Miles Christopher O, Wilkins Alistair L, Samdal Ingunn A, Sandvik Morten, Petersen Dirk, Quilliam Michael A, Naustvoll Lars J, Rundberget Thomas, Torgersen Trine, Hovgaard Peter, Jensen Dwayne J, Cooney Janine M
National Veterinary Institute, PB 8156 Dep., N-0033 Oslo, Norway.
Chem Res Toxicol. 2004 Nov;17(11):1423-33. doi: 10.1021/tx049870a.
Two novel pectenotoxins (PTXs) were detected by LC-MS in solid phase extracts of net hauls taken at Flødevigen, Norway, in June 2002 that were dominated by Dinophysis acuminata and Dinophysis norvegica. The new compounds were isolated as minor components from a large collection of a Dinophysis acuta-dominated bloom obtained from Skjer, Sognefjorden, Norway, in October 2002. LC-MS and NMR analyses revealed that the new components, 36S-PTX-12 and 36R-PTX-12, occurred as a pair of equilibrating diastereoisomers differing from PTX-2 in that they contained an exocylic olefinic methylene rather than a methyl group at C-38. Analyses of shellfish extracts revealed that PTX-12 accumulated in Norwegian blue mussels (Mytilus edulis) and cockles (Cerastoderma edule), along with PTX-12 seco acids occurring as a complex mixture of diastereoisomers. LC-MS analysis of algal cells picked from the net haul from Flødevigen revealed that PTX-12 predominated in D. acuta and D. norvegica, whereas PTX-2 was the predominant pectenotoxin in D. acuminata. Preliminary observations indicate that the relative contents of PTX-2 and PTX-12 vary between sites and years in Norway, even within a single species of Dinophysis. Our data also suggest that heterotrophic dinoflagellates may accumulate toxins from their prey.
2002年6月在挪威弗勒德维根采集的网捞固相提取物中，通过液相色谱 - 质谱联用仪（LC-MS）检测到两种新型pectenotoxins（PTXs），这些提取物中主要是尖刺菱形藻（Dinophysis acuminata）和挪威菱形藻（Dinophysis norvegica）。新化合物是从2002年10月从挪威松恩峡湾的斯基尔采集的大量以渐尖菱形藻（Dinophysis acuta）为主的水华中作为次要成分分离出来的。LC-MS和核磁共振（NMR）分析表明，新成分36S-PTX-12和36R-PTX-12是一对相互平衡的非对映异构体，与PTX-2不同的是，它们在C-38位含有一个环外烯丙基亚甲基而不是一个甲基。贝类提取物分析表明，PTX-12在挪威蓝贻贝（Mytilus edulis）和鸟蛤（Cerastoderma edule）中积累，同时PTX-12的裂合酸以非对映异构体的复杂混合物形式存在。对从弗勒德维根网捞中挑选的藻类细胞进行LC-MS分析表明，PTX-12在渐尖菱形藻和挪威菱形藻中占主导地位，而PTX-2是尖刺菱形藻中主要的pectenotoxin。初步观察表明，在挪威，即使在单一的菱形藻物种内，PTX-2和PTX-12的相对含量在不同地点和年份也有所不同。我们的数据还表明，异养甲藻可能会从其猎物中积累毒素。
