Structure yessotoxin

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.

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

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]. 

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... 

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... 

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. 

Daiguji, M., Satake, M., Ramstad, H., Aune, T, Naoki, H., and Yasumoto, T. 1998. Structure and fluorometric HPLC determination of 1-desulfoyessotoxin, a new yessotoxin analog isolated from mussels from Norway. Nat Toxins 6, 235—239. 

Ferrari, S., Ciminiello, P, Dell Aversano, C., Forino, M., Malaguti, C., Tubaro, A., Poletti, R., Yasumato, T, Fattorusso, E., and Rossini, G.E 2004. Structure-activity relationships of yessotoxins in cultured cells. Chem Res Toxicol 17,1251-1257. 

Naoki, H., Murata, M., and Yasumoto, T. 1993. Negative-ion fast-atom bombardment tandem mass spectrometry for the structural study of polyether compounds structural verification of yessotoxin. Rapid Commun. Mass Spectrom 7, 179-182. 

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. 

AU marine polyether ladders thus far characterized (e.g., maito-toxin 16 (Fig. 4a), the brevetoxins 12 and 13 and hemibreve-toxin B, the yessotoxins 14 (and the truncated adriatoxin), the Pacific and Caribbean ciguatoxins, the gambieric acids 15 and gamberiol (the gymnocins and brevenal) can be grouped into 14 backbone structures (3). 

An extract of the digestive glands of P. yessoensis, collected fiom the aforementioned location, upon fractionation gave a new polyether toxin, yessotoxin[114]. The structure of which was determined by spectroscopic methods (92) and has the chemical characteristics of dinoflagellate toxins isolated from Gymnodinium breve (93). Recently, toxic mussels collected from Ban try Bay, Ireland, were found to contain dinophysistoxin-2 (DTX2) [115] (94). 

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. 

Yessotoxins (YTXs) represent a group of polycyclic ether compounds, structurally closely related to brevetoxins and ciguatoxins. Several reviews on this topic have been previously published. Most of them report on YTXs within a wider survey including other biotoxins a review focused on the occurrence, detection, chemistry, and pharmacology of YTXs and structural analogs has been recently published. ... 

The parent compound of this class of marine toxins is yessotoxin (YTX, 1), whose structure was established first and which gave the basic framework to elucidate the structures of the other YTXs. 

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. 

FIGURE 13.1 Structures of yessotoxins, shown in their sulfonic acid forms, which were first reported from shellfish. The configuration at C-45 in 5 has been assigned by analogy with 2, as reported by Morohashi et al. ... 

FIGURE 13.3 Structures of yessotoxin methyl ketone analogs fromP. reticulatum. The structures are shown in their sulfonic acid forms. 

FIGURE 13.4 Structures of yessotoxins, shown in their sulfonic acid forms, which have been only found in... 

FIGURE 13.5 Structures of nor-ring A-yessotoxin and its heptanor-41-oxo-analogs. 

FIGURE 13.6 Structures of yessotoxins arabinosides from P. reticulatum... 

Successively, Miles et al during a large-scale isolation of YTX, confirmed the presence of 31 in extracts of Pr. reticulatum and in addition isolated 32-0-[P-l- arabinofuranosyl-(5 -> 1")-P-L-arabinofuranosyl]-yessotoxin (32, Figure 13.6), whose structure was confirmed by comparison of its NMR data with those established for its 1-homoYTX homologue (28). ... 

FIGURE 13.10 Structure of the two C-42 epimers from derivatization of yessotoxin with DMEQ-TAD. 

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