Esterification of okadaic acid in the mussel Mytilus galloprovincialis.

Okadaic acid and other toxins of the diarrheic shellfish poisoning (DSP) group are transformed mainly to their acyl-derivatives in bivalves. Some recent studies suggest that bacteria present in the bivalve gut could contribute substantially to the acylation of the toxins. By feeding microcapsules containing okadaic acid to mussels we have shown unequivocally that the ingested okadaic acid is nearly completely transformed to its fatty acid esters (acyl-derivatives). Treating mussels with antibiotics did not have any significant effect on the acylation of the supplied okadaic acid, suggesting that bacteria do not play any significant role in this process. The microsomal and mitochondrial subcellular fractions of the cells of the digestive gland have been shown to have contain enzymes that are able to transfer a fatty acid molecule from Coenzyme A to okadaic acid (so, that have Acyl-CoA:OA acyltransferase activity). This activity was related to that of the enzyme Cytochrome C reductase (NADPH), a marker of endoplasmic reticulum, suggesting that this organelle is the main responsible for the acylation process. Acylation of DSP toxins seems to be a key step in the depuration of these toxins from mussels, as these compounds are found in feces as acyl-derivatives. This is probably true for most bivalves. The proportion of acyl-derivatives accumulated can point to the key process of the depuration: acylation or excretion of acylated derivatives. In the mussels Mytilus galloprovincialis, Mytilus edulis and in Donax trunculus, the first process seems to be the most important, but in most bivalve species it seems to be the second one. Other aspects of the relationship between depuration and acylation are also discussed.