Five new alkaloids from the endophytic fungus Penicillium sizovae in Ferula sinkiangensis

IF 2.6 3区医学 Q3 CHEMISTRY, MEDICINAL Fitoterapia Pub Date : 2025-06-01 Epub Date: 2025-03-24 DOI:10.1016/j.fitote.2025.106498

Shuhui Tan , Leiling Shi , Xudong Xu , Guoping Wang , Jun Zhu , Yuan Li , Congzhao Fan , Yaqin Zhao

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Abstract

Five new alkaloids, ferupencines A–E, featuring a pyrrol-oxazine core with a C₃- C₄O₂N framework, were isolated from the secondary metabolites of the endophytic fungus Penicillium sizovae residing in Ferula sinkiangensis. Their structures were elucidated through comprehensive 1D and 2D NMR spectroscopy, along with mass spectrometric analysis, experimental and calculated (ECD) spectra, and other complementary methods. The absolute configuration of compound 1 was determined via X-ray crystallography, supported by experimental and calculated electronic circular dichroism (ECD) data. Notably, this is the first report of these compounds being isolated from endophytic fungi. The cytotoxicity of ferupencines A–E (1–5) was evaluated against three human tumor cell lines: HeLa, SGC-7901, and SHG-44. Compound 2 exhibited moderate cytotoxic activity against HeLa and SGC-7901 cells, with IC₅₀ values of 18.6 μM and 14.2 μM, respectively. Additionally, compound 5 showed an IC₅₀ value of 23.8 μM against HeLa cells, indicating moderate cytotoxic potential.

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新疆阿魏内生真菌青霉菌的5个新生物碱。

从栖息在沉香阿魏中的内生真菌青霉的次级代谢产物中分离出了五种新生物碱，即阿魏碱 A-E，其特点是具有 C3- C4O2N 框架的吡咯-恶嗪核心。通过全面的一维和二维核磁共振光谱、质谱分析、实验和计算（ECD）光谱以及其他补充方法阐明了它们的结构。化合物 1 的绝对构型是通过 X 射线晶体学确定的，并得到了实验和计算的电子圆二色性（ECD）数据的支持。值得注意的是，这是首次从内生真菌中分离出这些化合物的报道。研究人员评估了阿魏鹏嗪 A-E （1-5）对三种人类肿瘤细胞系的细胞毒性：HeLa、SGC-7901 和 SHG-44。化合物 2 对 HeLa 和 SGC-7901 细胞具有中等程度的细胞毒性活性，IC50 值分别为 18.6 μM 和 14.2 μM。此外，化合物 5 对 HeLa 细胞的 IC50 值为 23.8 μM，表明具有中等细胞毒性潜力。

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来源期刊

Fitoterapia 医学-药学

CiteScore

5.80

自引率

2.90%

发文量

198

审稿时长

1.5 months

期刊介绍： Fitoterapia is a Journal dedicated to medicinal plants and to bioactive natural products of plant origin. It publishes original contributions in seven major areas: 1. Characterization of active ingredients of medicinal plants 2. Development of standardization method for bioactive plant extracts and natural products 3. Identification of bioactivity in plant extracts 4. Identification of targets and mechanism of activity of plant extracts 5. Production and genomic characterization of medicinal plants biomass 6. Chemistry and biochemistry of bioactive natural products of plant origin 7. Critical reviews of the historical, clinical and legal status of medicinal plants, and accounts on topical issues.