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Tersaphilones A-E, cytotoxic chlorinated azaphilones from the deep-sea-derived fungus Phomopsis tersa FS441
Tetrahedron ( IF 2.1 ) Pub Date : 2020-11-30 , DOI: 10.1016/j.tet.2020.131806
Shanchong Chen , Zhaoming Liu , Yuchan Chen , Haibo Tan , Hongxin Liu , Weimin Zhang

Five new chlorinated azaphilone derivatives, tersaphilones A-E along with three known analogues were isolated from the deep-sea-derived fungus Phomopsis tersa FS441. Structures of the new compounds with absolute configurations were determined by comprehensive chemical analyses including spectroscopic techniques, ECD calculation, and single crystal X-ray diffraction. Among them, tersaphilone B possessed the unique 6/6-6 carbon skeleton with a cleaved tetrahydrofuranyl ring. Besides, tersaphilones D and E were a pair of diastereomers featuring a characteristic epoxide ring, which were rarely-occurring in azaphilones. Moreover, all compounds were evaluated for their anticancer activity using a panel of four tumor cell lines, wherein the novel tersaphilones D and E showed significant cytotoxicity against MCF-7, SF-268, and A549 cell lines with the IC50 values ranging from 5.4 to 8.3 μM.



中文翻译:

Tersaphilones AE,来自深海真菌Phomopsis tersa FS441的细胞毒性氯氮杂苯甲

从深海真菌Phomopsis tersa中分离出五个新的氯化氮杂苯甲酮衍生物,tersaphilones AE和三个已知类似物FS441。通过全面的化学分析,包括光谱技术,ECD计算和单晶X射线衍射,可以确定具有绝对构型的新化合物的结构。其中,地塞米松B具有独特的6 / 6-6碳骨架,带有裂解的四氢呋喃基环。此外,苯三氮酮D和E是一对具有特征性环氧环的非对映异构体,在氮杂苯酮中很少出现。此外,使用一组四个肿瘤细胞系对所有化合物的抗癌活性进行了评估,其中新的萜品类化合物D和E对MCF-7,SF-268和A549细胞系显示出显着的细胞毒性,IC 50值为5.4至 8.3μM .

更新日期:2020-12-17
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