Triantaspirols A-C and Paraphaeolactone Cs from Paraphaeosphaeria sp. KT4192: Sensitivity of CP3 in Distinguishing Close NMR Signals.

IF 3.3 2区生物学 Q2 CHEMISTRY, MEDICINAL Journal of Natural Products Pub Date : 2024-10-10 DOI:10.1021/acs.jnatprod.4c00935

Ryuhi Kanehara, Yuki Oinuma, Hayato Maeda, Kazuaki Tanaka, Masaru Hashimoto

引用次数: 0

Abstract

Hybridized spirobisnaphthalene derivatives, triantaspirols A-C (1-3) and paraphaeolactones C1 and C2 (4 and 5), were identified from the culture broth of the fungus Paraphaeosphaeria sp. KT4192. The NMR spectra of 2 and 3, as well as 4 and 5, closely resembled each other, indicating that these were pairs of diastereomers. Although this NMR spectral resemblance made it challenging to distinguish their relative configurations, detailed analysis of the electronic circular dichroism (ECD) spectra and NOE correlations allowed us to deduce them. The CP3 metric with the DFT-based NMR chemical shifts was found to distinguish configurations of diastereomers in a highly sensitive and accurate manner that DP4 could not account for because of the very close chemical shift differences in the experimental NMR spectra. The reliability of this method was assessed using 23 published examples which could not be distinguished by DP4 protocol.

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来自 Paraphaeosphaeria sp. KT4192 的 Triantaspirols A-C 和 Paraphaeolactone Cs：CP3 在区分近似 NMR 信号方面的灵敏度。

从真菌 Paraphaeosphaeria sp. KT4192 的培养液中鉴定出了杂化螺双萘衍生物--三烷螺 A-C（1-3）和副内酯 C1 和 C2（4 和 5）。2 和 3 以及 4 和 5 的核磁共振光谱非常相似，表明它们是一对非对映异构体。尽管核磁共振光谱的相似性使我们难以区分它们的相对构型，但通过对电子圆二色性（ECD）光谱和 NOE 相关性的详细分析，我们还是推断出了它们的相对构型。我们发现，CP3 指标与基于 DFT 的 NMR 化学位移能以高度灵敏和准确的方式区分非对映异构体的构型，而 DP4 则无法解释这一点，因为实验 NMR 光谱中的化学位移差异非常接近。使用 23 个已发表的实例评估了这种方法的可靠性，DP4 协议无法区分这些实例。

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.