Mass spectrometry of some amaryllidaceae alkaloids.

Jonquailine, a new pretazettine-type alkaloid isolated from Narcissus jonquilla quail, with activity against drug-resistant cancer

“…A final proof of the natural origin of jonquailine was found by extracting the bulbs of N. jonquilla quail described above but using ethanol and analyzing the crude extract by GC/MS as detailed in the experimental for alkaloids and corresponding isocarbostyril content. Lycorine, haemanthamine and narciclasine, the main components, as well as the new alkaloid jonquailine ( t R = 24.59 min) were identified also by co-injection with their standards and by comparing the mass spectral fragmentation with standard reference spectra reported in literature [41,42]. Minor components were identified as deoxytazettine, epi-macronine, trisphaeridine and tazettine [41,42].…”

“…The split ratio was 1:20. The alkaloids and narciclasine were identified by applying co-chromatography with standards previously isolated from N. jonquilla quail bulbs and other Amaryllidaceae plants, by comparing the mass spectral fragmentation with standard reference spectral data from NIST (NIST Mass Spectral Database, PC-Version 5.0 (2005), National Institute of Standardization and Technology, Gaithersburg, MD, USA), and by comparing mass spectral data with those of literature [41,42]. …”

Identification of Alkaloids from Hippeastrum aulicum (Ker Gawl.) Herb. (Amaryllidaceae) Using CGC-MS and Ambient Ionization Mass Spectrometry (PS‑MS and LS-MS)

“…Concerning the skeleton types found in H. aulicum, the EI mass fragmentation of homolycorine-type alkaloid D 3,4 -derivatives features a dominant retro-Diels Alder process and cleavage of ring C, yielding a very abundant ion peak characterized by the pyrrolidine ring (m/z 109). 33 Consequently, the alkaloids 9, 10, 12, 27, 29 and 30 show the base peak at m/z 109 (100%), with all remaining ion peaks displaying less than 10% of abundance. Otherwise, alkaloid 31 possesses a methoxyl group at C-2 and so displays the base peak at m/z 139, which is in agreement with the pyrrolidine residue along with the methoxyl substituent at C-2.…”

“…Otherwise, alkaloid 31 possesses a methoxyl group at C-2 and so displays the base peak at m/z 139, which is in agreement with the pyrrolidine residue along with the methoxyl substituent at C-2. 33 Lycorinetype compounds, which are biogenetically related to the homolycorine skeleton, also suffer a retro-Diels Alder process followed by the loss of C-1 and C-2, along with their substituents, yielding the base peak at m/z 228, 242 and 226 for compounds 14, 21 and 25, respectively. Alkaloid 26, which lacks the 3,4-unsaturation, possesses the base peak at m/z 332 (M-1) instead of the typical base peak after the retro-Diels Alder process.…”

Phytochemical and Biological Investigation of Hymenocallis littoralisSalisb.

“…The 1 H-NMR data of 2 showed the presence of two s at d(H) 6.92 and 7.46, assigned, respectively, to HÀC (11) and HÀC (8) of the benzopyran moiety, as well as three s typical for the methylenedioxy (d(H) 6.05, 6.06) and the N-methyl (d(H) 2.04) groups [7 -10]. These structural features were confirmed by 13 C-NMR, which showed, beside the signals of a tetrasubstituted aromatic ring, those of a lactone, a methylenedioxy moiety, and an N-methyl group at d(C) 164.6, 102.1, and 43.5, respectively [10].…”