| Title: | Odorant-Binding Protein 3-Oriented Rational Design and Discovery of Novel Jasmonate Derivatives as Potential Aphid-Repellent Agents |
| Author(s): | Li H; Zhu Z; Yang Z; Du S; Wang Y; Zhong H; Zhang R; Zhang C; Zhou JJ; Xu Z; Duan H; |
| Address: | "Innovation Center of Pesticide Research, Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193, China. State Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Huaxi, Guiyang 550025, China. CAS Key Laboratory of Receptor Research, Drug Discovery and Design Center, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, China" |
| ISSN/ISBN: | 1520-5118 (Electronic) 0021-8561 (Linking) |
| 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 muM. Most novel JA derivatives displayed better binding affinities than D1 (K(d) = 1-26 muM). 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 muM 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" |
| Keywords: | "Acetates/metabolism/pharmacology Animals *Aphids/chemistry Cyclopentanes Insect Proteins/metabolism *Insect Repellents Oxylipins Pheromones/metabolism *Receptors, Odorant/metabolism insect behavior regulators jasmonate derivatives odorant-binding protein;" |
| Notes: | "MedlineLi, Huilin Zhu, Ziwei Yang, Zhaokai Du, Shaoqing Wang, Yueran Zhong, Hanjing Zhang, Rulei Zhang, Chunrong Zhou, Jing-Jiang Xu, Zhijian Duan, Hongxia eng 2022/09/13 J Agric Food Chem. 2022 Sep 21; 70(37):11792-11803. doi: 10.1021/acs.jafc.2c04126. Epub 2022 Sep 12" |
