秦耀果, 杨朝凯, 张以涵, 周雨蓓, 潘世香, 刘彦, 石卓, 杨新玲. 新型2-烷氧基取代苯甲酸香叶酯类蚜虫报警信息素类似物的设计、合成及生物活性[J]. 农药学学报, 2022, 24(5): 1179-1188. DOI: 10.16801/j.issn.1008-7303.2022.0103
    引用本文: 秦耀果, 杨朝凯, 张以涵, 周雨蓓, 潘世香, 刘彦, 石卓, 杨新玲. 新型2-烷氧基取代苯甲酸香叶酯类蚜虫报警信息素类似物的设计、合成及生物活性[J]. 农药学学报, 2022, 24(5): 1179-1188. DOI: 10.16801/j.issn.1008-7303.2022.0103
    QIN Yaoguo, YANG Zhaokai, ZHANG Yihan, ZHOU Yubei, PAN Shixiang, LIU Yan, SHI Zhuo, YANG Xinling. Design, synthesis, bioactivities of novel geranyl 2-alkoxy-substitutedbenzoate as aphid alarm pheromone derivatives[J]. Chinese Journal of Pesticide Science, 2022, 24(5): 1179-1188. DOI: 10.16801/j.issn.1008-7303.2022.0103
    Citation: QIN Yaoguo, YANG Zhaokai, ZHANG Yihan, ZHOU Yubei, PAN Shixiang, LIU Yan, SHI Zhuo, YANG Xinling. Design, synthesis, bioactivities of novel geranyl 2-alkoxy-substitutedbenzoate as aphid alarm pheromone derivatives[J]. Chinese Journal of Pesticide Science, 2022, 24(5): 1179-1188. DOI: 10.16801/j.issn.1008-7303.2022.0103

    新型2-烷氧基取代苯甲酸香叶酯类蚜虫报警信息素类似物的设计、合成及生物活性

    Design, synthesis, bioactivities of novel geranyl 2-alkoxy-substitutedbenzoate as aphid alarm pheromone derivatives

    • 摘要: 为了发现结构新颖的蚜虫行为控制剂,以课题组发现的高活性化合物 3e (2-羟基-3-甲氧基苯甲酸香叶酯)为先导,利用活性亚结构拼接的方法,设计合成了15个未见文献报道的新型2-烷氧基取代苯甲酸香叶酯类蚜虫报警信息素(E)-β-farnesene (EβF)衍生物,其结构经过核磁共振氢谱(1H NMR)、红外光谱(IR)和高分辨质谱(HRMS)的确证。蚜虫驱避活性测定结果表明,部分目标化合物在5 µg剂量下对豌豆蚜Acyrthosiphon pisum表现出不同程度的驱避活性,其中化合物 6i 活性最高,驱避率达到60.9%,与先导化合物 3e 的活性没有显著性差异。靶标蛋白结合实验证明,部分目标化合物与气味结合蛋白ApisOBP9具有较好的结合活性,尤其是化合物 6i 与ApisOBP9的结合常数达到(4.92±0.18) µmol/L。进一步的分子对接结果表明, 6i 与靶标ApisOBP9具有较好的结合作用力,能很好地结合到靶标蛋白的活性位点,其结合模式和先导化合物相似。本研究对后续化合物的结构优化具有重要参考价值。

       

      Abstract: In order to discover aphid behavioral control agents with new structures, 15 novel geranyl 2-alkoxy-substitutedbenzoate aphid alarm pheromone (E)-β-Farnesene (EβF) derivatives were designed and synthesized by using the method of linking active substructures based on the lead compound 3e (geranyl 2-hydroxy-3-methoxybenzoate). The structures of the target compounds were confirmed by 1H NMR, IR and HRMS. Preliminary bioassay results showed that some target compounds had varied repellent activity against the pea aphid Acyrthosiphon pisum at the dosage of 5 µg. Among them, the compound 6i exhibited the highest repellent proportion of 60.9%, which was not significantly different from that of the lead 3e . The target protein binding experiments showed that some target compounds had good binding activities with the odorant binding proteins of ApisOBP9. Particularly, compound 6i displayed the best binding constant of (4.92±0.18) µmol/L with ApisOBP9. Further molecular docking study revealed that the representative compound 6i had a good binding affinity to the ApisOBP9, wherein it had the similar binding mode with ApisOBP9 like 3e . This study provides important clues for the further structure optimization.

       

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