Structural Aspects of Flavonoids as Inhibitors of Human Butyrylcholinesterase
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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During Alzheimer's disease progression, BChE activity can increase significantly, potentially contributing to aggregation of amyloid beta-peptides and formation of senile plaques.
“Notably, during the progression of AD, BChE activity can increase significantly, potentially contributing to the aggregation of amyloid beta-peptides and the formation of senile plaques, which are characteristic of the disease [90,91].”
From Cholinesterase Inhibitors from Plants and Their Potential in Alzheimer’s Treatment: Systematic Review (2025) · cites this paper as [90]
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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
- Venue
- European Journal of Medicinal Chemistry
- Publisher
- Elsevier BV
- Published
- 2010-01
- Volume
- 45
- Issue
- 1
- Pages
- 186-192
- ISSN
- 0223-5234 (ISSN-L)
- 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
- Locations
- European Journal of Medicinal Chemistry (publishedVersion)
- PubMed (publishedVersion)
- Topics
- Health Sciences › Medicine › Pharmacology › Cholinesterase and Neurodegenerative Diseases
- Health Sciences › Medicine › Pharmacology › Flavonoids in Medical Research
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › 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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