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Background and Aims:During wine ageing, a great variety of reactions take place, resulting in an immense variety of products whose structure sometimes remains unknown. The aim of this work is the study of different fragmentation patterns of flavanol-anthocyanin derivatives formed along the wine ageing; these patterns are useful for elucidating the different structures of these compounds and other new related ones. Methods and Results: Several wines from the Protected Denomination of Origin Rioja have been studied by an analytical method that combines column chromatography and high-performance liquid chromatography with diode array and mass and tandem mass spectrometric detections. Thirty-five coloured flavanol-anthocyanin compounds formed by direct reaction or by acetaldehyde-mediated condensation have been identified. For direct reaction derivatives, two different fragmentation patterns (one of them not previously reported) have been observed depending on the position of flavanol in the coloured derivative. Several compounds have been identified in aged wines for the first time to the authors' knowledge, like (+)-gallocatechin-cyanidin-3-glucoside and (+)-catechincyanidin-3-glucoside Conclusions: The developed analytical procedure has allowed the identification of some compounds for the first time, and two different fragmentation patterns have been observed depending on the position of flavanol in the pigment. Significance of the Study: The establishment of different fragmentation patterns allows the structural elucidation of unknown compounds.

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they exhibited a higher phenolic content than 'Meana' apple juice. Although flavan-3-ol, procyanidin and dihydrochalcone levels were similar to those observed in 'Meana' apple, flavonol levels increased slightly. Furthermore, it is worth noting that hydroxycinnamic acid concentration was up to three times higher. This fact could lead to an increase in cider astringency and color, as well as in cider aroma. Thus, this methodology is proposed to be applicable to the determination of the phenolic profile in other fruit and/or plant extracts.