{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,5]],"date-time":"2026-10-05T20:44:54Z","timestamp":1791233094846,"version":"4.1.0"},"reference-count":71,"publisher":"MDPI AG","issue":"7","license":[{"start":{"date-parts":[[2017,7,14]],"date-time":"2017-07-14T00:00:00Z","timestamp":1499990400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Alzheimer\u2019s 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\u2019s 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, (\u2013)-argemonine, allocryptopine, (\u2013)-platycerine, (\u2013)-munitagine, and (\u2013)-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 (\u2013)-munitagine, a pavine alkaloid, inhibited both acetylcholinesterase and prolyl oligopeptidase with IC50 values of 62.3 \u00b1 5.8 \u00b5M and 277.0 \u00b1 31.3 \u00b5M, respectively.<\/jats:p>","DOI":"10.3390\/molecules22071181","type":"journal-article","created":{"date-parts":[[2017,7,14]],"date-time":"2017-07-14T10:45:02Z","timestamp":1500029102000},"page":"1181","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":27,"title":["Cholinesterase and Prolyl Oligopeptidase Inhibitory Activities of Alkaloids from Argemone platyceras (Papaveraceae)"],"prefix":"10.3390","volume":"22","author":[{"given":"Tom\u00e1\u0161","family":"Siatka","sequence":"first","affiliation":[{"name":"Department of Pharmacognosy, Faculty of Pharmacy, Charles University, Akademika Heyrovsk\u00e9ho 1203, 500 05 Hradec Kr\u00e1lov\u00e9, Czech Republic"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Mark\u00e9ta","family":"Adamcov\u00e1","sequence":"additional","affiliation":[{"name":"Department of Pharmaceutical Botany and Ecology, ADINACO Research Group, Faculty of Pharmacy, Charles University, Akademika Heyrovsk\u00e9ho 1203, 500 05 Hradec Kr\u00e1lov\u00e9, Czech Republic"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Lubom\u00edr","family":"Opletal","sequence":"additional","affiliation":[{"name":"Department of Pharmaceutical Botany and Ecology, ADINACO Research Group, Faculty of Pharmacy, Charles University, Akademika Heyrovsk\u00e9ho 1203, 500 05 Hradec Kr\u00e1lov\u00e9, Czech Republic"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Lucie","family":"Cahl\u00edkov\u00e1","sequence":"additional","affiliation":[{"name":"Department of Pharmaceutical Botany and Ecology, ADINACO Research Group, Faculty of Pharmacy, Charles University, Akademika Heyrovsk\u00e9ho 1203, 500 05 Hradec Kr\u00e1lov\u00e9, Czech Republic"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Daniel","family":"Jun","sequence":"additional","affiliation":[{"name":"Department of Toxicology and Military Pharmacy, Faculty of Military Health Sciences, University of Defence, T\u0159ebe\u0161sk\u00e1 1575, 500 01 Hradec Kr\u00e1lov\u00e9, Czech Republic"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Martina","family":"Hrabinov\u00e1","sequence":"additional","affiliation":[{"name":"Department of Toxicology and Military Pharmacy, Faculty of Military Health Sciences, University of Defence, T\u0159ebe\u0161sk\u00e1 1575, 500 01 Hradec Kr\u00e1lov\u00e9, Czech Republic"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ji\u0159\u00ed","family":"Kune\u0161","sequence":"additional","affiliation":[{"name":"Department of Inorganic and Organic Chemistry, Faculty of Pharmacy, Charles University, Akademika Heyrovsk\u00e9ho 1203, 500 05 Hradec Kr\u00e1lov\u00e9, Czech Republic"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jakub","family":"Chlebek","sequence":"additional","affiliation":[{"name":"Department of Pharmaceutical Botany and Ecology, ADINACO Research Group, Faculty of Pharmacy, Charles University, Akademika Heyrovsk\u00e9ho 1203, 500 05 Hradec Kr\u00e1lov\u00e9, Czech Republic"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2017,7,14]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"550","DOI":"10.2174\/138920207783769549","article-title":"Current therapeutic options for Alzheimer\u2019s disease","volume":"8","year":"2007","journal-title":"Curr. Genom."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"1589","DOI":"10.1007\/s12272-010-1010-y","article-title":"Potential therapeutic agents against Alzheimer\u2019s disease from natural sources","volume":"33","author":"Park","year":"2010","journal-title":"Arch. Pharm. Res."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"7","DOI":"10.1155\/2014\/979730","article-title":"Recent updates in the treatment of neurodegenerative disorders using natural compounds","volume":"2014","author":"Rasool","year":"2014","journal-title":"Evid. Based Complement. Alternat. Med."},{"key":"ref_4","doi-asserted-by":"crossref","unstructured":"Nordberg, A., Ballard, C., Bullock, R., Darreh-Shori, T., and Somogyi, M. (2013). A Review of Butyrylcholinesterase as a Therapeutic Target in the Treatment of Alzheimer\u2019s disease. Prim. Care Companion CNS Disord., 15.","DOI":"10.4088\/PCC.12r01412"},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"615","DOI":"10.1016\/S0149-2918(04)90064-1","article-title":"Pharmacotherapeutic approaches to the treatment of Alzheimer\u2019s disease","volume":"26","author":"Standridge","year":"2004","journal-title":"Clin. Ther."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"159","DOI":"10.1185\/03007990152673800","article-title":"A New therapeutic target in Alzheimer\u2019s disease treatment: Attention to butyrylcholinesterase","volume":"17","author":"Greig","year":"2001","journal-title":"Curr. Med. Res. Opin."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"1402","DOI":"10.1111\/j.1471-4159.1984.tb02801.x","article-title":"Intralaminar neurochemical distributions in human midtemporal cortex: Comparison between Alzheimer\u2019s disease and the normal","volume":"42","author":"Perry","year":"1984","journal-title":"J. Neurochem."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"1457","DOI":"10.1136\/bmj.2.6150.1457","article-title":"Correlation of cholinergic abnormalities with senile plaques and mental test scores in senile dementia","volume":"2","author":"Perry","year":"1978","journal-title":"BMJ"},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"289","DOI":"10.1016\/j.phymed.2007.02.002","article-title":"Acetylcholinesterase inhibitors from plants","volume":"14","author":"Mukherjee","year":"2007","journal-title":"Phytomedicine"},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"57","DOI":"10.1016\/j.jep.2003.11.016","article-title":"Acetylcholinesterase and butyrylcholinesterase inhibitory activity of some Turkish medicinal plants","volume":"91","author":"Orhan","year":"2004","journal-title":"J. Ethnopharmacol."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"418","DOI":"10.1016\/j.jep.2005.09.032","article-title":"Screening of plants used in Danish folk medicine to treat memory dysfunction for acetylcholinesterase activity","volume":"104","author":"Adsersen","year":"2006","journal-title":"J. Ethnopharmacol."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"411","DOI":"10.1002\/pca.1066","article-title":"Rapid TLC\/GC-MS identification of acetylcholinesterase inhibitors in alkaloid extracts","volume":"19","author":"Berkov","year":"2008","journal-title":"Phytochem. Anal."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"235","DOI":"10.1016\/j.foodchem.2011.04.081","article-title":"Angiotensin-I-converting enzyme and prolyl endopeptidase inhibitory peptides from natural sources with a focus on marine processing by-products","volume":"129","author":"Wilson","year":"2011","journal-title":"Food Chem."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"1023","DOI":"10.1517\/13543776.2011.577416","article-title":"Low molecular weight inhibitors of prolyl oligopeptidase: A review of compounds patented from 2003 to 2010","volume":"21","author":"Giralt","year":"2011","journal-title":"Expert Opin. Ther. Pat."},{"key":"ref_15","doi-asserted-by":"crossref","unstructured":"M\u00e4nnist\u00f6, P.T., and Garc\u00eda-Horsman, J.A. (2017). Mechanism of Action of prolyl oligopeptidase (PREP) in degenerative brain diseases: Has peptidase activity only a modulatory role on the interactions of PREP with proteins?. Front. Aging Neurosci., 9.","DOI":"10.3389\/fnagi.2017.00027"},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"50","DOI":"10.1016\/j.cca.2006.09.001","article-title":"Suggested functions for prolyl oligopeptidase: A puzzling paradox","volume":"377","author":"Brandt","year":"2007","journal-title":"Clin. Chim. Acta"},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"31","DOI":"10.1111\/j.1527-3458.2002.tb00214.x","article-title":"S 17092: A prolyl endopeptidase inhibitor as a potential therapeutic drug for memory impairment. Preclinical and clinical studies","volume":"8","author":"Morain","year":"2002","journal-title":"CNS Drug Rev."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"271","DOI":"10.1016\/0006-3223(93)90083-P","article-title":"A peptide enhancement strategy in Alzheimer\u2019s disease; Pilot study with TRH_physostigmine infusions","volume":"34","author":"Mellow","year":"1993","journal-title":"Biol. Psychiatry"},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"403","DOI":"10.1007\/BF00451695","article-title":"Acute effects of high-dose thyrotrophin-releasing hormone infusions in Alzheimer\u2019s disease","volume":"98","author":"Mellow","year":"1989","journal-title":"Psychopharmacol."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"197","DOI":"10.1016\/S0944-7113(99)80009-9","article-title":"Screening of crude drug extracts for prolyl endopeptidase inhibitory activity","volume":"6","author":"Tezuka","year":"1999","journal-title":"Phytomedicine"},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"131","DOI":"10.1016\/0014-5793(90)80084-V","article-title":"Identification of a putative amyloid A4-generating enzyme as a prolyl endopeptidase","volume":"260","author":"Ishiura","year":"1990","journal-title":"FEBS Lett."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"3423","DOI":"10.1021\/jm901104g","article-title":"Inhibitors of prolyl oligopeptidases for the therapy of human diseases: Defining diseases and inhibitors","volume":"53","author":"Lawandi","year":"2010","journal-title":"J. Med. Chem."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"3309","DOI":"10.1097\/00001756-200110290-00032","article-title":"Brain prolyl oligopeptidase activity is associated with neuronal damage rather than \u03b2-amyloid accumulation","volume":"12","author":"Laitinen","year":"2001","journal-title":"Neuroreport"},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"350","DOI":"10.1046\/j.1365-2125.2000.00270.x","article-title":"Pharmacodynamic and pharmacokinetic profile of S 17092, a new orally active prolyl endopeptidase inhibitor, in elderly healthy volunteers. A phase I study","volume":"50","author":"Morain","year":"2000","journal-title":"Br. J. Clin. Pharmacol."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"176","DOI":"10.1159\/000107070","article-title":"Psychotropic Profile of S 17092, a prolyl endopeptidase inhibitor, Using quantitative EEG in young healthy volunteers","volume":"55","author":"Morain","year":"2007","journal-title":"Neuropsychobiology"},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"2252","DOI":"10.2174\/092986712800229032","article-title":"Current concepts on selected plant secondary metabolites with promising inhibitory effects against enzymes linked to Alzheimer\u2019s disease","volume":"19","author":"Orhan","year":"2012","journal-title":"Curr. Med. Chem."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"192","DOI":"10.1016\/j.fitote.2015.04.004","article-title":"Isoquinoline alkaloids as prolyl oligopeptidase inhibitors","volume":"103","author":"Chlebek","year":"2015","journal-title":"Fitoterapia"},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"91","DOI":"10.1002\/cbdv.201500033","article-title":"Isoquinoline alkaloids from Fumaria officinalis L. and their biological activities related to Alzheimer\u2019s disease","volume":"13","author":"Chlebek","year":"2016","journal-title":"Chem. Biodivers."},{"key":"ref_29","first-page":"1541","article-title":"Alkaloids from Chlidanthus fragrans and their acetylcholinesterase, butyrylcholinesterase and prolyl oligopeptidase","volume":"8","author":"Chlebek","year":"2013","journal-title":"Nat. Prod. Commun."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"257","DOI":"10.1007\/BF01089231","article-title":"Phylogeny of prickly poppies, Argemone (Papaveraceae), and the evolution of morphological and alkaloid characters based on ITS nrDNA sequence variation","volume":"218","author":"Schwarzbach","year":"1999","journal-title":"Plant Syst. Evol."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"108","DOI":"10.1016\/j.ejphar.2005.08.046","article-title":"Isoquercitrin from Argemone platyceras inhibits carbachol and leukotriene D4-induced contraction in guinea-pig airways","volume":"522","author":"Fernandez","year":"2005","journal-title":"Eur. J. Pharmacol."},{"key":"ref_32","first-page":"323","article-title":"Alkaloide aus Argemone platyceras","volume":"47","author":"Boit","year":"1960","journal-title":"Naturwissenschaften"},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"1728","DOI":"10.1135\/cccc19631728","article-title":"Alkaloide der Mohngew\u00e4chse (Papaveraceae) XII. \u00dcber die Alkaloide aus Argemone platyceras Link et Otto","volume":"28","year":"1963","journal-title":"Coll. Czech. Chem. Commun."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"2513","DOI":"10.1135\/cccc19732513","article-title":"Alkaloids of the Papaveraceae. L. On the quaternary alkaloids from Argemone platyceras Link et Otto","volume":"38","year":"1973","journal-title":"Coll. Czech. Chem. Commun."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"189","DOI":"10.1007\/BF00574736","article-title":"Alkaloids of four species of Argemone","volume":"22","author":"Israilov","year":"1986","journal-title":"Chem. Nat. Comp."},{"key":"ref_36","first-page":"580","article-title":"Alkaloids from several Argemone species","volume":"22","author":"Chelombitko","year":"1988","journal-title":"Pharm. Chem. J."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"285","DOI":"10.1135\/cccc19760285","article-title":"Quaternary alkaloids from the roots of Argemone platyceras Link et Otto","volume":"41","year":"1976","journal-title":"Coll. Czech. Chem. Commun."},{"key":"ref_38","first-page":"1279","article-title":"Identification of pavinane alkaloids in the genera Argemone and Eschscholzia by GC-MS","volume":"7","author":"Opletal","year":"2012","journal-title":"Nat. Prod. Commun."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"231","DOI":"10.1007\/s00044-008-9122-3","article-title":"Evaluation of new lead for acetylcholinesterase inhibition","volume":"18","author":"Khorana","year":"2009","journal-title":"Med. Chem. Res."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"375","DOI":"10.1093\/anatox\/35.6.375","article-title":"Suicide with cisatracurium and thiopental: Forensic and analytical aspects","volume":"35","author":"Castaing","year":"2011","journal-title":"J. Anal. Toxicol."},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"3331","DOI":"10.1016\/0031-9422(90)80210-8","article-title":"Assignments of 1H and 13C-NMR resonances of some isoquinoline alkaloids","volume":"29","author":"Janssen","year":"1990","journal-title":"Phytochemistry"},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"4775","DOI":"10.1248\/cpb.33.4775","article-title":"Utilization of protopine and related alkaloids. XVII. Spectroscopic studies on the ten-membered ring conformations of protopine and \u03b1-allocryptopine","volume":"33","author":"Takahashi","year":"1985","journal-title":"Chem. Pharm. Bull."},{"key":"ref_43","doi-asserted-by":"crossref","unstructured":"Leyva-Peralta, M.A., Robles-Zepeda, R.E., Garibay-Escobar, A., Ruiz-Bustos, E., Alvarez-Berber, L.P., and G\u00e1lvez-Ruiz, J.C. (2015). In vitro anti-proliferative activity of Argemone gracilenta and identification of some active components. BMC Complement. Alternat. Med., 15.","DOI":"10.1186\/s12906-015-0532-8"},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"3338","DOI":"10.1021\/ja00817a064","article-title":"A novel isoquinoline alkaloid group. The aporphine-pavine dimers","volume":"96","author":"Shamma","year":"1974","journal-title":"J. Am. Chem. Soc."},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"803","DOI":"10.1021\/np980311b","article-title":"Four dimeric aporphine-containing alkaloids from Thalictrum fauriei","volume":"62","author":"Lee","year":"1999","journal-title":"J. Nat. Prod."},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"2925","DOI":"10.1021\/jo01347a044","article-title":"Alkaloids of the Papaveraceae. IV. Argemone hispida and A. munita subspecies routundata","volume":"31","author":"Stermitz","year":"1966","journal-title":"J. Org. Chem."},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"1177","DOI":"10.1016\/S0040-4039(00)72391-4","article-title":"Alkaloids of Papaveraceae. III. Synthesis and structure of norargemonine","volume":"11","author":"Stermitz","year":"1966","journal-title":"Tetrahedron Lett."},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"461","DOI":"10.1016\/S0031-9422(00)90056-6","article-title":"Alkaloids of Argemone grandiflora","volume":"11","author":"Benn","year":"1972","journal-title":"Phytochemistry"},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"618","DOI":"10.1104\/pp.112.194886","article-title":"Characterization of three O-methyltransferases involved in noscapine biosynthesis in opium poppy","volume":"159","author":"Dang","year":"2012","journal-title":"Plant Physiol."},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"1773","DOI":"10.3987\/REV-10-673","article-title":"The chemical and biological properties of protopine and allocryptopine","volume":"81","author":"Vacek","year":"2010","journal-title":"Heterocycles"},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"293","DOI":"10.1021\/np50027a001","article-title":"The pavine and isopavine alkaloids","volume":"46","author":"Lantz","year":"1983","journal-title":"J. Nat. Prod."},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"1604","DOI":"10.1016\/j.clinthera.2015.05.510","article-title":"Current practices in the treatment of Alzheimer disease: Where is the evidence after the phase III Trials?","volume":"37","author":"Ehret","year":"2015","journal-title":"Clin. Ther."},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"27","DOI":"10.1016\/j.neuropharm.2013.07.004","article-title":"Therapeutics of Alzheimer\u2019s disease: Past, present and future","volume":"76","author":"Anand","year":"2014","journal-title":"Neuropharmacology"},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"251","DOI":"10.1111\/joim.12191","article-title":"Clinical trials and late-stage drug development for Alzheimer\u2019s disease: An appraisal from 1984 to 2014","volume":"275","author":"Schneider","year":"2014","journal-title":"J. Intern. Med."},{"key":"ref_55","doi-asserted-by":"crossref","first-page":"433","DOI":"10.1016\/j.phrs.2003.11.017","article-title":"Cholinesterase inhibitors: New roles and therapeutic alternatives","volume":"50","author":"Giacobini","year":"2004","journal-title":"Pharmacol. Res."},{"key":"ref_56","doi-asserted-by":"crossref","first-page":"697","DOI":"10.2147\/CIA.S129145","article-title":"Rivastigmine: The advantages of dual inhibition of acetylcholinesterase and butyrylcholinesterase and its role in subcortical vascular dementia and Parkinson\u2019s disease dementia","volume":"12","author":"Kandiah","year":"2017","journal-title":"Clin. Interv. Aging"},{"key":"ref_57","doi-asserted-by":"crossref","first-page":"88","DOI":"10.1016\/0006-2952(61)90145-9","article-title":"A new rapid colorimetric determination of acetylcholinesterase activity","volume":"7","author":"Ellman","year":"1961","journal-title":"Biochem. Pharmacol."},{"key":"ref_58","first-page":"1035","article-title":"Acetylcholinesterase and butyrylcholinesterase inhibitory compounds from Eschscholzia californica (Papaveraceae)","volume":"5","author":"Opletal","year":"2010","journal-title":"Nat. Prod. Commun."},{"key":"ref_59","doi-asserted-by":"crossref","first-page":"53","DOI":"10.1351\/pac200577010053","article-title":"Discovery of drug candidates from some Turkish plants and conservation of biodiversity","volume":"77","author":"Sener","year":"2005","journal-title":"Pure Appl. Chem."},{"key":"ref_60","first-page":"577","article-title":"Alkaloids from Peumus boldus and their acetylcholinesterase, butyrylcholinesterase and prolyl oligopeptidase inhibition activity","volume":"10","author":"Opletal","year":"2015","journal-title":"Nat. Prod. Commun."},{"key":"ref_61","first-page":"607","article-title":"Acetylcholinesterase and butyrylcholinesterase inhibitory compounds from Corydalis cava (Fumariaceae)","volume":"6","author":"Chlebek","year":"2011","journal-title":"Nat. Prod. Commun."},{"key":"ref_62","doi-asserted-by":"crossref","first-page":"2170","DOI":"10.1016\/j.bmcl.2006.01.067","article-title":"Isoquinoline derivatives as potential acetyl-cholinesterase inhibitors","volume":"16","author":"Markmee","year":"2006","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref_63","first-page":"313","article-title":"Molecular diversity in the bioactive compounds from Turkish plants\u2013evaluation of acetylcholinesterase inhibitory activity of Fumaria species","volume":"26","author":"Sener","year":"2004","journal-title":"J. Chem. Soc. Pak."},{"key":"ref_64","doi-asserted-by":"crossref","first-page":"6669","DOI":"10.1016\/j.bmc.2012.09.040","article-title":"Exploration of natural compounds as sources of new bifunctional scaffolds targeting cholinesterases and beta amyloid aggregation: The case of chelerythrine","volume":"20","author":"Brunhofer","year":"2012","journal-title":"Bioorg. Med. Chem."},{"key":"ref_65","doi-asserted-by":"crossref","first-page":"6732","DOI":"10.3390\/molecules16086732","article-title":"Berberine: A potential multipotent natural product to combat Alzheimer\u2019s disease","volume":"9","author":"Ji","year":"2011","journal-title":"Molecules"},{"key":"ref_66","doi-asserted-by":"crossref","first-page":"1433","DOI":"10.1248\/bpb.32.1433","article-title":"Anti-Alzheimer and antioxidant activities of Coptidis rhizoma alkaloids","volume":"32","author":"Jung","year":"2009","journal-title":"Biol. Pharm. Bull."},{"key":"ref_67","doi-asserted-by":"crossref","first-page":"2581","DOI":"10.1007\/s00216-015-8468-x","article-title":"Application of hydrostatic CCC-TLC-HPLC-ESI-TOF-MS for the bioguided fractionation of anticholinesterase alkaloids from Argemone mexicana L. roots","volume":"407","author":"Mroczek","year":"2015","journal-title":"Anal. Bioanal. Chem."},{"key":"ref_68","doi-asserted-by":"crossref","first-page":"642","DOI":"10.1021\/je0504360","article-title":"Solubility of berberine chloride in various solvents","volume":"51","author":"Lu","year":"2006","journal-title":"J. Chem. Eng. Data"},{"key":"ref_69","unstructured":"NCBI (2017, May 15). PubChem. Pubchem Compound, Available online: https:\/\/www.ncbi.nlm.nih.gov\/pccompound."},{"key":"ref_70","doi-asserted-by":"crossref","first-page":"172","DOI":"10.1016\/0076-6879(74)31019-1","article-title":"Preparation of impermeable ghosts and inside-out vesicles from human erythrocyte membranes","volume":"31","author":"Steck","year":"1974","journal-title":"Methods Enzymol."},{"key":"ref_71","doi-asserted-by":"crossref","first-page":"80114","DOI":"10.1039\/C6RA20205E","article-title":"Isolation of Amaryllidaceae alkaloids from Nerine bowdenii W. Watson and their biological activities","volume":"6","author":"Opletal","year":"2016","journal-title":"RSC Adv."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/22\/7\/1181\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T18:42:42Z","timestamp":1760208162000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/22\/7\/1181"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2017,7,14]]},"references-count":71,"journal-issue":{"issue":"7","published-online":{"date-parts":[[2017,7]]}},"alternative-id":["molecules22071181"],"URL":"https:\/\/doi.org\/10.3390\/molecules22071181","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2017,7,14]]}}}