Mass Spectrometry-Based Characterization of New Spirolides from Alexandrium ostenfeldii (Dinophyceae)
Spirolides belong to a group of marine phycotoxins produced by the marine planktonic dinophyte Alexandrium ostenfeldii. Composed of an imine moiety and a spiroketal ring system within a macrocylcle, spirolides are highly diverse with toxin types that vary among different strains. This study aims to...
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ftpubmed:oai:pubmedcentral.nih.gov:7599687 2023-05-15T16:29:53+02:00 Mass Spectrometry-Based Characterization of New Spirolides from Alexandrium ostenfeldii (Dinophyceae) Nieva, Joyce A. Tebben, Jan Tillmann, Urban Wohlrab, Sylke Krock, Bernd 2020-10-02 http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7599687/ http://www.ncbi.nlm.nih.gov/pubmed/33023163 https://doi.org/10.3390/md18100505 en eng MDPI http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7599687/ http://www.ncbi.nlm.nih.gov/pubmed/33023163 http://dx.doi.org/10.3390/md18100505 © 2020 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/). CC-BY Mar Drugs Article Text 2020 ftpubmed https://doi.org/10.3390/md18100505 2020-11-08T01:47:50Z Spirolides belong to a group of marine phycotoxins produced by the marine planktonic dinophyte Alexandrium ostenfeldii. Composed of an imine moiety and a spiroketal ring system within a macrocylcle, spirolides are highly diverse with toxin types that vary among different strains. This study aims to characterize the spirolides from clonal A. ostenfeldii strains collected from The Netherlands, Greenland and Norway by mass spectral techniques. The structural characterization of unknown spirolides as inferred from high-resolution mass spectrometry (HR-MS) and collision induced dissociation (CID) spectra revealed the presence of nine novel spirolides that have the pseudo-molecular ions m/z 670 (1), m/z 666 (2), m/z 696 (3), m/z 678 (4), m/z 694 (5), m/z 708 (6), m/z 720 (7), m/z 722 (8) and m/z 738 (9). Of the nine new spirolides proposed in this study, compound 1 was suggested to have a truncated side chain in lieu of the commonly observed butenolide ring in spirolides. Moreover, there is indication that compound 5 might belong to new spirolide subclasses with a trispiroketal ring configuration having a 6:5:6 trispiroketal ring system. On the other hand, the other compounds were proposed as C- and G-type SPX, respectively. Compound 7 is proposed as the first G-type SPX with a 10-hydroxylation as usually observed in C-type SPX. This mass spectrometry-based study thus demonstrates that structural variability of spirolides is larger than previously known and does not only include the presence or absence of certain functional groups but also involves the triketal ring system. Text Greenland PubMed Central (PMC) Greenland Norway Marine Drugs 18 10 505 |
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Article Nieva, Joyce A. Tebben, Jan Tillmann, Urban Wohlrab, Sylke Krock, Bernd Mass Spectrometry-Based Characterization of New Spirolides from Alexandrium ostenfeldii (Dinophyceae) |
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Spirolides belong to a group of marine phycotoxins produced by the marine planktonic dinophyte Alexandrium ostenfeldii. Composed of an imine moiety and a spiroketal ring system within a macrocylcle, spirolides are highly diverse with toxin types that vary among different strains. This study aims to characterize the spirolides from clonal A. ostenfeldii strains collected from The Netherlands, Greenland and Norway by mass spectral techniques. The structural characterization of unknown spirolides as inferred from high-resolution mass spectrometry (HR-MS) and collision induced dissociation (CID) spectra revealed the presence of nine novel spirolides that have the pseudo-molecular ions m/z 670 (1), m/z 666 (2), m/z 696 (3), m/z 678 (4), m/z 694 (5), m/z 708 (6), m/z 720 (7), m/z 722 (8) and m/z 738 (9). Of the nine new spirolides proposed in this study, compound 1 was suggested to have a truncated side chain in lieu of the commonly observed butenolide ring in spirolides. Moreover, there is indication that compound 5 might belong to new spirolide subclasses with a trispiroketal ring configuration having a 6:5:6 trispiroketal ring system. On the other hand, the other compounds were proposed as C- and G-type SPX, respectively. Compound 7 is proposed as the first G-type SPX with a 10-hydroxylation as usually observed in C-type SPX. This mass spectrometry-based study thus demonstrates that structural variability of spirolides is larger than previously known and does not only include the presence or absence of certain functional groups but also involves the triketal ring system. |
format |
Text |
author |
Nieva, Joyce A. Tebben, Jan Tillmann, Urban Wohlrab, Sylke Krock, Bernd |
author_facet |
Nieva, Joyce A. Tebben, Jan Tillmann, Urban Wohlrab, Sylke Krock, Bernd |
author_sort |
Nieva, Joyce A. |
title |
Mass Spectrometry-Based Characterization of New Spirolides from Alexandrium ostenfeldii (Dinophyceae) |
title_short |
Mass Spectrometry-Based Characterization of New Spirolides from Alexandrium ostenfeldii (Dinophyceae) |
title_full |
Mass Spectrometry-Based Characterization of New Spirolides from Alexandrium ostenfeldii (Dinophyceae) |
title_fullStr |
Mass Spectrometry-Based Characterization of New Spirolides from Alexandrium ostenfeldii (Dinophyceae) |
title_full_unstemmed |
Mass Spectrometry-Based Characterization of New Spirolides from Alexandrium ostenfeldii (Dinophyceae) |
title_sort |
mass spectrometry-based characterization of new spirolides from alexandrium ostenfeldii (dinophyceae) |
publisher |
MDPI |
publishDate |
2020 |
url |
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7599687/ http://www.ncbi.nlm.nih.gov/pubmed/33023163 https://doi.org/10.3390/md18100505 |
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Greenland Norway |
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Greenland Norway |
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Greenland |
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Greenland |
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Mar Drugs |
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http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7599687/ http://www.ncbi.nlm.nih.gov/pubmed/33023163 http://dx.doi.org/10.3390/md18100505 |
op_rights |
© 2020 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/). |
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CC-BY |
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https://doi.org/10.3390/md18100505 |
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Marine Drugs |
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