Structural study of spirolide marine toxins by mass spectrometry Part I. Fragmentation pathways of 13-desmethyl spirolide C by collision-induced dissociation and infrared multiphoton

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DOIResolve DOI: http://doi.org/10.1007/s00216-003-2297-z
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TypeArticle
Journal titleAnalytical and Bioanalytical Chemistry
Volume378
Issue4
Pages969976; # of pages: 8
SubjectTriple-quadrupole mass spectrometry; Quadrupole-linear ion-trap mass spectrometry; infrared multiphoton dissociation mass spectrometry; collision-induced dissociation mass spectrometry; Fourier-transform ion cyclotron resonance mass spectrometry; MS fragmentation pathways; charge-remote fragmentation; phytoplankton; Alexandrium ostenfeldii; spirolide marine toxins; 13-Desmethyl spirolide C
AbstractA novel group of toxins, the spirolides, has been investigated by several mass spectrometric (MS) methods to enable structure elucidation and metabolite identification. These macrocyclic compounds, produced by the dinoflagellate Alexandrium ostenfeldii, are a new class of marine phycotoxin with characteristic spiro-linked tricyclic ether and imine moieties. A crude phytoplankton extract has been shown to contain known spirolides and several unknown compounds, present at low yet significant levels. This study has focused on mass spectrometric characterization of the main component of this extract, 13-desmethyl spirolide C. Collision-induced dissociation (CID) spectra were collected on triple-quadrupole and quadrupole linear ion-trap instruments. High-resolution Fourier-transform ion cyclotron resonance MS data revealed the accurate masses of the protonated molecule and the product ions formed by infrared multiphoton dissociation. A fragmentation scheme for this toxin has been proposed to explain the formation of the collision-induced fragments. Charge-remote fragmentations dominate the CID spectra, because there is only one predominantly basic site in this molecule, and prove to be structurally informative. Extensive MS characterization of 13-desmethyl spirolide C will undoubtedly be useful in the characterization of known and unknown spirolides and other related compounds.
Publication date
PublisherSpringer International Publishing AG
LanguageEnglish
AffiliationNational Research Council Canada; NRC Institute for Marine Biosciences
Peer reviewedYes
IdentifierNRC-IMB-42397
NRC number1325
NPARC number3538163
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Record identifier2136b1d0-8f70-44da-ba8b-bba78e7a944b
Record created2009-03-01
Record modified2016-11-15
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