Discovery of nosokophic acid, a predicted intermediate of moenomycins, from nosokomycin-producing Streptomyces sp. K04-0144

Bioorg Med Chem Lett. 2013 Feb 1;23(3):860-3. doi: 10.1016/j.bmcl.2012.11.044. Epub 2012 Nov 29.

Abstract

A new actinomycete metabolite designated nosokophic acid was isolated from the culture broth of nosokomycin-producing Streptomyces sp. K04-0144, and the structure was elucidated by various NMR experiments. Nosokophic acid was found to be 3-phosphoglycosyl-2-sesquiterpenyl dihydroxypropionic acid, a predicted biosynthetic intermediate of nosokomycin-related moenomycins. The compound showed no activity against MRSA, but potentiated imipenem activity against MRSA by 512-fold.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology
  • Bambermycins / chemistry
  • Bambermycins / metabolism*
  • Drug Discovery*
  • Drug Synergism
  • Hexuronic Acids / chemistry*
  • Hexuronic Acids / pharmacology
  • Imipenem / pharmacology
  • Magnetic Resonance Spectroscopy
  • Methicillin-Resistant Staphylococcus aureus / drug effects
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Organophosphates / chemistry*
  • Organophosphates / pharmacology
  • Streptomyces / chemistry
  • Streptomyces / metabolism*

Substances

  • 3-phosphoglycosyl-2-sesquiterpenyl dihydroxypropionic acid
  • Anti-Bacterial Agents
  • Hexuronic Acids
  • Organophosphates
  • Bambermycins
  • Imipenem