New Prenylated Indole Homodimeric and Pteridine Alkaloids from the Marine-Derived Fungus Aspergillus austroafricanus Y32-2

Mar Drugs. 2021 Feb 9;19(2):98. doi: 10.3390/md19020098.

Abstract

Chemical investigation of secondary metabolites from the marine-derived fungus Aspergillus austroafricanus Y32-2 resulted in the isolation of two new prenylated indole alkaloid homodimers, di-6-hydroxydeoxybrevianamide E (1) and dinotoamide J (2), one new pteridine alkaloid asperpteridinate A (3), with eleven known compounds (4-14). Their structures were elucidated by various spectroscopic methods including HRESIMS and NMR, while their absolute configurations were determined by ECD calculations. Each compound was evaluated for pro-angiogenic, anti-inflammatory effects in zebrafish models and cytotoxicity for HepG2 human liver carcinoma cells. As a result, compounds 2, 4, 5, 7, 10 exhibited pro-angiogenic activity in a PTK787-induced vascular injury zebrafish model in a dose-dependent manner, compounds 7, 8, 10, 11 displayed anti-inflammatory activity in a CuSO4-induced zebrafish inflammation model, and compound 6 showed significant cytotoxicity against HepG2 cells with an IC50 value of 30 µg/mL.

Keywords: Aspergillus austroafricanus; anti-inflammatory effects; marine-derived fungus; novel bioactive metabolites; pro-angiogenesis.

MeSH terms

  • Angiogenesis Inducing Agents / pharmacology
  • Animals
  • Anti-Inflammatory Agents / pharmacology
  • Aspergillus / metabolism*
  • Hep G2 Cells
  • Humans
  • Indole Alkaloids / chemistry
  • Indole Alkaloids / isolation & purification*
  • Indole Alkaloids / pharmacology
  • Magnetic Resonance Spectroscopy
  • Pteridines / chemistry
  • Pteridines / isolation & purification*
  • Pteridines / pharmacology
  • Water Microbiology*
  • Zebrafish

Substances

  • Angiogenesis Inducing Agents
  • Anti-Inflammatory Agents
  • Indole Alkaloids
  • Pteridines

Supplementary concepts

  • Aspergillus austroafricanus