Two novel iboga alkaloids with neuroprotective effects from Tabernaemontana corymbosa

IF 4.7 2区化学 Q2 CHEMISTRY, PHYSICAL Journal of Molecular Structure Pub Date : 2025-03-07 DOI:10.1016/j.molstruc.2025.141973

Kun Fan , Cai-Feng Ding , Hua Lin , Meng-Zhen Sun , Khalid Hassan Mohamed , Bang-Yin Tan , Rong-Ping Zhang , Bao-Chun Shen , Wei-Yan Hu , Hao-Fei Yu

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Abstract

Two novel members of the iboga-alkaloid, tabcorymines A and B, were isolated from the stem bark of Tabernaemontana corymbosa. Tabcorymine A (1) features a unique diaza [5.5.6.6] fenestrane structure with six chiral centers, while tabcorymine B (2) possesses an indole-oxabicyclo[5.2.1] decane skeleton. We elucidated their structures and absolute configurations using extensive spectroscopy, the ACD/structure elucidator (ACD/SE), quantum chemical calculations, and DP4+ probability analyses. The C-19 chiral hydroxyl groups of both compounds were determined through CD data from the in situ formed [Rh₂(OCOCF₃)₄] complex and Mosher's method, respectively. Furthermore, we have shown that tabcorymine A (1) inhibits MPTP-induced SH-SY5Y cell injury. Western blot and molecular docking experiments demonstrated that tabcorymine A (1) reduces the expression of the Bax protein, thereby inhibiting neuronal apoptosis and providing neuronal protection.

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两种具有神经保护作用的新伊波加生物碱

从山竹（tabernamontana corymbosa）的茎皮中分离出了两个新的伊波加生物碱，tabcorymines A和B。Tabcorymine A(1)具有独特的具有六个手性中心的双链[5.5.6.6]窗烷结构，而Tabcorymine B(2)具有吲哚-不沙比环[5.2.1]癸烷骨架。我们利用广谱光谱、ACD/结构解析器（ACD/SE）、量子化学计算和DP4+概率分析等方法对它们的结构和绝对构型进行了解析。两种化合物的C-19手性羟基分别通过原位形成的[Rh2(OCOCF3)4]配合物的CD数据和Mosher法测定。此外，我们已经证明tabcorymine A(1)抑制mptp诱导的SH-SY5Y细胞损伤。Western blot和分子对接实验表明，tabcorymine A(1)可降低Bax蛋白的表达，从而抑制神经元凋亡，起到神经元保护作用。

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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.