Three new 12-carbamoylated streptothricins from Streptomyces sp. I08A 1776

Bioorg Med Chem Lett. 2012 Oct 1;22(19):6151-4. doi: 10.1016/j.bmcl.2012.08.003. Epub 2012 Aug 10.

Abstract

Two new streptothricins (1 and 2) and a new streptothricin acid derivative (3), all with the carbamoyl group substituted at C-12 of the gulosamine moiety, together with the known N(β)-acetylstreptothricin D acid (4), have been isolated from the culture broth of Streptomyces sp. I08A 1776. The structures of the new compounds were determined by MS, CD, and 1D and 2D NMR spectroscopic data analysis. The isolated compounds were evaluated for antibacterial and antifungal activities. Streptothricin E (6) showed potent activity against the clinically isolated extensively drug-resistant Mycobacterium tuberculosis with MIC values of 0.25-0.5μg/mL.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / isolation & purification
  • Anti-Bacterial Agents / pharmacology*
  • Antifungal Agents / chemistry
  • Antifungal Agents / isolation & purification
  • Antifungal Agents / pharmacology*
  • Bacteria / drug effects*
  • Dose-Response Relationship, Drug
  • Fungi / drug effects*
  • Magnetic Resonance Spectroscopy
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Stereoisomerism
  • Streptomyces / chemistry*
  • Streptothricins / chemistry
  • Streptothricins / isolation & purification
  • Streptothricins / pharmacology*

Substances

  • Anti-Bacterial Agents
  • Antifungal Agents
  • Streptothricins