medicine › Pharmacology (medical) › Flavonoids in Medical Research
Life Sciences › Pharmacology, Toxicology and Pharmaceutics › Drug Discovery › Bioactive natural compounds
Keywords: flavonoids, butyrylcholinesterase, acetylcholinesterase, enzyme inhibitors, structure-activity relationship, galangin, quercetin, kaempferol, myricetin, fisetin, apigenin, luteolin, rutin, molecular docking, hydrogen bonding, π-π stacking, cytotoxicity, THP-1 cells, HepG2 cells, A549 cells
MeSH terms: Acetylcholinesterase, Butyrylcholinesterase, Cholinesterase Inhibitors, Flavonoids, Humans, Models, Molecular, Protein Conformation, Substrate Specificity, Cell Line, Tumor

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Structural aspects of flavonoids as inhibitors of human butyrylcholinesterase

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