Chalcomycins from Marine-Derived Streptomyces sp. and Their Antimicrobial Activities

Mar Drugs. 2017 May 29;15(6):153. doi: 10.3390/md15060153.


Dihydrochalcomycin (1) and chalcomycin, (2), two known chalcomycins, and chalcomycin E (3), a new compound, were isolated from marine-derived Streptomyces sp. HK-2006-1. Their structures were elucidated by detailed spectroscopic and X-ray crystallographic analysis. The antimicrobial activities against Staphylococcus aureus, Escherichia coli, Candida albicans, and Aspergillus niger of 1-3 were evaluated. Compounds 1-2 exhibited activities against S. aureus with minimal inhibitory concentrations (MICs) of 32 µg/mL and 4 µg/mL, respectively. The fact that 1-2 showed stronger activity against S. aureus 209P than 3 indicated that the epoxy unit was important for antimicrobial activity. This structure-activity tendency of chalcomycins against S. aureus is different from that of aldgamycins reported in our previous research, which provide a valuable example for the phenomenon that 16-membered macrolides with different sugars do not have parallel structure-activity relationships.

Keywords: 16-membered macrolide; antimicrobial activity; chalcomycin E; marine-derived Streptomyces; secondary metabolite.

MeSH terms

  • Anti-Infective Agents / chemistry*
  • Anti-Infective Agents / pharmacology*
  • Aquatic Organisms / chemistry*
  • Aspergillus niger / drug effects
  • Candida albicans / drug effects
  • Escherichia coli / drug effects
  • Glycosides / chemistry
  • Glycosides / pharmacology
  • Macrolides / chemistry*
  • Macrolides / pharmacology*
  • Microbial Sensitivity Tests / methods
  • Staphylococcus aureus / drug effects
  • Streptomyces / chemistry*
  • Structure-Activity Relationship


  • Anti-Infective Agents
  • Glycosides
  • Macrolides
  • dihydrochalcomycin
  • chalcomycin