title: Alkaloids from Peumus boldus and their acetylcholinesterase, butyrylcholinesterase and prolyl oligopeptidase inhibition activity.
abstract: Eleven isoquinoline alkaloids (1-11) were isolated from dried leaves of Peumus boldus Mol. by standard chromatographic methods. The chemical structures were elucidated by MS, and 1D and 2D NMR spectroscopic analysis, and by comparison with literature data. Compounds isolated in sufficient amount were evaluated for their acetylcholinesterase, and butyrylcholinesterase inhibition activity using Ellman's method. In the prolyl oligopeptidase assay, Z-Gly-Pro-p-nitroanilide was used as substrate. Promising butyrylcholinesterase inhibition activities were demonstrated by two benzylisoquinoline alkaloids, reticuline (8) and N-methylcoclaurine (9), with IC50 values of 33.6 ± 3.0 µM and 15.0 ± 1.4 µM, respectively. Important prolyl oligopeptidase inhibition activities were shown by N-methyllaurotetanine (6) and sinoacutine (4) with IC50 values of 135.4 ± 23.2 µM and 143.1 ± 25.4 µM, respectively. Other tested compounds were considered inactive.
authors.forename: Anna
authors.initials: A
authors.lastname: Hošt'álková
authors.forename: Lubomír
authors.initials: L
authors.lastname: Opletal
authors.forename: Jiří
authors.initials: J
authors.lastname: Kuneš
authors.forename: Zdeněk
authors.initials: Z
authors.lastname: Novák
authors.forename: Martina
authors.initials: M
authors.lastname: Hrabinová
authors.forename: Jakub
authors.initials: J
authors.lastname: Chlebek
authors.forename: Lukáš
authors.initials: L
authors.lastname: Čegan
authors.forename: Lucie
authors.initials: L
authors.lastname: Cahlíková
mesh_terms: D000110:Acetylcholinesterase / Q000378:metabolism*; D000470:Alkaloids / Q000737:chemistry* / Q000494:pharmacology*; D002091:Butyrylcholinesterase / Q000378:metabolism*; D002800:Cholinesterase Inhibitors / Q000737:chemistry / Q000494:pharmacology*; D006801:Humans; D031611:Peumus / Q000737:chemistry*; D018515:Plant Leaves / Q000737:chemistry; D000085822:Prolyl Oligopeptidases; D012697:Serine Endopeptidases / Q000378:metabolism*; D013379:Substrate Specificity
chemical_list: D000470:Alkaloids; D002800:Cholinesterase Inhibitors; D000110:Acetylcholinesterase; D002091:Butyrylcholinesterase; D012697:Serine Endopeptidases; C000705287:PREPL protein, human; D000085822:Prolyl Oligopeptidases