Stachybotrysins A-G, Phenylspirodrimane Derivatives from the Fungus Stachybotrys chartarum

J Nat Prod. 2017 Jun 23;80(6):1819-1826. doi: 10.1021/acs.jnatprod.7b00014. Epub 2017 May 22.

Abstract

Seven new phenylspirodrimane derivatives named stachybotrysins A-G (2-8), together with five known compounds (1, 9-12), were isolated from Stachybotrys chartarum CGMCC 3.5365. Stachybotrysin D (5) is the first reported example of a naturally occurring alcoholic O-sulfation of a phenylspirodrimane, and stachybotrysins F and G (7 and 8) are the first examples possessing an isobenzotetrahydrofuran ring with an acetonyl moiety attached. The structures of these compounds were elucidated on the basis of extensive spectroscopic data analysis and by comparison with reported data. The absolute configurations of 1-8 were determined by X-ray single-crystal diffraction, electronic circular dichroism (ECD), and calculated ECD. Compounds 1 and 8 displayed anti-HIV activity with IC50 values of 15.6 and 18.1 μM, respectively, and 2, 7, 9, and 11 showed inhibitory effect on influenza A virus with IC50 values ranging from 12.4 to 18.9 μM.

MeSH terms

  • Anti-HIV Agents / chemistry
  • Anti-HIV Agents / isolation & purification*
  • Anti-HIV Agents / pharmacology
  • Antiviral Agents / chemistry
  • Antiviral Agents / isolation & purification*
  • Antiviral Agents / pharmacology
  • Crystallography, X-Ray
  • Drug Screening Assays, Antitumor
  • Influenza A virus / drug effects
  • Inhibitory Concentration 50
  • Molecular Conformation
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Polycyclic Sesquiterpenes
  • Sesquiterpenes / chemistry
  • Sesquiterpenes / isolation & purification*
  • Sesquiterpenes / pharmacology
  • Spiro Compounds / chemistry
  • Spiro Compounds / isolation & purification*
  • Stachybotrys / chemistry*
  • Structure-Activity Relationship

Substances

  • Anti-HIV Agents
  • Antiviral Agents
  • Polycyclic Sesquiterpenes
  • Sesquiterpenes
  • Spiro Compounds
  • drimane