Isotopic Exchange HPLC-HRMS/MS Applied to Cyclic Proanthocyanidins in Wine and Cranberries
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Cyclic B-type proanthocyanidins in red wines and grapes have been discovered recently. However, proanthocyanidins of a different chemical structure (non-cyclic A-type proanthocyanidins) already known to be present in cranberries and wine possess an identical theoretical mass. As a matter of fact, the retention times and the MS/MS fragmentations found for the proposed novel cyclic B-type tetrameric proanthocyanidin in red wine and the known tetrameric proanthocyanidin in a cranberry extract are herein shown to be identical. Thus, hydrogen/deuterium (H/D) exchange was applied to HPLC-HRMS/MS to confirm the actual chemical structure of the new oligomeric proanthocyanidins. The comparison of the results in water and deuterium oxide and between wine and cranberry extract indicates that the cyclic B-type tetrameric proanthocyanidin is the actual constituent of the recently proposed novel tetrameric species ([C60H49O24]+, m/z 1153.2608). Surprisingly, the same compound was also identified as the main tetrameric proanthocyanidin in cranberries. Finally, a totally new cyclic B-type hexameric proanthocyanidin ([C90H73O36]+, m/z 1729.3876) belonging to this novel class was identified for the first time in red wine.
KeywordsCyclic proanthocyanidins Hydrogen/deuterium exchange High-resolution mass spectrometry Wine Cranberries Cyclic B-type hexameric proanthocyanidin
The authors thank Kellerei Bozen (Bolzano, Italy) for providing the samples of Lagrein wine used for the analysis. The authors thank the Province of Bolzano (Italy) (Landesregierung mittels Beschluss Nr. 1472, 07.10.2013) for their financial support.
- 5.Jourdes, M., Zeng, L., Pons-Marcadé, P., Rivero Canosa, M., Richard, T., Teissèdre, P.-L.: A new procyanidin tetramer with unusual macrocyclic skeleton from grape and wine. Book of Abstracts of 39th World Vine and Wine Congress - Theme 2 Oenology, pp. 432/433, 24–28 October. Bento Gonçalves, Brazil (2016)Google Scholar
- 6.Jouin, A., Rossetti, F., Teissèdre, P.-L., Jourdes, M.: Evaluation of crown procyanidins contents in different variety and their accumulation kinetic during grape maturation. Book of Abstracts of 10th In Vino Analytica Scientia (IVAS) Symposium, 17–20 July, pp. 160, Salamanca, Spain (2017)Google Scholar
- 9.Vivas de Gaulejac, N., Vivas, N., Absalon, C., Nonier, M.F.: Merlot Noir and Cabernet Sauvignon. J. Int. des Sci. de la Vigne et du Vin 35, 51–56 (2001)Google Scholar
- 17.Carlson, E.E., Cravatt, B.F.: Chemoselective probes for metabolite enrichment and profiling. Nat. Methods. 4(5), 429–435 (2007)Google Scholar
- 22.Savini, S., Loizzo, M.R., Tundis, R., Mozzon, M., Foligni, R., Longo, E., Morozova, K., Scampicchio, M., Martin-Vertedor, D., Boselli, E.: Fresh refrigerated Tuber melanosporum truffle: effect of the storage conditions on the antioxidant profile, antioxidant activity, and volatile profile. Eur. Food Res. Technol. 1–9 (2017)Google Scholar
- 23.Zhang, S., Zhu, M.J.: Characterization of polyphenolics in grape pomace extracts using ESI Q-TOF MS/MS. J. Food Sci. Nutr. 1, 1–10 (2015)Google Scholar