Clarification of Plant Octadecanoide Signaling Pathway by using the Modified Probe of Phytotoxin, Coronatine

使用植物毒素冠菌素修饰探针阐明植物十八烷信号通路

基本信息

批准号：
13660102
负责人：
TOSHIMA Hiroaki
金额：
$ 1.98万
依托单位：
IBARAKI UNIVERSITY
依托单位国家：
日本
项目类别：
Grant-in-Aid for Scientific Research (C)
财政年份：
2001
资助国家：
日本
起止时间：
2001 至 2002
项目状态：
已结题

项目摘要

A phytotoxin, coronatine exhibits various biological activities induced by endogenous phytohormone-like regulators, octadecanoide/jasmonoide. Because the intensity of biological activity caused by coronatine is higher than those by octadecanoide/jasmonoide, it seems that coronatine is the most valuable probe to clarify plant octadecanoide signaling pathway.Coronafacic acid, the acid component of coranatine could be synthesized in 1-2 g scale by using the catalytic asymmetric synthesis. The modification of partial structure of coronafacic acid (reduction of conjugated double bond and/or carbonyl group) made it possible to provide chemically stable coronatine analogs, which possess various probe parts (fluorescent chromophore, photoaffinity labeling functional group, radioactive element, and biotin). Since the introduction of a linker to the coronamic acid, was achived, preparation of the affinity chromatography linked by coronatine analogs is possible.The synthesized coronatine analogs were subjected to the bioassay using rice leaves. After treatment of rice leaves with solution of coronatine analogs for 6 h, induced volatiles (terpenes) from leaves to headspace were quantitatively analyzed. Most of the coronatine analogs exhibited higher volatile-inducing activity than that caused by racemic jasmonic acid, which was used as the positive control in this assay. The activity of some coronatine analogs was higher than that of coronatine itself. Therefore, these results showed that coronatine analogs would be useful chemical probes to clarify coronatine binding protein, which might be octadecanoide/jasmonoide binding protein responsible for plant octadecanoide signaling pathway.The research on determination of coronatine binding protein is now in progress.

冠菌素是一种植物毒素，具有由内源性植物激素样调节剂十八烷苷/茉莉酮苷诱导的多种生物活性。由于冠菌素引起的生物活性强度高于十八烷酸/茉莉酸，因此冠菌素似乎是阐明植物十八烷酸信号通路最有价值的探针。冠酸，即冠菌素的酸性成分，可在1-2 g内合成。通过使用催化不对称合成进行规模化。冠发酸部分结构的修饰（共轭双键和/或羰基的还原）使得提供化学稳定的冠发酸类似物成为可能，其具有各种探针部分（荧光发色团、光亲和标记官能团、放射性元素和生物素）。由于实现了在冠酸上引入连接体，因此可以制备由冠菌素类似物连接的亲和色谱。使用稻叶对合成的冠菌素类似物进行生物测定。用冠菌素类似物溶液处理水稻叶子 6 小时后，对从叶子到顶部空间的诱导挥发物（萜烯）进行定量分析。大多数冠菌素类似物表现出比外消旋茉莉酸更高的挥发物诱导活性，外消旋茉莉酸在该测定中用作阳性对照。一些冠菌素类似物的活性高于冠菌素本身。因此，这些结果表明冠菌素类似物将成为阐明冠菌素结合蛋白的有用化学探针，该蛋白可能是负责植物十八烷酸信号通路的十八烷酸/茉莉酮结合蛋白。冠菌素结合蛋白测定的研究正在进行中。