Effects of carboxyl and acylamino linkers in synthetic derivatives of aphid alarm pheromone (E)-β-farnesene on repellent, binding and aphicidal activity

Qin, Yuchuan; Yang, Zhaokai; Zhou, Jing‐Jiang; Zhang, Shang-Yang; Pan, Shixiang; Liu, Yan; Gu, Shaohua; Duan, Hongxia; Yang, Xinling

doi:10.1016/j.molstruc.2022.133658

Cited by 5 publications

(4 citation statements)

References 41 publications

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“…In this work, more ligands including MeSA, GA, 4e and 4i were used to elucidate the binding mechanism between ligands and target ApisOBP9 through molecular docking, indicating hydrophobic interaction and H‐bond were vital for the derivatives binding with ApisOBP9. This result was consistent with that observed in our previous docking study for ApisOBP9 33,58 . The Arg126 was key residue for H‐bond receptor.…”

Section: Resultssupporting

confidence: 92%

“…This result was consistent with that observed in our previous docking study for ApisOBP9. 33,58 The Arg126 was key residue for H-bond receptor. Compound 3e had both hydrophobic interactions and H-bonds with ApisOBP9 and 4i had the most potent hydrophobic interactions suggesting why these two ligands showed the best binding affinity in our experiments.…”

Section: Molecular Docking 341 Molecular Docking Of Ligands To Apisobp9mentioning

confidence: 99%

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Aphid‐repellent, ladybug‐attraction activities, and binding mechanism of methyl salicylate derivatives containing geraniol moiety

Yang

Pan

et al. 2022

Pest Management Science

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BACKGROUND Aphids have been mainly controlled by traditional chemical insecticides, resulting in unamiable risk to the environment over the last decades. Push–pull strategy is regarded as a promising eco‐friendly approach for aphid management through repelling aphid away and attracting their natural enemy. Methyl salicylate (MeSA), one of typical HIPVs (herbivore‐induced plant volatiles), can repel aphids and attract ladybugs. Our previous studies discovered a new lead compound 3e, a salicylate‐substituted carboxyl (E)‐β‐farnesene derivative that had effective aphid‐repellent activity. However, whether 3e has attractive activity to ladybug like MeSA is unknown. Meanwhile, to discover a new derivative for both deterring aphid and recruiting ladybug is meaningful for green control of aphids. RESULTS Through the structural optimization of 3e, 14 new derivatives were designed and synthesized. Among them, compounds 4e and 4i had good aphid (Acyrthosiphon pisum) repellent activity, and compounds 3e, 4e and 4i had significant ladybug (Harmonia axyridis) attractive activity to males. Particularly, 4i exhibited manifest attractive effect on the females as well. Binding mechanism showed that 4i not only bound effectively with the aphid (Acyrthosiphon pisum) target ApisOBP9 thanks to its multiple hydrophobic interactions and hydrogen‐bond, but also had strong binding affinity with ladybug target HaxyOBP15 due to the suitable steric space. Additionally, 4i displayed low toxicity to bee Apis mellifera. CONCLUSION Compound 3e does exhibit attractive activity to male ladybug as MeSA. However, the new derivative 4i, with both pleasant aphid‐repellent and ladybug‐attraction activities, can be considered as a novel potential push–pull candidate for aphid control in sustainable agriculture. © 2022 Society of Chemical Industry.

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Section: Resultssupporting

confidence: 92%

Section: Molecular Docking 341 Molecular Docking Of Ligands To Apisobp9mentioning

confidence: 99%

Aphid‐repellent, ladybug‐attraction activities, and binding mechanism of methyl salicylate derivatives containing geraniol moiety

Yang

Pan

et al. 2022

Pest Management Science

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“…However, the result of the bioassay showed that they were not effective in repelling aphids [22]. Subsequently, we optimized the structure of those compounds by introducing the ortho-hydroxyl group and the compounds were evaluated to have an obvious promotion on repellent activities against aphids, but the repellent activities were greatly reduced by replacing the ester groups with the amide groups (Scheme 2) [23,25]. The above results indicated that the ester group was very important for maintaining the repellent activity of aphids.…”

Section: Introductionmentioning

confidence: 99%

“…In this work, to identify if the activity can be influenced by inverting ester groups, a series of novel geranic acid esters containing substituted aromatic rings were firstly designed by reversing the Scheme 2. Design strategy of the target compounds [22,23,25].…”

Section: Introductionmentioning

confidence: 99%

Discovery of Novel Potential Aphid Repellents: Geranic Acid Esters Containing Substituted Aromatic Rings

Pan

Qin

et al. 2022

Molecules

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Aphids are one of the most damaging agricultural pests. For the sake of novel eco-friendly compounds with good activity for aphid control, a series of novel geranic acid esters containing substituted aromatic rings were designed by inverting ester groups of lead compounds. All compounds were characterized by HRMS, 1H-NMR, and 13C-NMR. In order to identify the effect of inversion ester groups on activity, a bioassay was conducted. The results showed that the repellent activity against Acyrthosiphon pisum (A. pisum) and the binding affinity with the odorant-binding protein 9 from A. pisum (ApisOBP9) of the compounds were increased after inversion of the ester groups. Particularly, 5f showed the best repellent activity (repellency proportion: 55.6%) and binding affinity (1/Ki: 0.49 µM). Meanwhile, the structure–activity relationships revealed that the introduction of meta-substitution of the benzene ring and halogen atoms, such as Cl and Br, facilitated the biological activity. The further molecular docking results demonstrated that hydrogen bonding interactions and hydrophobic interactions were vital for the binding affinity with ApisOBP9. Additionally, all compounds were predicted to be eco-friendly and their volatile physicochemical properties have been enhanced compared to the leads. The present results provide valuable clues for the further rational design of aphids’ behavioral control agents.

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Rational design and discovery of novel oxalate-like derivatives as aphid-repellent candidates based on odorant-binding protein 3

Zhu,

Li,

Liu

et al. 2024

Journal of Molecular Structure

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Effects of carboxyl and acylamino linkers in synthetic derivatives of aphid alarm pheromone (E)-β-farnesene on repellent, binding and aphicidal activity

Cited by 5 publications

References 41 publications

Aphid‐repellent, ladybug‐attraction activities, and binding mechanism of methyl salicylate derivatives containing geraniol moiety

Aphid‐repellent, ladybug‐attraction activities, and binding mechanism of methyl salicylate derivatives containing geraniol moiety

Discovery of Novel Potential Aphid Repellents: Geranic Acid Esters Containing Substituted Aromatic Rings

Rational design and discovery of novel oxalate-like derivatives as aphid-repellent candidates based on odorant-binding protein 3

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