New sugar-mimic alkaloids from the pods of Angylocalyx pynaertii

J Nat Prod. 2002 Feb;65(2):198-202. doi: 10.1021/np010360f.

Abstract

Chromatographic separation of the pod extract of Angylocalyx pynaertii resulted in the isolation of 13 sugar-mimic alkaloids (1-13). The structures of the new alkaloids were elucidated by spectroscopic methods as the 6-O-beta-D-glucoside (10) and N-hydroxyethyl derivative (11) of 1,4-dideoxy-1,4-imino-D-arabinitol (DAB) (1), 1,6-dideoxynojirimycin (12), and 1,3,4-trideoxynojirimycin (13). 2,5-Imino-1,2,5-trideoxy-L-glucitol (7), 2,5-dideoxy-2,5-imino-D-fucitol (8), and beta-homofuconojirimycin (9), isolated from the pods as well as the bark, were very specific inhibitors of alpha-L-fucosidase with no significant inhibitory activity toward other glycosidases. In this work, 1,4-dideoxy-1,4-imino-D-ribitol (6) was found to be a better inhibitor of lysosomal beta-mannosidase than 2,5-imino-1,2,5-trideoxy-D-mannitol (2). N-Hydroxyethyl-1-deoxynojirimycin (miglitol), which is commercially available for the treatment of diabetes, retained its inhibitory potential toward rat intestinal maltase and sucrase, whereas 11 and the synthetic N-hydroxyethyl derivative of 2,5-dideoxy-2,5-imino-D-mannitol markedly lowered or abolished their inhibition toward all enzymes tested.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / chemistry
  • Alkaloids / isolation & purification*
  • Alkaloids / pharmacology
  • Animals
  • Cameroon
  • Carbohydrates / chemistry*
  • Cattle
  • Coffee / enzymology
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / isolation & purification*
  • Enzyme Inhibitors / pharmacology
  • Fabaceae / chemistry*
  • Glucan 1,4-alpha-Glucosidase / antagonists & inhibitors
  • Glycoside Hydrolases / antagonists & inhibitors*
  • Intestines / enzymology
  • Liver / enzymology
  • Molecular Conformation
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Oryza / enzymology
  • Plant Bark
  • Plants, Medicinal / chemistry*
  • Rats
  • Stereoisomerism
  • Structure-Activity Relationship
  • Yeasts / enzymology

Substances

  • Alkaloids
  • Carbohydrates
  • Coffee
  • Enzyme Inhibitors
  • Glycoside Hydrolases
  • Glucan 1,4-alpha-Glucosidase