Shielding Effects of Aromatic (Indole) Ring for Structural Analysis

IF 3.3 2区 生物学 Q2 CHEMISTRY, MEDICINAL Journal of Natural Products Pub Date : 2023-08-30 DOI:10.1021/acs.jnatprod.3c00434
Jian-Zi Liu, Hao-Di Sun, Lin Chen and Gang Ding*, 
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Abstract

This review provides a critical analysis of shielding effects induced by an aromatic (indole) ring of small molecules mainly including three members of naturally occurring secondary metabolites asterric acid analogs, diketopiperazines (DKPs) possessing an aromatic or an indole ring, and rubrolides. Empirical rules about the shielding effects induced by an aromatic (indole) ring are classified, based on which some 1H NMR chemical shift values in the A-ring and structures of asterric acid analogs are revised, and the relative configurations of some DKPs possessing an indole ring are also assigned or revised. The empirical rules could provide an efficient and convenient method for NMR data analysis and configuration determination for the three members of small molecules mentioned above.

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结构分析中芳香(吲哚)环的屏蔽效应
这篇综述对小分子的芳香(吲哚)环诱导的屏蔽作用进行了批判性分析,主要包括三种天然次级代谢产物——紫苑酸类似物、具有芳香或吲哚环的二酮哌嗪(DKPs)和红内酯。对芳香(吲哚)环屏蔽效应的经验规律进行了分类,在此基础上修正了A环的一些1H NMR化学位移值和星形类似物的结构,并对一些具有吲哚环的DKP的相对构型进行了分配或修正。该经验规则为上述三个小分子的核磁共振数据分析和构型测定提供了一种高效方便的方法。
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来源期刊
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.
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