Isolation and Identification of Three New Sterigmatocystin Derivatives from the Fungus Aspergillus versicolor Guided by Molecular Networking Approach

Chem Biodivers. 2020 Jun;17(6):e2000208. doi: 10.1002/cbdv.202000208. Epub 2020 May 19.

Abstract

Molecular networking approach was applied for the targeted isolation of new sterigmatocystin derivatives, sterigmatocystins A-C, from the marine sponge-derived fungus Aspergillus versicolor. Sterigmatocystin A features a rare 6/6/6/6/5 polycyclic system. The structures of sterigmatocystins A-C, including absolute configurations, were determined on the basis of spectroscopic data and ECD calculations. Sterigmatocystin A showed more stronger promoting angiogenesis activity than the positive control at 1.25 μM level in transgenic fluorescent zebrafish. Sterigmatocystins A-C also exhibited moderate antiviral activity by the inhibition of HSV-2.

Keywords: 6/6/6/6/5 polycyclic system; Aspergillus versicolor; antiviral activity; molecular networking; promoting angiogenesis activity; sterigmatocystins A-C.

MeSH terms

  • Angiogenesis Inhibitors / chemistry
  • Angiogenesis Inhibitors / isolation & purification
  • Angiogenesis Inhibitors / pharmacology
  • Animals
  • Animals, Genetically Modified / metabolism
  • Antiviral Agents / chemistry*
  • Antiviral Agents / isolation & purification
  • Antiviral Agents / pharmacology
  • Aspergillus / chemistry*
  • Aspergillus / metabolism
  • Circular Dichroism
  • Herpesvirus 2, Human / drug effects
  • Humans
  • Magnetic Resonance Spectroscopy
  • Molecular Conformation
  • Neovascularization, Physiologic / drug effects
  • Porifera / microbiology
  • Sterigmatocystin / analogs & derivatives*
  • Sterigmatocystin / isolation & purification
  • Sterigmatocystin / pharmacology
  • Zebrafish / metabolism

Substances

  • Angiogenesis Inhibitors
  • Antiviral Agents
  • Sterigmatocystin

Supplementary concepts

  • Aspergillus versicolor