44-Methylgambierone, a new gambierone analogue isolated from Gambierdiscus australes

[Display omitted] •Novel secondary metabolite identified from Gambierdiscus australes.•Isolation and purification protocols developed.•NMR and MS experiments confirmed molecular structure as 44-methylgambierone.•Compound previously identified as maitotoxin-3. A new analogue of gambierone, 44-methylg...

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Bibliographic Details
Published in:Tetrahedron letters 2019-02, Vol.60 (8), p.621-625
Main Authors: Murray, J. Sam, Selwood, Andrew I., Harwood, D. Tim, van Ginkel, Roel, Puddick, Jonathan, Rhodes, Lesley L., Rise, Frode, Wilkins, Alistair L.
Format: Article
Language:English
Subjects:
Ciguatera fish poisoning
Gambierone
Liquid chromatography
Maitotoxin-3
Mass spectrometry
Nuclear magnetic resonance spectroscopy
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Summary:[Display omitted] •Novel secondary metabolite identified from Gambierdiscus australes.•Isolation and purification protocols developed.•NMR and MS experiments confirmed molecular structure as 44-methylgambierone.•Compound previously identified as maitotoxin-3. A new analogue of gambierone, 44-methylgambierone, was isolated from the benthic dinoflagellate Gambierdiscus australes collected from Raoul Island (Rangitahua/Kermadec Islands). This molecule has been previously reported as maitotoxin-3. The structure of 44-methylgambierone was elucidated using 1D- and 2D-nuclear magnetic resonance spectroscopy and mass spectrometry techniques. The nine-ring polyether backbone (A–I) and functional groups (carbonyl, terminal diol, 1,3-diene and monosulphate) are the same for both compounds with the addition of an olefinic methyl group being the only modification in 44-methylgambierone.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2019.01.043