HPLC-DAD-Directed Isolation of Linearly Fused Prenylated Indole Alkaloids from a Soil-Derived Aspergillus versicolor
HPLC-DAD-Directed Isolation of Linearly Fused Prenylated Indole Alkaloids from a Soil-Derived Aspergillus versicolor
复制标题
DOI：
10.1021/acs.jnatprod.9b00183
复制
发表时间：
2019-08-01
影响因子：
5.1
通讯作者：
Zhang, Yonghui
中科院分区：
文献类型：
--
作者：
Li, Huaqiang;Xu, Dan;Zhang, Yonghui
对土生真菌杂色曲霉QC812进行了高效液相色谱-化学分析，分离和鉴定了8个新的线性融合的戊烯基吲哚生物碱I-P(1-8)和一个同系物H(9)。通过HRESIMS、一维和二维核磁共振、电子圆二色谱和单晶X-射线衍射谱等波谱分析确定了它们的结构和绝对构型。天冬酰胺I(1)是第一个由D-脯氨酸和L色氨酸衍生而来的二酮基哌嗪，具有前所未有的C-11螺环稠合6/6/5/5/6/5六环体系。天冬酰胺J(2)是首次报道的线性稠合的6/6/5三环戊烯基吲哚生物碱。化合物1和2对HeLa细胞具有中等抑制活性，IC50值分别为7.3和6.4mU/L。
An HPLC-DAD-directed chemical investigation of the soil-derived fungus Aspergillus versicolor QC812 resulted in the isolation and identification of eight new linearly fused prenylated indole alkaloids, asperversiamides I-P (1-8), along with a congener, asperversiamide H (9). Their structures and absolute configurations were determined by spectroscopic analysis including HRESIMS and 1D and 2D NMR, electronic circular dichroism analysis, and single-crystal X-ray diffraction. Asperversiamide I (1), the first diketopiperazine derived from D-proline and L-tryptophan, possesses an unprecedented C-11-spiro-fused 6/6/5/5/6/5 hexacyclic ring system. Asperversiamide J (2) is the first linearly fused 6/6/5 tricyclic prenylated indole alkaloid to be reported. 1 and 2 showed moderate inhibitory activities against HeLa cells with IC50 values of 7.3 and 6.4 mu M, respectively.