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

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.

Repellent and Antifeedant Activities of Citral-Derived Lactones against the Peach Potato Aphid

“…Under natural conditions, the high proportion of salivation during the consumption of the phloem sap is typical for aphid behavior on unsuitable or non-host plants [51][52][53]. Similar effects on aphid behavior during the phloem phase were revealed when aphids were offered plants treated with natural and synthetic compounds, e.g., piperitone-derived lactones, cis-jasmone and its derivatives, β-thujone and its derivatives, or farnesol and nerolidol [32,[54][55][56]. The settling deterrent activities of β,γ-dimethyllactone (4) and α,γ-dimethylenelactone (7) were probably due to the post-ingestive inhibition.…”

Induced Systemic Resistance by a Plant Growth-Promoting Rhizobacterium Impacts Development and Feeding Behavior of Aphids

“…Third, +E aphids salivated longer in the phloem before the first E2 on +PGPR plants. Because various jasmonate components can be detected in the phloem and influence aphid feeding behavior [65], it seems that +E aphids were able to recognize the primed state of V. faba once it reached the phloem sap, and to adapt, in consequence, its salivation behavior. In A. pisum, some salivary proteins were identified as effectors that modulate insect feeding and survival on V. faba [66,67], and potentially inhibit plant immune responses in phloem sieve elements [64,68,69].…”

Effect of Naringenin and Its Derivatives on the Probing Behavior of Myzus persicae (Sulz.)

“…We have established that the potency and persistence of behavioral effects on aphid probing of piperitone-, β -damascone-, xanthohumol-, isoxanthohumol-, and cis -jasmone-derived compounds depended on their substituents. Certain modifications caused shifts from attractant to deterrent properties, or vice versa [ 24 , 25 , 26 , 29 ]. In the present study, we also revealed specific structure–activity relationships.…”

“…Therefore, the synthesis of natural compound analogues is one of the most promising ways leading to their practical use in insect pest population control [ 24 ]. Structural transformations of the natural molecule usually change the mode of action and potency of its activity [ 25 , 26 ]. The possibility of reducing aphid infestation of crop plants by naringenin and its analogues application has never been explored.…”