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Molecules 2018, 23(9), 2362; https://doi.org/10.3390/molecules23092362

Novel Hydroxy- and Epoxy-cis-Jasmone and Dihydrojasmone Derivatives Affect the Foraging Activity of the Peach Potato Aphid Myzus persicae (Sulzer) (Homoptera: Aphididae)

1
Department of Botany and Ecology, University of Zielona Góra, Szafrana 1, 65-516 Zielona Góra, Poland
2
Department of Chemistry, Wrocław University of Environmental and Life Sciences, Norwida 25, 50-375 Wrocław, Poland
*
Author to whom correspondence should be addressed.
Received: 13 July 2018 / Revised: 29 August 2018 / Accepted: 11 September 2018 / Published: 15 September 2018
(This article belongs to the Section Chemical Biology)
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Abstract

Jasmonates show great potential in sustainable agriculture due to their various roles in natural mechanisms of plant defense, and because they are non-toxic, non-mutagenic, and easily metabolized. The aim of the study was to explore structure–activity relationships of dihydrojasmone, cis-jasmone, and their derivatives at the plant–aphid interface. We focused on the behavioral responses of aphids, following the exogenous application of natural jasmonates and their derivatives to the host plants. Aphid probing behavior was examined using an electrical penetration graph technique (EPG). The chemoenzymatic transformation of cis-jasmone and the activity of two new derivatives are described. The application of cis-jasmone, dihydrojasmone, the hydroxyderivatives, epoxyderivatives, and alkyl-substituted δ-lactones hindered the foraging activity of Myzus persicae (Sulz.) (Hemiptera: Aphididae) during early stages of probing at the level of non-phloem tissues. The application of saturated bicyclic epoxy-δ-lactone enhanced plant acceptance by M. persicae. Jasmonate derivatives containing a hydroxy group, especially in correlation with a lactone ring, were more active than natural compounds and other derivatives studied. Jasmonates of the present study are worth considering as elements of sustainable aphid control as components of the “push–pull” strategy. View Full-Text
Keywords: aphid probing behavior; antifeedant; structure-activity relationships aphid probing behavior; antifeedant; structure-activity relationships
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Paprocka, M.; Gliszczyńska, A.; Dancewicz, K.; Gabryś, B. Novel Hydroxy- and Epoxy-cis-Jasmone and Dihydrojasmone Derivatives Affect the Foraging Activity of the Peach Potato Aphid Myzus persicae (Sulzer) (Homoptera: Aphididae). Molecules 2018, 23, 2362.

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