Selective extraction of gambierone and related metabolites in Gambierdiscus silvae using m-aminophenylboronic acid–agarose gel and liquid chromatography–high-resolution mass spectrometric detection
| Autor: | Christopher O. Miles, Alexander K. Leynse, Alison Robertson, Elizabeth M. Mudge, Pearse McCarron |
|---|---|
| Jazyk: | angličtina |
| Rok vydání: | 2023 |
| Předmět: |
LC-HRMS
Ciguatoxin Gambierdiscus boronic acid gel Clinical Biochemistry Secondary metabolite vic-diol Mass spectrometry Biochemistry Article Mass Spectrometry Analytical Chemistry chemistry.chemical_compound Biotransformation medicine Sample preparation ciguatera Chromatography gambierone Sepharose Extraction (chemistry) Cell Biology General Medicine Boronic Acids Solvent chemistry Dinoflagellida Agarose Chromatography Liquid Ethers medicine.drug |
| Zdroj: | J Chromatogr B Analyt Technol Biomed Life Sci |
| Popis: | Gambierdiscus spp. are epi-benthic dinoflagellates that have been associated with ciguatera poisoning. These microalgae can have complex secondary metabolite profiles including ciguatoxins, maitotoxins, and gambierones, with varying compositions and toxicities across species and strains. Given this chemical diversity there is a need to develop selective and sensitive methods for secondary metabolite profiling. In this study, we used a cultured Caribbean strain of Gambierdiscus silvae to develop sample preparation and analysis strategies for characterizing vic-diol containing secondary metabolites. A pooled cellular extract was first screened by liquid chromatography–high–resolution mass spectrometry (LC–HRMS) for ciguatoxin-related compounds, which resulted in the confirmation of gambierone (1) and tentative identification of 29-methylgambierone (3). Treatment of the extract with periodate confirmed that the gambierones each contained one reactive vic-diol, which was exploited for the development of a selective extraction procedure using m-aminophenylboronic acid gel and the non-aqueous binding solvent chloroform. Using this non-traditional boronate affinity procedure, LC-HRMS also revealed the presence of additional sulfated polycyclic ethers in the gambierone-containing vic-diol fraction, while pigments and other contaminants were removed. The developed tools could be applied to screen collections of Gambierdiscus and other benthic algae to provide additional chemical characterization of gambierone-related compounds. The selective extraction procedure may also prove useful as a step in the isolation of these sulfated polyethers for structural, toxicological and biotransformation studies. |
| Databáze: | OpenAIRE |
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