Structural elucidation of aculeximycin. I. Further purification and glycosidic bond cleavage of aculeximycin

J Antibiot (Tokyo). 1989 May;42(5):691-700. doi: 10.7164/antibiotics.42.691.

Abstract

A new insecticidal antibiotic, aculeximycin (ACM), was produced by an actinomycete identified as Streptosporangium albidum. ACM has been successfully isolated from culture filtrate by a combination of Diaion HP-20, Amberlite CG-50, reversed phase silica gel and Sephadex LH-20 chromatographies. It was found that ACM is a basic glycosidic antibiotic with a molecular weight of 1,672 including five monosaccharide units, three double bonds and a hemiketal ring by preliminary spectral analyses. Treatment of ACM with 1,8-diazabicyclo[5,4,0]undecene-7 caused a glycosidic bond cleavage to give aculexitriose, pseudoaglycones I and II.

MeSH terms

  • Actinomycetales / metabolism
  • Aminoglycosides
  • Anti-Bacterial Agents* / isolation & purification
  • Anti-Bacterial Agents* / metabolism
  • Bridged Bicyclo Compounds
  • Bridged Bicyclo Compounds, Heterocyclic*
  • Chemical Phenomena
  • Chemistry, Physical
  • Chromatography
  • Chromatography, High Pressure Liquid
  • Glycosides
  • Insecticides
  • Macrolides*
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Molecular Weight
  • Spectrophotometry

Substances

  • Aminoglycosides
  • Anti-Bacterial Agents
  • Bridged Bicyclo Compounds
  • Bridged Bicyclo Compounds, Heterocyclic
  • Glycosides
  • Insecticides
  • Macrolides
  • aculeximycin
  • 1,8-diazabicyclo(5.4.0)undec-7-ene