新型2,3-二氢喹啉-4(1H)-酮类独角金内酯类似物的合成及其对分枝列当的防治效果

    Synthesis of novel strigolactone analogues with 2,3-dihydroquinolin-4(1H)-one scaffold and efficacy for the Phelipanche aegyptiaca

    • 摘要: 分枝列当 (Phelipanche aegyptiaca) 为一年生全寄生杂草,广泛分布于我国西北部地区,主要寄生在番茄、马铃薯等茄科作物上。当前,国内外仍无针对分枝列当防治的有效药剂。基于天然独角金内酯刺激诱导分枝列当种子萌发的能力,本研究设计、合成了一系列二氢喹啉酮类独角金内酯类似物用于诱导分枝列当自杀性萌发,从而实现对分枝列当的有效防治。研究结果表明,化合物5a5b5i5m5n的生物活性优于阳性对照化合物rac-GR24。其中化合物5m对分枝列当种子的有效抑制中浓度(EC50)为0.00358 mg/L,是阳性对照rac-GR24 (0.04158 mg/L) 的1/12左右。温室盆栽试验结果表明,化合物5m在10 mg/L下对分枝列当的防治效果最好,平均每盆寄生1.62株,而空白对照组平均每盆寄生13.60株。通过对化合物5m进行分子对接计算,确定了其在蛋白空腔中的有效结合模式。这些研究结果为开发二氢喹啉酮类独角金内酯类似物用于分枝列当寄生杂草防治提供了理论基础。

       

      Abstract: As an annual holoparasitic weed, Phelipanche aegyptiaca is widely distributed in the northwest area of China, primarily parasitizing solanaceous crops such as tomato and potato. Currently, there is no effective herbicide for controlling P. aegyptiaca. Based on the seed germination property of natural strigolactones, herein we synthesized a series of strigolactone analogues derived from 2,3-dihydroquinolin-4(1H)-one scaffold applied to P. aegyptiaca control. Compounds 5a, 5b, 5i, 5m, and 5n showed higher bioactivity than the positive control rac-GR24 (EC50 = 0.04158 mg/L). Particularly, compound 5m (EC50 = 0.00358 mg/L) displayed a 12-fold higher seed germination activity than rac-GR24 towards the parasitic P. aegyptiaca seeds. The greenhouse experiment revealed that compound 5m exhibited a robust potential in P. aegyptiaca control. Compared to the control group (13.60 per pot), the number of P. aegyptiaca plant infected to the tomato plant crashed to 1.62 per pot at the dosage of 10 mg/L. Finally, to better understand the structure-activity relationship on these novel quinoline-4-one derivatives, we performed molecular docking of compound 5m. The results of this study provide a promising basis for using quinoline-4-one-derived strigolactone analogues for the P. aegyptiaca control.

       

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