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Sesquiterpenes from a deep-sea-derived fungus Graphostroma sp. MCCC 3A00421
Tetrahedron ( IF 2.1 ) Pub Date : 2017-11-08 , DOI: 10.1016/j.tet.2017.11.013
Siwen Niu , Chun-Lan Xie , Tianhua Zhong , Wei Xu , Zhu-Hua Luo , Zongze Shao , Xian-Wen Yang

Two structurally corrected sesquiterpenes (1 and 2) and nine new ones (311) were isolated from Graphostroma sp. MCCC 3A00421, a deep-sea-derived fungus obtained from hydrothermal sulfide deposits of the Atlantic Ocean. Their structures were elucidated mainly by extensive analyses of NMR and MS spectroscopic data, and their absolute configurations were determined by Cu-Kα single-crystal X-ray diffraction, the modified Mosher's method, as well as ECD spectra. Xylariterpenoid E (3) is the first example of trinor-bergamotane and graphostromabisabol B (11) is the first trinor-bisabolane found in nature. Interestingly, khusinol B (6) exhibited significant anti-inflammatory effect with IC50 value of 17 μM, which was stronger than that of the positive control, aminoguanidine, whose IC50 value was 23 μM. In addition, it also showed weak anti-allergic effect (IC50 = 150 μM).



中文翻译:

来自深海真菌Graphostroma sp。的倍半萜。MCCC 3A00421

两个结构校正倍半萜烯(12)和9级新的(3 - 11)从分离Graphostroma藻。MCCC 3A00421,一种深海来源的真菌,得自大西洋的热液硫化物矿床。主要通过对NMR和MS光谱数据的广泛分析来阐明其结构,并通过Cu-Kα单晶X射线衍射,改进的Mosher方法以及ECD光谱确定其绝对构型。Xylariterpenoid E(3)是trinor-佛手柑的第一个例子,而graphostromabisabol B(11)是自然界中发现的第一个trinor-bisabolane。有趣的是,khusinol B(6)显示出显着的抗炎作用,IC 50值为 17μM,比阳性对照氨基胍(IC 50值为 23μM)强。此外,它还显示出较弱的抗过敏作用(IC 50  = 150  μ M)。

更新日期:2017-11-08
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