Alkaloids from Narcissus poeticus cv. Pink Parasol of various structural types and their biological activity

Fifteen Amaryllidaceae alkaloids ( 1 – 15 ) of various structural types were isolated by standard chromatographic methods from fresh bulbs of Narcissus poeticus cv. Pink Parasol. The chemical structures were elucidated by MS, and 1D and 2D NMR spectroscopic analyses, and by comparison with literature data. Narcipavline ( 5 ) and narcikachnine ( 6 ) are reported here for the first time. In their structure are combined two basic structural types of Amaryllidaceae alkaloids (galanthamine- and galanthindole-structural types), which represent a new structural type of these compounds. Alkaloids isolated in sufficient amounts were evaluated for their human erythrocytic acetylcholinesterase, and human serum butyrylcholinesterase (HuBuChE) inhibition activity using Ellman’s method. Z -Gly-Pro- p -nitroanilide was used as substrate in the prolyl oligopeptidase (POP) assay. Untested alkaloids were also screened for their cytotoxic activity against a small panel of human cancer cells, which spanned cell lines from different tissue types. In parallel, MRC-5 human fibroblasts were employed to determine overall toxicity against noncancerous cells. Some compounds were evaluated for their antiprotozoal activity. The newly isolated alkaloid narcipavline ( 5 ) showed interesting HuBuChE inhibition activity (IC 50 = 24.4 ± 1.2 µM), and norlycoramine ( 11 ) demonstrated promising POP inhibition (IC 50 = 0.21 ± 0.01 mM).