Activity-guided fractionation of the leaves of Ormosia sumatrana using a proteasome inhibition assay

J Nat Prod. 2004 Nov;67(11):1911-4. doi: 10.1021/np040134g.

Abstract

Activity-guided fractionation of a chloroform-soluble extract of the leaves of Ormosia sumatrana, using a proteasome inhibition assay, led to the isolation of a new A-type proanthocyanidin derivative, 3'-O-cinnamoylprocyanidin A-2 (1), and a new cerebroside, sumatranoside (2). The structures of these two isolates were determined as epicatechin-(2 beta-->O-->7',4 beta-->8')-epicatechin-3'-O-cinnamate (1) and 1-O-(beta-d-glucopyranosyl)-(2S,3S,4R)-2N-[(2'R)-2'-hydroxy-tetracosanoyl]-9Z-octadecene-1,3,4-triol (2), respectively, by spectroscopic and chemical methods. Sumatranoside (2) exhibited proteasome inhibitory activity with an IC(50) value of 30 microM.

Publication types

  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Catechin / analogs & derivatives*
  • Catechin / chemistry
  • Catechin / isolation & purification*
  • Catechin / pharmacology
  • Cerebrosides / chemistry
  • Cerebrosides / isolation & purification*
  • Cerebrosides / pharmacology
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / isolation & purification*
  • Enzyme Inhibitors / pharmacology
  • Fabaceae / chemistry*
  • Indonesia
  • Inhibitory Concentration 50
  • Molecular Structure
  • Plant Leaves / chemistry
  • Proteasome Inhibitors*
  • Stereoisomerism

Substances

  • 3'-O-cinnamoylprocyanidin A-2
  • Cerebrosides
  • Enzyme Inhibitors
  • Proteasome Inhibitors
  • sumatranoside
  • Catechin