A new tetracyclic triterpenoid from endophytic fungus Fusarium sporotrichioides

IF 4.7 4区医学 Q1 CHEMISTRY, MEDICINAL Chinese Herbal Medicines Pub Date : 2024-04-01 DOI:10.1016/j.chmed.2022.10.007

Yajing Wang, Chunyue Liu, Yihui Yang, Chang Li, Yuehu Pei

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Abstract

Objective

To isolate bioactive compounds from the endophytic fungus Fusarium sporotrichioides isolated from Rauwolfia yunnanensis, and investigate their pharmacological activities.

Methods

The chemical constituents were isolated and purified by combining with ODS column chromatography, silica gel column chromatography and by performing semipreparative HPLC. Their structures were established on the basis of 1D NMR (¹H-NMR and ¹³C-NMR) and 2D NMR (¹H–¹H COSY, HSQC, HMBC and NOESY), as well as HRESIMS and comparison with literature data. In addition, the absolute configuration of compound 1 was determined by calculated ECD data.

Results

One previously undescribed tetracyclic triterpenoid derivative, named as integracide L (1), 12α-acetoxy-4,4-dimethyl-24-methylene-5α-cholesta-8,14-diene-2α,3β,11β-triol (2), 12α-acetoxy-4,4-dimethyl-24-methylene-5α-cholesta-8-momoene-2α,3β,11β-triol (3), 12α-acetoxy-4,4-dimethyl-24-methylene-5α-cholesta-8,14-diene-3β,11β-triol (4), and 12α-acetoxy-4,4-dimethyl-24-methylene-5α-cholesta-8-momoene-3β,11β-triol (5) were isolated from F. sporotrichioide. Moreover, compound 1 was rare tetracyclic triterpenoid with single methyl replacement at C-4 position.

Conclusion

Compound 1 was a new tetracyclic triterpenoid isolated from the endophytic fungus F. sporotrichioides. In addition, compound 2 could inhibit the growth of three different human cancer cells significantly. Compounds 3 and 5 were found to possess better cytotoxic activities on HepG-2 cells than the other compounds, with IC₅₀ values of (2.8 ± 0.1) and (6.3 ± 0.3) μmol/L respectively.

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内生真菌孢毛镰刀菌的一个新的四环三萜

方法结合ODS柱层析、硅胶柱层析和半制备高效液相色谱法，分离纯化了云南芒萁内生真菌中的化学成分。根据一维核磁共振（1H-NMR 和 13C-NMR）、二维核磁共振（1H-1H COSY、HSQC、HMBC 和 NOESY）、HRESIMS 以及与文献数据的比较，确定了它们的结构。此外，还通过计算 ECD 数据确定了化合物 1 的绝对构型。结果一种以前未曾描述过的四环三萜类衍生物被命名为 integracide L (1)，即 12α-acetoxy-4,4-dimethyl-24-methylene-5α-cholesta-8,14-diene-2α,3β,11β-triol (2)，12α-acetoxy-4,4-dimethyl-24-methylene-5α-cholesta-8-momoene-2α、3β,11β-三醇（3）、12α-乙酰氧基-4,4-二甲基-24-亚甲基-5α-胆甾烯-8,14-二烯-3β,11β-三醇（4）和 12α-乙酰氧基-4,4-二甲基-24-亚甲基-5α-胆甾烯-8-亚甲基-3β,11β-三醇（5）从 F. sporotrichioide 分离出来。sporotrichioide.结论化合物 1是从内生真菌 F. sporotrichioides 中分离出的一种新的四环三萜类化合物。此外，化合物 2 能显著抑制三种不同人类癌细胞的生长。与其他化合物相比，化合物 3 和 5 对 HepG-2 细胞具有更好的细胞毒性活性，其 IC50 值分别为 (2.8 ± 0.1) 和 (6.3 ± 0.3) μmol/L。

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