Isolation, identification and stability of acylated derivatives of apigenin 7-O-glucoside from chamomile (Chamomilla recutita [L.] Rauschert)

Phytochemistry. 2004 Aug;65(16):2323-32. doi: 10.1016/j.phytochem.2004.07.011.

Abstract

The major flavonoids in the white florets of chamomile (Chamomilla recutita [L.] Rauschert) were rapidly purified using a combination of polyamide solid-phase extraction and preparative HPLC. From the combined LC/MS, LC/MS/MS, and NMR data the apigenin glucosides were identified as apigenin 7-O-glucoside (Ap-7-Glc), Ap-7-(6"-malonyl-Glc), Ap-7-(6"-acetyl-Glc), Ap-7-(6"-caffeoyl-Glc), Ap-7-(4"-acetyl-Glc), Ap-7-(4"-acetyl,6"-malonyl-Glc), and a partially characterised apigenin-7-(mono-acetyl/mono-malonylglucoside) isomer. Malonyl and caffeoyl derivatives of Ap-7-Glc have not previously been identified in chamomile. The two mono-acetyl/mono-malonyl flavonoids have not previously been reported in any plant species. These acylated glucosides are unstable and degrade to form acetylated compounds or Ap-7-Glc. The degradation products formed are dependent on the extraction and storage conditions, i.e. temperature, pH and solvent.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetylation
  • Anti-Inflammatory Agents / chemistry
  • Anti-Inflammatory Agents / isolation & purification*
  • Anti-Inflammatory Agents / pharmacology
  • Apigenin / chemistry
  • Apigenin / isolation & purification*
  • Apigenin / pharmacology
  • Biodegradation, Environmental
  • Chromatography, High Pressure Liquid
  • Drug Stability
  • Gas Chromatography-Mass Spectrometry
  • Glucosides / chemistry
  • Glucosides / isolation & purification*
  • Glucosides / pharmacology
  • Hydrogen-Ion Concentration
  • Isomerism
  • Magnetic Resonance Spectroscopy
  • Matricaria / chemistry*
  • Solvents
  • Temperature

Substances

  • Anti-Inflammatory Agents
  • Glucosides
  • Solvents
  • Apigenin