Biologicky aktivní metabolity rostlin VII. Alkaloidy Eschscholtzia californica CHAM. a jejich biologická aktivita

Univerzita Karlova v Praze, Farmaceutická fakulta v Hradci Králové Katedra: Katedra farmaceutické botaniky a ekologie Kandidát: Mgr. Lucia Bednaříková Konzultant: Ing. Lucie Cahlíková, Ph.D. Názov rigoróznej práce: Biologicky aktivní metabolity rostlin VII. Alkaloidy Eschscholtzia californica CHAM. a jejich biologická aktivita Predmetom rigoróznej práce bolo spracovanie bázického výtrepku kvartérnych alkaloidov vo forme jodidov z Eschscholtzia californica CHAM. (Papaveraceae). Pomocou bežných chromatografických metód boli izolované tri alkaloidy v čistej forme, ktoré boli následne podrobené štruktúrnej analýze (MS a NMR štúdie). Prvou izolovanou látkou bol terciárny alkaloid allokryptopín, druhá izolovaná látka bola identifikovaná ako kvartérna báza (-)-7-O- metyl-éterneokaryachín-N-metyljodid, tretím izolovaným alkaloidom bola kvartérna báza kalifornidín. Všetky tri alkaloidy boli z E. californica už v minulosti izolované. Všetky izolované látky boli testované na ich inhibičnú aktivitu voči ľudskej erytrocytárnej acetylcholinesteráze (HuAChE) a ľudskej sérovej butyrylcholinesteráze (HuBuChE). Pre allokryptopín boli namerané hodnoty IC50 (HuAChE) = 114,4 ± 3,2 μM a IC50 (HuBuChE) = 655 ± 12 μM. Inhibičné hodnoty získané pre (-)-7-O-metyl-éterneokaryachín-N-metyljodid boli IC50 (HuAChE) = 148,2 ±...Charles University in Prague, Faculty of Pharmacy in Hradec Králové Department: Department of Pharmaceutical Botany and Ecology Candidate: Mgr. Lucia Bednaříková Consultant: Ing. Lucie Cahlíková, Ph.D. Title of Thesis: Biologically active metabolites of plants VII. Alkaloids from Eschscholtzia californica CHAM. and their biological activity The aim of the thesis was to process the alkaline fraction of quaternary alkaloids in the form of their iodides from Eschscholtzia californica CHAM. (Papaveraceae). By means of common chromatographic methods three alkaloids were isolated in pure form and subsequently subjected to structural analysis (MS and NMR studies). The first isolated substance was a tertiary alkaloid allocryptopine, the second one was identified as a quaternary base (-)-7-O-methyl- etherneocaryachine-N-methiodide and the third one was a quaternary base californidine. All the isolated alkaloids have previously been isolated from E. californica. The isolated substances were tested for their inhibitory activity against human erythrocyte acetylcholinesterase (HuAChE) and human plasma butyrylcholinesterase (HuBuChE). The measured values for allocryptopine were IC50 (HuAChE) = 114.4 ± 3.2 μM and IC50 (HuBuChE) = 655 ± 12 μM. The values for (-)-7-O-methyl-etherneocaryachine-N-methiodide were IC50...Katedra farmaceutické botanikyDepartment of Pharmaceutical BotanyFaculty of Pharmacy in Hradec KrálovéFarmaceutická fakulta v Hradci Králov