TOXIC SUBSTANCES, HETEROCAPSATOXIN A AND B TOWARDS OYSTER FROM RED TIDES, HETEROCAPSA CIRCULARISQUAMA, APPREARED IN SETO INLAND SEA

濑户内海赤潮中发现的有毒物质异辣椒素 A 和 B 对牡蛎的影响

基本信息

批准号：
14380275
负责人：
HIRAGA Yoshikazu
金额：
$ 4.54万
依托单位：
HIROSHIMA UNIVERSITY
依托单位国家：
日本
项目类别：
Grant-in-Aid for Scientific Research (B)
财政年份：
2002
资助国家：
日本
起止时间：
2002 至 2004
项目状态：
已结题

项目摘要

Harmful phytoplankton blooms have caused serious social and environmental problems and heavy damage to fisheries throughout the world. In recent years, a novel dinoflagellate Heterocapsa circularisquama has caused mass mortality of bivalves, e.g. oysters and pearl oysters, in several inner bay of Japan. In our research the toxic substance in this plankton, two novel compounds exhibit the toxicity towards oyster were isolated.The algae of cultured H.circularisquama was extracted with 1-BuOH, and the 1-BuOH extract was partitioned between hexane and 80% MeOH. The residue from the 80% MeOH-soluble fraction was subjected to column chromatography on reversed phase silica gel to afford the biologically active fractions. Further separation by silica gel column chromatography, gel permeation chromatography, and HPLC (reverse phase) yielded two toxic substances named heterocapsatoxin A (HTX-A, molecular weight 5024) and heterocapsatoxin B (HTX-B, molecular weight 1980). Analysis of ^1H and ^<13>C NMR spectra of HTX-A and HTX-B, they have a very similar structures which contained the several C=C double bonds and many oxygen functionalities.In order to elucidate the structure of HTX-A,HTX-A was subjected to ozonolysis to give two major products, which were named HTX-A1 and HTX-A2. HTX-A1 was determined to have the molecular formula C_<46>H_<84>O_<22> by high-resolution FABMS. The structural elucidation of HTX-A1 was performed mainly by NMR experiments consisting ^1H and ^<13>C NMR,COSY,HMQC, and HMBC.

有害的浮游植物盛开造成了严重的社会和环境问题，并对全世界的渔业造成了严重破坏。近年来，一种新型的鞭毛鞭毛杂质圆形圆形曲霉造成了双壳类的质量死亡，例如日本内湾的牡蛎和珍珠牡蛎。在我们的研究中，该浮游物质中的有毒物质分离出了两种新型化合物对牡蛎的毒性。培养的H. circularisquama的藻类用1-BuOH提取，1-BuOH提取物在己烷和80％MEOH之间分配。从80％MeOH可溶性馏分中的残留物在反向相硅凝胶上进行柱色谱法，以负担生物学活性的馏分。通过硅胶柱色谱，凝胶渗透色谱法和HPLC（反相）进一步分离，产生了两种有毒物质，称为Heterocapsatoxin A（HTX-A，分子量5024）和Heterocapsapapsatoxin b（HTX-B，HTX-B，HTX-B，分子量1980）。分析HTX-A和HTX-B的 ^1H和 ^<13> C NMR光谱，它们具有非常相似的结构，其中包含几个C = C双键和许多氧功能。为了阐明HTX-A的结构，HTX-A的结构，HTX-A的结构受到了两种主要产物，以给出了两种主要产物，以给出了两种命名为HTX-A1和HTX-A1和Htx-A1和HTX-A1和HTX-A1和HTX-AA。确定HTX-A1的分子公式C_ <46> H_ <84> O_ <22>通过高分辨率FABMS。 HTX-A1的结构阐明主要是通过NMR实验进行的，其NMR实验和 ^1H和 ^<13> C NMR，COZY，HMQC和HMBC进行。