A new flavanone glycoside from the dried immature fruits of Poncirus trifoliata

Chem Pharm Bull (Tokyo). 2007 Aug;55(8):1270-3. doi: 10.1248/cpb.55.1270.

Abstract

A new flavanone glycoside, (2R)-5-hydroxy-4'-methoxyflavanone-7-O-{beta-glucopyranosyl-(1-->2)-beta-glucopyranoside} (1), was isolated from the EtOAc extract of dried immature fruit of Poncirus trifoliata, together with three known compounds, (2S)-poncirin (2), (2S)-naringin (3), and (2S)-poncirenin (4). The structure of compound 1 was elucidated by spectroscopic data analysis, including 1D and 2D NMR experiments. Among the isolates, compound 2 exhibited considerable inhibitory activity against lipopolysaccharide (LPS)-induced prostaglandin E(2) (PGE(2)) and interleukin-6 (IL-6) production, and mRNA expression in RAW 264.7 murine macrophage cells.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Cell Survival / drug effects
  • Dinoprostone / biosynthesis
  • Flavanones / chemistry*
  • Flavanones / pharmacology
  • Fruit / chemistry*
  • Glycosides / chemistry
  • Glycosides / isolation & purification
  • Glycosides / pharmacology*
  • Interleukin-6 / antagonists & inhibitors
  • Interleukin-6 / biosynthesis
  • Lipopolysaccharides / antagonists & inhibitors
  • Lipopolysaccharides / toxicity
  • Macrophages / drug effects
  • Macrophages / metabolism
  • Magnetic Resonance Spectroscopy
  • Mice
  • Poncirus / chemistry*
  • Prostaglandin Antagonists / pharmacology
  • RNA, Messenger / biosynthesis
  • Reverse Transcriptase Polymerase Chain Reaction
  • Spectrophotometry, Infrared
  • Spectrophotometry, Ultraviolet
  • Tetrazolium Salts
  • Thiazoles

Substances

  • (2R)-5-hydroxy-4'-methoxyflavanone-7-O-(beta-glucopyranosyl-(1-2)-beta-glucopyranoside)
  • Flavanones
  • Glycosides
  • Interleukin-6
  • Lipopolysaccharides
  • Prostaglandin Antagonists
  • RNA, Messenger
  • Tetrazolium Salts
  • Thiazoles
  • thiazolyl blue
  • Dinoprostone