Structural study of spirolide marine toxins by mass spectrometry |
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Authors: | Lekha?Sleno Anthony?J?Windust Email author" target="_blank">Dietrich?A?VolmerEmail author |
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Institution: | (1) Institute for Marine Biosciences, National Research Council, 1411 Oxford Street, Halifax, Nova Scotia, B3H 3Z1, Canada |
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Abstract: | A 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. |
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Keywords: | Triple-quadrupole mass spectrometry Quadrupole-linear ion-trap mass spectrometry Collision-induced dissociation mass spectrometry Infrared multiphoton 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 |
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