Cyclopeptide Avellanins D-O with Antimalarial Activity from the Mariana Trench Anemone-Derived Hamigera ingelheimensis MSC5.

IF 3.3 2区生物学 Q2 CHEMISTRY, MEDICINAL

Journal of Natural Products Pub Date : 2024-11-27 DOI:10.1021/acs.jnatprod.4c00740

Hao Li, Yuling Chen, Bingqing Tang, Zhengjie Liu, Bo Peng, Jiajun Li, Han Gao, Sibao Wang, Zhiyong Li

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引用次数: 0

Abstract

Marine microorganisms are a treasure trove of natural products, especially those in extreme marine environments, which may produce novel natural products. Herein, biosynthetic gene cluster analysis combined with an integrated metabolomic strategy incorporating matrix-assisted laser desorption ionization-time-of-flight mass spectrometry (MALDI-TOF MS), nuclear magnetic resonance (NMR), and liquid chromatography-mass spectrometry/mass spectrometry (LC-MS/MS) based Global Natural Products Social Molecular Networking (GNPS) was used to discover new compounds from the Mariana trench anemone-derived fungus Hamigera ingelheimensis MSC5. As a result, 12 new cyclic pentapeptides, avellanins D-O (1-12), were isolated, together with a known cyclic pentapeptide avellanin C (13). All the structures and absolute configurations were elucidated using NMR, mass spectrometry, X-ray diffraction analysis, and Marfey's method. A plausible biosynthetic pathway for the avellanins was proposed based on the gene cluster analysis of H. ingelheimensis MSC5. Bioassay revealed that compound 6 exhibited potent antimalarial activity with an IC₅₀ value of 0.19 ± 0.09 μM.

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从马里亚纳海沟天葵提取的 Hamigera ingelheimensis MSC5 中提取的具有抗疟活性的环肽 Avellanins D-O。

海洋微生物是天然产物的宝库，尤其是极端海洋环境中的微生物，可能会产生新型天然产物。本文采用生物合成基因簇分析法，结合基于全球天然产品社会分子网络（GNPS）的基质辅助激光解吸电离飞行时间质谱（MALDI-TOF MS）、核磁共振（NMR）和液相色谱-质谱/质谱（LC-MS/MS）的综合代谢组学策略，从马里亚纳海沟天葵源真菌Hamigera ingelheimensis MSC5中发现了新化合物。结果分离出了 12 种新的环状五肽，即vellanins D-O (1-12)，以及已知的环状五肽 avellanin C (13)。利用核磁共振、质谱、X 射线衍射分析和马菲法阐明了所有的结构和绝对构型。根据 H. ingelheimensis MSC5 的基因簇分析，提出了vellanins 的合理生物合成途径。生物测定显示，化合物 6 具有很强的抗疟活性，其 IC50 值为 0.19 ± 0.09 μM。

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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.