Diarrhetic shellfish poisoning

Figure 5.59 Molecular structures of the diarrhetic shellfish poisons (a) pectenotoxin-6 (PTX6) (b) okadaic acid (OA) (c) dinophysistoxin-1 (DTXl) (d) yessotoxin (YTX). Reprinted from J. Chromatogr., A, 943, Matrix effect and correction by standard addition in quantitative liquid chromatographic-mass spectrometric analysis of diarrhetic shellfish poisoning toxins , Ito, S. and Tsukada, K., 39-46, Copyright (2002), with permission from Elsevier Science.

Three classes of polyethers, okadaic acid derivatives, pectenotoxins, and yessotoxin were isolated from bivalves in connection with diarrhetic shellfish poisoning. The etiology of the toxins, toxicological properties, and determination methods are described. 

Diarrhetic shellfish poisoning is an illness caused by polyether toxins produced by dinoflagellates and accumulated in shellfish (31). Patients suffer from diarrhea, nausea, and stomach pain but recover within three days without serious aftereffects. Despite the relatively mild symptoms, careful attention should be paid to the... 

In addition to okadaic acid, dinophysistoxin-1 (i.e., 35-methylokadaic acid), 7-0-palmitoyl-okadaic acid, and pectenotoxin 2 are reported to be diarrhetic toxins from shellfish 34). Application of 1 xg of dinophysistoxin-1 to mouse ear caused as strong irritation as the same dose of okadaic acid. Interestingly, the potencies of these compounds in the irritant test on mouse ear correlated well with their potencies as diarrhetic shellfish poisons. Dinophysistoxin-1 induced ODC activity as strongly as okadaic acid. Recently, we found that dinophysistoxin-1 is also a new non-TPA type tumor promoter with as high activity as okadaic acid 35). 

DMS Dimethylsulfide DMSP Dimethylsulfoniopropionate DSP Diarrhetic shellfish poisoning PSP Paralytic shellfish poisoning PUFA Polyunsaturated fatty acid... 

The toxins responsible for DSP include a series of polyether molecules (including okadaic acid and six derivatives of dinophysistoxin), four pecteno-toxins (polyether lactones), and yessotoxins (including two sulfate esters that resemble brevetoxins) (Murata, 1982 Murata, 1987 Tachibana et al., 1981 Yasumoto, 1989). Diarrhetic shellfish poisons are produced primarily by dinoflagellates from the genera Dinophysis, although Prorocentrum lima also produces both okadaic acid and dinophysistoxin-1 (Heredia-Tapia et al., 2002). 

The biological activities of the other diarrhetic shellfish poisons are not well understood, and some of the toxins included in the DSP complex may not be... 

AZP, the most-recently characterized marine seafood poisoning, is associated with eating shellfish contaminated with azaspiracids. The first human intoxications attributed to AZP occurred in the Netherlands, and the symptoms included those similar to DSP (i.e., nausea, vomiting, severe diarrhea, and stomach cramps). However, although chemical analyses did not identify significant levels of the diarrhetic shellfish poisons, they identified a new class of toxins (James et ah, 2003a). 

Aune, T. and Yndestad, M., Diarrhetic shellfish poisoning, in Falconer, I.R., ed.. Algal Toxins in Seafood and Drinking Water, Academic Press, San Diego, 1993. Australia New Zealand Food Authority, Shellfish Toxins in Food, A Toxicological Review and Risk Assessment, Australia New Zealand Food Authority, Canberra, 2001. 

Murata, M., Isolation and structural elucidation of the causative toxin of the diarrhetic shellfish poisoning, Bull. Jpn. Soc.Sci. Fish, 48, 549, 1982. 

Murata, M., Isolation and structure of yessotoxin, a novel polyether compound implicated in diarrhetic shellfish poisoning, Tet. Lett., 28, 5869, 1987. 

In addition to the proven production of 35S-methyl okadaic acid (Dinophysistoxin -1) by D. fortii (52), with resulting diarrhetic shellfish poisoning (DSP) in Japan, there is strong circumstantial evidence that D. acuminata and possibly other Dinophysis species have produced DSP in Dutch and Spanish waters (53) These species are very widespread and comnK)n in both tropical and temperate waters, but they are not often abundant. They are very difficult to culture and so it is difficult to determine if populations in other areas are toxigenic. 

Yessotoxin (214) is a polyether from the scallop Patinopecten yessoensis and has been implicated in diarrhetic shellfish poisoning (DSP). The structure and partial stereochemistry of yessotoxin were deduced from spectral data [219]. The relative stereochemistry of yessotoxin and the structures of two new analogues, 45-hydroxyyessotoxin (215) and 45,46,47-trinoryessotoxin (216) were also established [220]. The absolute stereochemistry of yessotoxin (214) was determined by NMR spectroscopy using a chiral anisotropic reagent [221]. The absolute configuration at C45 in 45-hydroxyyessotoxin (215), isolated from P. yessoensis, was determined by the use of a modified Mosher s method [222]. 

Additionally, a number of marine toxins with medical and toxicological importance have been isolated from marine flora and fauna. Okadaic acid, Fig. (62) is the main toxin produced by dinoflagellates, which can accumulate in the hepatopancreas of mussels and caused diarrhetic shellfish poisoning in consumers [505,506], However, this toxin is also a tumor promoter and a specific potent inhibitor of protein phosphatases which may provokes mitotic arrest and apoptosis of leukemia cells [507-509], These types of compounds have been reported in shellfish and phytoplankton, and more recently, in Spanish mussels [510], Portuguese bivalves [511], and the diatom Thalassiosira weissflogii [512],... 

Ito, S. and Tsukada, K., Matrix effect and correlation by standard addition in quantitative liquid chromatographic spectrometric analysis of diarrhetic shellfish poisoning toxins, J. Chromatogr., 943, 39 16, 2002. 

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