CP-78,545, a new monocarboxylic acid ionophore antibiotic related to zincophorin and produced by a Streptomyces

J Antibiot (Tokyo). 1989 Aug;42(8):1213-20. doi: 10.7164/antibiotics.42.1213.

Abstract

A new monocarboxylic acid ionophore antibiotic related to zincophorin, CP-78,545 (1), was found in the culture broth of Streptomyces sp. N731-45. CP-78,545 was extracted with organic solvents and purified by column chromatography. The metabolite, which is active in vitro against certain Gram-positive bacteria, as well as the anaerobe Treponema hyodysenteriae, and a coccidium Eimeria tenella, was isolated as a water insoluble magnesium salt (2) in 2:1 (ligand/metal) stoichiometry. The structure of CP-78,545 was elucidated by spectroscopic (NMR and MS) methods, and the relative stereochemistry was determined by single-crystal X-ray analysis of the cadmium salt (3). CP-78,545, i.e., 24-dehydrozincophorin, is unique since its molecular backbone contains a terminal double bond previously not found in other polyether ionophores.

MeSH terms

  • Animals
  • Anti-Bacterial Agents / biosynthesis
  • Anti-Bacterial Agents / isolation & purification*
  • Carboxylic Acids / biosynthesis
  • Carboxylic Acids / isolation & purification*
  • Carboxylic Acids / pharmacology
  • Chemical Phenomena
  • Chemistry, Physical
  • Chickens
  • Coccidiostats / biosynthesis
  • Coccidiostats / isolation & purification*
  • Fermentation
  • Ionophores / biosynthesis
  • Ionophores / isolation & purification*
  • Magnetic Resonance Spectroscopy
  • Microbial Sensitivity Tests
  • Models, Molecular
  • Molecular Conformation
  • Molecular Structure
  • Streptomyces / metabolism
  • X-Ray Diffraction

Substances

  • Anti-Bacterial Agents
  • Carboxylic Acids
  • Coccidiostats
  • Ionophores
  • CP 78545