Tentative identification of pyranoanthocyanins in Rioja aged red wines by high-performance liquid chromatography and tandem mass spectrometry
Version of Record online: 3 JAN 2014
© 2014 Australian Society of Viticulture and Oenology Inc.
Australian Journal of Grape and Wine Research
Volume 20, Issue 1, pages 31–40, February 2014
How to Cite
Sánchez-Ilárduya, M.B., Sánchez-Fernández, C., Garmón-Lobato, S., Viloria-Bernal, M., Abad-García, B., Berrueta, L.Á. and Gallo, B. (2014), Tentative identification of pyranoanthocyanins in Rioja aged red wines by high-performance liquid chromatography and tandem mass spectrometry. Australian Journal of Grape and Wine Research, 20: 31–40. doi: 10.1111/ajgw.12061
- Issue online: 26 JAN 2014
- Version of Record online: 3 JAN 2014
- Manuscript Accepted: 27 JUN 2013
- Manuscript Revised: 20 APR 2013
- Manuscript Received: 19 MAR 2013
- Agricultural, Industrial and Education Departments of the Basque Government (GV/EJ). Grant Numbers: PA08/09, PA09/11, PA10/13, S–PE06UN14, S–PE07UN34, S–PE08UN05, S–PE09UN03, IT413-10
- Universidad del País Vasco/Euskal Herriko Unibertsitatea (UPV/EHU)
- Education Department of Basque Government (GV/EJ)
Background and Aims
Pyranoanthocyanins are a type of derivative formed by the cycloaddition reaction of different compounds with anthocyanins during wine maturation and ageing, and show a characteristic pyranic ring. This ring provides a high stability to the pigment, and the ring does not fragment in mass spectrometric experiments. Thus, aglycone ions of these derivatives in tandem mass spectrometry show the same fragmentation pattern as that of the corresponding precursor anthocyanin. The aim of this work was the identification of pyranoanthocyanins present in Rioja aged wines using mass spectrometric features to differentiate among isomeric compounds.
Methods and Results
The application to three Rioja aged red wines of a methodology that combines column chromatography, solid-phase extraction and high-performance liquid chromatography–diode array detection–electrospray ionisation collision-induced dissociation–tandem mass spectrometry has allowed the identification of 72 pyranoanthocyanin derivatives.
This paper provides an overview of pyranoanthocyanin derivatives present in aged red wines with the identification of 72 compounds, some of them derivatives that appear in low concentration, and it assesses the importance of mass spectrometric analysis in the differentiation among isomeric derivatives.
Significance of the Study
The methodology described allows the identification of derivatives at low concentration and the establishment of characteristic fingerprints of native anthocyanins, which provide an effective tool for pyranoanthocyanin identification, allowing the differentiation among isomeric derivatives.