Sulfated diesters of okadaic acid and DTX-1: self-protective precursors of diarrhetic shellfish poisoning (DSP) toxins

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DOIResolve DOI: http://doi.org/10.1016/j.hal.2017.01.012
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TypeArticle
Journal titleHarmful Algae
ISSN1568-9883
Volume63
Pages8593
SubjectDSP toxins; okadaic acid; DTX-1; diol esters; sulfated diesters; toxin storage
AbstractMany toxic secondary metabolites used for defense are also toxic to the producing organism. One important way to circumvent toxicity is to store the toxin as an inactive precursor. Several sulfated diesters of the diarrhetic shellfish poisoning (DSP) toxin okadaic acid have been reported from cultures of various dinoflagellate species belonging to the genus Prorocentrum. It has been proposed that these sulfated diesters are a means of toxin storage within the dinoflagellate cell, and that a putative enzyme mediated two-step hydrolysis of sulfated diesters such as DTX-4 and DTX-5 initially leads to the formation of diol esters and ultimately to the release of free okadaic acid. However, only one diol ester and no sulfated diesters of DTX-1, a closely related DSP toxin, have been isolated leading some to speculate that this toxin is not stored as a sulfated diester and is processed by some other means. DSP components in organic extracts of two large scale Prorocentrum lima laboratory cultures have been investigated. In addition to the usual suite of okadaic acid esters, as well as the free acids okadaic acid and DTX-1, a group of corresponding diol- and sulfated diesters of both okadaic acid and DTX-1 have now been isolated and structurally characterized, confirming that both okadaic acid and DTX-1 are initially formed in the dinoflagellate cell as the non-toxic sulfated diesters.
Publication date
PublisherElsevier
LanguageEnglish
AffiliationNRC Institute for Marine Biosciences; Measurement Science and Standards; National Research Council Canada
Peer reviewedYes
NPARC number23001792
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Record identifiercfcfa5e7-5a20-4eb3-a1bc-5e5c7d414a84
Record created2017-04-07
Record modified2017-04-07
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