title: Acetylcholinesterase and butyrylcholinesterase inhibitory compounds from Chelidonium majus (Papaveraceae).
abstract: The roots and aerial parts of Chelidonium majus L. were extracted with EtOH and fractionated using CHCl3 and EtOH. Repeated column chromatography, preparative TLC and crystallization led to the isolation of five isoquinoline alkaloids, stylopine (3), chelidonine (4), homochelidonine (5), protopine (6), and allocryptopine (7), along with two isolation artifacts 6-ethoxydihydrosanguinarine (1) and 6-ethoxydihydrochelerythrine (2). All isolated compounds were tested for human blood acetylcholinesterase (HuAChE) and human plasma butyrylcholinesterase (HuBuChE) inhibitory activity. The isolation artifacts exhibited the highest activity against HuAChE and HuBuChE with IC50 values of 0.83 +/- 0.04 microM and 4.20 +/- 0.19 microM for 6-ethoxydihydrochelerythrine and 3.25 +/- 0.24 microM and 4.51 +/- 0.31 microM for 6-ethoxydihydrosanguinarine. The most active of the naturally-occurring alkaloids was chelidonine, which inhibited both HuAChE and HuBuChE in a dose-dependent manner with IC50 values of 26.8 +/- 1.2 microM and 31.9 +/- 1.4 microM, respectively.
authors.affiliation: Department of Pharmaceutical Botany and Ecology, Faculty of Pharmacy, Charles University, Heyrovského 1203, 500 05 Hradec Králové, Czech Republic. cahlikova@faf.cuni.cz
authors.forename: Lucie
authors.initials: L
authors.lastname: Cahlíková
authors.forename: Lubomír
authors.initials: L
authors.lastname: Opletal
authors.forename: Milan
authors.initials: M
authors.lastname: Kurfürst
authors.forename: Katerina
authors.initials: K
authors.lastname: Macáková
authors.forename: Andrea
authors.initials: A
authors.lastname: Kulhánková
authors.forename: Anna
authors.initials: A
authors.lastname: Hostálková
mesh_terms: D000110:Acetylcholinesterase / Q000378:metabolism*; D002091:Butyrylcholinesterase / Q000378:metabolism*; D028281:Chelidonium / Q000737:chemistry*; D002800:Cholinesterase Inhibitors / Q000737:chemistry* / Q000494:pharmacology; D004910:Erythrocyte Membrane / Q000187:drug effects; D006801:Humans; D035261:Plant Components, Aerial / Q000737:chemistry; D018517:Plant Roots / Q000737:chemistry
chemical_list: D002800:Cholinesterase Inhibitors; D000110:Acetylcholinesterase; D002091:Butyrylcholinesterase