Phenolic C-Glycosides and Aglycones from Marine-Derived Aspergillus sp. and Their Anti-Inflammatory Activities

J Nat Prod. 2019 May 24;82(5):1098-1106. doi: 10.1021/acs.jnatprod.8b00744. Epub 2019 Apr 23.


A chemical investigation of the secondary metabolites of a marine-derived Aspergillus sp. led to the isolation and characterization of 13 phenolic compounds, including 10 new compounds (1-10). Seven new compounds (1-7) are unusual phenolic C-glycosides, while the other new compounds (8-10) are structurally related aglycones. The chemical structures of these new compounds were elucidated by 1D and 2D NMR and HRESIMS spectroscopic analyses. The absolute configurations of these new C-glycosides were determined by comparison of experimental electronic circular dichroism spectra with those of calculated ones. In addition, the anti-inflammatory activities of these compounds were evaluated, and compound 9 significantly inhibited nitric oxide production with an IC50 value of 6.0 ± 0.5 μM in lipopolysaccharide-induced RAW264.7 cells. Moreover, compound 9 also showed anti-inflammatory activity by inhibiting the NF-κB-activated pathway.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Anti-Inflammatory Agents / isolation & purification*
  • Aspergillus / chemistry*
  • Glycosides / chemistry
  • Glycosides / isolation & purification*
  • Glycosides / pharmacology
  • Magnetic Resonance Spectroscopy
  • Mice
  • NF-kappa B / antagonists & inhibitors
  • Nitric Oxide / antagonists & inhibitors
  • Phenols / isolation & purification*
  • RAW 264.7 Cells


  • Anti-Inflammatory Agents
  • Glycosides
  • NF-kappa B
  • Phenols
  • Nitric Oxide