30591-44-7Relevant academic research and scientific papers
Construction of Cholesterol Oxime Ether Derivatives Containing Isoxazoline/Isoxazole Fragments and Their Agricultural Bioactive Properties/Control Efficiency
Xu, Hui,Zhang, Kong,Lv, Min,Hao, Meng
, p. 8098 - 8109 (2021)
To explore natural-product-based pesticidal candidates and high value-added application of cholesterol in agriculture, oximinoether derivatives of cholesterol-containing isoxazoline/isoxazole fragments (I-1～I-16 and II-1～II-18) were semiprepared by structural optimization of cholesterol. Their structures were characterized by optical rotation, high-resolution mass spectrometry (HRMS), IR, and 1H NMR spectroscopy. Particularly, the Z configurations of oxime fragments at the C-7 position of target compounds were undoubtedly determined by X-ray crystallography. Against Mythimna separata Walker, compounds 3e, I-8, I-14, and II-3 showed 2.4-2.7-fold growth inhibitory activity of the precursor cholesterol. Against Plutella xylostella Linnaeus, compounds I-6, I-7, and I-9 showed 2.4-2.7-fold oral toxicity of cholesterol. Against Aphis citricola Van der Goot, compounds 2e and II-15 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 1) against A. citricola 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.
Natural-product-based pesticides: Semisynthesis, structural elucidation, and evaluation of new cholesterol–matrine conjugates as pesticidal agents
Hao, Meng,Li, Tianze,Lv, Min,Xu, Hui,Xu, Jianwei,Zhang, Shaoyong
, (2021/09/07)
To develop new potential pesticide candidates from low value-added natural bioactive products, a series of new cholesterol–matrine conjugates (I(a–e)–IV(a–e)) were prepared from two lead compounds cholesterol and matrine. Against Mythimna separata Walker, compound IVa exhibited 3.0 and 2.6 folds promising insecticidal activity of cholesterol and matrine, respectively; against Aphis citricola Van der Goot, compound IVd showed 4.3 and 2.2 folds potent aphicidal activity of their precursors; notably, it also showed good control effects in the greenhouse; against Plutella xylostella Linnaeus at a dose of 20 μg/nymph, compound IIIe exhibited 2.8 and 2.0 folds oral toxicity of cholesterol and matrine, respectively. Compounds IIIe, IVd and IVe can be used as the leads for further structural optimization as the insecticidal and aphicidal agents.
