Acetylcholinesterase and butyrylcholinesterase inhibitory compounds from Eschscholzia californica (Papaveraceae).
The roots and aerial parts of Eschscholzia californica Cham. (Papaveraceae) were extracted with ethanol. Repeated column chromatography, preparative TLC, and crystallization led to the isolation of fourteen isoquinoline alkaloids, the structures of which were determined on the basis of spectroscopic techniques and by comparison with literature values. One of the compounds isolated, 1-(3-hydroxy-4-methoxybenzyl)-2-methyl-6,7-methylenedioxy-1,2,3,4-tetrahydroisoquinoline (14), has not previously been isolated from a natural source. All isolated compounds were tested for human blood acetylcholinesterase (HuAChE) and human plasma butyrylcholinesterase (HuBuChE) inhibition activity. None of the compounds isolated significantly inhibited both HuAChE and HuBuChE, but the two benzylisoquinoline alkaloids, reticuline 9 and 14, showed promising inhibitory activity against HuBuChE.
Cahlíková
Lucie
L
Department of Pharmaceutical Botany and Ecology, Faculty of Pharmacy, Charles University, Heyrovského 1203, 500 05 Hradec Králové, Czech Republic. cahlikova@faf.cuni.cz
Macáková
Katerina
K
Kunes
Jirí
J
Kurfürst
Milan
M
Opletal
Lubomír
L
Cvacka
Josef
J
Chlebek
Jakub
J
Blundene
Gerald
G
D000110:Acetylcholinesterase / Q000378:metabolism*; D044182:Benzylisoquinolines / Q000737:chemistry / Q000494:pharmacology; D002091:Butyrylcholinesterase / Q000378:metabolism*; D004789:Enzyme Activation / Q000187:drug effects; D004791:Enzyme Inhibitors / Q000737:chemistry / Q000494:pharmacology; D031675:Eschscholzia / Q000737:chemistry*; D006801:Humans; D044005:Tetrahydroisoquinolines / Q000737:chemistry / Q000494:pharmacology
D044182:Benzylisoquinolines; D004791:Enzyme Inhibitors; D044005:Tetrahydroisoquinolines; C014843:1,2,3,4-tetrahydroisoquinoline; D000110:Acetylcholinesterase; D002091:Butyrylcholinesterase; C003298:reticuline