GC‐MS of amaryllidaceous galanthamine‐type alkaloids |
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Authors: | Strahil Berkov Francesc Viladomat Carles Codina Sergio Suárez Angel Ravelo Jaume Bastida |
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Institution: | 1. Departament de Productes Naturals, Biologia Vegetal i Edafologia, Facultat de Farmàcia, Universitat de Barcelona, , 08028 Barcelona, Spain;2. AgroBioInstitute, , 8 Dragan Tzankov Blvd., 1164 Sofia, Bulgaria;3. Instituto Universitario de Bio‐Orgánica Antonio González, Avenida Astrofísico Francisco Sánchez 2, , 38206 La Laguna, Tenerife, Spain |
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Abstract: | Galanthamine‐type alkaloids produced by plants of the Amaryllidaceae family are potent acetylcholinesterase inhibitors. One of them, galanthamine, has been marketed as a hydrobromide salt for the treatment of Alzheimer's disease. In the present work, gas chromatography with electron impact mass spectrometry (GC‐EIMS) fragmentation of 12 reference compounds isolated from various amaryllidaceous plants and identified by spectroscopic methods (1D and 2D nuclear magnetic resonance, circular dichroism, high‐resolution MS (HRMS) and EIMS) was studied by tandem mass spectrometry (GC‐MS/MS) and accurate mass measurements (GC‐HRMS). The studied compounds showed good peak shape and efficient GC separation with a GC‐MS fragmentation pattern similar to that obtained by direct insertion probe. With the exception of galanthamine‐N‐oxide and N‐formylnorgalanthamine, the galanthamine‐type compounds showed abundant M]+. and M‐H]+ ions. A typical fragmentation pattern was also observed, depending on the substituents of the skeleton. Based on the fragmentation pathways of reference compounds, three other galanthamine‐type alkaloids, including 3‐O‐(2′‐butenoyl)sanguinine, which possesses a previously unelucidated structure, were identified in Leucojum aestivum ssp. pulchelum, a species endemic to the Balearic islands. GC‐MS can be successfully applied to Amaryllidaceae plant samples in the routine screening for potentially new or known bioactive molecules, chemotaxonomy, biodiversity and identification of impurities in pharmaceutical substances. Copyright © 2012 John Wiley & Sons, Ltd. |
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Keywords: | Amaryllidaceae alkaloids galanthamine GC‐MS tandem mass spectrometry |
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