New esters of okadaic acid in seawater and blue mussels (Mytilus edulis). 2008

Trine Torgersen, and Christopher O Miles, and Thomas Rundberget, and Alistair L Wilkins
Department of Feed and Food Hygiene, National Veterinary Institute, P.O. Box 750 Sentrum, NO-0106 Oslo, Norway. trine.torgersen@vetinst.no

Marine algal toxins of the okadaic acid (OA) group can occur as diol esters and sulfated diol esters in algae and as fatty acid esters in shellfish. Several of these ester forms have been identified, but the most common procedure for detecting OA group toxin esters is by measuring the increase in parent toxin after alkaline hydrolysis. Use of this alkaline hydrolysis method led to the discovery of high levels of conjugates of OA and dinophysistoxins-2 (DTX2) in seawater and of OA, DTX1, and DTX2 in blue mussel hepatopancreas (HP) from Flødevigen, Norway, during a bloom of Dinophysis spp. In the water sample, a C 8-diol ester, a C 9-diol ester, and a previously undescribed C 8-triol ester of OA were characterized using HPLC-MS (2), -MS (3), and -MS (4) in combination with various derivatization procedures. Palmitic acid (16:0) ester derivatives of these diol/triol esters were found in mussel HP and characterized using HPLC-MS (2), -MS (3), and -MS (4). To the authors' knowledge, hybrid diol-fatty acid esters of OA have not been previously described. Mass spectral analysis showed the presence of two forms of hybrid esters: one with the fatty acid conjugated to the 7-OH of the OA moiety and the other with the fatty acid conjugated to the OH group in the "diol" moiety. In the water sample, the C 8-diol ester was the most abundant, whereas in the mussels, the 16:0-C 9-diol hybrid ester was most abundant, and only minor amounts of the 16:0-C 8-diol hybrid ester were detected, suggesting that C 8- and C 9-diol esters of OA may be metabolized differently in blue mussels. 7- O-acyl esters of OA, DTX1, and DTX2 are thought to contribute to shellfish toxicity by being hydrolyzed in the human stomach to the parent toxins, and the newly characterized hybrid esters are likely to contribute similarly.

UI MeSH Term Description Entries
D004952 Esters Compounds derived from organic or inorganic acids in which at least one hydroxyl group is replaced by an –O-alkyl or another organic group. They can be represented by the structure formula RCOOR’ and are usually formed by the reaction between an acid and an alcohol with elimination of water. Ester
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
D012623 Seawater The salinated water of OCEANS AND SEAS that provides habitat for marine organisms. Sea Water,Sea Waters,Seawaters,Water, Sea,Waters, Sea
D049872 Bivalvia A class in the phylum MOLLUSCA comprised of mussels; clams; OYSTERS; COCKLES; and SCALLOPS. They are characterized by a bilaterally symmetrical hinged shell and a muscular foot used for burrowing and anchoring. Mussels,Bivalves,Clams,Bivalve,Bivalvias,Clam,Mussel
D056890 Eukaryota One of the three domains of life (the others being BACTERIA and ARCHAEA), also called Eukarya. These are organisms whose cells are enclosed in membranes and possess a nucleus. They comprise almost all multicellular and many unicellular organisms, and are traditionally divided into groups (sometimes called kingdoms) including ANIMALS; PLANTS; FUNGI; and various algae and other taxa that were previously part of the old kingdom Protista. Eukaryotes,Eucarya,Eukarya,Eukaryotas,Eukaryote
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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