赭曲菌素A - C，从内生真菌赭黄拟青霉SLJB - 2培养物中分离得到的三种新型吲哚二酮哌嗪。
Ochrolines A-C, three new indole diketopiperazines from cultures of endophytic fungi Bionectria ochroleuca SLJB-2.
作者信息
Zheng Yuting, Qin Siyu, Xu Li, Sang Zihuan, Chen Chen, Tan Jianbing, Huang Yuantao, Li Meifang, Zou Zhenxing
机构信息
Xiangya School of Pharmaceutical Sciences, Central South University, Changsha 410013, China; Hunan Key Laboratory of Diagnostic and Therapeutic Drug Research for Chronic Diseases, Central South University, Changsha 410013, China.
Affiliated Haikou Hospital of Xiangya School of Medicine, Central South University, Haikou 570100, China.
出版信息
Fitoterapia. 2024 Mar;173:105809. doi: 10.1016/j.fitote.2023.105809. Epub 2023 Dec 31.
Three new indole diketopiperazines, ochrolines A-C (1-3), along with three known compounds (4-6), were isolated and identified from the EtOAc extract of the solid fermentation of Bionectria ochroleuca SLJB-2. Notably, compound 1 featured a natural rarely-occurring caged skeleton with a 6/5/6/7 heterotetracyclic bridged ring system. The structures including absolute configurations of 1-3 were fully accomplished by extensive spectroscopic analyses, DFT GIAO C NMR and electronic circular dichroism (ECD) calculations. The plausible biogenetic pathways of these new indole diketopiperazines were also proposed. Moreover, the cytotoxic activity screening revealed that compound 2 exhibited moderate inhibitory effect against A549 with inhibition rate of 57.44% at the concentration of 50 μM and compound 1 exhibited mild inhibitory activities against A549, Hela and MCF-7.
从赭黄丝葚霉SLJB-2固体发酵的乙酸乙酯提取物中分离并鉴定出三种新的吲哚二酮哌嗪类化合物，赭曲菌素A-C（1-3），以及三种已知化合物（4-6）。值得注意的是，化合物1具有天然罕见的笼状骨架，带有6/5/6/7杂四环桥环体系。通过广泛的光谱分析、DFT GIAO C NMR和电子圆二色性（ECD）计算，完全确定了1-3的结构，包括其绝对构型。还提出了这些新的吲哚二酮哌嗪类化合物可能的生物合成途径。此外，细胞毒性活性筛选显示，化合物2对A549表现出中等抑制作用，在浓度为50 μM时抑制率为57.44%，化合物1对A549、Hela和MCF-7表现出轻度抑制活性。
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