2-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.

Three classes of polyethers, okadaic acid derivatives, pectenotoxins, and yessotoxin were isolated from bivalves in connection with diarrhetic shellfish poisoning. The etiology of the toxins, toxicological properties, and determination methods are described. 

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

Not all these polyether occur together in the same shellfish samples. OA was the major toxin in the mussel specimens from most of the European countries (42), while DTXl was the major toxin in mussel in Japan and in Sogndal, Norway (43). Scallops in Japan show the most complicated toxin profile. Furthermore, the relative ratio of the toxins varied regionally, seasonally, and annually. Pectenotoxins were detected, however, only in Japanese shellfish. Distribution of toxins is summarized in Table I. 

In addition to okadaic acid, dinophysistoxin-1 (i.e., 35-methylokadaic acid), 7-0-palmitoyl-okadaic acid, and pectenotoxin 2 are reported to be diarrhetic toxins from shellfish 34). Application of 1 xg of dinophysistoxin-1 to mouse ear caused as strong irritation as the same dose of okadaic acid. Interestingly, the potencies of these compounds in the irritant test on mouse ear correlated well with their potencies as diarrhetic shellfish poisons. Dinophysistoxin-1 induced ODC activity as strongly as okadaic acid. Recently, we found that dinophysistoxin-1 is also a new non-TPA type tumor promoter with as high activity as okadaic acid 35). 

Suzuki et al. [480] developed a solid-phase extraction LC-MS method for determining pectenotoxin-2 and pectenotoxin-6 in seawater. These are toxins produced from toxic phytoplankton. 

Terao, K., et al., Histopathological studies on experimental marine toxin poisoning. I. Ultrastructural changes in the small intestine and liver of suckling mice induced by dinophysistoxin-1 and pectenotoxin-1, Toxicon, 24, 11-12, 1141, 1986. 

Okadaic acid (OA), dinophysistoxins (DTXs), pectenotoxins (PTXs), azaspiracids (AZAs) and spirolides Shellfish 9-2,012 ng/g (mainly OA group toxins) [204]... 

Pectenotoxins were easily discernible by their strong UV absorption. The presence of 5 components was recognized by TLC and HPLC. Pectenotoxin-1 was isolated as white crystalline solid m.p. 208-209 ... 

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. 

Table 9.1. Worldwide occurrence of pectenotoxins in identified algal species... 

Table 9.2. Levels of pectenotoxins (pg/cell) in Dinophysis spp. determined by analysis of extracts from Dinophysis blooms or by analysis of picked Dinophysis cells... 

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