Cawthron Institute, Private Bag 2, Nelson, New Zealand.
J Agric Food Chem. 2010 May 26;58(10):6532-42. doi: 10.1021/jf100267a.
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 LD(50) 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.
扇贝毒素和翼足类毒素是一组环状亚胺毒素，迄今为止仅从日本贝类中分离出来。与其他环状亚胺贝类毒素一样，扇贝毒素在脂溶性贝类毒素的小鼠生物测定中会导致快速死亡，但没有直接证据将这些化合物与人类疾病联系起来。我们使用 LC-MS 在来自澳大利亚和新西兰的一系列贝类和环境样本中鉴定了已知的扇贝毒素 A（1）和 D（6），以及新型扇贝毒素 E（7）、F（8）和 G（5）。从太平洋牡蛎的消化腺中分离出来后，通过质谱和 NMR 光谱确定了新型扇贝毒素的结构，并通过腹腔注射对其 LD50 值进行了评估。毒素结构的检查以及环境样本的分析表明，扇贝毒素 F 和 G 是由不同的甲藻分别产生的。此外，似乎很可能的是，扇贝毒素 F（8）是扇贝毒素 D（6）和 E（7）的前体，而扇贝毒素 G（6）是扇贝毒素 A-C（1 和 2）和翼足类毒素 A-C（3 和 4）的前体，通过贝类中的代谢和水解转化。
