A new linear peptide, higapeptin, isolated from the mud flat-derived fungus Acremonium persicinum inhibits mitochondrial energy metabolism

IF 2.5 4区医学 Q3 CHEMISTRY, MEDICINAL

Journal of Natural Medicines Pub Date : 2024-02-29 DOI:10.1007/s11418-024-01784-4

Ahmed H. El-Desoky, Yuki Hitora, Yoshitomo Nishime, Yusaku Sadahiro, Teppei Kawahara, Sachiko Tsukamoto

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Abstract

A combination of LC–MS/MS and feature-based molecular networking analyses led to the isolation of a new adenopeptin analog, higapeptin (1), and four known peptides, adenopeptin (2), adenopeptins B and C (3 and 4), and acremopeptin (5), from the rice culture of the fungus Acremonium persicinum (18F04103) isolated from a mud flat of the Ariake Sea in Kyushu, Japan. The structure of 1 was determined by NMR and MS/MS fragmentation analyses. The absolute configuration of the constituent amino acids was determined by Marfey’s analysis after acid hydrolysis. The C-terminal residue was synthesized, and its absolute configuration was established by Marfey’s analysis. Compounds 1 and 2 were found to inhibit mitochondrial energy metabolism, similar to efrapeptin D (6), a known mitochondrial ATPase inhibitor.

Graphical abstract

Abstract Image

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从泥滩真菌 Acremonium persicinum 中分离出的一种新的线性肽--higapeptin--可抑制线粒体能量代谢。

结合 LC-MS/MS 和基于特征的分子网络分析，从日本九州有明海域泥滩分离出的真菌 Acremonium persicinum (18F04103) 的水稻培养物中分离出了一种新的腺肽类似物 higapeptin (1)，以及四种已知的肽，腺肽 (2)、腺肽 B 和 C (3 和 4) 以及 acremopeptin (5)。通过核磁共振和 MS/MS 片段分析确定了 1 的结构。组成氨基酸的绝对构型是通过酸水解后的马菲分析确定的。合成了 C 端残基，并通过 Marfey 分析确定了其绝对构型。研究发现，化合物 1 和 2 可抑制线粒体的能量代谢，与已知的线粒体 ATP 酶抑制剂 efrapeptin D（6）相似。

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来源期刊

Journal of Natural Medicines 医学-药学

CiteScore

6.90

自引率

3.00%

发文量

审稿时长

1.7 months

期刊介绍： The Journal of Natural Medicines is an international journal publishing original research in naturally occurring medicines and their related foods and cosmetics. It covers: -chemistry of natural products -biochemistry of medicinal plants -pharmacology of natural products and herbs, including Kampo formulas and traditional herbs -botanical anatomy -cultivation of medicinal plants. The journal accepts Original Papers, Notes, Rapid Communications and Natural Resource Letters. Reviews and Mini-Reviews are generally invited.