Sulfated diesters of okadaic acid and DTX-1: Self-protective precursors of diarrhetic shellfish poisoning (DSP) toxins
| Autor: | Wendy K. Strangman, Pearse McCarron, Jeremy E. Melanson, Jeffrey L. C. Wright, Tingmo Hu, Patricia LeBlanc, John A. Walter, Ian W. Burton |
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| Rok vydání: | 2017 |
| Předmět: |
DSP toxins
toxin storage 0106 biological sciences Diol Plant Science Aquatic Science medicine.disease_cause 01 natural sciences DTX-1 Hydrolysis chemistry.chemical_compound sulfated diesters Sulfation okadaic acid medicine Animals Shellfish Poisoning Pyrans chemistry.chemical_classification biology 010405 organic chemistry Toxin 010604 marine biology & hydrobiology Dinoflagellate Okadaic acid biology.organism_classification 0104 chemical sciences Enzyme chemistry Biochemistry Dinoflagellida diol esters Marine Toxins Diarrhetic shellfish poisoning |
| Zdroj: | Harmful Algae. 63:85-93 |
| ISSN: | 1568-9883 |
| DOI: | 10.1016/j.hal.2017.01.012 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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