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Structure Elucidation and Relative Toxicity of (24R)-24-Hydroxyyessotoxin from a Namibian Isolate of Gonyaulax spinifera
- Isabelle Rajotte, Cheryl Rafuse, Elliott J. Wright, John C. Achenbach, Lee D. Ellis, Pearse McCarron
- Journal of natural products 2019 v.82 no.7 pp. 1945-1952
- Danio rerio, Gonyaulax, biomass, hydroxylation, liquid chromatography, mass spectrometry, nuclear magnetic resonance spectroscopy, solvents, toxicity, yessotoxin
- Liquid chromatography–high-resolution mass spectrometry (LC-HRMS) analysis of a Namibian strain of Gonyaulax spinifera showed the presence of a number of yessotoxins (YTXs). Principal among these were YTX (1), homoYTX (2), and a tentative hydroxylated analogue that did not correspond to any previously confirmed YTX structures. Culturing the G. spinifera strain afforded sufficient biomass for purification of the new analogue through a series of solvent partitioning and chromatographic steps, yielding ∼0.9 mg as a solid. NMR spectroscopy, ion-trap mass spectrometry, and HRMS identified the new analogue as 24-hydroxyYTX (7). Purified 24-hydroxyYTX was quantitated by NMR, and its relative toxicity evaluated using two embryonic zebrafish toxicity assays. 24-HydroxyYTX demonstrated reduced toxicity compared to YTX.