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Pest Manag Sci

Title:		Bioactivities of synthetic salicylate-substituted carboxyl (E)-beta-Farnesene derivatives as ecofriendly agrochemicals and their binding mechanism with potential targets in aphid olfactory system
Author(s):		Qin YG; Yang ZK; Song DL; Wang Q; Gu SH; Li WH; Duan HX; Zhou JJ; Yang XL;
Address:		"Department of Applied Chemistry, College of Science, China Agricultural University, Beijing, China. State Key Laboratory for Biology of Plant Diseases and Insect Pests, Institute of Plant Protection, Chinese Academy of Agricultural Sciences, Beijing, China. Department of Entomology, College of Plant Protection, China Agricultural University, Beijing, China. Department of Biological Chemistry and Crop Protection, Rothamsted Research, Harpenden, Hertfordshire, UK"
Journal Title:		Pest Manag Sci
Year:		2020
Volume:		20200226
Issue:		7
Page Number:		2465 - 2472
DOI:		10.1002/ps.5787
ISSN/ISBN:		1526-4998 (Electronic) 1526-498X (Linking)
Abstract:		"BACKGROUND: The aphid alarm pheromone, (E)-beta-farnesene (EbetaF), 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 EbetaF as more economic and stable aphid control agents, EbetaF 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: EbetaF 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 mug 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. EbetaF 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 EbetaF 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 EbetaF and EbetaF 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"
Keywords:		Agrochemicals Animals *Aphids Molecular Docking Simulation Pheromones Salicylic Acid Sesquiterpenes (E)-beta-farnesene molecular docking odorant-binding proteins repellent activity;
Notes:		"MedlineQin, Yao-Guo Yang, Zhao-Kai Song, Dun-Lun Wang, Qian Gu, Shao-Hua Li, Wen-Hao Duan, Hong-Xia Zhou, Jing-Jiang Yang, Xin-Ling eng 2017YFD0200504/the National Key Research and Development Plan of China/ 31772164/the National Natural Science Foundation of China/ 31772207/the National Natural Science Foundation of China/ England 2020/02/16 Pest Manag Sci. 2020 Jul; 76(7):2465-2472. doi: 10.1002/ps.5787. Epub 2020 Feb 26"