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Isolation, Structural Determination and Acute Toxicity of Pinnatoxins E, F and G

Abstract
Pinnatoxins and pteriatoxins are a group of cyclic imine toxins that have hitherto only been isolated from Japanese shellfish. As with other cyclic imine shellfish toxins, pinnatoxins cause rapid death in the mouse bioassay for lipophilic shellfish toxins, but there is no evidence directly linking these compounds to human illness. We have identified the known pinnatoxins A (1) and D (6), and the novel pinnatoxins E (7), F (8) and G (5), in a range of shellfish and environmental samples from Australia and New Zealand using LC−MS. After isolation from the digestive glands of Pacific oysters, the structures of the novel pinnatoxins were determined by mass spectrometry and NMR spectroscopy, and their LD50 values were evaluated by ip administration to mice. Examination of the toxin structures, together with analysis of environmental samples, suggests that pinnatoxins F and G are produced separately in different dinoflagellates. Furthermore, it appears probable that pinnatoxin F (8) is the progenitor of pinnatoxins D (6) and E (7), and that pinnatoxin G (6) is the progenitor of both pinnatoxins A−C (1 and 2) and pteriatoxins A−C (3 and 4), via metabolic and hydrolytic transformations in shellfish.
Type
Journal Article
Type of thesis
Series
Citation
Selwood, A.I., Miles, C.O., Wilkins, A.L., van Ginkel, R., Munday, R., Rise, F. & McNabb, P. (2010). Isolation, Structural Determination and Acute Toxicity of Pinnatoxins E, F and G. Journal of Agricultural and Food Chemistry, 58(10), 6532-6542.
Date
2010
Publisher
American Chemical Society
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