Novel alpha-glucosidase inhibitors, CKD-711 and CKD-711a produced by Streptomyces sp. CK-4416. III. Physico-chemical properties and structure elucidation

J Antibiot (Tokyo). 2002 May;55(5):467-71. doi: 10.7164/antibiotics.55.467.

Abstract

We have isolated two novel a-glucosidase inhibitors, O-[4-deoxy-4-(2,3-epoxy-3-hydroxymethyl-4,5,6-trihydroxycyclohexane-1-yl-amino)-alpha-D-glucopyranosyl]-(1-->4)-O-alpha-D-glucopyranosyl-(1-->4)-alpha-D-glucopyranose (named CKD-711) and its hexameric analog CKD-711a, from the fermentation broth of Streptomyces sp. CK-4416. HRFAB-MS and NMR analyses reveal that molecular formulae of CKD-711 and CKD-711a are C25H43NO20 and C37H63NO30, respectively with the latter containing two more glucose moieties than the former. Detailed chemical structures of both compounds have been characterized by high-resolution two-dimensional NMR methods.

MeSH terms

  • Enzyme Inhibitors / chemistry*
  • Enzyme Inhibitors / isolation & purification
  • Enzyme Inhibitors / metabolism
  • Glycoside Hydrolase Inhibitors*
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry / methods
  • Molecular Structure
  • Streptomyces / metabolism*

Substances

  • Enzyme Inhibitors
  • Glycoside Hydrolase Inhibitors