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Isolation of alkaloid galanthin from Narcissus poeticus recurvus and its semi-synthetic derivatives
Lojkásek, Matěj ; Suchánková, Daniela (advisor) ; Kučera, Tomáš (referee)
Charles University Faculty of Pharmacy in Hradec Králové Department of Pharmacognosy Candidate: Matěj Lojkásek Instructor: Pharm.Dr. Daniela Hulcová, Ph.D. Title of thesis: Isolation of alkaloids from Narcissus poeticus recurvus and its semi-synthetic derivatives Key words: Amaryllidaceae, galanthin, semi-synthetic derivatives, Alzheimer's disease, acetylcholinesterase, butyrylcholinesterase, cytotoxicity. As part of the thesis, two alkaloid substances (galanthin and cherylline) were isolated from the bulbs of the mother plant Narcissus poeticus recurvus using preparative TLV chromatography. The obtained galanthin was subsequently used for the preparation of 6 derivatives of this alkaloid, namely esters. Galanthine esters were prepared by acylation of the hydroxyl group. The derivatives were identified by NMR, HMRS and the optical rotation was measured. In the end, only 5 of the prepared substances were recovered in sufficient quantity and purity. Derivative G2 could not be retained. In the case of G1, G4 and G6, the yield of the reaction was higher than 50%, whereas for G3 it was 49.55%, G2 19.23% and G5 39.79%. All prepared derivatives except G2 were tested for inhibitory activity against cholinesterases by the Ellman method using recombinant enzymes. Unfortunately, according to the IC50 values...
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