具有抗神经炎潜能的紫杉叶c32 -环artane型三萜的1H nmr引导分离

IF 4.7 2区化学 Q2 CHEMISTRY, PHYSICAL

Journal of Molecular Structure Pub Date : 2025-09-25 DOI:10.1016/j.molstruc.2025.144169

Qi Gao , Xiaoxiao Chong , Lan Pan , Yuqian Xue , Yingzhan Tang , Min Yang , Jianlin Li , Andong Wang , Wenli Wang , Guangtong Chen , Boyi Fan

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引用次数: 0

摘要

c32 -环artane型三萜由于其环丙烷环体系而表现出独特的1H NMR信号，使其与结构相关的类似物区别开来。本研究利用1H核磁共振引导分离技术，成功从紫杉叶中分离到7个新的典型环artane三萜，分别命名为Taxodium ascendens A-G(1-7)，以及2个首次从植物中分离到的天然产物Taxodium H和I(8和9)，以及2个已知的产物Taxodium ascendens 10和11。通过综合光谱技术，包括一维和二维核磁共振，严格阐明了这些未报道的分子的平面结构和绝对构型，并通过单晶x射线分析证实。生物活性评估显示，化合物7对BV-2小胶质细胞中lps诱导的一氧化氮（NO）产生具有有效的抑制作用，IC₅₀值为9.02 μM。进一步研究表明，化合物7可抑制IL-1β、TNF-α、COX-2、iNOS和IL-6 mRNA的表达，且呈剂量依赖性。后续研究进一步发现，化合物7能有效诱导BV-2细胞的炎性自噬。

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$1H NMR-guided fractionation of C32-cycloartane type triterpenes from the leaves of Taxodium ascendens with anti-neuroinflammatory potential$

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1H NMR-guided fractionation of C32-cycloartane type triterpenes from the leaves of Taxodium ascendens with anti-neuroinflammatory potential

C₃₂-cycloartane type triterpenes exhibit distinctive ¹H NMR signals attributable to their cyclopropane ring system, setting them apart from structurally related analogs. In this study, seven new typical cycloartane triterpenes, designated as taxcycloterpenes A-G (1–7), along with two natural products taxcycloterpenes H and I (8 and 9) isolated from plant for the first time, and two known ones (10 and 11), were successfully obtained from the leaves of Taxodium ascendens with the aid of ¹H NMR-guided isolation. The planar structures and absolute configurations of these unreported identified molecules were rigorously elucidated through comprehensive spectroscopic techniques, including 1D and 2D NMR, and confirmed by single-crystal X-ray analysis. Bioactivity assessments revealed that compound 7 demonstrated a potent inhibitory effect on LPS-induced nitric oxide (NO) production in BV-2 microglial cells, with an IC₅₀ value of 9.02 μM. Further research indicated that compound 7 could inhibit the mRNA expression of IL-1β, TNF-α, COX-2, iNOS, and IL-6 in a dose-dependent manner. Subsequent investigations further revealed that compound 7 effectively induced the inflammatory autophagy in BV-2 cells.

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来源期刊

Journal of Molecular Structure 化学-物理化学

CiteScore

7.10

自引率

15.80%

发文量

2384

审稿时长

45 days

期刊介绍： The Journal of Molecular Structure is dedicated to the publication of full-length articles and review papers, providing important new structural information on all types of chemical species including: • Stable and unstable molecules in all types of environments (vapour, molecular beam, liquid, solution, liquid crystal, solid state, matrix-isolated, surface-absorbed etc.) • Chemical intermediates • Molecules in excited states • Biological molecules • Polymers. The methods used may include any combination of spectroscopic and non-spectroscopic techniques, for example: • Infrared spectroscopy (mid, far, near) • Raman spectroscopy and non-linear Raman methods (CARS, etc.) • Electronic absorption spectroscopy • Optical rotatory dispersion and circular dichroism • Fluorescence and phosphorescence techniques • Electron spectroscopies (PES, XPS), EXAFS, etc. • Microwave spectroscopy • Electron diffraction • NMR and ESR spectroscopies • Mössbauer spectroscopy • X-ray crystallography • Charge Density Analyses • Computational Studies (supplementing experimental methods) We encourage publications combining theoretical and experimental approaches. The structural insights gained by the studies should be correlated with the properties, activity and/ or reactivity of the molecule under investigation and the relevance of this molecule and its implications should be discussed.