ArticleJournal of chromatography. B, Analytical technologies in the biomedical and life sciences2022
Selective extraction of gambierone and related metabolites in Gambierdiscus silvae using m-aminophenylboronic acid-agarose gel and liquid chromatography-high-resolution mass spectrometric detection.
Article in Journal of chromatography. B, Analytical technologies in the biomedical and life sciences, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.
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9 citing papers in PubMed, 18 citations in OpenAlex.
- Automatic MS/MS Data Mining Strategy for Rapid Screening of Polyether Toxins Derived fromAnalytical chemistry · 2025Article
- Isolation of Caribbean Ciguatoxin-5 (C-CTX5) and confirmation of its structure by NMR spectroscopy.Tetrahedron · 2024Article
- Targeted Metabolite Fingerprints of ThirteenMarine drugs · 2024Article
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- Article
- Gambierone and Sodium Channel Specific Bioactivity Are Associated with the Extracellular Metabolite Pool of the Marine DinoflagellateMarine drugs · 2023Article
- Characterization of New Gambierones Produced byMarine drugs · 2022Article
- Comparative Study on the Performance of Three Detection Methods for the Quantification of Pacific Ciguatoxins in French Polynesian Strains ofMarine drugs · 2022Article
- Production and stability of Oxygen-18 labeled Caribbean ciguatoxins and gambierones.Toxicon : official journal of the International Society on Toxinology · 2022Article
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Authors and funding
5 authors at 3 institutions in 2 countries.
Funding
Abstract
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 a novel isomer of 44-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.
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