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Protoilludane, Illudalane, and Botryane Sesquiterpenoids from the Endophytic Fungus Phomopsis sp. TJ507A
Journal of Natural Products ( IF 3.3 ) Pub Date : 2018-05-17 00:00:00 , DOI: 10.1021/acs.jnatprod.7b00889 Shuangshuang Xie 1 , Ye Wu 2 , Yuben Qiao 1 , Yi Guo 1 , Jianping Wang 1 , Zhengxi Hu 1 , Qing Zhang 1 , Xiaonian Li 3 , Jinfeng Huang 1 , Qun Zhou 1 , Zengwei Luo 1 , Junjun Liu 1 , Hucheng Zhu 1 , Yongbo Xue 1 , Yonghui Zhang 1
Journal of Natural Products ( IF 3.3 ) Pub Date : 2018-05-17 00:00:00 , DOI: 10.1021/acs.jnatprod.7b00889 Shuangshuang Xie 1 , Ye Wu 2 , Yuben Qiao 1 , Yi Guo 1 , Jianping Wang 1 , Zhengxi Hu 1 , Qing Zhang 1 , Xiaonian Li 3 , Jinfeng Huang 1 , Qun Zhou 1 , Zengwei Luo 1 , Junjun Liu 1 , Hucheng Zhu 1 , Yongbo Xue 1 , Yonghui Zhang 1
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To explore the chemical diversity of metabolites from endophytic fungi, the strain Phomopsis sp. TJ507A, isolated from the medicinal plant Phyllanthus glaucus, was investigated. A 2,3-seco-protoilludane-type sesquiterpenoid (1), eight protoilludane-type sesquiterpenoids (2–9), four illudalane-type sesquiterpenoids (10a/10b, 11, and 12), and a botryane-type sesquiterpenoid (13) in addition to seven known sesquiterpenoids (14–20) were identified from the liquid culture of the fungus. Structures of the isolated compounds, including their absolute configurations, were elucidated based on extensive spectroscopic analyses, a modified Mosher analysis, electronic circular dichroism (ECD) calculations, and [Rh2(OCOCF3)4]-induced ECD spectra as well as X-ray crystallographic analyses. Compound 1 represents the first example of a naturally occurring sesquiterpenoid containing the unusual 2,3-seco-protoilludane scaffold. Compounds 1 (p < 0.001); 2–6, 15, and 18 (p < 0.01); and 7, 9, and 20 (p < 0.05) displayed β-site amyloid precursor protein cleaving enzyme 1 (BACE1) inhibitory activities ranging from 19.4% to 43.8% at the concentration of 40 μM. LY2811376 was used as the positive control with an inhibitory activity of 38.6% (p < 0.01). Furthermore, none of these compounds showed obvious hepatotoxicity at concentration of 40 μM.
中文翻译：
内生真菌Phomopsis sp。的原illudaneane，Illudalane和Botryane倍半萜类化合物。TJ507A
为了探索内生真菌代谢产物的化学多样性，菌株Phomopsis sp。研究了从药用植物余甘子（Phyllanthus glaucus）分离的TJ507A 。2,3-开环-protoilludane型倍半萜类（1），八原伊鲁型倍半萜类（2 - 9），四illudalane型倍半萜（10A / 10B，11，和12），和一个botryane型倍半萜类（13），以及七个已知的倍半萜（14 – 20）是从真菌的液体培养物中鉴定出来的。基于广泛的光谱分析，改进的Mosher分析，电子圆二色性（ECD）计算和[Rh 2（OCOCF 3）4 ]诱导的ECD光谱以及X ，对分离出的化合物的结构（包括其绝对构型）进行了阐明。射线晶体学分析。化合物1表示含有不寻常2,3-天然存在的倍半萜类的第一实施例开环-protoilludane支架。化合物1（p <0.001）; 2 - 6，15，和18（p<0.01）; 和7，9，和20（p <0.05）显示β位淀粉样前体蛋白裂解酶1（BACE1）的抑制活性，在40μM的浓度范围从19.4％至43.8％。LY2811376用作阳性对照，抑制活性为38.6％（p <0.01）。此外，这些化合物在40μM的浓度下均未显示出明显的肝毒性。
更新日期：2018-05-17
中文翻译：
内生真菌Phomopsis sp。的原illudaneane，Illudalane和Botryane倍半萜类化合物。TJ507A
为了探索内生真菌代谢产物的化学多样性，菌株Phomopsis sp。研究了从药用植物余甘子（Phyllanthus glaucus）分离的TJ507A 。2,3-开环-protoilludane型倍半萜类（1），八原伊鲁型倍半萜类（2 - 9），四illudalane型倍半萜（10A / 10B，11，和12），和一个botryane型倍半萜类（13），以及七个已知的倍半萜（14 – 20）是从真菌的液体培养物中鉴定出来的。基于广泛的光谱分析，改进的Mosher分析，电子圆二色性（ECD）计算和[Rh 2（OCOCF 3）4 ]诱导的ECD光谱以及X ，对分离出的化合物的结构（包括其绝对构型）进行了阐明。射线晶体学分析。化合物1表示含有不寻常2,3-天然存在的倍半萜类的第一实施例开环-protoilludane支架。化合物1（p <0.001）; 2 - 6，15，和18（p<0.01）; 和7，9，和20（p <0.05）显示β位淀粉样前体蛋白裂解酶1（BACE1）的抑制活性，在40μM的浓度范围从19.4％至43.8％。LY2811376用作阳性对照，抑制活性为38.6％（p <0.01）。此外，这些化合物在40μM的浓度下均未显示出明显的肝毒性。
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