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

IF 3.3 2区生物学 Q2 CHEMISTRY, MEDICINAL

Journal of Natural Products Pub 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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引用次数: 0

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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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.