New indole derivatives from endophytic fungus Colletotruchum sp. HK-08 originated from leaves of Nerium indicum

IF 4.7 4区医学 Q1 CHEMISTRY, MEDICINAL Chinese Herbal Medicines Pub Date : 2024-04-01 DOI:10.1016/j.chmed.2023.07.004

Huiqin Chen , Hao Zheng , Caihong Cai , Hao Wang , Cuijuan Gai , Zhiqiong Tan , Haofu Dai , Wenli Mei

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Abstract

Objective

To study secondary metabolites from endophytic fungus Colletotruchum sp. HK-08 originated from the leaves of Nerium indicum.

Methods

The compounds were isolated by various column chromatographic techniques, and their structures were elucidated by spectroscopic techniques [high resolution electrospray ionization mass spectroscopy (HRESIMS), one-dimensional (1D) and two-dimensional (2D) nuclear magnetic resonance spectroscopy (NMR)], as well as comparison with literature data. The Ellman method was used to determine the acetylcholinesterase (AChE) inhibitory activity.

Results

Four indole derivatives were identified from Colletotruchum sp. HK-08, including 6′-hydroxymonaspiloindole (1), 2-(2-oxoindolin-3-yl)ethyl 2-(4-hydroxyphenyl) acetate (2), 2-(2-oxoindolin-3-yl)ethyl 2-(2-hydroxyphenyl)acetate (3), and monaspiloindole (4). Compound 4 presented weak AChE inhibitory activity with IC₅₀ value of (69.30 ± 6.27) μmol/L [tacrine as the positive control, with IC₅₀ value of (0.61 ± 0.07) μmol/L].

Conclusion

Compounds 1–3 were new compounds, and compound 4 had weak AChE inhibitory activity.

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源自 Nerium indicum 叶子的内生真菌 Colletotruchum sp.

方法采用不同的柱层析技术分离化合物，通过光谱技术[高分辨率电喷雾离子化质谱（HRESIMS）、一维（1D）和二维（2D）核磁共振波谱（NMR）]以及与文献数据的比较阐明其结构。结果从 Colletotruchum sp.HK-08 中鉴定出四种吲哚衍生物，包括 6′-羟基单天冬氨醛（1）、2-(2-氧代吲哚啉-3-基)乙基 2-(4-羟基苯基)乙酸酯（2）、2-(2-氧代吲哚啉-3-基)乙基 2-(2-羟基苯基)乙酸酯（3）和单天冬氨醛（4）。化合物 4 具有较弱的 AChE 抑制活性，IC50 值为 (69.30 ± 6.27) μmol/L [他克林作为阳性对照，IC50 值为 (0.61 ± 0.07) μmol/L]。

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