Isolation and structure of vanitaracin A, a novel anti-hepatitis B virus compound from Talaromyces sp

Bioorg Med Chem Lett. 2015 Oct 1;25(19):4325-8. doi: 10.1016/j.bmcl.2015.07.067. Epub 2015 Jul 26.

Abstract

Two new tricyclic polyketides, vanitaracin A (1) and B (2), together with three novel compounds 3, 4 and 5, were isolated from a culture broth of a fungus, Talaromyces sp. The chemical structures of these compounds were determined from spectroscopic data (1D/2D NMR, MS and IR). The five isolated compounds were then tested for anti-hepatitis B virus (HBV) activity and vanitaracin A was found to exhibit an IC50 value of 10.5 μM using a HBV-susceptible cell line. By contrast, the derivative 2 displayed weak anti-HBV action, which suggested that the substituents at C-9 in 1 are likely to be important for its antiviral activity. We believe the two vanitaracin derivatives constitute a new class of anti-HBV agents.

Keywords: HBV; Infection; Natural products; Structure determination.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antiviral Agents / chemistry
  • Antiviral Agents / isolation & purification
  • Antiviral Agents / pharmacology*
  • Cell Line, Tumor
  • Dose-Response Relationship, Drug
  • Hep G2 Cells
  • Hepatitis B virus / drug effects*
  • Humans
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Polyketides / chemistry
  • Polyketides / isolation & purification
  • Polyketides / pharmacology*
  • Structure-Activity Relationship
  • Talaromyces / chemistry*

Substances

  • Antiviral Agents
  • Polyketides
  • vanitaracin A