Disambiguation of Isomeric Procyanidins with Cyclic B-Type and Non-cyclic A-Type Structures from Wine and Peanut Skin with HPLC-HDX-HRMS/MS
Hydrogen/deuterium exchange coupled with high-resolution mass spectrometry was successfully applied for the identification of A-type tetrameric, pentameric, and hexameric procyanidins in peanut skin. This extended a previous study on isomeric cyclic B-type unconventional tetramer, pentamer, and hexamer procyanidins found in wine and cranberries. Not only had the method successfully identified the procyanidins with a single A-linkage (e.g., tetrameric m/z 1153.2608) by means of distinguishing them from their isomeric cyclic B-type analogues, but this method also worked for procyanidins with two or more A-linkages (such as the tetrameric m/z 1151.2452). As a further consequence, B-type cyclic pentamers and hexamers in wine have been elucidated with hydrogen/deuterium exchange (HDX) for the first time.
KeywordsIsotopic exchange Cyclic procyanidins Wine Peanut skin A-type procyanidins
The authors wish to thank Kellerei Bozen (Gries, Bolzano, Italy) for providing the samples of Lagrein wine used for the analysis.
The authors thank the Province of Bolzano (Italy) (Beschluss No. 1472, 07.10.2013) for their financial support.
- 1.Vivas de Gaulejac, N., Vivas, N., Absalon, C., Nonier, M.F.: Identification of Procyanidin A2 in grape and wine of Vitis vinifera LCV. Merlot Noir and Cabernet Sauvignon. J Int des Sci de la Vigne et du Vin. 35, 51–56 (2001)Google Scholar
- 4.Hollands, W.J., Voorspoels, S., Jacobs, G., Aaby, K., Meisland, A., Garcia-Villalba, R., Tomas-Barberan, F., Piskula, M.K., Mawson, D., Vovk, I., Needs, P.W., Kroon, P.A.: Development, validation and evaluation of an analytical method for the determination of monomeric and oligomeric procyanidins in apple extracts. J. Chromatogr. A. 1495, 46–56 (2017)CrossRefGoogle Scholar
- 5.Robbins, R.J., Leonczak, J., Johnson, J.C., Li, J., Kwik-Uribe, C., Prior, R.L., Gu, L.: Method performance and multi-laboratory assessment of a normal phase high pressure liquid chromatography-fluorescence detection method for the quantitation of flavanols and procyanidins in cocoa and chocolate containing samples. J. Chromatogr. A. 1216, 4831–4840 (2009)CrossRefGoogle Scholar
- 7.Falleh, H., Oueslati, S., Guyot, S., Ben, A., Magné, C., Abdelly, C., Ksouri, R.: LC / ESI-MS / MS characterisation of procyanidins and propelargonidins responsible for the strong antioxidant activity of the edible halophyte Mesembryanthemum edule L. Food Chem. 127, 1732–1738 (2011)CrossRefGoogle Scholar
- 12.(2011) Scientific Opinion on the substantiation of health claims related to polyphenols in olive and protection of LDL particles from oxidative damage (ID 1333, 1638, 1639, 1696, 2865), maintenance of normal blood HDL-cholesterol concentrations (ID 1639), mainte. EFSA J 9:2033. doi: https://doi.org/10.2903/j.efsa.2011.2033
- 14.Jourdes M, Zeng L, Pons-Marcadé P, Rivero Canosa M, Richard T, Teissèdre P-L (2016) A new procyanidin tetramer with unusual macrocyclic skeleton from grape and wine. 39’ World Vine Wine Congr. - Theme 2 Oenology, p. 432-433, 24-28 October, Bento Gonçalves, BrazilGoogle Scholar
- 15.Jouin A, Rossetti F, Teissèdre P-L, Jourdes M (2017) Evaluation of crown procyanidins contents in different variety and their accumulation kinetic during grape maturation. 10th Vino Anal. Sci. Symp. 17-20 July, p. 160, Salamanca, SpainGoogle Scholar