Elucidation and partial NMR assignment of monosulfated maitotoxins from the Caribbean

Eugene P Mazzola; Jonathan R Deeds; Whitney L Stutts; Clark D Ridge; Robert W Dickey; Kevin D White; R Thomas Williamson; Gary E Martin

doi:10.1016/j.toxicon.2019.03.026

Elucidation and partial NMR assignment of monosulfated maitotoxins from the Caribbean

Toxicon. 2019 Jun:164:44-50. doi: 10.1016/j.toxicon.2019.03.026. Epub 2019 Apr 4.

Authors

Eugene P Mazzola¹, Jonathan R Deeds², Whitney L Stutts², Clark D Ridge³, Robert W Dickey⁴, Kevin D White², R Thomas Williamson⁵, Gary E Martin⁵

Affiliations

¹ University of Maryland-FDA Joint Institute, College Park, MD, 20742, USA.
² Food and Drug Administration, Center for Food Safety and Applied Nutrition, Office of Regulatory Science, College Park, MD, 20740, USA.
³ Food and Drug Administration, Center for Food Safety and Applied Nutrition, Office of Regulatory Science, College Park, MD, 20740, USA. Electronic address: clark.ridge@fda.hhs.gov.
⁴ Food and Drug Administration Gulf Coast Seafood Laboratory, Office of Food Safety, Dauphin Island, AL, 36528, USA.
⁵ Merck Research Laboratories, Process and Analytical Chemistry, NMR Structure Elucidation Group, Rahway, NJ, 07065, USA.

PMID: 30954452
DOI: 10.1016/j.toxicon.2019.03.026

Abstract

Compounds similar to maitotoxin (MTX) have been isolated from several laboratory strains of the dinoflagellate Gambierdiscus spp. from the Caribbean. Mass spectral results suggest that these compounds differ from MTX by the loss of one sulfate group and, in some cases, the loss of one methyl group with the addition of one degree of unsaturation. NMR experiments, using approximately 50 nmol of one of these compounds, have demonstrated that the 9-sulfo group of MTX is still present, suggesting that these compounds are 40-desulfo congeners of MTX.

Keywords: Dinoflagellate; Gambierdiscus; High resolution mass spectrometry; Liquid chromatography–mass spectrometry; NMR spectroscopy.

MeSH terms

Caribbean Region
Chromatography, Liquid
Dinoflagellida / chemistry*
Magnetic Resonance Spectroscopy
Marine Toxins / chemistry*
Mass Spectrometry
Molecular Structure
Oxocins / chemistry*

Substances

Marine Toxins
Oxocins
maitotoxin