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      Semisynthesis of S-Desoxybrevetoxin-B2 and Brevetoxin-B2, and Assessment of Their Acute Toxicities

      Selwood, Andrew I.; van Ginkel, Roel; Wilkins, Alistair L.; Munday, Rex; Ramsdell, John S.; Jensen, Dwayne J.; Cooney, Janine M.; Miles, Christopher O.
      DOI
       10.1021/tx700441w
      Link
       pubs.acs.org
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      Citation
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      Selwood, A. I., van Ginkel, R., Wilkins, A. L., et al. (2008). Semisynthesis of S-Desoxybrevetoxin-B2 and Brevetoxin-B2, and Assessment of Their Acute Toxicities. Chemical Research in Toxicology, 21(4), 944-950.
      Permanent Research Commons link: https://hdl.handle.net/10289/2840
      Abstract
      animals and people consuming seafood. Brevetoxin-B2 (5) is a toxic metabolite produced in shellfish exposed to algae that contain brevetoxin-B (1). S-Desoxybrevetoxin-B2 (4) has been proposed as a cometabolite produced during this transformation, and while LC-MS analyses suggest its presence in shellfish, it has not yet been isolated and characterized. Studies on these materials are severely constrained by the difficulty of obtaining and purifying them from natural sources. We have developed a convenient one-pot conversion of commercially available brevetoxin-B (1) into S-desoxybrevetoxin-B2 (4), and a simple method for converting 4 into brevetoxin-B2 (5). Full NMR and mass-spectral characterization of 4 and 5 confirmed their structures and showed that the ratio of diastereoisomers in the synthetic 4 and 5 was similar to that observed in naturally contaminated shellfish. The LD50 values for 4, 5, and dihydrobrevetoxin-B (6) by ip injection in mice were 211, 400, and 250 µg/kg, respectively. The methodology for synthesis of brevetoxin metabolites should greatly facilitate toxicological, biochemical and immunochemical studies of these substances, as well as the production of analytical standards.
      Date
      2008
      Publisher
      American Chemical Society
      Collections
      • Science and Engineering Papers [3124]
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