Peng Fei, Hou Shao-Yang, Zhang Tian-Yuan, Wu Ying-Ying, Zhang Meng-Yue, Yan Xi-Meng, Xia Ming-Yu, Zhang Yi-Xuan
School of Life Science and Biopharmaceutics, Shenyang Pharmaceutical University Shenyang 110016 PR China
Quanzhou Medical College Quanzhou PR China.
RSC Adv. 2019 Sep 12;9(49):28754-28763. doi: 10.1039/c9ra04747f. eCollection 2019 Sep 9.
Two new compounds chetoseminudin F (1) and G (2) together with eleven known compounds were isolated from the solid fermentation products of the endophytic fungus sp. SYP-F7950. The structures of the isolated compounds were elucidated by extensive spectroscopic analyses, including 1D and 2D NMR, and HRFABMS experiments. The absolute configurations of chetoseminudin F (1) and G (2) were determined by comparing the electronic circular dichroism (ECD) spectrum with those of the reported references. A plausible biogenetic pathway for compounds 1-6 and 9-13 was proposed. These isolates were also evaluated for their antimicrobial and antitumor activity, revealing that chetoseminudin F (1) displayed more potent cytotoxicity against MDA-MB-231 cells with an IC value of 26.49 μmol L more than the common chemotherapeutic agent (paclitaxel). In antimicrobial assay, compounds 6, 9, 11 and 12 had strong antibacterial activity against , , and antifungal activity against with minimum inhibitory concentration (MIC) values ranging from 0.12 to 9.6 μg mL; meanwhile compounds 6, 8, 9 and 12 exhibited strong cytotoxicity with IC values of 2.75-8.68 μmol L against tumor cell lines A549 and MDA-MB-231. In addition, morphological observation showed that treatment with compounds 6, 9 and 12 increased the mean length of by 1.6 to 1.8-fold. molecular docking was applied to study the binding interactions between the compounds and the active sites of filamentous temperature-sensitive protein Z (FtsZ) from . Compounds 6, 9 and 12 displayed the low binding energies, strong H-bond interactions with FtsZ. On the basis of the antimicrobial activities, cellular phenotype observation and docking studies, compounds 6, 9 and 12 are considered to be a promising antimicrobial inhibitor of FtsZ.
从内生真菌sp. SYP-F7950的固体发酵产物中分离出两种新化合物chetoseminudin F(1)和G(2)以及十一种已知化合物。通过广泛的光谱分析,包括一维和二维核磁共振以及高分辨快原子轰击质谱实验,阐明了分离出的化合物的结构。通过将电子圆二色光谱(ECD)与报道的参考文献进行比较,确定了chetoseminudin F(1)和G(2)的绝对构型。提出了化合物1-6和9-13可能的生物合成途径。还对这些分离物的抗菌和抗肿瘤活性进行了评估,结果表明chetoseminudin F(1)对MDA-MB-231细胞表现出更强的细胞毒性,IC值为26.49 μmol/L,比常用化疗药物(紫杉醇)更强。在抗菌试验中,化合物6、9、11和12对 、 具有较强的抗菌活性,对 具有抗真菌活性,最低抑菌浓度(MIC)值范围为0.12至9.6 μg/mL;同时,化合物6、8、9和12对肿瘤细胞系A549和MDA-MB-231表现出较强的细胞毒性,IC值为2.75-8.68 μmol/L。此外,形态学观察表明,用化合物6、9和12处理使 的平均长度增加了1.6至1.8倍。应用分子对接研究化合物与来自 的丝状温度敏感蛋白Z(FtsZ)活性位点之间的结合相互作用。化合物6、9和12表现出低结合能,与FtsZ有强氢键相互作用。基于抗菌活性、细胞表型观察和对接研究,化合物6、9和12被认为是一种有前途的FtsZ抗菌抑制剂。