Testing a chemical series inspired by plant stress oxylipin signalling agents for herbicide safening activity.
Testing a chemical series inspired by plant stress oxylipin signalling agents for herbicide safening activity.
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DOI：
10.1002/ps.4859
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发表时间：
2018-04
影响因子：
4.1
通讯作者：
Edwards R
中科院分区：
文献类型：
--
作者：
Brazier-Hicks M;Knight KM;Sellars JD;Steel PG;Edwards R
谷物中的除草剂安全化与快速的异生素反应（XR）有关，涉及谷胱甘肽转移酶（GST）的诱导。XR也被植物胁迫期间释放的氧化脂肪酸（oxylipins）所调用，表明这些信号传导剂与安全化之间存在联系。为了研究这种关系，合成了一系列以氧脂12-氧代植物二烯酸和植物前列烷1为模型的化合物，其亲脂性和亲电性不同。然后测试化合物在拟南芥中激发XR的能力，并与安全剂fenclorim相比，保护暴露于除草剂丙草胺的水稻幼苗。在测试的21种化合物中，有三种化合物引起了与fenclorim相关的快速GST诱导。所有化合物具有两个亲电碳中心和一个亲脂性基团的特征都oxylipins和fenclorim。在保护水稻幼苗免受除草剂损害方面观察到的轻微效果与XR呈正相关，但没有提供功能性安全化。基于氧脂素特征的安全剂的设计被证明成功地衍生出在拟南芥中引起快速XR的化合物，但在谷物中不能提供经典的安全化。这些结果进一步支持了安全剂和氧脂素信号传导之间的联系，但也强调了对这些化合物的反应的物种依赖性差异。版权所有© 2018作者.由John Wiley & Sons有限公司代表化学工业协会出版的《害虫管理科学》。
Herbicide safening in cereals is linked to a rapid xenobiotic response (XR), involving the induction of glutathione transferases (GSTs). The XR is also invoked by oxidized fatty acids (oxylipins) released during plant stress, suggesting a link between these signalling agents and safening. To examine this relationship, a series of compounds modelled on the oxylipins 12‐oxophytodienoic acid and phytoprostane 1, varying in lipophilicity and electrophilicity, were synthesized. Compounds were then tested for their ability to invoke the XR in Arabidopsis and protect rice seedlings exposed to the herbicide pretilachlor, as compared with the safener fenclorim. Of the 21 compounds tested, three invoked the rapid GST induction associated with fenclorim. All compounds possessed two electrophilic carbon centres and a lipophilic group characteristic of both oxylipins and fenclorim. Minor effects observed in protecting rice seedlings from herbicide damage positively correlated with the XR, but did not provide functional safening. The design of safeners based on the characteristics of oxylipins proved successful in deriving compounds that invoke a rapid XR in Arabidopsis but not in providing classical safening in a cereal. The results further support a link between safener and oxylipin signalling, but also highlight species‐dependent differences in the responses to these compounds. © 2018 The Authors. Pest Management Science published by John Wiley & Sons Ltd on behalf of Society of Chemical Industry.
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