Investigation of a Quantitative Method for the Analysis of Chiral Monoterpenes in White Wine by HS-SPME-MDGC-MS of Different Wine Matrices

Abstract

A valid quantitative method for the analysis of chiral monoterpenes in white wine using head-space solid phase micro-extraction-MDGC-MS (HS-SPME-MDGC-MS) with stable isotope dilution analysis was established. Fifteen compounds: (S)-(−)-limonene, (R)-(+)-limonene, (+)-(2R,4S)-cis-rose oxide, (−)-(2S,4R)-cis-rose oxide, (−)-(2R,4R)-trans-rose oxide, (+)-(2S,4S)-cis-rose oxide, furanoid (+)-trans-linalool oxide, furanoid (−)-cis-linalool oxide, furanoid (−)-trans-linalool oxide, furanoid (+)-cis-linalool oxide, (−)-linalool, (+)-linalool, (−)-α-terpineol, (+)-α-terpineol and (R)-(+)-β-citronellol were quantified. Two calibration curves were plotted for different wine bases, with varying residual sugar content, and three calibration curves for each wine base were investigated during a single fiber’s lifetime. This was needed as both sugar content and fiber life impacted the quantification of the chiral terpenes. The chiral monoterpene content of six Pinot Gris wines and six Riesling wines was then analyzed using the verified method. ANOVA with Tukey multiple comparisons showed significant differences for each of the detected chiral compounds in all 12 wines. PCA score plots showed a clear separation between the Riesling and Pinot Gris wines. Riesling wines had greater number of chiral terpenes in comparison to Pinot Gris wines. Beyond total terpene content it is possible that the differences in chiral terpene content may be driving the aromatic differences in white wines.

Free Monoterpene Isomer Profiles of Vitis Vinifera L. cv. White Wines

“…D3-(±)-α-terpineol and d3-(±)-linalool (≥99.4%) were obtained from CDN Isotopes (Pointe-Claire, QC, Canada). D3-(±)-limonene was synthesized in the lab via diels-alder and wittig reactions [ 16 ]. Milli-Q water was obtained from a Millipore Continental water system (EMD-Millipore, Billerica, MA, USA).…”

Addition of fast gas chromatography to selected ion flow tube mass spectrometry for analysis of individual monoterpenes in mixtures

“…Gas chromatography mass spectrometry (GC-MS) coupled with pre-concentration techniques has been developed to successfully identify and quantify different atmospheric monoterpenes (Janson, 1993;Räisänen et al, 2009;Song et al, 2015). However, the requirements of pre-concentration and long cycle time (more than 1 h) are obviously unsuitable for real-time measurements.…”

Reliable HPLC separation, vibrational circular dichroism spectra, and absolute configurations of isoborneol enantiomers

“…Enantiomers show significant differences in sensory qualities, odor threshold, pharmacology activities, metabolic processes, and toxicities . Since chiral monoterpene compounds possess few or no functional groups and high volatility, their chiral analysis studies have been mainly performed by gas chromatography with cyclodextrin derivatives as chiral selectors . In order to obtain optically active stereoisomers in batch, several research groups tried to develop direct HPLC separation methods with chiral columns.…”

“…[7][8][9] Since chiral monoterpene compounds possess few or no functional groups and high volatility, their chiral analysis studies have been mainly performed by gas chromatography with cyclodextrin derivatives as chiral selectors. 7,[10][11][12] In order to obtain optically active stereoisomers in batch, several research groups tried to develop direct HPLC separation methods with chiral columns. In Zukowski's work, complete separation of (±)-pinene with a selectivity factor of 1.53 was obtained by HPLC with α-cyclodextrin as the mobile phase additive.…”