Bioactivities of synthetic salicylate-substituted carboxyl (E)-beta-Farnesene derivatives as ecofriendly agrochemicals and their binding mechanism with potential targets in aphid olfactory system

文献类型： 外文期刊

第一作者： Qin, Yao-Guo

作者： Qin, Yao-Guo;Yang, Zhao-Kai;Li, Wen-Hao;Yang, Xin-Ling;Zhou, Jing-Jiang;Qin, Yao-Guo;Wang, Qian;Gu, Shao-Hua;Duan, Hong-Xia;Song, Dun-Lun;Gu, Shao-Hua

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关键词： (E)-beta-farnesene; salicylic acid; repellent activity; odorant-binding proteins; molecular docking

期刊名称：PEST MANAGEMENT SCIENCE （ 影响因子：4.845； 五年影响因子：4.674 ）

ISSN： 1526-498X

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收录情况： SCI

摘要： BACKGROUND The aphid alarm pheromone, (E)-beta-farnesene (E beta F), is a natural product secreted from the aphid cornicle as a signal to warn companions of danger. Odorant binding proteins (OBPs) are the vital targets in insect signal transduction pathways. To improve bioactivity of E beta F as more economic and stable aphid control agents, E beta F derivatives containing an active substructure, salicylic acid moiety, were designed, synthesized, and evaluated for their bioactivities in a structure-function study under laboratory conditions. RESULTS E beta F derivatives, (E)-3,7-dimethylocta-2,6-dien-1-yl-2-hydroxy-3-methylbenzoate and (E)-3,7-dimethylocta-2,6-dien-1-yl-2-hydroxy-3-methoxybenzoate showed outstanding aphid-repellent activity at a dose of 5 mu g against Acyrthosiphon pisum (repellency proportions of 67.3% and 71.2%, respectively) and Myzus persicae (repellency proportions of 80.0% and 74.4%, respectively) in laboratory. E beta F and most of its derivatives bound strongly to ApisOBP9 with a higher affinity than those of the reported potential targets AphisOBP3 and ApisOBP7. The binding affinities to these three ApisOBPs were generally consistent with the in vivo aphid-repellent activity. A molecular docking study suggested that the hydrophobic effect was crucial for the interactions between the derivatives and the OBPs. CONCLUSION New E beta F derivatives containing salicylic acid moiety and their repellent activity, binding mechanism with three potential OBPs are presented. A new OBP, ApisOBP9, was characterized as a potential E beta F and E beta F derivatives binding protein for the first time. The hydrophobic nature of these analogues is responsible for their activity. Two analogues 3b and 3e with outstanding aphid-repellent activity could be new leads for aphid control agents.

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