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

Marlena Paprocka,Anna Gliszczyńska,Katarzyna Dancewicz,Beata Gabryś

doi:10.3390/molecules23092362

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.

Highlights

Jasmonates form a family of compounds that are synthesized in plants via the octadecanoid pathway [1]
We focused on the hydroxyderivative of dihydrojasmone was an aphid settling deterrent while the original compound behavioral responses of aphids, following the exogenous application of natural jasmonates and their was not, and the hydroxyderivative of cis-jasmone was more active than the starting compound [31]
The present study revealed that cis-jasmone (1), dihydrojasmone (2), and basically all derivatives of these natural compounds (3–7 and 9–10) affected the course of the pre-ingestive phase of M. persicae probing: the first probe was significantly several times shorter than on the control plants, the probes were more numerous and separated by 2–16 min non-probing intervals, which resulted in significantly longer time when aphid stylets were outside of the plant (Tables 1 and 2)

Summary

Introduction

Jasmonates form a family of compounds that are synthesized in plants via the octadecanoid pathway [1]. The naturally occurring jasmonates participate in plant developmental processes as phytohormones, are involved in interactions of plants with other organisms, and are vital signaling molecules in plant responses to various abiotic and biotic stresses, including stresses caused by insect feeding [5,6,7,8]. The Food and Agriculture Organization (FAO) estimates that between 20 and 40 percent of global crop yields are reduced each year due to the damage caused by plant pests and diseases Pre-harvest crop loss caused by Molecules 2018, 23, 2362; doi:10.3390/molecules23092362 www.mdpi.com/journal/molecules

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