Galloylglucosides from berries of Pimenta dioica

J Nat Prod. 2000 Jun;63(6):749-52. doi: 10.1021/np9906121.

Abstract

Three new galloylglucosides, (4S)-alpha-terpineol 8-O-beta-D-(6-O-galloyl)glucopyranoside (1); (4R)-alpha-terpineol 8-O-beta-D-(6-O-galloyl)glucopyranoside (2), and 3-(4-hydroxy-3-methoxyphenyl)propane-1,2-diol 2-O-beta-D-(6-O-galloyl)glucopyranoside (3), were isolated from the berries of Pimenta dioica together with three known compounds, gallic acid (4), pimentol (5), and eugenol 4-O-beta-D-(6-O-galloyl)glucopyranoside (6). The structures of 1-3 were elucidated on the basis of MS and NMR spectral data and enzymatic hydrolysis. These galloylglucosides (1-3, 5, and 6) showed radical-scavenging activity nearly equivalent to that of gallic acid (4) against 1,1-diphenyl-2-picrylhydrazyl radical.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cyclohexane Monoterpenes
  • Free Radicals
  • Fruit / chemistry*
  • Glucosides / chemistry
  • Glucosides / isolation & purification*
  • Magnetic Resonance Spectroscopy
  • Models, Chemical
  • Monoterpenes*
  • Plant Extracts / chemistry
  • Plants, Medicinal / chemistry*
  • Rosales / chemistry*
  • Terpenes / chemistry
  • Terpenes / isolation & purification*

Substances

  • Cyclohexane Monoterpenes
  • Free Radicals
  • Glucosides
  • Monoterpenes
  • Plant Extracts
  • Terpenes
  • terpineol-8-O-(6-O-galloyl)glucopyranoside