The structures of three metabolites of the algal hepatotoxin okadaic acid produced by oxidation with human cytochrome P450

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DOIResolve DOI: http://doi.org/10.1016/j.bmc.2012.04.046
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TypeArticle
Journal titleBioorganic & Medicinal Chemistry
ISSN0968-0896
Volume20
Issue12
Pages37423745; # of pages: 4
SubjectOkadaic acid; Dinoflagellate; Algal toxin; Xenobiotic metabolism; Cytochrome P450
AbstractFour metabolites of okadaic acid were generated by incubation with human recombinant cytochrome P450 3A4. The structures of two of the four metabolites have been determined by MS/MS experiments and 1D and 2D NMR methods using 94 and 133 μg of each metabolite. The structure of a third metabolite was determined by oxidation to a metabolite of known structure. Like okadaic acid, the metabolites are inhibitors of protein phosphatase PP2A. Although one of the metabolites does have an α,β unsaturated carbonyl with the potential to form adducts with an active site cysteine, all of the metabolites are reversible inhibitors of PP2A.
Publication date
LanguageEnglish
AffiliationMeasurement Science and Standards; National Research Council Canada
Peer reviewedYes
IdentifierS0968089612003434
NPARC number21268677
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Record identifier8ee836b4-a377-41b3-9f12-c8fcf64c92ac
Record created2013-11-07
Record modified2016-05-09
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