Chapter 3 Chemical and Biological Aspects of Narcissus Alkaloids

Revised NMR data for Incartine: an Alkaloid from Galanthus elwesii

“…The complete assignment of the 1 H-NMR spectrum (Table 1), performed by 2D COSY and NOESY experiments, revealed a compound with a lycorine type structure whose chemical shifts were closely comparable with those of galanthine [6]. The absence of an olefinic proton in 1, characteristic of the lycorine type compounds [5], as well as the similarity of the chemical shifts of the H-11 and H-12 protons with those of the homolycorine type C3 -C4 epoxy derivatives, galwesine and 9-O-demethylgalwesine [4] indicated a C3 -C4 epoxy ring. On the basis of the 1 H-NMR spectral data, 1 was identified as incartine, an alkaloid that has been isolated only once from the flowers of Lycoris incarnata [7].…”

“…The HRMS of compound 1, with a parent ion at m/z 333.1572 (calc. mass -333.1576), suggested the molecular formula C 18 H 23 NO 5 . The complete assignment of the 1 H-NMR spectrum (Table 1), performed by 2D COSY and NOESY experiments, revealed a compound with a lycorine type structure whose chemical shifts were closely comparable with those of galanthine [6].…”

“…A wide range of bioactivities have been reported for compounds 2-5 [5,8]. Alkaloids with the lycorine type skeleton possess significant antiviral and cytotoxic activities.…”

“…Earlier investigations in Galanthus elwesii have resulted in the isolation of a large variety of Amaryllidaceae alkaloids [2][3][4]. Many of these compounds have been found to exhibit among others, strong acetylcholinesterase inhibitory, cytotoxic and antiviral activities [5].…”

The Genus Galanthus: A Source of Bioactive Compounds

“…As a result of extensive phytochemical studies, over 500 alkaloids have been isolated from the amaryllidaceous plants (Zhong, 2005). The Amaryllidaceae type alkaloids have been structurally classified into nine main subgroups, namely lycorine, crinine, haemanthamine, narciclasine, galanthamine, tazettine, homolycorine, montanine www.intechopen.com and norbelladine (Bastida et al, 2006). In the genus Galanthus, however, two new structural subgroups, graciline and plicamine type alkaloids, have been found (Ünver, 2007).…”