Phialomyces macrosporus: Chemical Constituents, Antimicrobial Activity and Complete NMR Assignments for the 7,7'-Biphyscion

Chem Biodivers. 2019 Sep;16(9):e1900353. doi: 10.1002/cbdv.201900353. Epub 2019 Aug 20.

Abstract

Five known secondary metabolites, chrysophanol (1), 7,7'-biphyscion (2), secalonic acid D (3), mannitol (4) and trehalose (5) were isolated for the first time from the extracts of the fungus Phialomyces macrosporus. Their structures were elucidated by NMR methods (1D and 2D NMR analysis), optical activity and ESI-MS. Complete 1 H and 13 C assignments were performed for compound 2. The antimicrobial activity was evaluated by serial microdilution assay for compounds 2 and 3 and results showed that compound 3 exhibited a significant growth inhibition at concentrations of 15.6 mg/ml (S. aureus and S. choleraesius) and 0.97 mg/mL (B. subtilis), comparable to the positive control.

Keywords: 7,7′-biphyscion, secalonic acid D; Phialomyces macrosporus; antimicrobial activity; biological activity; chrysophanol; mannitol; trehalose.

MeSH terms

  • Anthraquinones / chemistry
  • Anthraquinones / isolation & purification
  • Anthraquinones / pharmacology
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / isolation & purification
  • Anti-Bacterial Agents / pharmacology*
  • Bacillus subtilis / drug effects*
  • Bacillus subtilis / growth & development
  • Dose-Response Relationship, Drug
  • Magnetic Resonance Spectroscopy
  • Mannitol / chemistry
  • Mannitol / isolation & purification
  • Mannitol / pharmacology
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Salmonella / drug effects*
  • Salmonella / growth & development
  • Staphylococcus aureus / drug effects*
  • Staphylococcus aureus / growth & development
  • Trehalose / chemistry
  • Trehalose / isolation & purification
  • Trehalose / pharmacology
  • Xanthones / chemistry
  • Xanthones / isolation & purification
  • Xanthones / pharmacology

Substances

  • Anthraquinones
  • Anti-Bacterial Agents
  • Xanthones
  • 7,7'-biphyscion
  • Mannitol
  • secalonic acid
  • Trehalose