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

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.

Ectopic Odorant Receptor Responding to Flavor Compounds: Versatile Roles in Health and Disease

“…Airway smooth muscle (ASM) is located in the bronchial tree, where it plays a pivotal role in the modulation of bronchomotor tone, and ASM abnormalities are associated with many airway diseases including asthma [ 86 ]. Commonly used anti-obstructive drugs for asthma treatment, such as albuterol and fenoterol (both are β2-adrenergic receptor agonists), work by generating cAMP [ 87 ].…”

“…ORs and their key downstream signaling elements like Gαolf and Adcy3 are also expressed in the heart [ 85 , 86 ]. In human stem cell-derived cardiomyocytes, OR51E1 ligand nonanoic acid induces a negative chronotropy.…”

“…In human stem cell-derived cardiomyocytes, OR51E1 ligand nonanoic acid induces a negative chronotropy. This observed physiological effect of nonanoic acid is mediated by OR51E1 as indicated by antagonist and siRNA knock-down experiments [ 86 ]. Regarding downstream signaling cascade, OR51E1 stimulation may predominantly involve the G protein activation in stem cell-derived cardiomyocytes.…”

Current Developments in Analyzing Food Volatiles by Multidimensional Gas Chromatographic Techniques

“…In the field of food adulteration, Langen et al proposed an interesting application of H/C MDGC for quantitative determinations of α- and β-ionone and β-damascenone and enantiomeric separation of α-ionone in wine samples. These potent odorants, deriving from carotenoid cleavage, are reminiscent of violet, raspberry, and floral flavor attributes and generally are present as key odorants in raspberries, tea, and tobacco.…”

Corylus avellana L. Natural Signature: Chiral Recognition of Selected Informative Components in the Volatilome of High-Quality Hazelnuts

“…Enantiomeric recognition of chiral components and enantiomeric excess and/or ratio determinations are therefore important aspects not only to correlate chemical patterns to the sensory profile of food, but also to authenticate geographical origin for quality assurance purposes. Moreover, enantiomeric recognition enables conformity monitoring vs. legal requirements while objectively supporting fraud/adulteration counteractions ( Marchelli et al, 1996 ; Cagliero et al, 2016 ; Langen et al, 2016 ; Zhu et al, 2017 ; Sgorbini et al, 2019b ).…”