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Article

Cholinesterase and Prolyl Oligopeptidase Inhibitory Activities of Alkaloids from Argemone platyceras (Papaveraceae)

by
Tomáš Siatka
1,
Markéta Adamcová
2,
Lubomír Opletal
2,
Lucie Cahlíková
2,
Daniel Jun
3,
Martina Hrabinová
3,
Jiří Kuneš
4 and
Jakub Chlebek
2,*
1
Department of Pharmacognosy, Faculty of Pharmacy, Charles University, Akademika Heyrovského 1203, 500 05 Hradec Králové, Czech Republic
2
Department of Pharmaceutical Botany and Ecology, ADINACO Research Group, Faculty of Pharmacy, Charles University, Akademika Heyrovského 1203, 500 05 Hradec Králové, Czech Republic
3
Department of Toxicology and Military Pharmacy, Faculty of Military Health Sciences, University of Defence, Třebešská 1575, 500 01 Hradec Králové, Czech Republic
4
Department of Inorganic and Organic Chemistry, Faculty of Pharmacy, Charles University, Akademika Heyrovského 1203, 500 05 Hradec Králové, Czech Republic
*
Author to whom correspondence should be addressed.
Molecules 2017, 22(7), 1181; https://doi.org/10.3390/molecules22071181
Submission received: 20 May 2017 / Revised: 30 June 2017 / Accepted: 10 July 2017 / Published: 14 July 2017
(This article belongs to the Section Medicinal Chemistry)
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Abstract

Alzheimer’s disease is an age-related, neurodegenerative disorder, characterized by cognitive impairment and restrictions in activities of daily living. This disease is the most common form of dementia with complex multifactorial pathological mechanisms. Many therapeutic approaches have been proposed. Among them, inhibition of acetylcholinesterase, butyrylcholinesterase, and prolyl oligopeptidase can be beneficial targets in the treatment of Alzheimer’s disease. Roots, along with aerial parts of Argemone platyceras, were extracted with ethanol and fractionated on an alumina column using light petrol, chloroform and ethanol. Subsequently, repeated preparative thin-layer chromatography led to the isolation of (+)-laudanosine, protopine, (–)-argemonine, allocryptopine, (–)-platycerine, (–)-munitagine, and (–)-norargemonine belonging to pavine, protopine and benzyltetrahydroisoquinoline structural types. Chemical structures of the isolated alkaloids were elucidated by optical rotation, spectroscopic and spectrometric analysis (NMR, MS), and comparison with literature data. (+)-Laudanosine was isolated from A. platyceras for the first time. Isolated compounds were tested for human blood acetylcholinesterase, human plasma butyrylcholinesterase and recombinant prolyl oligopeptidase inhibitory activity. The alkaloids inhibited the enzymes in a dose-dependent manner. The most active compound (–)-munitagine, a pavine alkaloid, inhibited both acetylcholinesterase and prolyl oligopeptidase with IC50 values of 62.3 ± 5.8 µM and 277.0 ± 31.3 µM, respectively.
Keywords: Argemone platyceras; alkaloids; acetylcholinesterase; butyrylcholinesterase; prolyl oligopeptidase; Alzheimer’s disease Argemone platyceras; alkaloids; acetylcholinesterase; butyrylcholinesterase; prolyl oligopeptidase; Alzheimer’s disease
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MDPI and ACS Style

Siatka, T.; Adamcová, M.; Opletal, L.; Cahlíková, L.; Jun, D.; Hrabinová, M.; Kuneš, J.; Chlebek, J. Cholinesterase and Prolyl Oligopeptidase Inhibitory Activities of Alkaloids from Argemone platyceras (Papaveraceae). Molecules 2017, 22, 1181. https://doi.org/10.3390/molecules22071181

AMA Style

Siatka T, Adamcová M, Opletal L, Cahlíková L, Jun D, Hrabinová M, Kuneš J, Chlebek J. Cholinesterase and Prolyl Oligopeptidase Inhibitory Activities of Alkaloids from Argemone platyceras (Papaveraceae). Molecules. 2017; 22(7):1181. https://doi.org/10.3390/molecules22071181

Chicago/Turabian Style

Siatka, Tomáš, Markéta Adamcová, Lubomír Opletal, Lucie Cahlíková, Daniel Jun, Martina Hrabinová, Jiří Kuneš, and Jakub Chlebek. 2017. "Cholinesterase and Prolyl Oligopeptidase Inhibitory Activities of Alkaloids from Argemone platyceras (Papaveraceae)" Molecules 22, no. 7: 1181. https://doi.org/10.3390/molecules22071181

APA Style

Siatka, T., Adamcová, M., Opletal, L., Cahlíková, L., Jun, D., Hrabinová, M., Kuneš, J., & Chlebek, J. (2017). Cholinesterase and Prolyl Oligopeptidase Inhibitory Activities of Alkaloids from Argemone platyceras (Papaveraceae). Molecules, 22(7), 1181. https://doi.org/10.3390/molecules22071181

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