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Isoquinoline Alkaloid Contents in Macleaya cordata Extracts and Their Acetylcholinesterase and Butyrylcholinesterase Inhibition
Open accessAbstract
An important strategy for treating neurodegenerative disorders is to maintain the levels of acetylcholine in the synaptic cleft by blocking the cholinesterases. Searching for new effective compounds with inhibited acetylcholinesterase and butyrylcholinesterase activity is one of the most significant challenges of the modern scientific research. The aim of this study was the optimization of the condition for cholinesterase activity determination by high-performance liquid chromatography coupled with diode array detector (HPLC-DAD) in terms of concentrations of enzymatic reaction mixture components, temperature of incubation, and incubation time. In vitro investigation of acetylcholinesterase and butyrylcholinesterase activity inhibition by some isoquinoline alkaloids and extracts obtained from the aerial part and roots of Macleaya cordata collected in May, July, and September. Acetylcholinesterase and butyrylcholinesterase activity inhibition of the extracts obtained from the plant had not been tested previously. The application of the HPLC method allowed eliminating absorption of interfering components, for example, alkaloids such as sanguinarine and berberine. The HPLC method was successfully applied for the evaluation of the acetylcholinesterase inhibitory activity in samples such as plant extracts, especially those containing colored components adsorbing at the same wavelength as the adsorption wavelength of 5-thio-2-nitro-benzoic acid, which is the product of the reaction between thiocholine (product of the hydrolysis of acetyl/butyrylthiocholine reaction) with Ellman’s reagent. Moreover, liquid chromatography coupled with a triple quadrupole mass spectrometer (LC–QqQ–ESI–MS/MS) analysis allowed evaluating the identification of relevant bioactive compounds in the obtained plant extracts. The investigated alkaloids, especially sanguinarine and chelerythrine, and all the Macleaya cordata extracts, especially the extract obtained from the aerial part collected in May, exhibited very high cholinesterase activity inhibition. HPLC-DAD was also applied for the kinetics study of the most active alkaloids sanguinarine and chelerythrine. Our investigations demonstrated that these plant extracts can be recommended for further in vivo experiments to confirm their cholinesterase inhibition activity.
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“While AChE is primarily responsible for terminating cholinergic neurotransmission, BChE has been shown to hydrolyze ACh as well, albeit with lower catalytic efficiency [89].”
From Cholinesterase Inhibitors from Plants and Their Potential in Alzheimer’s Treatment: Systematic Review (2025) · cites this paper as [89]
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Sanguinarine and chelerythrine: assessment of safety on pigs in ninety days feeding experiment
Kosina, P., Daniela Walterová, B., Jitka Ulrichová, A., Lichnovský, V., Stiborová, M., Dračínská, H., Vičar, J., Krecman, V., Brabec, M. J., & Šimánek, V. (2003) · Food and Chemical Toxicology · doi:10.1016/j.fct.2003.08.007 · Cited by 179
Plazas, E., Hagenow, S., Murillo, M. C. Á., Stark, H., & Suárez, L. E. C. (2020) · Bioorganic Chemistry · doi:10.1016/j.bioorg.2020.103722 · Cited by 67
Hulcová, D., Maříková, J., Korábečný, J., Hošťálková, A., Jun, D., Kuneš, J., Chlebek, J., Opletal, L., Simone, A. D., Nováková, L., et al. (2019) · Phytochemistry · doi:10.1016/j.phytochem.2019.112055 · Cited by 61
Othman, W. N. N. W., Liew, S. Y., Khaw, K. Y., Murugaiyah, V., Litaudon, M., & Awang, K. (2016) · Bioorganic & Medicinal Chemistry · doi:10.1016/j.bmc.2016.07.043 · Cited by 60
Chemistry and Biological Activity of Alkaloids from the Genus Lycoris (Amaryllidaceae)
Cahlíková, L., Breiterova, K. H., & Opletal, L. (2020) · Molecules · doi:10.3390/molecules25204797 · Cited by 55
Cortés, N., Sierra, K., Álzate, F., Osorio, E. H., & Osorio, E. (2017) · Phytochemical Analysis · doi:10.1002/pca.2736 · Cited by 49
Plazas, E., Casoti, R., Murillo, M. C. Á., Costa, F. B. D., & Suárez, L. E. C. (2019) · Phytochemistry · doi:10.1016/j.phytochem.2019.112128 · Cited by 46
Ka, S., Masi, M., Mérindol, N., Lecce, R. D., Plourde, M. B., Seck, M., Górecki, M., Pescitelli, G., Desgagné‐Penix, I., & Evidente, A. (2020) · Phytochemistry · doi:10.1016/j.phytochem.2020.112390 · Cited by 46
Petruczynik, A., Plech, T., Tuzimski, T., Misiurek, J., Kaproń, B., Misiurek, D., Szultka‐Młyńska, M., Buszewski, B., & Waksmundzka‐Hajnos, M. (2019) · Toxins · doi:10.3390/toxins11100575 · Cited by 43
Self-citationMamun, A. A., Maříková, J., Hulcová, D., Janoušek, J., Šafratová, M., Nováková, L., Kučera, T., Hrabinová, M., Kuneš, J., Korábečný, J., et al. (2020) · Biomolecules · doi:10.3390/biom10050800 · Cited by 43
Cited by
ALNasser, M. N., Alboraiy, G. M., Alsowig, E. M., & Alqattan, F. M. (2025) · Brain Sciences · doi:10.3390/brainsci15020215 · Cited by 35
Medicinal Plants - Chemical, Biochemical, and Pharmacological Approaches
de Oliveira, M. S., Andrade, E. H. D. A., Kumar, R., & Mali, S. N. (2023) · IntechOpen eBooks · doi:10.5772/intechopen.107682 · Cited by 17
Sayğı, T. K., Tan, N., Toraman, G. Ö. A., Ünsal, Ç., Tuğay, O., & Topçu, G. (2023) · Pharmaceutical Biology · doi:10.1080/13880209.2023.2218881 · Cited by 11
Tuzimski, T., Petruczynik, A., Kaproń, B., Plech, T., Makuch‐Kocka, A., Janiszewska, D., Sugajski, M., Buszewski, B., & Szultka‐Młyńska, M. (2024) · Molecules · doi:10.3390/molecules29051048 · Cited by 9
Self-citationŞenol, F. S., Salmas, R. E., Emerce, E., Şener, B., & Orhan, İ. E. (2023) · CNS & Neurological Disorders - Drug Targets · doi:10.2174/1871527322666230417083053 · Cited by 8
Metadata
- Authors
- Tuzimski, T., Petruczynik, A., Szultka-Młyńska, M., Sugajski, M., & Buszewski, B.
- Affiliations
- Medical University of Lublin (PL)
- Department of Environmental Chemistry and Bioanalytics, Faculty of Chemistry, Nicolaus Copernicus University, Gagarina 7, 87-100 Torun, Poland
- Nicolaus Copernicus University (PL)
- Corresponding author
- Tuzimski, Tomasz
- Petruczynik, Anna
- ORCID
- Venue
- Molecules
- Publisher
- MDPI AG
- Published
- 2022-06-03
- Volume
- 27
- Issue
- 11
- Pages
- 3606
- ISSN
- 1420-3049 (ISSN-L)
- PMC
- PMC9182188
- OpenAlex
- W4281674146
- Cited by
- 21
- References
- 41
- Citations by year
- 2026: 2 · 2025: 7 · 2024: 5 · 2023: 6 · 2022: 1
- FWCI
- 2.84
- Type
- journal article
- Language
- en
- Open access
- gold
- doi.org
- Licence
- Locations
- Molecules (publishedVersion, cc-by)
- PubMed Central (publishedVersion, cc-by)
- PubMed (publishedVersion)
- DOAJ (DOAJ: Directory of Open Access Journals) (submittedVersion, cc-by-sa)
- Topics
- Health Sciences › Medicine › Pharmacology (medical) › Cholinesterase and Neurodegenerative Diseases
- Life Sciences › Agricultural and Biological Sciences › Plant Science › Phytochemistry and Biological Activities
- Health Sciences › Medicine › Complementary and alternative medicine › Medicinal Plants and Neuroprotection
- Keywords
- Macleaya cordata, isoquinoline alkaloids, acetylcholinesterase inhibition, butyrylcholinesterase inhibition, sanguinarine, chelerythrine, Ellman's reagent, neurodegenerative diseases, plant extracts, aerial parts, roots
- MeSH terms
- Acetylcholinesterase, Alkaloids, Antineoplastic Agents, Butyrylcholinesterase, Cholinesterase Inhibitors, Isoquinolines, Plant Extracts, Papaveraceae, Tandem Mass Spectrometry
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- Tuzimski, T., Petruczynik, A., Szultka-Młyńska, M., Sugajski, M., & Buszewski, B. (2022). Isoquinoline Alkaloid Contents in Macleaya cordata Extracts and Their Acetylcholinesterase and Butyrylcholinesterase Inhibition. Molecules. https://doi.org/10.3390/molecules27113606
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