Potential Antiviral Xanthones from a Coastal Saline Soil Fungus Aspergillus iizukae

Mar Drugs. 2018 Nov 15;16(11):449. doi: 10.3390/md16110449.

Abstract

Five new (15) and two known xanthones (6 and 7), one of the latter (6) obtained for the first time as a natural product, together with three known anthraquinones, questin, penipurdin A, and questinol, were isolated from the coastal saline soil-derived Aspergillus iizukae by application of an OSMAC (one strain many compounds) approach. Their structures were determined by interpretation of nuclear magnetic resonance (NMR) and high-resolution electrospray ionization mass spectroscopy (HRESIMS) data, as well as comparison of these data with those of related known compounds. Antiviral activity of xanthones 1-7 was evaluated through the cytopathic effect (CPE) inhibition assay, and compound 2 exhibited distinctly strong activity towards influenza virus (H1N1), herpes simplex virus types 1 (HSV-1) and 2 (HSV-2) with IC50 values of 44.6, 21.4, and 76.7 μM, respectively, which indicated that it was worth to further investigate it as a potential lead compound. The preliminary structure-activity relationship of the xanthones is discussed.

Keywords: Aspergillus iizukae; antiviral activity; structure-activity relationship; xanthones.

MeSH terms

  • Animals
  • Antiviral Agents / chemistry
  • Antiviral Agents / isolation & purification
  • Antiviral Agents / pharmacology*
  • Aspergillus / chemistry*
  • Dogs
  • Herpesvirus 1, Human / drug effects
  • Herpesvirus 2, Human / drug effects
  • Influenza A Virus, H1N1 Subtype / drug effects
  • Inhibitory Concentration 50
  • Madin Darby Canine Kidney Cells
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Soil / chemistry
  • Soil Microbiology
  • Spectrometry, Mass, Electrospray Ionization
  • Structure-Activity Relationship
  • Xanthones / chemistry
  • Xanthones / isolation & purification
  • Xanthones / pharmacology*

Substances

  • Antiviral Agents
  • Soil
  • Xanthones