Synergistic Combination of NAPROC-13 and NMR 13C DFT Calculations: A Powerful Approach for Revising the Structure of Natural Products

IF 3.3 2区生物学 Q2 CHEMISTRY, MEDICINAL Journal of Natural Products Pub Date : 2023-09-07 DOI:10.1021/acs.jnatprod.3c00437

Hugo A. Sánchez-Martínez, Juan A. Morán-Pinzón, Esther del Olmo Fernández, David López Eguiluz, José F. Adserias Vistué, José L. López-Pérez* and Estela Guerrero De León*,

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引用次数: 1

Abstract

This article describes the structure revision of nine triterpenoids that have been reported corresponding to the same ¹³C NMR data set. In addition, ¹³C NMR calculation shows that some chemical shift assignments must be swapped. Our analysis improves the fit between the experimental and calculated data. Correcting misassigned structures and correctly assigning each signal is essential for elucidating new structurally related compounds. Furthermore, the ambiguity of several compounds, the structure of which differs in the literature and the Sci-Finder database, has been eliminated. Misassigned structures were found by chemical shift searches in NAPROC-13, and the results provide two or more different compounds with the same ¹³C NMR data. The process to determine the correct, most likely structural proposal in agreement with the experimental ¹³C NMR data was carried out by DFT calculations.

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NAPROC-13和NMR 13C DFT计算的协同组合：一种修改天然产物结构的有力方法

本文描述了9种三萜类化合物的结构修订，这些化合物已被报道对应于相同的13C NMR数据集。此外，13C NMR计算表明，一些化学位移分配必须互换。我们的分析改进了实验数据和计算数据之间的拟合。纠正错误分配的结构并正确分配每个信号对于阐明新的结构相关化合物至关重要。此外，一些化合物的结构在文献和Sci-Finder数据库中有所不同，其模糊性已经消除。NAPROC-13中的化学位移搜索发现了错位结构，结果提供了两种或多种具有相同13C NMR数据的不同化合物。通过DFT计算来确定与实验13C NMR数据一致的正确的、最有可能的结构方案的过程。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Journal of Natural Products 生物-药学

CiteScore

9.10

自引率

5.90%

发文量

294

审稿时长

2.3 months

期刊介绍： The Journal of Natural Products invites and publishes papers that make substantial and scholarly contributions to the area of natural products research. Contributions may relate to the chemistry and/or biochemistry of naturally occurring compounds or the biology of living systems from which they are obtained. Specifically, there may be articles that describe secondary metabolites of microorganisms, including antibiotics and mycotoxins; physiologically active compounds from terrestrial and marine plants and animals; biochemical studies, including biosynthesis and microbiological transformations; fermentation and plant tissue culture; the isolation, structure elucidation, and chemical synthesis of novel compounds from nature; and the pharmacology of compounds of natural origin. When new compounds are reported, manuscripts describing their biological activity are much preferred. Specifically, there may be articles that describe secondary metabolites of microorganisms, including antibiotics and mycotoxins; physiologically active compounds from terrestrial and marine plants and animals; biochemical studies, including biosynthesis and microbiological transformations; fermentation and plant tissue culture; the isolation, structure elucidation, and chemical synthesis of novel compounds from nature; and the pharmacology of compounds of natural origin.