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

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dc.contributor.authorSelwood, Andrew I.
dc.contributor.authorvan Ginkel, Roel
dc.contributor.authorWilkins, Alistair L.
dc.contributor.authorMunday, Rex
dc.contributor.authorRamsdell, John S.
dc.contributor.authorJensen, Dwayne J.
dc.contributor.authorCooney, Janine M.
dc.contributor.authorMiles, Christopher O.
dc.date.accessioned2009-08-17T23:14:19Z
dc.date.available2009-08-17T23:14:19Z
dc.date.issued2008
dc.description.abstractanimals 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.en
dc.identifier.citationSelwood, 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.en
dc.identifier.doi10.1021/tx700441wen
dc.identifier.urihttps://hdl.handle.net/10289/2840
dc.language.isoen
dc.publisherAmerican Chemical Societyen_NZ
dc.relation.isPartOfChemical Research in Toxicologyen_NZ
dc.relation.urihttp://pubs.acs.org/doi/abs/10.1021/tx700441wen
dc.subjectchemistryen
dc.titleSemisynthesis of S-Desoxybrevetoxin-B2 and Brevetoxin-B2, and Assessment of Their Acute Toxicitiesen
pubs.begin-page944en_NZ
pubs.elements-id34265
pubs.end-page950en_NZ
pubs.issue4en_NZ
pubs.volume21en_NZ
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