HPLC-DAD-Directed Isolation of Linearly Fused Prenylated Indole Alkaloids from a Soil-Derived <i>Aspergillus versicolor</i> Huaqiang Li Dan Xu Weiguang Sun Beiye Yang Fengli Li Mengting Liu Jianping Wang Yongbo Xue Zhengxi Hu Yonghui Zhang 10.1021/acs.jnatprod.9b00183.s003 https://acs.figshare.com/articles/dataset/HPLC-DAD-Directed_Isolation_of_Linearly_Fused_Prenylated_Indole_Alkaloids_from_a_Soil-Derived_i_Aspergillus_versicolor_i_/9336335 An HPLC-DAD-directed chemical investigation of the soil-derived fungus <i>Aspergillus versicolor</i> QC812 resulted in the isolation and identification of eight new linearly fused prenylated indole alkaloids, asperversiamides I–P (<b>1</b>–<b>8</b>), along with a congener, asperversiamide H (<b>9</b>). 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 (<b>1</b>), 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 (<b>2</b>) is the first linearly fused 6/6/5 tricyclic prenylated indole alkaloid to be reported. <b>1</b> and <b>2</b> showed moderate inhibitory activities against HeLa cells with IC<sub>50</sub> values of 7.3 and 6.4 μM, respectively. 2019-08-07 17:06:11 7.3 single-crystal X-ray diffraction l-tryptophan -11-spiro dichroism analysis HPLC-DAD-directed chemical investigation HPLC-DAD-Directed Isolation prenylated indole alkaloids soil-derived fungus Aspergillus versicolor QC 812 identification Soil-Derived Aspergillus versicolor IC 50 values configuration HeLa cells 2 D NMR d-proline congener hexacyclic asperversiamide H diketopiperazine 1 D isolation tricyclic 6.4 μ M spectroscopic analysis Linearly Fused Prenylated Indole Alkaloids HRESIMS Asperversiamide J