Sulfated diesters of okadaic acid and DTX-1: Self-protective precursors of diarrhetic shellfish poisoning (DSP) toxins. 2017

Tingmo Hu, and Patricia LeBlanc, and Ian W Burton, and John A Walter, and Pearse McCarron, and Jeremy E Melanson, and Wendy K Strangman, and Jeffrey L C Wright
Institute for Marine Biosciences, National Research Council of Canada, 1411 Oxford Street, Halifax, NS B3H 3Z1, Canada.

Many 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.

UI MeSH Term Description Entries
D008387 Marine Toxins Toxic or poisonous substances elaborated by marine flora or fauna. They include also specific, characterized poisons or toxins for which there is no more specific heading, like those from poisonous FISHES. Marine Biotoxins,Phycotoxins
D011714 Pyrans Pyran
D004141 Dinoflagellida Flagellate EUKARYOTES, found mainly in the oceans. They are characterized by the presence of transverse and longitudinal flagella which propel the organisms in a rotating manner through the water. Dinoflagellida were formerly members of the class Phytomastigophorea under the old five kingdom paradigm. Amphidinium,Dinoflagellata,Dinophyceae,Dinophycidae,Dinophyta,Dinophytes,Gambierdiscus toxicus,Gonyaulax,Gymnodinium,Peridinium,Pyrrhophyta,Pyrrophyta,Dinoflagellates
D000818 Animals Unicellular or multicellular, heterotrophic organisms, that have sensation and the power of voluntary movement. Under the older five kingdom paradigm, Animalia was one of the kingdoms. Under the modern three domain model, Animalia represents one of the many groups in the domain EUKARYOTA. Animal,Metazoa,Animalia
D057096 Shellfish Poisoning Poisoning from toxins present in bivalve mollusks that have been ingested. Four distinct types of shellfish poisoning are recognized based on the toxin involved. Amnesic Shellfish Poisoning,Diarrhetic Shellfish Poisoning,Neurotoxic Shellfish Poisoning,Paralytic Shellfish Poisoning,Amnesic Shellfish Poisonings,Diarrhetic Shellfish Poisonings,Neurotoxic Shellfish Poisonings,Paralytic Shellfish Poisonings,Poisoning, Amnesic Shellfish,Poisoning, Diarrhetic Shellfish,Poisoning, Neurotoxic Shellfish,Poisoning, Paralytic Shellfish,Poisoning, Shellfish,Poisonings, Amnesic Shellfish,Poisonings, Diarrhetic Shellfish,Poisonings, Neurotoxic Shellfish,Poisonings, Paralytic Shellfish,Poisonings, Shellfish,Shellfish Poisoning, Amnesic,Shellfish Poisoning, Diarrhetic,Shellfish Poisoning, Neurotoxic,Shellfish Poisoning, Paralytic,Shellfish Poisonings,Shellfish Poisonings, Amnesic,Shellfish Poisonings, Diarrhetic,Shellfish Poisonings, Neurotoxic,Shellfish Poisonings, Paralytic
D019319 Okadaic Acid A specific inhibitor of phosphoserine/threonine protein phosphatase 1 and 2a. It is also a potent tumor promoter. It is produced by DINOFLAGELLATES and causes diarrhetic SHELLFISH POISONING. Ocadaic Acid

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