Discovery of Novel Potential Aphid Repellents: Geranic Acid Esters Containing Substituted Aromatic Rings

文献类型： 外文期刊

第一作者： Pan, Shixiang

作者： Pan, Shixiang;Li, Wenhao;Yang, Zhaokai;Liu, Yan;Shi, Zhuo;Yang, Xinling;Qin, Yaoguo;Qu, Cheng;Luo, Chen

作者机构：

关键词： molecular design; ester; aphids; repel; odorant-binding proteins; molecular docking

期刊名称：MOLECULES （ 影响因子：4.927； 五年影响因子：5.11 ）

ISSN：

年卷期： 2022 年 27 卷 18 期

页码：

收录情况： SCI

摘要： Aphids are one of the most damaging agricultural pests. For the sake of novel eco-friendly compounds with good activity for aphid control, a series of novel geranic acid esters containing substituted aromatic rings were designed by inverting ester groups of lead compounds. All compounds were characterized by HRMS, H-1-NMR, and C-13-NMR. In order to identify the effect of inversion ester groups on activity, a bioassay was conducted. The results showed that the repellent activity against Acyrthosiphon pisum (A. pisum) and the binding affinity with the odorant-binding protein 9 from A. pisum (ApisOBP9) of the compounds were increased after inversion of the ester groups. Particularly, 5f showed the best repellent activity (repellency proportion: 55.6%) and binding affinity (1/Ki: 0.49 mu M). Meanwhile, the structure-activity relationships revealed that the introduction of meta-substitution of the benzene ring and halogen atoms, such as Cl and Br, facilitated the biological activity. The further molecular docking results demonstrated that hydrogen bonding interactions and hydrophobic interactions were vital for the binding affinity with ApisOBP9. Additionally, all compounds were predicted to be eco-friendly and their volatile physicochemical properties have been enhanced compared to the leads. The present results provide valuable clues for the further rational design of aphids' behavioral control agents.

分类号：

  • 相关文献
作者其他论文 更多>>

微信小程序