Design, Synthesis and Bioactivity of Novel 2-Phenylethanol Ester Derivatives Containing Monoterpene Fragments

文献类型： 外文期刊

第一作者： Pan, Shixiang

作者： Pan, Shixiang;Liu, Yan;Shi, Zhuo;Lu, Xingxing;Chen, Chen;Yang, Xinling;Qin, Yaoguo;Qu, Cheng

作者机构：

关键词： 2-phenylethanol; odorant binding protein; repel aphid; attract ladybug; eco-friendliness

期刊名称：CHINESE JOURNAL OF ORGANIC CHEMISTRY （ 影响因子：2.2； 五年影响因子：1.5 ）

ISSN： 0253-2786

年卷期： 2025 年 45 卷 1 期

页码：

收录情况： SCI

摘要： To discover novel aphid control agents, taking plant volatile 2-phenylethanol as a lead, 16 ester derivatives of 2-phenylethanol containing monoterpenoid fragments were designed and synthesized by the method of active substructure splicing. The binding affinity of target compounds to odorant binding proteins (OBP) of Acyrthosiphon pisum and Harmonia axyridis was measured via fluorescent competitive binding assay. All compounds showed good binding affinity to both proteins, better than 2-phenylethanol. Behavioral experiments showed that all target compounds had repelling activity against A. pisum (35.9%similar to 57.7%) with 3-methoxyphenethyl (E)-3,7-dimethylocta-2,6-dienoate (3f) exhibiting the best repellency. In addition, 3f also showed significant attractive activity to H. axyridis. The binding mode of 3f with the OBP protein was investigated by molecular docking, revealing that the introduction of the monoterpenoid fragment significantly enhanced the hydrophobic interactions between compounds and proteins. Preliminary toxicity tests indicated that 3f was safe to H. axyridis, showing great application prospects in the green control of aphids.

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