1-氨基环丙烷羧酸多肽类似物的合成及乙烯生理效应评价

    Synthesis of 1-aminocyclopropane-1-carboxylic acid peptide analogues and evaluation of their ethylene physiological effects

    • 摘要: 多肽农药因具有高活性、靶标精准及环境友好等优点,已成为农药领域的研究热点。本研究基于1-氨基环丙烷羧酸(ACC)的特殊分子结构,设计并合成了16个线性寡聚1-氨基环丙烷羧酸多肽及其衍生物,以及3个环状二肽及其衍生物。其结构经核磁共振氢谱(1H NMR)、碳谱(13C NMR)和高分辨质谱(HRMS)确证。通过观测黄化豌豆幼苗的乙烯“三重反应”现象评价目标化合物的乙烯生理效应。结果表明:部分化合物能够诱导豌豆幼苗产生乙烯反应表型,且该效应具有浓度依赖性。其中化合物6a表现最为突出,当测试浓度为0.5 mmol/L时,6a对豌豆幼苗的茎生长抑制率为21.23%,胚轴增粗率为15.38%,略高于对照药剂ACC。此外,基于乙烯生理效应评价结果进行了初步的构效关系分析。这些研究成果为1-氨基环丙烷羧酸类似物和新型多肽农药的开发提供了理论基础。

       

      Abstract: Peptide pesticides have become a research hotspot in pesticide science owing to their high activity, precise target selectivity, and environmental friendliness. Based on the unique structure of 1-aminocyclopropane-1-carboxylic acid (ACC), 16 linear oligomeric ACC peptide derivatives along with 3 cyclic dipeptide derivatives were designed and synthesized in this study. Their structures were confirmed by 1H NMR, 13C NMR, and HRMS. The ethylene physiological effects of the target compounds were evaluated by observing the "triple response" phenomenon in etiolated pea seedlings. The results showed that some compounds induced ethylene response phenotypes in pea seedlings and this induction was concentration-dependent. Among them, 6a exhibited the most prominent activity. At a test concentration of 0.5 mmol/L, 6a showed a stem growth inhibition rate of 21.23% and an epicotyl thickening rate of 15.38%, which were slightly higher than those of the control agent ACC. Furthermore, a preliminary structure-activity relationship analysis was conducted based on the evaluation results of their ethylene physiological effects. These findings provide a theoretical basis for the further development of ACC analogs and novel peptide pesticides.

       

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