Systematic Modification of Zingerone Reveals Structural Requirements for Attraction of Jarvis’s Fruit Fly

Abstract

Tephritid fruit flies are amongst the most significant horticultural pests globally and male chemical lures are important for monitoring and control. Zingerone has emerged as a unique male fruit fly lure that can attract dacine fruit flies that are weakly or non-responsive to methyl eugenol and cuelure. However, the key features of zingerone that mediate this attraction are unknown. As Jarvis’s fruit fly, Bactrocera jarvisi (Tryon), is strongly attracted to zingerone, we evaluated the response of B. jarvisi to 37 zingerone analogues in a series of field trials to elucidate the functional groups involved in attraction. The most attractive analogues were alkoxy derivatives, with isopropoxy being the most attractive, followed by ethoxy and trifluoromethoxy analogues. All of the phenolic esters tested were also attractive with the response typically decreasing with increasing size of the ester. Results indicate that the carbonyl group, methoxy group, and phenol of zingerone are key sites for the attraction of B. jarvisi and identify some constraints on the range of structural modifications that can be made to zingerone without compromising attraction. These findings are important for future work in developing and optimising novel male chemical lures for fruit flies.

Vapor Pressures and Thermodynamic Properties of Phenylpropanoid and Phenylbutanoid Attractants of Male Bactrocera, Dacus, and Zeugodacus Fruit Flies at Ambient Temperatures

“…Clausius–Clapeyron plot for (a) RK and (b) ZG. The full circles are the DSC data from Park et al for RK and Hanssen et al for ZG. The triangles are the measured data from the saturator.…”

“…We here report on the construction of a simple saturator, the vapor pressures obtained by the saturation method, and estimated thermodynamic properties for seven male fruit fly attractants, which were selected based on recent field trials. ,,− …”

Recent Advancements in Studies on Chemosensory Mechanisms Underlying Detection of Semiochemicals in Dacini Fruit Flies of Economic Importance (Diptera: Tephritidae)

“…Furthermore, both ME-and RK-sensitive fruit fly species are attracted to zingerone owing to its structural resemblance to ME and RK [23]. A recent study on the chemical modification of zingerone has shown the structural properties required for the attraction of B. jarvisi [154]. Therefore, it will be interesting to study partial structures in ME-and RK-receptors that are necessary for binding to zingerone.…”

“…A recent study on the chemical modification of zingerone has shown the structural properties required for the attraction of B . jarvisi [ 154 ]. Therefore, it will be interesting to study partial structures in ME- and RK-receptors that are necessary for binding to zingerone.…”

Male-lure type, lure dosage, and fly age at feeding all influence male mating success in Jarvis’ fruit fly

“…In the laboratory, dose-response curves demonstrate that the species is approximately 1,500 times more responsive to zingerone than raspberry ketone: the species is also attracted to zingerone at a much younger age than to raspberry ketone 11 . The carbonyl group, methoxy group, and phenolic of zingerone are considered the key structural elements which make that chemical so attractive to B. jarvisi 25 . However, despite detailed knowledge on the relative attractiveness of B. jarvisi to raspberry ketone and zingerone, what role, if any, the two chemicals play in sexual selection in the species is not known.…”