Structure pectenotoxin

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.

Pectenotoxin-4 and -5 were isolated in pure forms, but attempts for structural... 

The secondary ionization mass spectra of pectenotoxin-3 and -4 gave a (M+ +H) ion at m/z 875, indicating that they share the same formula with pectenotoxin-1. The mass spectrum of pectenotoxin-5 gave a (M +H) ion at m/z 877, suggesting that it is a dihydro derivative of either of pectenotoxin-1,-3, and -4. Further structural elucidation of these components is under way. 

Figure 9.1. Pectenotoxins whose structures have been definitively identified. Key +, reported not reported , possible artifact found only as an acid-induced artifact (see Figure 9.2).

Daiguji, M., Satake, M., James, K.J., Bishop, A., MacKenzie, L., Naoki, H., and Yasumoto, T. 1998. Structures of new pectenotoxin analogs, pectenotoxin-2 seco acid and 7-e/7z-pectenotoxin-2 seco acid, isolated from a dinoflagellate and greenshell mussels. Chem Lett 653-654. 

The consumption of shellfish (scallops and mussels) harvested during late spring to early summer fiom the northeastern region of Japan quite often results in what is commonly known as diarrhetic shellfish poisoning. An initial chemical investigation of the toxic mussels resulted in the identification (86) of okadaic acid [108], dinophysistoxin 1 (DTXj) [109] and two toxins of unknown structures. In a later study (87), chemical structures of three new polyether toxins, dinophysistoxin- 3 (DTX3)[110], pectenotoxin-1 [111 ] and pectenotoxin-2 [112] were reported. 

Allingham, J.S. et al., A structural basis for regulation of actin polymerization by pectenotoxins, J Mol Biol Press, 2007. 

Murata, M. et al. The structure of pectenotoxin-3, a new constituent of diarrhetic shellfish toxins, Agric. Biol. Chem. 50, 2693, 1986. 

C55H82O21S2, Mr 1143.38, [a]p +3° (CHjOH), amorphous solid as disodium salt. Y. and pectenotoxin (PTX, pectenotoxin 1 C47H70O15, Mr 875.06, cryst., [a]0 +17.1°) are isolated as DSP toxins from the digestive glands of the scallop Patinopecten yessoensis the factual producer is the dinoflagellate Dinophysis fortii that is taken up with food and accumulated in the scallop the toxins cause poisonings in humans. Pectenotoxin is hepatotoxic and induces a rapid necrosis of hepatocytes Its behavior is similar to that of phal-loidin (see phallotoxins) while the structure rather resembles those of the brevetoxins. 

The structures of PTX-5 and PTX-10 have not yet been reported. Figure 23.37 Structures of some pectenotoxins. 

Figure 148. (a) Structure of Pectenotoxin-6, (b) values in C5D5N, (c) values in CDCI3, and (d) structure of Tanikolide lactone. 

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