Diarrhetic shellfish poisoning DSP

Table 5.17 Quantitative results obtained for the determination of four diarrhetic shellfish poisons (DSPs) using external standards and the method of standard additions. 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...

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]. 

Madigan, T.L., Lee, K.G., Padula, D. J., McNabb, R, and Pointon, A.M. 2006. Diarrhetic shellfish poisoning (DSP) toxins in South Australian shellfish. Harmful Algae, in press. 

Suzuki, T, Jin, T, Shirota, Y, Mitsuya, T, Okumura, Y, and Kamiyama, T. 2005b. Quantification of lipophilic toxins associated with diarrhetic shellfish poisoning (DSP) in Japanese bivalves by liquid chromatography-mass spectrometry (LC-MS) and comparison with mouse bioassay (MBA) as the official testing method in Japan. Fish Sci 71, 1370-1378. 

Yessotoxin (YTX) was first postulated as a causative agent of severe clinical signs and symptoms of diarrhetic shellfish poisoning (DSP) (Terao et al. 1990). However, no diarrhogenic properties of this toxin have been reported (Draisci et al. 2000). The mechanism of action of YTX is not completely clarified even though several studies in this sense have been done. 

Quilliam, M.A., Hardstaff, W.R., Ishida, N., McLachlan, XL., Reeves, A.R., Ross, N.W., and Windust, A.X 1996a. Production of diarrhetic shellfish poisoning (DSP) toxins by Prorocentrum lima in culture and development of analytical mefliods. In Harmful and Toxic Algal Blooms, ed. Yasumoto, T, Oshima, Y, and Fukuyo. Y.I.O.C. of UNESCO, 289-292. 

In 1995, a report of human illness with diarrhetic shellfish poisoning (DSP)-like symptoms in the Netherlands was eventually found to result from the consumption of poisoned mussels (Mytilus edulis) harvested from Killary Harbour, Ireland (McMahon 1996). Yasumoto, Satake, and co-workers eventually isolated and proposed a stracture for the causative agent of this condition azaspiracid-1 (la. Fig. 16.1). The unique polyether stracture of azaspiracid-1 (la) is characterized by several spiro-cyclic systems, including an azaspiro ring fused to a 2,9-dioxabicyclo[3.3.1]nonane system and a terminal carboxylic acid. In total, there are nine rings and twenty stereogenic centers within the structure proposed by Yasumoto and co-workers in 1998 (Satake 1998). This stracture was based primarily on NMR spectroscopic data and did not include absolute stereochemistry, nor did it specify relative stereochemistry between the ABCDE and FGHI domains. 

The sponge Halichondria okadai contains a polyether metabohte named okadaic acid (16) that was also isolated as a causative agent of diarrhetic shellfish poisoning (DSP) from mussels and other bivalves (14). However, the real producers are dinoflagellates of the genus Dinophysis. It is a potent cancer promoter that was found to be caused by inhibition of protein phosphatases 1 and 2A at nanomolar levels. Pectenotoxins are also involved in DSP and are produced by Dinophysis spp. pectenotoxin 2 (17) inhibits actin polymerization (14). 

Okadaic acid 11 is a potent and specific inhibitor of protein phosphatases produced by the dinoflagellates Prorocentrum lima, Dinophysisfortii, and Dirwphysis accuminata. It accumulates in bivalves and is one of the main toxins responsible for diarrhetic shellfish poisoning (DSP) (11). It has a highly unusual biosynthesis that has generated a lot of speculation because of the presence of isolated acetate chain methyl carbon atoms (10). Okadaic acid is a potent inhibitor of protein phosphatase A (11). 

Cyclic imine acting at nicotinic AcH receptor. Low oral toxicity Diarrhetic shellfish poisoning (DSP) toxins. Inhibitors of protein phosphatases (after hydrolysis of ester forms)... 

Koike, K. et ah. Evidence of phagotrophy in Dinophysis fortii (Dinophysiales, Dinophyceae), a dino-flagellate that causes diarrhetic shellfish poisoning (DSP), PhycoL Res., 48, 121, 2000. 

Subba Rao, D.V. et ah, Diarrhetic shellfish poisoning (DSP) associated with a subsurface bloom of Dinophysis norvergica in Bedford Basin, eastern Canada, Mar. Ecol. Prog. Ser, 97, 117, 1993. 

Marcaillou-Le Baut, C., Toxins involved in diarrhetic shellfish poisoning DSP, Oceanis, 16, 359, 1990. 

Azaspiracid poisoning (AZP) is the most recently discovered of the toxic syndromes from shellfish consumption. The symptoms of acute AZP intoxication closely resembles those associated with diarrhetic shellfish poisoning (DSP), and include diarrhea, vomiting, and headache and the first confirmed incident was in 1995 (Netherlands), following the consumption of mussels (Mytilus edulis) that were cultivated in Ireland (Satake et al., 1998). Since these symptoms are similar to bacterial enterotoxin poisoning, and analytical methods for the detection of these toxins have only been developed in recent years, it is probable that there have been many unreported cases of this poisoning. The first azaspiracid to be identified was AZAl (Figure 35.1, = H R = CH3),... 

Marine toxin from mussels (Mytilus edulis) cultivated in Ireland, C47H7.NO12, Mr 842.07, colorless, amorphous solid, [ ]d -21° (CH3OH), LD50 (mouse i.p.) 0.2 mg/kg. People who became ill in 1995 after consumption of mussels presented with symptoms very similar to those of diarrhetic shellfish poisoning (DSP) nausea, vomiting, severe diarrhea and stomach cramps. Lir. J. Am. Chem. Soc. 120,9967 (1998). - [CAS214899-2I-5]... 

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