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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

作者： Qin, Yao-Guo 1 ; Yang, Zhao-Kai 1 ; Song, Dun-Lun 4 ; Wang, Qian 3 ; Gu, Shao-Hua 3 ; Li, Wen-Hao 1 ; Duan, Hong-Xia 3 ;

作者机构： 1.China Agr Univ, Coll Sci, Dept Appl Chem, Beijing, Peoples R China

2.Rothamsted Res, Dept Biol Chem & Crop Protect, Harpenden AL5 2JQ, Herts, England

3.Chinese Acad Agr Sci, Inst Plant Protect, State Key Lab Biol Plant Dis & Insect Pests, Beijing, Peoples R China

4.China Agr Univ, Dept Entomol, Coll Plant Protect, Beijing, Peoples R China

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

年卷期：

页码：

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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