Aspulvinones from a mangrove rhizosphere soil-derived fungus Aspergillus terreus Gwq-48 with anti-influenza A viral (H1N1) activity

Bioorg Med Chem Lett. 2013 Mar 15;23(6):1776-8. doi: 10.1016/j.bmcl.2013.01.051. Epub 2013 Jan 25.

Abstract

A new butenolide isoaspulvinone E (1), together with two known butenolides aspulvinone E (2) and pulvic acid (3) were isolated from the marine-derived fungus, Aspergillus terreus Gwq-48. They showed significant anti-influenza A H1N1 virus activities, with IC50 values of 32.3, 56.9, and 29.1μg/mL, respectively. Moreover, only compound 1 exhibited effective inhibitory activity against H1N1 viral neuraminidase (NA), and docking of two isomers (1-2) into the active sites of NA showed that the E double bond Δ(5(10)) was essential to achieve activity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • 4-Butyrolactone / analogs & derivatives*
  • 4-Butyrolactone / chemistry
  • 4-Butyrolactone / isolation & purification
  • 4-Butyrolactone / pharmacology
  • Animals
  • Antiviral Agents / chemistry*
  • Antiviral Agents / isolation & purification
  • Antiviral Agents / pharmacology
  • Aspergillus / isolation & purification
  • Aspergillus / metabolism*
  • Benzylidene Compounds / chemistry*
  • Benzylidene Compounds / isolation & purification
  • Benzylidene Compounds / pharmacology
  • Binding Sites
  • Catalytic Domain
  • Cell Line
  • Cell Survival / drug effects
  • Dogs
  • Humans
  • Influenza A Virus, H1N1 Subtype / drug effects
  • Influenza A Virus, H1N1 Subtype / metabolism*
  • Magnetic Resonance Spectroscopy
  • Molecular Conformation
  • Molecular Docking Simulation
  • Neuraminidase / antagonists & inhibitors*
  • Neuraminidase / metabolism
  • Rhizosphere
  • Soil Microbiology

Substances

  • Antiviral Agents
  • Benzylidene Compounds
  • isoaspulvinone E
  • butenolide
  • Neuraminidase
  • 4-Butyrolactone