Secondary metabolites from the endophytic fungus Aspergillus fumigatus 06T03 from the soil of Aegiceras corniculatum and studies on their biological activity
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摘要 目的： 研究红树植物桐花树土壤内生真菌 Aspergillus fumigatus 06T03的次生代谢产物的分离纯化及其潜在的生物活性。方法： 菌株采用大米培养基经规模发酵，乙酸乙酯浸泡提取后经减压浓缩得到乙酸乙酯粗提物。采用多种现代色谱技术如硅胶柱色谱、Sephadex LH-20凝胶柱色谱、高效液相色谱等对粗提物进行化学成分分离。通过高分辨质谱，核磁共振波谱等综合谱学技术确定单体化合物结构。采用CCK-8法和Griess法初步评估单体化合物的抗肿瘤活性和抗炎活性。结果： 从As-pergillus fumigatus 06T03大米发酵产物中分离鉴定出9个化合物，分别为：Monomethylsulochrin（1）；Questin（2）；Demethylsulo-chrin（3）；Fumiquinazoline C（4）；Fumiquinazoline J （5）；Azaspirofurans A（6）；Pseurotin A（7）；N-[2-(4-hydroxyphenyl) ethenyl]formamide （8）；Pyripyropene A（9）。其中，化合物1～3属于蒽醌类化合物，4～9属于生物碱类化合物。活性结果显示，化合物1～9对肝癌细胞（Huh7）、卵巢癌细胞（A2780）、乳腺癌细胞（MDA-MB-231）未发现有明显抗肿瘤活性，化合物1、3、6、7、8和9具有一定抗炎活性。结论： 从桐花树土壤内生真菌 Aspergillus fumigatus 06T03中分离得到 9个单体化合物，除化合物 2，其余化合物均为首次从桐花树内生真菌中分离得到，化合物1、3、6、7、8和9具有一定的抗炎活性。本研究丰富了桐花树土壤内生真菌次生代谢产物的化学多样性，为后续深入开发提供了基础数据。Abstract Objective: To investigate the isolation and purification of the secondary metabolites and their potential biological activity in the endophytic fungus Aspergillus fumigatus 06T03 from the soil of Aegiceras corniculatum. Methods: The strain was fermented on a large scale using rice medium, and then extracted by soaking ethyl acetate and concentrated under reduced pressure to obtain a crude extract of ethyl acetate. A variety of modern chromatographic techniques such as silica gel column chromatography, Sephadex LH-20 gel column chromatography, high -performance liquid chromatography were used to separate the chemical components of the crude extract. Their structures were determined by using comprehensive spectral techniques such as high-resolution mass spectra (MS) and nuclear magnetic resonance (NMR) spectroscopy. The antineoplastic and anti-inflammatory activities of the monomers were evaluated using cell counting kit-8 (CCK-8) assay and Griess assays. Results: Nine compounds were isolated from the rice fermentation products of Aspergillus fumigatus 06T03 and identified as Monomethylsulochrin (1), Questin (2), Demethylsulochrin (3), Fumiquinazoline C (4), Fumiquinazoline J (5), Azaspirofurans A (6), Pseurotin A (7), N-[2-(4-hydroxyphenyl) ethenyl]formamide (8), and Pyripyropene A (9). Among them, compounds 1-3 belonged to anthraquinones, and 4-9 belonged to alkaloids. The results showed that compounds 1-9 failed to exhibit obvious antineoplastic activity against hepatoma carcinoma cells (Huh7), ovarian carcinoma cells (A2780), and breast cancer cells (MDA-MB-231), while compounds 1, 3, 6, 7, 8, and 9 had certain anti-inflammatory activities. Conclusion: Nine monomeric compounds, except compound 2 which has been isolated before, have been isolated for the first time from the endophytic fungus Aspergillus fumigatus 06T03 from the soil of Aegiceras corniculatum. Compounds 1, 3, 6, 7, 8, and 9 have certain anti-inflammatory activities. This study enriches the chemical diversity of the secondary metabolites of endophytic fungus from the soil of Aegiceras corniculatum, and provides basic data for subsequent further development.
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