Fitoterapia ( IF 2.5 ) Pub Date : 2021-03-19 , DOI: 10.1016/j.fitote.2021.104882 Mengyi Deng 1 , Xia Chen 1 , Zhengyi Shi 1 , Shuangshuang Xie 1 , Yuben Qiao 1 , Gang Chen 2 , Xiaosheng Tan 2 , Yuanyuan Lu 3 , Changxing Qi 1 , Yonghui Zhang 1
Six new metabolites, including two diphenolic derivatives (1 and 2), one pseurotin (3), one butenolide derivative (4), one benzopyran (5) and one isochromane lactone (6), together with ten known compounds (7–16) were isolated from an endophytic fungus Aspergillus sp. Their planar structures and absolute configurations were established based on techniques of MS, NMR, IR, UV, [Rh2(OCOCF3)4] complex-induced ECD, quantum chemical electronic circular dichroism (ECD) calculations, and single crystal X-ray diffraction. Structurally, compound 2 represents the first example of diphenolic derivative possessing an unusual 1-oxaspiro[2.4]heptane core bearing a 5/3 bicyclic skeleton; compound 3 represents the first example of pseurotin type natural products that only one hydroxy group is substituted at side chain. In bioassay, compounds 3, 7 and 8 exhibited potential inhibitory effect on the proliferation of anti-CD3/anti-CD28 monoclonal antibodies (mAbs) induced murine T cells, with IC50 values of (7.81 ± 0.71), (8.25 ± 0.78) and (8.84 ± 0.81) μM, respectively.
中文翻译:
来自内生真菌曲霉属的新型免疫抑制次级代谢产物。
六种新代谢物,包括两种双酚衍生物(1 和 2)、一种假素(3)、一种丁烯内酯衍生物(4)、一种苯并吡喃(5)和一种异色烷内酯(6),以及十种已知化合物(7-16)是从内生真菌曲霉菌中分离出来的。基于MS、NMR、IR、UV、[Rh2(OCOCF3)4]配合物诱导ECD、量子化学电子圆二色性(ECD)计算和单晶X射线衍射技术建立了它们的平面结构和绝对构型。在结构上,化合物 2 代表了第一个双酚衍生物的例子,它具有一个不寻常的 1-氧杂螺[2.4]庚烷核心,带有一个 5/3 双环骨架;化合物3代表假素类天然产物的第一个实例,其侧链仅被一个羟基取代。在生物测定中,化合物 3,