Flavanone glycosides from Miconia trailii

J Nat Prod. 2003 Jan;66(1):39-41. doi: 10.1021/np020429z.

Abstract

Assay-guided fractionation of the ethanol extract of the twigs and leaves of Miconia trailii yielded two new flavanone glycosides, matteucinol 7-O-alpha-l-arabinopyranosyl(1-->6)-beta-d-glucopyranoside (miconioside A, 1) and farrerol 7-O-beta-d-apiofuranosyl(1-->6)-beta-d-glucopyranoside (miconioside B, 2), along with the known compounds matteucinol 7-O-beta-d-apiofuranosyl(1-->6)-beta-d-glucopyranoside (3), matteucinol (4), 2alpha,3beta,19alpha-trihydroxyolean-12-ene-24,28-dioic acid (bartogenic acid, 5), 2alpha,3beta,23-trihydroxyolean-12-ene-28-oic acid (arjunolic acid, 6), 2alpha,3alpha,19alpha, 23-tetrahydroxyurs-12-ene-28-oic acid (myrianthic acid, 7), and stigmast-4-ene-3,6-dione (8). The structures of 1-8 were elucidated by spectroscopic methods, including 2D NMR.

Publication types

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

MeSH terms

  • Cholestenones / chemistry
  • Cholestenones / isolation & purification
  • Chromones / chemistry
  • Chromones / isolation & purification
  • Flavonoids / chemistry
  • Flavonoids / isolation & purification*
  • Glycosides / chemistry
  • Glycosides / isolation & purification*
  • Hydrolysis
  • Melastomataceae / chemistry*
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Peru
  • Plants, Medicinal / chemistry*
  • Stereoisomerism

Substances

  • Cholestenones
  • Chromones
  • Flavonoids
  • Glycosides
  • farrerol 7-O-beta-D-apiofuranosyl(1-6)-beta-D-glucopyranoside
  • matteucinol 7-O-alpha-L-arabinopyranosyl(1-6)-beta-glucopyranoside
  • stigmast-4-ene-3,6-dione
  • matteucinol