New sesquiterpenoids with anti-inflammatory effects from phytopathogenic fungus Bipolaris sorokiniana 11134

IF 4.8 3区化学 Q1 CHEMISTRY, MEDICINAL

Natural Products and Bioprospecting Pub Date : 2025-05-09 DOI:10.1007/s13659-025-00508-9

Qiang Yin, Jianying Han, Guixiang Yang, Zhijun Song, Keke Zou, Kangjie Lv, Zexu Lin, Lei Ma, Miaomiao Liu, Yunjiang Feng, Ronald J. Quinn, Tom Hsiang, Lixin Zhang, Xueting Liu, Guoliang Zhu, Jingyu Zhang

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引用次数: 0

Abstract

Sesquiterpenoids represent a structurally diverse class of natural products widely recognized for their ecological significance and pharmacological potential, including antimicrobial, anti-inflammatory, and anticancer properties. As part of our efforts to explore bioactive secondary metabolites from phytopathogenic fungi, we conducted a molecular networking-based analysis of Bipolaris sorokiniana isolate BS11134, which was fermented on a rice medium. This analysis led to the identification of three new seco-sativene-type sesquiterpenoids (1–3) and seven known analogues (4–10), with the NMR data of compound 4 being reported for the first time. The structures of these compounds were elucidated using HR-ESI-MS and extensive spectroscopic data analysis. Notably, compound 9 significantly inhibited nitrous oxide expression in lipopolysaccharide (LPS)-treated RAW264.7 cells in vitro (inhibition rate: 84.7 ± 1.7% at 10 μM), while compound 1 (10 μM) showed a weak inhibitory effect (inhibition rate = 28.0 ± 2.4%). Additionally, we proposed a biosynthetic pathway for these compounds. This study not only expands the chemical space of the helminthoporene class of molecules but also underscores the untapped potential of phytopathogenic fungi as promising sources of structurally unique and biologically active natural products.

Graphical Abstract

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植物病原真菌双星菌11134中具有抗炎作用的新型倍半萜类化合物

倍半萜是一类结构多样的天然产物，因其生态意义和药理潜力而被广泛认可，包括抗菌、抗炎和抗癌特性。作为我们探索植物病原真菌生物活性次生代谢物的一部分，我们对在水稻培养基上发酵的Bipolaris sorokiniana分离物BS11134进行了分子网络分析。通过分析鉴定出3个新的次生半萜类化合物（1-3）和7个已知的类似物（4 - 10），其中化合物4的NMR数据为首次报道。这些化合物的结构通过HR-ESI-MS和广泛的光谱数据分析得以阐明。值得注意的是，化合物9在体外脂多糖（LPS）处理的RAW264.7细胞中显著抑制氧化亚氮的表达（10 μM抑制率为84.7±1.7%），而化合物1 （10 μM）的抑制作用较弱（抑制率为28.0±2.4%）。此外，我们提出了这些化合物的生物合成途径。这项研究不仅扩大了甲基二烯类分子的化学空间，而且强调了植物病原真菌作为结构独特和具有生物活性的天然产物的有希望的来源的未开发潜力。图形抽象

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来源期刊

Natural Products and Bioprospecting CHEMISTRY, MEDICINAL-

CiteScore

8.30

自引率

2.10%

发文量

审稿时长

13 weeks

期刊介绍： Natural Products and Bioprospecting serves as an international forum for essential research on natural products and focuses on, but is not limited to, the following aspects: Natural products: isolation and structure elucidation Natural products: synthesis Biological evaluation of biologically active natural products Bioorganic and medicinal chemistry Biosynthesis and microbiological transformation Fermentation and plant tissue cultures Bioprospecting of natural products from natural resources All research articles published in this journal have undergone rigorous peer review. In addition to original research articles, Natural Products and Bioprospecting publishes reviews and short communications, aiming to rapidly disseminate the research results of timely interest, and comprehensive reviews of emerging topics in all the areas of natural products. It is also an open access journal, which provides free access to its articles to anyone, anywhere.