Herbicidal Activity of Monoterpenes Is Associated with Disruption of Microtubule Functionality and Membrane Integrity
Herbicidal Activity of Monoterpenes Is Associated with Disruption of Microtubule Functionality and Membrane Integrity
复制标题
DOI：
10.1614/ws-d-16-00044.1
复制
发表时间：
2017-01-01
期刊：
影响因子：
2.5
通讯作者：
Dudai, Nativ
中科院分区：
文献类型：
--
作者：
Chaimovitsh, David;Shachter, Alona;Dudai, Nativ
芳香植物及其挥发性化合物影响种子萌发和植物生长，因此具有作为植物生长调节剂和生物除草剂的农业用途的潜力。本研究选择了17种主要的单萜类化合物，并以不同生长阶段的转基因拟南芥为材料，对其植物毒性机制进行了研究。微管蛋白和植物细胞膜被确定为植物毒性和除草活性作用的焦点靶标。观察到单萜机制的变异性。柠檬烯和（+）-香茅醛具有强的抗微管功效，而柠檬醛、香叶醇、（-）-薄荷酮、（+）-香芹酮和（-）-香茅醛表现出中等的抗微管功效。胡薄荷酮、（-）-香芹酮、香芹酚、橙花醇、香叶酸、（+）/（-）-香茅醇和香茅酸缺乏抗微管能力。记录了（+）/（-）-香茅醛和（+）/（-）-香芹酮对微管组装的对映选择性破坏。（+）对映体比（-）对映体更有效。柠檬醛，柠檬烯，香芹酚，和胡薄荷酮也进行了测试的植物毒性和除草活性。胡薄荷酮对微管或膜没有可检测的影响。柠檬醛破坏微管，但不引起膜损伤。香芹酚对微管缺乏可检测的作用，但会引起膜渗漏，柠檬烯会破坏微管和膜渗漏。因此，在测试浓度下仅柠檬烯是除草剂。在植物中残留物的定量显示，柠檬醛被生物转化成橙花醇和香叶醇，柠檬烯被转化成香芹酚，这可以解释其相对于微管和膜功能的双重能力。所获得的结果是一个重要的附加值的商业努力，在选择适当的芳香族植物的生物除草化合物的来源，可持续的杂草管理与除草剂抗性进化的杂草种群的潜力有限。
Aromatic plants and their volatile compounds affect seed germination and plant growth, and therefore hold potential for agriculture uses as plant growth regulators and bioherbicides. In the present study 17 major monoterpenes were selected, and their mechanisms of plant toxicity were elucidated using transgenic Arabidopsis thaliana at various growth stages. Microtubulin and the plant cell membrane were identified as the focal targets through which phytotoxicity and herbicidal activity acted. Variability in monoterpene mechanisms was observed. Limonene and (+)-citronellal had strong antimicrotubule efficacy, whereas citral, geraniol, (-)-menthone, (+)-carvone, and (-)-citronellal demonstrated moderate antimicrotubule efficacy. Pulegone, (-)-carvone, carvacrol, nerol, geranic acid, (+)/(-)-citronellol, and citronellic acid lacked antimicrotubule capacity. An enantioselective disruption of microtubule assembly was recorded for (+)/(-)-citronellal and (+)/(-)-carvone. The (+) enatiomers were more potent than their (-) counterparts. Citral, limonene, carvacrol, and pulegone were also tested for phytotoxicity and herbicidal activity. Pulegone had no detectable effect on microtubules or membranes. Citral disrupted microtubules but did not cause membrane damage. Carvacrol lacked a detectable effect on microtubules but incited membrane leakage, and limonene disrupted microtubules and membrane leakage. Therefore, only limonene was herbicidal at the tested concentrations. In planta quantification of residues revealed that citral was biotransformed into nerol and geraniol, and limonene was converted into carvacrol, which could explain its dual capacity with respect to microtubules and membrane functionality. The results obtained are an important added value to commercial efforts in selecting appropriate aromatic plants to be sources of bioherbicidal compounds for sustainable weed management with a limited potential for herbicide resistance evolution in weed populations.