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.
Huiling Wen  1  2 ,  Chunmei Chen  1 ,  Weiguang Sun  1 ,  Yi Zang  1 ,  Qin Li  1 ,  Wenxuan Wang  3 ,  Fanrong Zeng  1 ,  Junjun Liu  1 ,  Yuan Zhou  1 ,  Qun Zhou  1 ,  Jianping Wang  1 ,  Zengwei Luo  1 ,  Hucheng Zhu  1 ,  Yonghui Zhang  1
Affiliations
  • 1. Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation and Department of Pharmacology, School of Pharmacy, Tongji Medical College , Huazhong University of Science and Technology , Wuhan 430030 , People's Republic of China.
  • 2. School of Pharmaceutical Sciences , Gannan Medical University , Ganzhou 341000 , People's Republic of China.
  • 3. School of Pharmaceutical Sciences , South-Central University for Nationalities , Wuhan , Hubei 430074 , People's Republic of China.
PMID: 31012585 DOI: 10.1021/acs.jnatprod.8b00744
Abstract

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.