Bioactive alkaloid extracts from Narcissus broussonetii: mass spectral studies.
Plants of the Amaryllidaceae family are a well-known source of tetrahydroisoquinoline alkaloids with a wide range of biological activities, including antiviral, antitumoral, antiparasitic, psychopharmacological, and acetylcholinesterase inhibitory, among others. Recent advances in the use of GC or LC coupled to MS have allowed a chemically guided isolation of uncommon and bioactive alkaloids. In the present work, analytical methods were applied to study the alkaloid profile of Narcissus broussonetii, a plant endemic to North Africa. Using the GC-MS technique and an in-home mass fragmentation database, twenty-three alkaloids were identified, including the very rare dinitrogenous alkaloids obliquine, plicamine, and secoplicamine. Applying LC-ESI-LTQ-Orbitrap-MS, fragmentation profiles were found to be similar for obliquine and plicamine but different for secoplicamine. Pretazettine, a potent cytotoxic alkaloid, was also isolated from N. broussonetii, although its identification by GC-MS was only possible after a BSTFA-derivatization. The silylated crude methanolic extract only showed the presence of pretazettine-TMS, confirming that tazettine was formed after the alkaloid extraction. The same observation was made in Narcissus cultivars in which tazettine had been detected as the major alkaloid. As part of an ongoing project on MS of Amaryllidaceae alkaloids, the silylated tazettine and pretazettine were studied by GC-MS/MS, and found to differ in their fragmentation routes. Finally, the EtOAc extract of N. broussonetii showed notable in vitro activity against Trypanosoma cruzi, with an IC(50) value of 1.77 μg/ml.
Department of Natural Products, Plant Biology and Soil Science, Faculty of Pharmacy, Av. Diagonal 643, 08028 Barcelona, Spain.
Jean Paulo
JP
de Andrade
Natalia Belén
NB
Pigni
Laura
L
Torras-Claveria
Strahil
S
Berkov
Carles
C
Codina
Francesc
F
Viladomat
Jaume
J
Bastida
D047151:Amaryllidaceae Alkaloids / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D000818:Animals; D000977:Antiparasitic Agents / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D002460:Cell Line; D008401:Gas Chromatography-Mass Spectrometry; D006576:Heterocyclic Compounds, 4 or More Rings / Q000737:chemistry; D020128:Inhibitory Concentration 50; D007546:Isoquinolines / Q000737:chemistry; D007893:Leishmania donovani / Q000187:drug effects / Q000254:growth & development; D051379:Mice; D015394:Molecular Structure; D031427:Narcissus / Q000737:chemistry*; D021261:Parasitic Sensitivity Tests; D010936:Plant Extracts / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D018517:Plant Roots; D010963:Plasmodium falciparum / Q000187:drug effects / Q000254:growth & development; D051381:Rats; D012997:Solvents / Q000737:chemistry; D021241:Spectrometry, Mass, Electrospray Ionization; D053719:Tandem Mass Spectrometry; D014349:Trypanosoma cruzi / Q000187:drug effects / Q000254:growth & development
D047151:Amaryllidaceae Alkaloids; D000977:Antiparasitic Agents; D006576:Heterocyclic Compounds, 4 or More Rings; D007546:Isoquinolines; D010936:Plant Extracts; D012997:Solvents; C473532:obliquine; C544217:plicamine; C011361:tazettine