Odorant-Binding Protein 3-Oriented Rational Design and Discovery of Novel Jasmonate Derivatives as Potential Aphid-Repellent Agents

Abstract

Odorant-binding protein (OBP) is a potential target for developing insect behavior control agents due to its properties in transporting semiochemicals. In this study, 12 novel jasmonic acid (JA) derivatives were rationally designed and synthesized based on the binding features between Acyrthosiphon pisum OBP3 (ApisOBP3) and compound D1 [(E)-3,7-dimethylocta-2,6-dien-1-yl 2-(3-oxo-2-pentylcyclopentyl)­acetate] with a binding affinity (K d) of 26.79 μM. Most novel JA derivatives displayed better binding affinities than D1 (K d = 1–26 μM). Among them, compound 6b [(E)-3,7-dimethylocta-2,6-dien-1-yl-2-((Z)-3-((acryloyloxy)­imino)-2-pentylcyclopentyl)­acetate] is the most promising compound with an excellent K d of 1.33 μM and a significant repellent activity with repellent rates of 50–60% against A. pisum and Myzus persicae. Both hydrophobic and electrostatic interactions were found to contribute significantly to the binding of 6b to ApisOBP3. This study provides significant guidance for the rational design and efficient identification of novel aphid repellents based on aphid OBPs.

Development of Sustainable Insecticide Candidates for Protecting Pollinators: Insight into the Bioactivities, Selective Mechanism of Action and QSAR of Natural Coumarin Derivatives against Aphids

“…6 Unexpectedly, as shown in Figure 2I, after 6methylcoumarin treatment for 24, 48, and 72 h, there was no difference in the proportion of aphids on the treated or control side of cotton leaves, demonstrating that 6-methylcoumarin exhibited no repellent activity against aphids. It has been reported that most of the natural products with repellent activity against aphids are volatile, such as lemon, 40 jasmonic acid, 41 and farnesol. 39 However, in this study, 6-methylcoumarin does not possess these properties, which may be the reason for its lack of repellent activity.…”

Discovery and properties of novel analogues of the aphid pheromones nepetalactone and nepetalactol

“…1(a,b). [8][9][10][11][12][13][14][15] (E)-⊎-farnesene (EBF) is the main component of aphid alarm pheromones, which are emitted by aphids to warn their conspecifics to leave the area in case of danger. 9 This pheromone also serves as a signal for natural enemies of aphids to locate their prey.…”

“…To improve the stability of EBF, researchers have extensively modified the conjugated diene in EBF that is susceptible to oxidation by increasing the molecular weight, reducing unsaturation, and introducing active fragments of other plant volatiles. [10][11][12][13][14][15][20][21][22][23] Furthermore, studies on EBF have been conducted to better understand the mechanisms of action. Odorant binding proteins 3 (OBP3), OBP5, and OBP9 in aphids have been found to have high binding affinity to EBF.…”

“…Considerable progress has been made in elucidating the properties and functions of aphid alarm pheromones, as evidenced by some extensive research findings on compounds shown in Fig. 1(a,b) 8–15 …”

“…However, the inherent instability of EBF poses a challenge to its practical application in pest control. To improve the stability of EBF, researchers have extensively modified the conjugated diene in EBF that is susceptible to oxidation by increasing the molecular weight, reducing unsaturation, and introducing active fragments of other plant volatiles 10–15,20–23 . Furthermore, studies on EBF have been conducted to better understand the mechanisms of action.…”