Immunosuppressive Nor-isopimarane Diterpenes from Cultures of the Fungicolous Fungus Xylaria longipes HFG1018
Immunosuppressive Nor-isopimarane Diterpenes from Cultures of the Fungicolous Fungus Xylaria longipes HFG1018
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来自真菌 Xylaria longipes HFG1018 培养物的免疫抑制性正异海松烷二萜
DOI：
10.1021/acs.jnatprod.9b00889
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发表时间：
2020-02-01
影响因子：
5.1
通讯作者：
Liu, Ji-Kai
中科院分区：
文献类型：
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作者：
Chen, He-Ping;Zhao, Zhen-Zhu;Liu, Ji-Kai
从真菌 Xylaria longipes 的培养物中分离出 18 种新的去甲异海松二萜，xylarinorditerpenes A-R (1-18)，以及两种先前报道的化合物，14 alpha,16-epoxy-18-norisopimar-7-en-4 alpha-ol (19) 和 Labdane 型二萜 Agatadiol (20)。 HFG1018 从腐木担子菌 Fomitopsis betulinus 中分离出来。 1-18的结构阐明和相对构型分配是通过光谱数据的解释和计算方法完成的。通过单晶X射线衍射确定了1、4和16的绝对构型。化合物1-16具有18-或19-去甲异海松烷骨架，并且化合物17和18具有18，19-二降-异海松烷骨架。化合物2-5、9、14、19和20显示出免疫抑制活性，但对刀豆球蛋白A诱导的T淋巴细胞和脂多糖诱导的B淋巴细胞的细胞增殖缺乏细胞毒性，IC50值分别为1.0至27.2μM和16.1至51.8μM。
Eighteen new nor-isopimarane diterpenes, xylarinorditerpenes A-R (1-18), along with two previously reported compounds, 14 alpha,16-epoxy-18-norisopimar-7-en-4 alpha-ol (19) and the labdane-type diterpene agatadiol (20), were isolated from cultures of the fungicolous fungus Xylaria longipes HFG1018 isolated from the wood-rotting basidiomycete Fomitopsis betulinus. The structure elucidation and relative configuration assignments of 1-18 were accomplished by interpretation of spectroscopic data and through computational methods. The absolute configurations of 1, 4, and 16 were determined by single-crystal X-ray diffraction. Compounds 1-16 possess an 18- or 19-nor-isopimarane skeleton, and compounds 17 and 18 possess an 18,19-dinor-isopimarane skeleton. Compounds 2-5, 9, 14, 19, and 20 showed immunosuppressive activity but were devoid of cytotoxicity against the cell proliferation by concanavalin A-induced T lymphocytes and lipopolysaccharide-induced B lymphocytes, with IC50 values varying from 1.0 to 27.2 mu M and from 16.1 to 51.8 mu M, respectively.