Cited by 22Cholinesterase and Neurodegenerative DiseasesPhytochemistry and Biological ActivitiesMedicinal Plants and Neuroprotection

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Isoquinoline Alkaloid Contents in Macleaya cordata Extracts and Their Acetylcholinesterase and Butyrylcholinesterase Inhibition

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Tuzimski, Tomasz, Petruczynik, Anna, Szultka-Młyńska, Małgorzata, Sugajski, Mateusz, Buszewski, Bogusław·2022·Molecules

DOI 10.3390/molecules27113606PMC PMC9182188

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Abstract

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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Figure 1 (A) HPLC-DAD chromatogram obtained for a mixture of alkaloid standards, (B) HPLC-DAD chromatogram obtained for the extract from the Macleaya cordata aerial part collected in May, (C) HPLC-DAD chromatogram obtained for the extract from the Macleaya cordata root collected in May. Chlr: chelerythrine; Pr: protopine; S: Ssnguinarine. The acquisition wavelength was set at 240 nm.CC BY · PubMed Central

Figure 2 Representative full-scan MS spectra obtained with the use of ESI–Q-TOF–MS/MS for chelerythrine from the Macleaya cordata’s extracts: (A) aerial part collected in May, (B) root collected in May, (C) aerial part collected in July, (D) root collected in July, as well as representative product ion MS/MS spectra obtained with the use of ESI-Q-TOF-MS/MS for chelerythrine (E), protopine (f), and sanguinarine (G) from the Macleaya cordata extracts.CC BY · PubMed Central

Figure 3 (A) Dependence of concentration of cholinesterases on the peak area. Error bars represent standard errors. (B) Dependence of ACTI and BCTI concentrations in the reaction with cholinesterases on the peak area. Error bars represent standard errors. (C) Dependence of the DTNB concentration in reaction with cholinesterases on the peak area. Error bars represent standard errors. (D) Dependence of the temperature of incubation in reaction with cholinesterases on the peak area. Error bars represent standard errors. (E) Dependence of the incubation time in reaction with acetylcholinesterases on the peak area. Error bars represent standard errors.CC BY · PubMed Central

Figure 4 Correlation between the sum of chelerythrine and sanguinarine contents and butyrylcholinesterase activity inhibition as IC50 of the investigated plant extracts.CC BY · PubMed Central

Figure 5 (A) Lineweaver–Bulk plot of acetylcholinesterase activity over a range of substrate concentration for chelerythrine, (B) determination of inhibition constants (Ki) by plotting the slope of the primary Lineweaver–Burk plot vs. chelerythrine concentration.CC BY · PubMed Central

Figure 6 (A) Lineweaver–Bulk plot of acetylcholinesterase activity over a range of substrate concentrations for sanguinarine, (B) determination of inhibition constants (Ki) by plotting the slope of the primary Lineweaver–Burk plot vs. sanguinarine concentration.CC BY · PubMed Central

Figure 7 Interactions between AChE and ligands: (A) chelerythrine, (B) protopine, (C) sanguinarine.CC BY · PubMed Central

Figure 8 Interactions between BChE and ligands: (A) chelerythrine, (B) protopine, (C) sanguinarine.CC BY · PubMed Central

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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: Tuzimski, Tomasz
Petruczynik, Anna
Szultka-Młyńska, Małgorzata
Sugajski, Mateusz
Buszewski, Bogusław
Venue: Molecules
Publisher: MDPI AG
Published: 2022-06-03
Volume: 27
Issue: 11
Pages: 3606
ISSN: 1420-3049 (ISSN-L)
DOI: 10.3390/molecules27113606
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: cc-by
creativecommons.org/licenses/by/4.0/ (vor)
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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Isoquinoline Alkaloid Contents in Macleaya cordata Extracts and Their Acetylcholinesterase and Butyrylcholinesterase Inhibition

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