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NMR-Based Quantum Mechanical Analysis Builds Trust and Orthogonality in Structural Analysis: The Case of a Bisdesmosidic Triglycoside as Withania somnifera Aerial Parts Marker
Journal of Natural Products ( IF 3.3 ) Pub Date : 2021-02-24 , DOI: 10.1021/acs.jnatprod.0c01131
Sitaram Bhavaraju 1 , David Taylor 1 , Matthias Niemitz 2 , David C Lankin 3 , Anton Bzhelyansky 1 , Gabriel I Giancaspro 1 , Yang Liu 1 , Guido F Pauli 3
Affiliation  

The present study demonstrates the relationship between conventional and quantum mechanical (QM) NMR spectroscopic analyses, shown here to assist in building a convincingly orthogonal platform for the solution and documentation of demanding structures. Kaempferol-3-O-robinoside-7-O-glucoside, a bisdesmosidic flavonol triglycoside and botanical marker for the aerial parts of Withania somnifera, served as an exemplary case. As demonstrated, QM-based 1H iterative full spin analysis (HiFSA) advances the understanding of both individual nuclear resonance spin patterns and the entire 1H NMR spectrum of a molecule and establishes structurally determinant, numerical HiFSA profiles. The combination of HiFSA with regular 1D 1H NMR spectra allows for simplified yet specific identification tests via comparison of high-quality experimental with QM-calculated spectra. HiFSA accounts for all features encountered in 1H NMR spectra: nonlinear high-order effects, complex multiplets, and their usually overlapped signals. As HiFSA replicates spectrum patterns from field-independent parameters with high accuracy, this methodology can be ported to low-field NMR instruments (40–100 MHz). With its reliance on experimental NMR evidence, the QM approach builds up confidence in structural characterization and potentially reduces identity analyses to simple 1D 1H NMR experiments. This approach may lead to efficient implementation of conclusive identification tests in pharmacopeial and regulatory analyses: from simple organics to complex natural products.

中文翻译:


基于 NMR 的量子力学分析在结构分析中建立信任和正交性:以双锁链三糖苷作为睡茄空中部分标记的案例



本研究展示了传统核磁共振波谱分析与量子力学 (QM) 核磁共振波谱分析之间的关系,此处所示的分析有助于建立一个令人信服的正交平台,用于解决高要求结构的问题并进行记录。 Kaempferol-3- O -robinoside-7- O- glucoside 是一种双锁链黄酮醇三糖苷,也是睡茄地上部分的植物学标记,是一个典型案例。正如所证明的,基于 QM 的1 H 迭代全自旋分析 (HiFSA) 增进了对单个核共振自旋模式和分子的整个1 H NMR 谱的理解,并建立了结构决定性的数值 HiFSA 谱。 HiFSA 与常规 1D 1 H NMR 光谱相结合,通过将高质量实验与 QM 计算的光谱进行比较,可以进行简化但具体的鉴定测试。 HiFSA 考虑了1 H NMR 谱中遇到的所有特征:非线性高阶效应、复杂多重态及其通常重叠的信号。由于 HiFSA 可以高精度地复制与场无关的参数的频谱模式,因此该方法可以移植到低场 NMR 仪器 (40–100 MHz)。凭借对实验 NMR 证据的依赖,QM 方法建立了对结构表征的信心,并有可能将身份分析简化为简单的 1D 1 H NMR 实验。这种方法可能会导致药典和监管分析中结论性鉴定测试的有效实施:从简单的有机物到复杂的天然产品。
更新日期:2021-03-26
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