Isolation and structure assignment of an iminotetrasaccharide from a cultured filamentous cyanobacterium Anabaena sp

J Nat Prod. 2006 Mar;69(3):365-8. doi: 10.1021/np050401y.

Abstract

In search of bioactive metabolites in cultured microalgae, a novel acylated iminopseudotetrasaccharide was isolated from a filamentous cyanobacterium Anabaena sp., and its structure was established by NMR, chemical degradation, and X-ray crystallography. The compound consists of glucose, glucuronic acid, arabinose, and 1,4,6-trideoxy-1,4-imino-D-allitol, which is closely related to potent glucosidase inhibitors such as nojirimycin. The tetrasaccharide itself showed moderate inhibitory activity against beta-D-glucuronidase.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • 1-Deoxynojirimycin / analogs & derivatives
  • Anabaena / chemistry*
  • Australia
  • Crystallography, X-Ray
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / isolation & purification*
  • Enzyme Inhibitors / pharmacology
  • Glucosamine / analogs & derivatives
  • Glucosamine / chemistry
  • Glucosamine / pharmacology
  • Glucuronidase / antagonists & inhibitors*
  • Molecular Conformation
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Oligosaccharides / chemistry*
  • Oligosaccharides / isolation & purification*
  • Oligosaccharides / pharmacology

Substances

  • Enzyme Inhibitors
  • Oligosaccharides
  • 1-Deoxynojirimycin
  • Glucuronidase
  • Glucosamine
  • nojirimycin