Yessotoxin from Patinopecten yessoensis

Terao, K., et al., Histopathological studies on experimental marine toxin poisoning - 5. The effects in mice of yessotoxin isolated from Patinopecten yessoensis and of a desulfated derivative, Toxicon, 28, 9, 1095, 1990. 

Yessotoxin (YTX) 46, isolated from Patinopecten yessoensis, is a marine polyether toxin (Figure 7.15). The molecular structures of YTX (C55Hg202iS2Na2) consisting of 6/6/6/6/7/6/8/6/6/676 ether rings trans-fused, was determined by MS and NMR. 

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]. 

The main structural features of yessotoxin (YTX, 1) (Figure 13.1) consist of a ladder-shaped polycyclic ether skeleton, an unsaturated terminal side chain of nine carbons, and two sulfate groups. It was first isolated from scallops, Patinopecten yessoensis, that were implicated in a DSP episode in Japan. The planar structure of YTX was elucidated by means of 2D nuclear magnetic resonance (NMR) techniques, and confirmed by fast atom bombardment mass spectrometry/mass spectrometry (FAB MS/MS) experiments " the stereochemical details were successively determined by assigning the relative and then the absolute stereochemistry. YTX has subsequently been isolated from shellfish collected along the coasts of several different countries such as Norway, Chile, New Zealand, Italy, suggesting the spread of this toxin worldwide. 

Yessotoxin, a disulfated polyether, was first reported as a contaminant of the scallop, Patinopecten yessoensis, in Japan in 1987 [1]. Since then, yessotoxin has been identified in shellfish from Norway... 

Yessotoxin (YTX) is a cyclic polyether similar to the brevetoxins, but whose activity is of diarrhetic shellfish poison (DSP) type. This compound was isolated in 1986 from the Japanese scallop Patinopecten yessoensis, it was later shown that this toxin came from the dinoflagellate Protoceratium reticulatum (Murata et al., 1987 Satake, MacKenzie, and Yasumoto, 1997a Takahashi et al., 1996). 

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