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oai:gredos.usal.es:10366/1394362026-01-14T10:55:04Zcom_10366_4182com_10366_4055com_10366_3946com_10366_3823col_10366_4183

Escribano Bailón, María Teresa Dangles, Olivier Brouillard, Raymond Flavylium ions Biochemistry Anthocyanins Tannins Catechin Acetaldehyde Copigmentation Self-association Red wine pigments [EN] In order to model natural polymeric pigments present in old red wines, new covalent adducts have been synthesized upon condensation of synthetic flavylium ions (models of anthocyanins) with catechin (model of tannins) in the presence and in the absence of acetaldehyde. These new pigments have been investigated by 1D and 2D NMR, HPLC, FAB-mass and UV-visible spectroscopies and molecular modelling. The two flavylium salts used in this work (3,4'-dimethoxy-7-hydroxyflavylium chloride and 5,7-dihydroxy-3,4'-dimethoxyflavylium chloride) display quite different reactivities toward catechin. The electronic donating effect of the catechin moiety and the formation of noncovalent dimers in acidic aqueous or methanolic solution should be mainly responsible for the improved stability of the flavylium chromophore in the new pigments. 2019-04-03 2019-04-03 1996 info:eu-repo/semantics/article Escribano-Bailón, T., Dangles, O., Brouillard, R. (1996). Coupling reactions between flavylium ions and catechin. Phytochemistry, 41 (6), pp. 1583-1592 Teresa Escribano-Bailón, Olivier Dangles, Raymond Brouillard, Coupling reactions between flavylium ions and catechin, Phytochemistry, Volume 41, Issue 6, 1996, Pages 1583-1592, ISSN 0031-9422, https://doi.org/10.1016/0031-9422(95)00811-X. (https://www.sciencedirect.com/science/article/pii/003194229500811X) 0031-9422 http://hdl.handle.net/10366/139436 10.1016/0031-9422(95)00811-X eng https://doi.org/10.1016/0031-9422(95)00811-X https://creativecommons.org/licenses/by-nc-nd/3.0/ info:eu-repo/semantics/openAccess Attribution-NonCommercial-NoDerivs 3.0 Unported