Phytochemical and Biological Investigation of Narcissus pseudonarcissus Cultivated in Egypt

A phytochemical investigation of the alkaloidal content of the bulbs of Narcissus pseudonarcissus cultivated in Egypt resulted in the isolation of the alkaloid; 9-O-demethyl-7-O-methyllycorenine (5) in addition to the eight known alkaloids; homolycorine (1), 7-O-methyloduline (2), 7-O-methyllycorenine (3), hippeastrine (4), 9-O-demethylhomolycorine (6), galanthamine (7), haemanthamine (8) and lycorine. Structural determination of the isolated alkaloids was established by different spectral analyses (UV, MS, NMR and 2D-NMR). The isolation of 9-O-demethyl-7-O-methyllycorenine (5) is reported here for the first time from family Amaryllidaceae. The chemotaxonomic significance of the isolated alkaloids was also studied; six of the isolated alkaloids belong to the homolycorine series which is a distinctive feature for the section Pseudonarcissi. The alkaloids of the homolycorine series are absent from some tribes of the Amaryllidaceae, such as the Amaryllideae or Hemantheae. Moreover, all the Narcissus alkaloids of the homolycorine series display a B/C ring junction with a cis stereochemistry Furthermore, the antimicrobial activity of some isolated alkaloids has been studied. It is noteworthy that this is the first phytochemical and biological investigation to be carried out on the Amaryllidaceae plant N. pseudonarcissus grown in Egypt.