Aspergoterpenins A⁻D: Four New Antimicrobial Bisabolane Sesquiterpenoid Derivatives from an Endophytic Fungus Aspergillus versicolor

Molecules. 2018 May 28;23(6):1291. doi: 10.3390/molecules23061291.

Abstract

Aspergoterpenins A⁻D (14), four new bisabolane sesquiterpenoid derivatives, were obtained from the endophytic fungus, Aspergillus versicolor, together with eight known compounds (512), and their structures were elucidated by a comprehensive analysis of their NMR (Nuclear Magnetic Resonance), MS (Mass Spectrum) and CD (Circular Dichroism) spectra. Aspergoterpenin A (1) was the first example with a characteristic ketal bridged-ring part in the degraded natural bisabolane-type sesquiterpene structures. The compounds 112 displayed no significant activities against four cancer cell lines (A549, Caski, HepG2 and MCF-7). Further, the antimicrobial activities to Erwinia carotovora sub sp. Carotovora were evaluated, and the results showed that compounds 112 displayed antimicrobial activities with MIC values ranging from 15.2 to 85.2 μg/mL.

Keywords: Aspergillus versicolor; antimicrobial activities; bisabolanese squiterpenoid; endophytic fungus; structural elucidation.

MeSH terms

  • A549 Cells
  • Anti-Infective Agents / chemistry
  • Anti-Infective Agents / pharmacology*
  • Aspergillus / chemistry*
  • Cell Line, Tumor
  • Hep G2 Cells
  • Humans
  • MCF-7 Cells
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Pectobacterium carotovorum / drug effects*
  • Sesquiterpenes / chemistry
  • Sesquiterpenes / pharmacology*

Substances

  • Anti-Infective Agents
  • Sesquiterpenes