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Production of 7-epi-Pectenotoxin-2 Seco Acid and Assessment of Its Acute Toxicity to Mice

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journal contribution
posted on 22.02.2006 by Christopher O. Miles, Alistair L. Wilkins, John S. Munday, Rex Munday, Allan D. Hawkes, Dwayne J. Jensen, Janine M. Cooney, Veronica Beuzenberg
Pectenotoxins (PTXs) accumulate in shellfish feeding on dinoflagellates of the genus Dinophysis, so that humans can be exposed to these toxins through shellfish consumption. Some PTXs are toxic to experimental animals, whereas others are of much lower toxicity. Pectenotoxin-2, the most abundant PTX from most Dinophysis spp., is rapidly metabolized by most shellfish to a mixture of pectenotoxin-2 seco acid (2) and 7-epi-pectenotoxin-2 seco acid (1). A mixture of 1 and 2 was produced during purification of an extract from in vitro enzymatic hydrolysis of pectenotoxin-2. These were separated by preparative HPLC, and the structure of 1 was confirmed by one- and two-dimensional 1H and 13C NMR spectroscopy and LC-MS3 analyses. No toxic changes were recorded in mice injected intraperitoneally with 1 or 2 at a dose of 5000 μg/kg. PTX seco acids are therefore unlikely to be of consequence to human consumers at the concentrations found in contaminated shellfish. Keywords: pectenotoxin; seco acid; PTX-2 seco acid; Dinophysis; toxicology; mussel