Department of Life and Environmental Sciences, University of Cagliari , via Ospedale 72, 09124 Cagliari, Italy.
J Agric Food Chem. 2015 Nov 18;63(45):9970-6. doi: 10.1021/acs.jafc.5b04815. Epub 2015 Nov 10.
A series of aryl hydrazones were synthesized and in vitro assayed for their activity on the root-knot nematode Meloidogyne incognita. The phenylhydrazones of thiophene-2-carboxyaldehyde 5, 3-methyl-2-thiophenecarboxyaldehyde, 6, and salicylaldehyde, 2, were the most potent with EC50/48h values of 16.6 ± 2.2, 23.2 ± 2.7, and 24.3 ± 1.4 mg/L, respectively. A GC-MS metabolomics analysis, after in vitro nematode treatment with hydrazone 6 at 100 mg/L for 12 h, revealed elevated levels of fatty acids such as lauric acid, stearic acid, 2-octenoic acid, and palmitic acid. Whereas control samples showed the highest levels of monoacylglycerols such as monostearin and 2-monostearin, surprisingly, 2 h after treatment with hydrazone 6, nematodes excreted 3 times the levels of ammonia eliminated in the same conditions by controls. Thus, phenylhydrazones may represent a good scaffold in the discovery and synthesis of new nematicidal compounds, and a metabolomics approach may be helpful in understanding their mechanisms of toxicity and mode of action.
合成了一系列芳基腙，并在体外对其对根结线虫 Meloidogyne incognita 的活性进行了测定。噻吩-2-甲醛、3-甲基-2-噻吩甲醛和水杨醛的苯腙具有最强的活性，其 EC50/48h 值分别为 16.6±2.2、23.2±2.7 和 24.3±1.4 mg/L。在体外线虫处理 12 h 后，用 100 mg/L 的腙 6 处理后，通过 GC-MS 代谢组学分析发现，脂肪酸如月桂酸、硬脂酸、2-辛烯酸和棕榈酸的水平升高。而对照样品中单酰基甘油如单硬脂酸甘油酯和 2-单硬脂酸甘油酯的水平最高，令人惊讶的是，在用 6 号腙处理 2 h 后，线虫排出的氨的水平是对照样品在相同条件下排出的氨的水平的 3 倍。因此，苯腙可能是发现和合成新杀线虫化合物的良好支架，代谢组学方法可能有助于理解其毒性机制和作用模式。
