HPLC-DAD-Directed Isolation of Linearly Fused Prenylated Indole Alkaloids from a Soil-Derived Aspergillus versicolor
2019-08-07T17:06:10Z (GMT)
by
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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