Berkov_2012_J.Mass.Spectrom_47_1065

Reference

Title : GC-MS of amaryllidaceous galanthamine-type alkaloids - Berkov_2012_J.Mass.Spectrom_47_1065
Author(s) : Berkov S , Viladomat F , Codina C , Suarez S , Ravelo A , Bastida J
Ref : J Mass Spectrom , 47 :1065 , 2012
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.
ESTHER : Berkov_2012_J.Mass.Spectrom_47_1065
PubMedSearch : Berkov_2012_J.Mass.Spectrom_47_1065
PubMedID: 22899516

Related information

Inhibitor SanguinineGalanthamine

Citations formats

Berkov S, Viladomat F, Codina C, Suarez S, Ravelo A, Bastida J (2012)
GC-MS of amaryllidaceous galanthamine-type alkaloids
J Mass Spectrom 47 :1065

Berkov S, Viladomat F, Codina C, Suarez S, Ravelo A, Bastida J (2012)
J Mass Spectrom 47 :1065

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    [paper] => Berkov_2012_J.Mass.Spectrom_47_1065
    [author] => Berkov S || Viladomat F || Codina C || Suarez S || Ravelo A || Bastida J
    [year] => 2012
    [title] => GC-MS of amaryllidaceous galanthamine-type alkaloids
    [journal] => J Mass Spectrom
    [volume] => 47
    [page] => 1065
    [medline] => 22899516
    [abstract] => Berkov_2012_J.Mass.Spectrom_47_1065
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            [content] => 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.
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