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

Abstract

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 = 24.4 ± 1.2 µM), and norlycoramine (11) demonstrated promising POP inhibition (IC = 0.21 ± 0.01 mM).

Amaryllidaceae Alkaloids as Potential Glycogen Synthase Kinase-3β Inhibitors

“…All Amaryllidaceae alkaloids tested have been previously isolated at the Department of Pharmaceutical Botany, Faculty of Pharmacy in Hradec Králové from various Amaryllidaceae plant species ( Zephyranthes robusta [ 39 , 40 ], Chlidanthus fragrans [ 27 , 41 ], Nerine bowdenii [ 42 ], Narcissus poeticus cv. Pink Parasol [ 43 ], and N. poeticus cv. Brackenhurst [ 44 ]).…”

Biologically active isoquinoline alkaloids covering 2014–2018

“…Ancistrocladus tectorius [84] Ancistrocladus ealaensis [86] Ancistrocladus ealaensis [32] T A B L E 1 (Continued) Amaryllidaceae family [98] Narcissus poeticus cv. Pink Parasol [99] (Continues) The alkaloids in this classification have the simplest structures and are distributed mainly in the genera Papaver,…”

“…24,103 The pyrrolophenanthridine alkaloids seco-isopowellaminone (336), haemanthamine (326), and incartine (337) also exhibited weak anti-human AChE activity. 99 (+)-Parfumidine (79), a spirobenzylisoquinoline alkaloid, exhibited POP inhibitory activity with an IC 50 value of 99 µM, compared with 3.27 µM for the positive drug (Z)-pro-prolinal. 24 The known benzophenanthridine alkaloid chelerythrine potently and selectively inhibited an isoform of recombinant human monoamine oxidase A (MAO-A) with an IC 50 value of 0.55 μM.…”

Amaryllidaceae Alkaloids of Different Structural Types from Narcissus L. cv. Professor Einstein and Their Cytotoxic Activity

“…The AA are classified into 9 main structural types (crinine, galanthamine, haemanthamine, homolycorine, lycorine, montanine, narciclasine, norbelladine, and tazettine) alongside more than 10 others (plicamine, galanthindole, augustamine, graciline, etc.). These minor structure types are usually found in trace amounts and are most often represented by single alkaloids [9,10]. Galanthamine, a selective, competitive acetylcholinesterase inhibitor with antioxidant properties is the most important AA identified so far.…”

“…For commercial production of AAs, the cultivars are preferred over native species because of their availability. Some Narcissus cultivars have been already studied in detail, and a number of AAs have been isolated throughout the years [7,10,21]. From previous phytochemical studies of 40 differing Narcissus cultivars, 14 AAs were identified in the alkaloid extract of Narcissus cv.…”