Isolation of 6,7-iso-Felinone A: A Configurational Reinvestigation of Related Fungal Metabolites.

IF 3.6 2区生物学 Q2 CHEMISTRY, MEDICINAL Journal of Natural Products Pub Date : 2025-04-25 Epub Date: 2025-03-30 DOI:10.1021/acs.jnatprod.5c00194

Rui Kanehira, Hideki Abe, Hisanaka Ito, Ryuhi Kanehara, Hayato Maeda, Kazuaki Tanaka, Masaru Hashimoto

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Abstract

An azaphilone, 6,7-iso-felinone A (2), was isolated from Diaporthales sp. KT3922 along with the known felinone A (1). While compound 2 exhibited weak Cotton effects, its naphthoate derivative (2a) displayed pronounced Cotton effects, enabling the determination of its absolute configuration through electronic circular dichroism (ECD) spectral analysis. Interestingly, the spectroscopically derived relative structure of compound 2 proved identical to previously reported hypoillexidiol (3) and xylariphilone (4). However, substantial differences in ¹H nuclear magnetic resonance data among these compounds warranted structural reinvestigation of the entire series, including the structurally related fungal metabolites, fusaraisochromenone (5) and aspergillusone C (6). Comparative analysis revealed identical relative configurations of compounds 1, 3, 4, and 5. Furthermore, compounds 1 and 3 were determined to have an identical absolute configuration, whereas the absolute configuration of compound 4 remained inconclusive due to a significant mismatch in its ECD spectral profile compared to compound 1. Compound 5 was identified as the enantiomer of compounds 1 and 3. Additionally, we discussed the stereochemistry of the 6,7-cis-diol isomer, aspergillusone C (6).

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6,7-iso- felinone A的分离：相关真菌代谢产物的构型再研究。

从Diaporthales sp. KT3922中与已知的felinone A(1)一起分离得到一种氮唑酮，6,7- isofelinone A(2)。化合物2表现出较弱的棉花效应，而其萘酸衍生物（2a）表现出明显的棉花效应，可以通过电子圆二色性（ECD）光谱分析确定其绝对结构。有趣的是，化合物2的光谱衍生相对结构被证明与先前报道的次ilillexidiol(3)和xylariphilone(4)相同。然而，这些化合物之间的1H核磁共振数据存在实质性差异，需要对整个系列进行结构重新研究，包括结构相关的真菌代谢物，fusaraisochromenone(5)和aspergillusone C(6)。对比分析显示化合物1,3，4和5。此外，化合物1和3被确定具有相同的绝对构型，而化合物4的绝对构型仍然不确定，因为与化合物1相比，其ECD谱线存在明显的不匹配。化合物5为化合物1和3的对映体。此外，我们还讨论了6,7-顺式二醇异构体曲霉菌C(6)的立体化学性质。

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.