Total Synthesis and Antimicrobial Evaluation of 23-Demethyleushearilide and Extensive Antimicrobial Evaluation of All Synthetic Stereoisomers of (16 Z,20 E)-Eushearilide and (16 E,20 E)-Eushearilide

Molecules. 2019 Sep 22;24(19):3437. doi: 10.3390/molecules24193437.


A novel stereoisomer of eushearilide, 23-demethyleushearilide, was synthesized, and the structure-activity relationships of this compound along with known eushearilide stereoisomers were investigated in order to design novel lead compounds for the treatment of fungal infections. It was discovered that all of these congeners, together with the natural product, exhibited a wide range of antimicrobial activity against not only fungi but also against bacteria, including methicillin-resistant Staphylococcus aureus (MRSA) and vancomycin-resistant enterococci (VRE).

Keywords: MNBA; antimicrobial activity; demethyl congener; eushearilide; lactonization; total synthesis.

MeSH terms

  • Anti-Infective Agents / chemical synthesis
  • Anti-Infective Agents / chemistry
  • Anti-Infective Agents / pharmacology
  • Macrolides / chemical synthesis*
  • Macrolides / chemistry
  • Macrolides / pharmacology*
  • Methicillin-Resistant Staphylococcus aureus / drug effects
  • Microbial Sensitivity Tests
  • Phosphorylcholine / analogs & derivatives*
  • Phosphorylcholine / chemical synthesis
  • Phosphorylcholine / chemistry
  • Phosphorylcholine / pharmacology
  • Stereoisomerism
  • Vancomycin Resistance
  • Vancomycin-Resistant Enterococci / drug effects


  • Anti-Infective Agents
  • Macrolides
  • eushearilide
  • Phosphorylcholine