Absolute configuration of volicitin from the regurgitant of lepidopteran caterpillars and biological activity of volicitin-related compounds
Absolute configuration of volicitin from the regurgitant of lepidopteran caterpillars and biological activity of volicitin-related compounds
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DOI：
10.1271/bbb.60133
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发表时间：
2006-09-01
影响因子：
1.6
通讯作者：
Mori, Naoki
中科院分区：
文献类型：
--
作者：
Sawada, Yoshitsugu;Yoshinaga, Naoko;Mori, Naoki
Volicitin [N-（17-hydroxylinolenoyl）-L-glutamine]和N-linolenoyl-L-glutamine是昆虫产生的植物挥发性激发子。测定了三种夜蛾科物种（棉铃虫、粘虫和斜纹夜蛾）volicitin的羟基亚麻酰基部分的绝对构型，均为17 S，且对映体过量较高。当用30 pmol的（17 S）-和（17 R）-volicitin处理时，诱导玉米幼苗释放挥发物，两种异构体之间释放的量没有显著差异。另一方面，N-亚麻酰-L-谷氨酰胺的活性仅为volicitin的约30%。在几种合成的N-亚麻酸氨基酸共轭物中，只有L-谷氨酰胺共轭物诱导挥发性有机化合物的排放。这些结果表明，volicitin的L-谷氨酰胺部分发挥了更关键的作用比羟基部分，虽然这两个部分影响诱导挥发物释放的激发子活性。
Volicitin [N-(17-hydroxylinolenoyl)-L-glutamine] and N-linolenoyl-L-glutamine are known as insect-produced plant volatile elicitors. The absolute configuration of the hydroxylinolenoyl moiety of volicitin from three noctuid species, Helicoverpa armigera, Mythimna separata and Spodoptera litura, was determined to be all 17S in high enantiomeric excess. When treated with 30 pmol of (17S)- and (17R)-volicitin, corn seedlings were induced, to release volatiles, there being no significant difference in the amount released between the two isomers. On the other hand, N-linolenoyl-L-glutamine was only about 30% as active as volicitin. Among several synthesized N-linolenoylamino acid conjugates, only the L-glutamine conjugate induced the emission of volatile organic compounds. These results show that the L-glutamine moiety of volicitin played a more critical role than the hydroxyl moiety, although both moieties affected the elicitor activity inducing the release of volatiles.