Quantitative determination of α-ionone, β-ionone, and β-damascenone and enantiodifferentiation of α-ionone in wine for authenticity control using multidimensional gas chromatography with tandem mass spectrometric detection

Anal Bioanal Chem. 2016 Sep;408(23):6483-96. doi: 10.1007/s00216-016-9767-6. Epub 2016 Jul 14.

Abstract

Native concentrations of α-ionone, β-ionone, and β-damascenone were studied in various authentic and commercial wines. In addition, the enantiomeric distribution of α-ionone was determined and its merits as a potential marker for aroma adulteration in wine were discussed. For extraction of volatiles, headspace solid-phase microextraction (HS-SPME) was applied, followed by heart-cut multidimensional gas chromatography coupled to tandem mass spectrometric detection for trace-level analysis. The enantioselective analysis of α-ionone was achieved with octakis(2,3-di-O-pentyl-6-O-methyl)-γ-cyclodextrin as the chiral selector in the separation column for gas chromatography (GC). In all the authentic wines studied, α-ionone showed a high enantiomeric ratio in favor of the (R)-enantiomer. Since an illegal addition of α-ionone in a racemic form changes the enantiomeric ratio, this ratio may serve as an adulteration marker. Concentrations varied between <LOD to 0.081 μg/L for α-ionone, <LOD to 1.0 μg/L for β-ionone, and 0.03-10.3 μg/L for β-damascenone. Commercial wines of suspiciously strong flavor yielded concentrations up to 4.6 μg/L for α-ionone, 3.6 μg/L for β-ionone, and 4.3 μg/L for β-damascenone. Elevated α- and β-ionone concentrations serve as additional indicators for a potential adulteration. In order to classify the concentrations of the analytes in the context of their odor activity in wine, odor thresholds were determined. Graphical abstract Trace-level analysis of authenticity markers in wine.

Keywords: Adulteration; Authenticity; C13-Norisoprenoids; Enantiodifferentiation; Heart-cut multidimensional gas chromatography; Odor threshold determination; Tandem mass spectrometry.

Publication types

  • Validation Study

MeSH terms

  • Gas Chromatography-Mass Spectrometry / methods*
  • Limit of Detection
  • Norisoprenoids / analysis*
  • Odorants / analysis
  • Solid Phase Microextraction / methods
  • Stereoisomerism
  • Tandem Mass Spectrometry / methods
  • Wine / analysis*

Substances

  • Norisoprenoids
  • beta-ionone
  • alpha-ionone
  • beta-damascenone