Cholinesterase and Prolyl Oligopeptidase Inhibitory Activities of Alkaloids from Argemone platyceras (Papaveraceae)
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 propose...
Main Authors: | , , , , , , , |
---|---|
Format: | Article |
Language: | English |
Published: |
MDPI AG
2017-07-01
|
Series: | Molecules |
Subjects: | |
Online Access: | https://www.mdpi.com/1420-3049/22/7/1181 |
id |
doaj-2dc14400728245b2928137ec59f4c886 |
---|---|
record_format |
Article |
spelling |
doaj-2dc14400728245b2928137ec59f4c8862020-11-24T21:34:42ZengMDPI AGMolecules1420-30492017-07-01227118110.3390/molecules22071181molecules22071181Cholinesterase and Prolyl Oligopeptidase Inhibitory Activities of Alkaloids from Argemone platyceras (Papaveraceae)Tomáš Siatka0Markéta Adamcová1Lubomír Opletal2Lucie Cahlíková3Daniel Jun4Martina Hrabinová5Jiří Kuneš6Jakub Chlebek7Department of Pharmacognosy, Faculty of Pharmacy, Charles University, Akademika Heyrovského 1203, 500 05 Hradec Králové, Czech RepublicDepartment of Pharmaceutical Botany and Ecology, ADINACO Research Group, Faculty of Pharmacy, Charles University, Akademika Heyrovského 1203, 500 05 Hradec Králové, Czech RepublicDepartment of Pharmaceutical Botany and Ecology, ADINACO Research Group, Faculty of Pharmacy, Charles University, Akademika Heyrovského 1203, 500 05 Hradec Králové, Czech RepublicDepartment of Pharmaceutical Botany and Ecology, ADINACO Research Group, Faculty of Pharmacy, Charles University, Akademika Heyrovského 1203, 500 05 Hradec Králové, Czech RepublicDepartment of Toxicology and Military Pharmacy, Faculty of Military Health Sciences, University of Defence, Třebešská 1575, 500 01 Hradec Králové, Czech RepublicDepartment of Toxicology and Military Pharmacy, Faculty of Military Health Sciences, University of Defence, Třebešská 1575, 500 01 Hradec Králové, Czech RepublicDepartment of Inorganic and Organic Chemistry, Faculty of Pharmacy, Charles University, Akademika Heyrovského 1203, 500 05 Hradec Králové, Czech RepublicDepartment of Pharmaceutical Botany and Ecology, ADINACO Research Group, Faculty of Pharmacy, Charles University, Akademika Heyrovského 1203, 500 05 Hradec Králové, Czech RepublicAlzheimer’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.https://www.mdpi.com/1420-3049/22/7/1181Argemone platycerasalkaloidsacetylcholinesterasebutyrylcholinesteraseprolyl oligopeptidaseAlzheimer’s disease |
collection |
DOAJ |
language |
English |
format |
Article |
sources |
DOAJ |
author |
Tomáš Siatka Markéta Adamcová Lubomír Opletal Lucie Cahlíková Daniel Jun Martina Hrabinová Jiří Kuneš Jakub Chlebek |
spellingShingle |
Tomáš Siatka Markéta Adamcová Lubomír Opletal Lucie Cahlíková Daniel Jun Martina Hrabinová Jiří Kuneš Jakub Chlebek Cholinesterase and Prolyl Oligopeptidase Inhibitory Activities of Alkaloids from Argemone platyceras (Papaveraceae) Molecules Argemone platyceras alkaloids acetylcholinesterase butyrylcholinesterase prolyl oligopeptidase Alzheimer’s disease |
author_facet |
Tomáš Siatka Markéta Adamcová Lubomír Opletal Lucie Cahlíková Daniel Jun Martina Hrabinová Jiří Kuneš Jakub Chlebek |
author_sort |
Tomáš Siatka |
title |
Cholinesterase and Prolyl Oligopeptidase Inhibitory Activities of Alkaloids from Argemone platyceras (Papaveraceae) |
title_short |
Cholinesterase and Prolyl Oligopeptidase Inhibitory Activities of Alkaloids from Argemone platyceras (Papaveraceae) |
title_full |
Cholinesterase and Prolyl Oligopeptidase Inhibitory Activities of Alkaloids from Argemone platyceras (Papaveraceae) |
title_fullStr |
Cholinesterase and Prolyl Oligopeptidase Inhibitory Activities of Alkaloids from Argemone platyceras (Papaveraceae) |
title_full_unstemmed |
Cholinesterase and Prolyl Oligopeptidase Inhibitory Activities of Alkaloids from Argemone platyceras (Papaveraceae) |
title_sort |
cholinesterase and prolyl oligopeptidase inhibitory activities of alkaloids from argemone platyceras (papaveraceae) |
publisher |
MDPI AG |
series |
Molecules |
issn |
1420-3049 |
publishDate |
2017-07-01 |
description |
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. |
topic |
Argemone platyceras alkaloids acetylcholinesterase butyrylcholinesterase prolyl oligopeptidase Alzheimer’s disease |
url |
https://www.mdpi.com/1420-3049/22/7/1181 |
work_keys_str_mv |
AT tomassiatka cholinesteraseandprolyloligopeptidaseinhibitoryactivitiesofalkaloidsfromargemoneplatyceraspapaveraceae AT marketaadamcova cholinesteraseandprolyloligopeptidaseinhibitoryactivitiesofalkaloidsfromargemoneplatyceraspapaveraceae AT lubomiropletal cholinesteraseandprolyloligopeptidaseinhibitoryactivitiesofalkaloidsfromargemoneplatyceraspapaveraceae AT luciecahlikova cholinesteraseandprolyloligopeptidaseinhibitoryactivitiesofalkaloidsfromargemoneplatyceraspapaveraceae AT danieljun cholinesteraseandprolyloligopeptidaseinhibitoryactivitiesofalkaloidsfromargemoneplatyceraspapaveraceae AT martinahrabinova cholinesteraseandprolyloligopeptidaseinhibitoryactivitiesofalkaloidsfromargemoneplatyceraspapaveraceae AT jirikunes cholinesteraseandprolyloligopeptidaseinhibitoryactivitiesofalkaloidsfromargemoneplatyceraspapaveraceae AT jakubchlebek cholinesteraseandprolyloligopeptidaseinhibitoryactivitiesofalkaloidsfromargemoneplatyceraspapaveraceae |
_version_ |
1725947897769361408 |