Yessotoxin analogues

Two analogues of yessotoxin, homoyessotoxin (217) and 45-hydroxyhomoyessotoxin (218) were isolated from the digestive glands of mussels from the Adriatic Sea. Their structures were determined by NMR spectroscopy and mass spectrometry [223]. Adriatoxin (219), a further yessotoxin analogue, was isolated from the digestive glands of the mussel... 

Global Distribution, Levels, and Profiles of Yessotoxin Analogues... 

Ciminiello, E, Eattorusso, E., Eorino, M., Poletti, R., and Viviani, R. 2000a. Structure determination of carboxyhomoyesso-toxin, a new yessotoxin analogue isolated from adriatic mussels. Chem Res Toxicol 13,110-11 A. 

Samdal, I.A., Olseng, c.D., Sandvik, M., Miles, C.O., Briggs, L.R., Torgersen, T, and Jensen, D.J. 2006. Profile of yessotoxin analogues in a Norwegian strain of Protoceratium reticulatum. Pp. 242-247 in Proc. 5th, Inti. Conf Mollusc. Shell/. Safety, June 14—18, 2004, Galway, Ireland. Published hy Marine Institute. 

Satake, M., Eiki, K., Ichimura, T., Ota, S., Sekiguchi, K., and Oshima, Y, Structure of 45,46,47-trinorhomoyessotoxin, a new yessotoxin analogue from Protoceratium reticulatum which represents the first detection of a homoyessotoxin in Japan. Harmful Algae, 5, 731, 2006. 

Ciminiello P. et al. Structure determination of carboxyhomoyessotoxin, a new yessotoxin analogue isolated from Adriatic mussels, Chem. Res. Toxicol. 13, 770, 2000. 

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]. 

Yessotoxin and its analogues are disulfonated polyether toxins reported from shellfish from different countries, but a new derivative lacking a 1-sulfated substituent, 1-desulfoyessotoxin (YTX with R =H), has been isolated from mussels from Norway <1998MI235>. Its ESI-MS spectrum showed that this compound is 102 Da smaller than YTX 17, implying that one of the sulfate esters in YTX was desulfonated. The NMR data of 1-desulfoyessotoxin are similar to that of YTX 17 except for the 1-methylenic protons where desulfonation occurred they are shifted to upheld by 0.49ppm and their chemical shifts (3.72 and 3.78ppm) are typical of hydroxymethyl protons. 

Numerous studies have been conducted with cultures of the marine dinoflagellate Protoceratium reticulatum not only to confirm the biogenetic origin of yessotoxin 17 and 45,46,47-trinoryessotoxin 20 <1997MI164, 1999MI147>, but also to isolate and assign the structure of known and new YTX analogues, such as 27 (a l-en-3-one isomer of... 

Satake, M., Eiki K., Oshima Y, Mitsuya T, Sekiguchi K., Koike K., and Ogata T. 2002. Yessotoxin production hy Protoceratium reticulatum in Japan and structures of its new analogues. In 10th Inti. Conf. Harm/Algae, St. Pete Beach, FL, USA. 

Kinetic analysis of the interaction between yessotoxin and analogues and immobilized phosphodiesterases... 

Yessotoxins (YTXs) were discovered in shellfish extracts together with toxins from the OA group in 1987 [46]. Since the YTXs contribute to the outcome of the MBA for DSP toxins, they were initially included in the DSP toxin complex. The main producer of YTXs is the dinoflagellate Protoceratium reticulatum. YTXs are detected in bivalve mollusks in many parts of the world, like Japan, New Zealand, Australia, Canada, Norway, Italy, and the United Kingdom [3]. Many analogues of YTX are described, and new ones are frequently reported. 

Kleivdal, H., Briggs, L.R., and Miles, C.O., YTX ELISA for determination of yessotoxins and its analogues in shellfish and environmental samples. Submission from Biosense Laboratories AS to Food Safety Dept., WHO, Geneva, May 31, 2004. 

Ciminieho, R, Dell Aversano, C., Fattorusso, E., Forino, M., Magno, S., and Poletti, R., Direct detection of yessotoxin and its analogues by hquid chromatography coupled with electrospray ion trap mass spectrometry, J. Chromatogr. A, 968, 61, 2002. 

Briggs, L.R. et al.. Enzyme-linked immunosorbent assay for the detection of yessotoxin and its analogues, JAgric Food Chem, 52, 5836, 2004. 

Although no human intoxication is known to be caused by consumption of shellfish contaminated with yessotoxin or its analogues, because of the widespread occurrence of these compounds and their high levels in shellfish, their toxicity both in vitro and in vivo has been extensively studied. 

Ciminiello P. et al. Isolation of adriatoxin, a new analogue of yessotoxin from mussels of the Adriatic Sea, Tetrahedron Lett. 39, 8897, 1998. 

Pazos M.J. et al. Kinetic analysis of the interaction between yessotoxin and analogues and immobilized phosphodiesterases using a resonant mirror optical biosensor, Chem. Res. Toxicol. 18, 1155, 2005. 

P. Hess and J. Aasen, Chemistry, origins and distribution of yessotoxin and its analogues, in L.M. Botana (Ed.), Phytotoxins, Chemistry and Biochemistry, Blackwell Publishing, Ames, Iowa, 2007, pp. 187-202. 

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