Ceramidastin, a novel bacterial ceramidase inhibitor, produced by Penicillium sp. Mer-f17067

J Antibiot (Tokyo). 2009 Feb;62(2):63-7. doi: 10.1038/ja.2008.10. Epub 2009 Jan 9.

Abstract

Decrease of ceramide in the skin is one of the aggravating factors of atopic dermatitis. The skin is often infected by ceramidase-producing bacteria, such as Pseudomonas aeruginosa. The bacterial ceramidase then degrades ceramide in the skin. To develop anti-atopic dermatitis drugs, we searched for ceramidase inhibitors, which led to the discovery of ceramidastin, a novel inhibitor of bacterial ceramidase, from the culture broth of Penicillium sp. Mer-f17067. Ceramidastin inhibited the bacterial ceramidase with an IC(50) value of 6.25 microg ml(-1). Here we describe the isolation, physicochemical properties, structure determination and biological activity of ceramidastin.

MeSH terms

  • Animals
  • Antibiotics, Antineoplastic / isolation & purification
  • Antibiotics, Antineoplastic / pharmacology
  • Antibiotics, Antineoplastic / toxicity
  • Cell Line, Tumor
  • Cell Survival / drug effects
  • Ceramidases / antagonists & inhibitors*
  • Cyclooctanes / isolation & purification*
  • Cyclooctanes / pharmacology*
  • Cyclooctanes / toxicity
  • Dermatitis, Atopic / drug therapy
  • Dermatitis, Atopic / enzymology
  • Enzyme Inhibitors / isolation & purification*
  • Enzyme Inhibitors / pharmacology*
  • Enzyme Inhibitors / toxicity
  • Female
  • Fermentation
  • Humans
  • Magnetic Resonance Spectroscopy
  • Maleic Anhydrides / isolation & purification*
  • Maleic Anhydrides / pharmacology*
  • Maleic Anhydrides / toxicity
  • Mice
  • Mice, Inbred ICR
  • Molecular Conformation
  • Penicillium / classification
  • Penicillium / metabolism*
  • Pseudomonas / enzymology
  • Spectrometry, Mass, Electrospray Ionization
  • Spectrophotometry, Ultraviolet
  • Tetrazolium Salts
  • Thiazoles

Substances

  • Antibiotics, Antineoplastic
  • Cyclooctanes
  • Enzyme Inhibitors
  • Maleic Anhydrides
  • Tetrazolium Salts
  • Thiazoles
  • ceramidastin
  • Ceramidases
  • thiazolyl blue