HPLC-DAD-Directed Isolation of Linearly Fused Prenylated
Indole Alkaloids from a Soil-Derived Aspergillus versicolor
Posted on 2019-08-07 - 17:06
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 μM, respectively.
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Li, Huaqiang; Xu, Dan; Sun, Weiguang; Yang, Beiye; Li, Fengli; Liu, Mengting; et al. (2019). HPLC-DAD-Directed Isolation of Linearly Fused Prenylated
Indole Alkaloids from a Soil-Derived Aspergillus versicolor. ACS Publications. Collection. https://doi.org/10.1021/acs.jnatprod.9b00183
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AUTHORS (10)
HL
Huaqiang Li
DX
Dan Xu
WS
Weiguang Sun
BY
Beiye Yang
FL
Fengli Li
ML
Mengting Liu
JW
Jianping Wang
YX
Yongbo Xue
ZH
Zhengxi Hu
YZ
Yonghui Zhang
KEYWORDS
7.3single-crystal X-ray diffractionl-tryptophan-11-spirodichroism analysisHPLC-DAD-directed chemical investigationHPLC-DAD-Directed Isolationprenylated indole alkaloidssoil-derived fungus Aspergillus versicolor QC 812identificationSoil-Derived Aspergillus versicolorIC 50 valuesconfigurationHeLa cells2 D NMRd-prolinecongenerhexacyclicasperversiamide Hdiketopiperazine1 Disolationtricyclic6.4 μ Mspectroscopic analysisLinearly Fused Prenylated Indole AlkaloidsHRESIMSAsperversiamide J