Isolation, identification and stability of acylated derivatives of apigenin 7-O-glucoside from chamomile (Chamomilla recutita [L.] Rauschert).
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.
Svehliková
Vanda
V
Department of Biology and Ecology, P.J. Safárik University, Mánesova 23, SK-04154 Kosice, Slovakia.
Bennett
Richard N
RN
Mellon
Fred A
FA
Needs
Paul W
PW
Piacente
Sonia
S
Kroon
Paul A
PA
Bao
Yongping
Y
D000107:Acetylation; D000893:Anti-Inflammatory Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D047310:Apigenin / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D001673:Biodegradation, Environmental; D002851:Chromatography, High Pressure Liquid; D004355:Drug Stability; D008401:Gas Chromatography-Mass Spectrometry; D005960:Glucosides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D006863:Hydrogen-Ion Concentration; D007536:Isomerism; D009682:Magnetic Resonance Spectroscopy; D031168:Matricaria / Q000737:chemistry*; D012997:Solvents; D013696:Temperature
D000893:Anti-Inflammatory Agents; D005960:Glucosides; D012997:Solvents; D047310:Apigenin