title: Isolation, identification and stability of acylated derivatives of apigenin 7-O-glucoside from chamomile (Chamomilla recutita [L.] Rauschert).
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.
authors.affiliation: Department of Biology and Ecology, P.J. Safárik University, Mánesova 23, SK-04154 Kosice, Slovakia.
authors.forename: Vanda
authors.initials: V
authors.lastname: Svehliková
authors.forename: Richard N
authors.initials: RN
authors.lastname: Bennett
authors.forename: Fred A
authors.initials: FA
authors.lastname: Mellon
authors.forename: Paul W
authors.initials: PW
authors.lastname: Needs
authors.forename: Sonia
authors.initials: S
authors.lastname: Piacente
authors.forename: Paul A
authors.initials: PA
authors.lastname: Kroon
authors.forename: Yongping
authors.initials: Y
authors.lastname: Bao
mesh_terms: 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
chemical_list: D000893:Anti-Inflammatory Agents; D005960:Glucosides; D012997:Solvents; D047310:Apigenin