College of Plant Protection, Northwest A&F University, Yangling 712100, Shaanxi, China.
School of Marine Sciences, Ningbo University, Ningbo 315211, Zhejiang, China.
J Agric Food Chem. 2021 Jul 28;69(29):8098-8109. doi: 10.1021/acs.jafc.1c01884. Epub 2021 Jul 19.
To explore natural-product-based pesticidal candidates and high value-added application of cholesterol in agriculture, oximinoether derivatives of cholesterol-containing isoxazoline/isoxazole fragments ( and ) were semiprepared by structural optimization of cholesterol. Their structures were characterized by optical rotation, high-resolution mass spectrometry (HRMS), IR, and H NMR spectroscopy. Particularly, the configurations of oxime fragments at the C-7 position of target compounds were undoubtedly determined by X-ray crystallography. Against Walker, compounds , , , and showed 2.4-2.7-fold growth inhibitory activity of the precursor cholesterol. Against Linnaeus, compounds -, , and showed 2.4-2.7-fold oral toxicity of cholesterol. Against Van der Goot, compounds and exhibited 4.9 and 5.8-fold aphicidal activity of cholesterol, respectively. Notably, they showed good control effects (3.0-5.0-fold promising control efficiency of ) against in the greenhouse. Structure-activity relationships (SARs) suggested that the C-3 hydroxyl group and the C-7 position of cholesterol are two important modification sites. It will pave the way for future structural optimization and application of cholesterol derivatives as potential pesticidal agents in agriculture.
为了探索基于天然产物的杀虫剂候选物和胆固醇在农业中的高附加值应用，通过对胆固醇进行结构优化，半制备了含胆固醇的异恶唑啉/异噁唑片段的肟醚衍生物（和）。它们的结构通过旋光度、高分辨率质谱（HRMS）、IR 和 H NMR 光谱进行了表征。特别是，通过 X 射线晶体学无疑确定了目标化合物 C-7 位肟片段的构型。针对 Walker，化合物、、、和表现出 2.4-2.7 倍的前体胆固醇生长抑制活性。针对 Linnaeus，化合物-、、和表现出 2.4-2.7 倍的胆固醇口服毒性。针对 Van der Goot，化合物和分别表现出 4.9 和 5.8 倍的杀蚜活性，是胆固醇的 4.9 和 5.8 倍。值得注意的是，它们在温室中对表现出良好的防治效果（3.0-5.0 倍有希望的防治效率）。构效关系（SAR）表明，胆固醇的 C-3 羟基和 C-7 位是两个重要的修饰位点。这将为未来作为农业中潜在杀虫剂的胆固醇衍生物的结构优化和应用铺平道路。
