Phenolic glycosides from berries of Pimenta dioica

J Nat Prod. 2008 May;71(5):861-5. doi: 10.1021/np0705615. Epub 2008 Mar 4.

Abstract

Four new phenolic glycosides, (2-hydroxy-3-methoxy-5-allyl)phenyl beta- d-(6-O-E-sinapoyl)glucopyranoside (1), (1' R,5' R)-5-(5-carboxymethyl-2-oxocyclopentyl)-3 Z-pentenyl beta-D-(6-O-galloyl)glucopyranoside (2), (S)-alpha-terpinyl [alpha-L-(2-O-galloyl)arabinofuranosyl]-(1-->6)-beta-D-glucopyranoside (3), and (R)-alpha-terpinyl [alpha-L-(2-O-galloyl)arabinofuranosyl]-(1-->6)-beta-D-glucopyranoside (4), were isolated from the berries of Pimenta dioica together with eight known flavonoids. The structures of 1-4 were elucidated on the basis of MS and NMR data and enzymatic hydrolysis. All four glycosides showed radical-scavenging activity against 1,1-diphenyl-2-picrylhydrazyl (DPPH) radicals.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Biphenyl Compounds
  • Flavonoids / chemistry
  • Flavonoids / isolation & purification
  • Flavonoids / pharmacology
  • Free Radical Scavengers
  • Fruit / chemistry
  • Glycosides / chemistry
  • Glycosides / isolation & purification*
  • Glycosides / pharmacology
  • Jamaica
  • Molecular Structure
  • Phenols / chemistry
  • Phenols / isolation & purification*
  • Phenols / pharmacology
  • Picrates / pharmacology
  • Pimenta / chemistry*
  • Plants, Medicinal / chemistry*

Substances

  • Biphenyl Compounds
  • Flavonoids
  • Free Radical Scavengers
  • Glycosides
  • Phenols
  • Picrates
  • 1,1-diphenyl-2-picrylhydrazyl