Chartarlactams Q-T, Dimeric Phenylspirodrimanes with Antibacterial and Antiviral Activities

Chem Biodivers. 2020 Jun;17(6):e2000170. doi: 10.1002/cbdv.202000170. Epub 2020 Jun 8.

Abstract

Four new phenylspirodrimane-type dimers, namely chartarlactams Q-T, along with stachyin B were isolated from the fermentation broth of a sponge-derived fungus Stachybotrys chartarum WGC-25 C-6. Chartarlactams Q-T were structurally featured by the dimerization of two units of phenylspirodrimane linked by a C-N bond. Their structures were determined on the basis of extensive spectroscopic analysis, while quantum ECD calculation and modified Mosher's method were used for the assignment of absolute configurations. Chartarlactams Q-S and stachyin B showed moderate inhibition against bacterial pathogen Staphylococcus aureus with MIC values ranging from 4 μg/mL to 16 μg/mL, and chartarlactam T exhibited significant inhibition toward ZIKV virus.

Keywords: Stachybotrys chartarum; antibacterial activity; antivirus activity; chartarlactams Q−T; structure elucidation.

MeSH terms

  • Anti-Bacterial Agents / chemistry*
  • Anti-Bacterial Agents / isolation & purification
  • Anti-Bacterial Agents / pharmacology
  • Antiviral Agents / chemistry*
  • Antiviral Agents / isolation & purification
  • Antiviral Agents / pharmacology
  • Circular Dichroism
  • Dimerization
  • Gram-Negative Bacteria / drug effects
  • Gram-Positive Bacteria / drug effects
  • Lactams / chemistry*
  • Lactams / isolation & purification
  • Lactams / pharmacology
  • Magnetic Resonance Spectroscopy
  • Microbial Sensitivity Tests
  • Molecular Conformation
  • Polycyclic Sesquiterpenes / chemistry*
  • Polycyclic Sesquiterpenes / isolation & purification
  • Polycyclic Sesquiterpenes / pharmacology
  • Stachybotrys / chemistry*
  • Stachybotrys / metabolism
  • Zika Virus / drug effects

Substances

  • Anti-Bacterial Agents
  • Antiviral Agents
  • Lactams
  • Polycyclic Sesquiterpenes
  • drimane

Supplementary concepts

  • Stachybotrys chartarum