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

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Qin, Y‐G., Yang, Z‐K., Song, D-L., Wang, Q., Gu, S-H., Li, W-H., Duan, H-W., Zhou, J-J. and Yang, X‐L. 2020. Bioactivities of synthetic salicylate‐substituted carboxyl (E)‐β‐Farnesene derivatives as ecofriendly agrochemicals and their binding mechanism with potential targets in aphid olfactory system . Pest Management Science. 76 (7), pp. 2465-2472. https://doi.org/10.1002/ps.5787

AuthorsQin, Y‐G., Yang, Z‐K., Song, D-L., Wang, Q., Gu, S-H., Li, W-H., Duan, H-W., Zhou, J-J. and Yang, X‐L.
Abstract

BACKGROUND:The aphid alarm pheromone,(E)-β-farnesene (EβF), is a natural product secreted from the aphid cornicle as a signal to warn companions of danger. Odorant binding proteins (OBPs) are the vitaltargetsin insect signal transduction pathways. To improve bioactivity of EβFasmore economic and stable aphid control agents, EβF derivatives containing an active substructure,salicylic acid moiety,were designed, synthesized, and evaluated for theirbioactivitiesina structure-function study underlaboratory conditions. RESULTS:EβFderivatives, (E)-3,7-dimethylocta-2,6-dien-1-yl-2-hydroxy-3-methylbenzoateand(E)-3,7-dimethylocta-2,6-dien-1-yl-2-hydroxy-3-methoxybenzoateshowed outstanding aphid-repellent activity at a dose of 5 µgagainst Acyrthosiphon pisum(repellency proportions of 67.3% and 71.2%, respectively) and Myzus persicae(repellency proportionsof 80.0% and 74.4%, respectively)in laboratory. EβF and most of its derivatives bound strongly to ApisOBP9with a higheraffinity than thoseof the reported potential targetsAphisOBP3 and ApisOBP7. The binding affinitiesto these three ApisOBPswere generally consistentwith the in vivoaphid-repellent activity. A molecular docking study suggested that the hydrophobic effectwas crucial fortheinteractions between the derivatives and the OBPs.
CONCLUSION: New EβFderivatives containing salicylic acid moietyand their repellent activity, binding mechanism with three potential OBPs are presented. A new OBP, ApisOBP9, was characterizedas a potentialEβF and EβF derivativesbinding proteinfor the first time. The hydrophobic nature of these analogues is responsible for their activity. Two analogues 3band 3ewith outstanding aphid-repellent activity could be newleadsfor aphid control agents.

Keywords(E)-β-farnesene ; Salicylic acid; Repellent activity; Molecular docking; Odorant-binding proteins
Year of Publication2020
JournalPest Management Science
Journal citation76 (7), pp. 2465-2472
Digital Object Identifier (DOI)https://doi.org/10.1002/ps.5787
Open accessPublished as non-open access
FunderBiotechnology and Biological Sciences Research Council
National Key Research and Development Plan of China
National Natural Science Foundation of China
Funder project or code2017YFD0200504
31772164
31772207
Output statusPublished
Publication dates
Online07 Jun 2020
Publication process dates
Accepted15 Feb 2020
PublisherWiley
ISSN1526-498X

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