Studies on the constituents of Broussonetia species. VII. Four new pyrrolidine alkaloids, broussonetines M, O, P, and Q, as inhibitors of glycosidase, from Broussonetia kazinoki SIEB

Chem Pharm Bull (Tokyo). 2000 Sep;48(9):1281-5. doi: 10.1248/cpb.48.1281.

Abstract

Four new pyrrolidine alkaloids, broussonetines M, O, P, and Q, were isolated from the branches of Broussonetia kazinoki SIEB, (Moraceae). Broussonetines M, O, P, and Q were formulated as (2R,3R,4R,5R)-2-hydroxymethyl-3,4-dihydroxy-5-[(10S)-10,13-dihydroxy-tri decyl]pyrrolidine (1), (2R,3R,4R,5R)-2-hydroxymethyl-3,4-dihydroxy-5-[(E)9-oxo-13-hydroxy-3- tridecenyl]pyrrolidine (2), (2R,3R,4R,5R)-2-hydroxymethyl-3,4-dihydroxy-5-[(E)10-oxo-13-hydroxy-3-++ +tridecenyl]pyrrolidine (3), and (2R,3S,4R,5R)-2-hydroxymethyl-3-hydroxy-4-(beta-D-glucopyranosyloxy++ +)-5-[10-oxo-13-(beta-D-glucopyranosyloxy)tridecyl]pyrrolidine (4) respectively, by spectroscopic and chemical methods. 1-4 inhibited beta-glucosidase, beta-galactosidase and beta-mannosidase.

MeSH terms

  • Alkaloids / isolation & purification*
  • Alkaloids / pharmacology
  • Chromatography, Thin Layer
  • Enzyme Inhibitors / isolation & purification*
  • Enzyme Inhibitors / pharmacology
  • Glycoside Hydrolases / antagonists & inhibitors*
  • Hydrolysis
  • Magnetic Resonance Spectroscopy
  • Mannosidases / antagonists & inhibitors
  • Mass Spectrometry
  • Plants, Medicinal / chemistry*
  • Pyrrolidines / isolation & purification*
  • Pyrrolidines / pharmacology
  • beta-Galactosidase / antagonists & inhibitors
  • beta-Glucosidase / antagonists & inhibitors
  • beta-Mannosidase

Substances

  • Alkaloids
  • Enzyme Inhibitors
  • Pyrrolidines
  • Glycoside Hydrolases
  • Mannosidases
  • beta-Glucosidase
  • beta-Galactosidase
  • beta-Mannosidase