Cyclo(Pro-DOPA), a third identified bioactive metabolite produced by Streptomyces sp. 8812

J Antibiot (Tokyo). 2018 Aug;71(8):757-761. doi: 10.1038/s41429-018-0059-6. Epub 2018 Apr 26.

Abstract

A new metabolite, cyclic dipeptide, cis-(3S,8aS)-3-(3,4-dihydroxybenzyl)hexahydropyrrolo[1,2-a]pyrazine-1,4-dione, named JS-3 was isolated from Streptomyces sp. 8812 fermentation broth. Its chemical structure was established by means of spectroscopic analysis. A wide-range-screening study, which included inhibition assay of DD-carboxypeptidase/transpeptidase activity, determination of antibacterial, antifungal, and antiproliferative activities as well as free-radical scavenging was performed. To authors knowledge, this is the first isolation of such compound from natural sources and the first one from bacteria, Streptomyces.

MeSH terms

  • Anti-Bacterial Agents / isolation & purification
  • Anti-Bacterial Agents / pharmacology*
  • Antifungal Agents / isolation & purification
  • Antifungal Agents / pharmacology*
  • Bacteria / drug effects
  • Carboxypeptidases / antagonists & inhibitors*
  • Diketopiperazines / isolation & purification
  • Diketopiperazines / metabolism
  • Diketopiperazines / pharmacology*
  • Dipeptides / isolation & purification
  • Dipeptides / metabolism
  • Dipeptides / pharmacology*
  • Fermentation
  • Fungi / drug effects
  • Peptidyl Transferases / antagonists & inhibitors*
  • Streptomyces / metabolism*

Substances

  • Anti-Bacterial Agents
  • Antifungal Agents
  • Diketopiperazines
  • Dipeptides
  • Peptidyl Transferases
  • Carboxypeptidases