Coupling reactions between flavylium ions and catechin

Teresa Escribano-Bailón; Olivier Dangles; Raymond Brouillard

doi:10.1016/0031-9422(95)00811-X

Coupling reactions between flavylium ions and catechin

Teresa Escribano-Bailón
, Olivier Dangles
, Raymond Brouillard^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

135 Scopus citations

Abstract

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.

Original language	English
Pages (from-to)	1583-1592
Number of pages	10
Journal	Phytochemistry
Volume	41
Issue number	6
DOIs	https://doi.org/10.1016/0031-9422(95)00811-X
State	Published - 1996
Externally published	Yes

Keywords

Acetaldehyde
Anthocyanins
Catechin
Copigmentation
Flavylium ions
Red wine pigments
Self-association
Tannins

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10.1016/0031-9422(95)00811-X

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title = "Coupling reactions between flavylium ions and catechin",

abstract = "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.",

keywords = "Acetaldehyde, Anthocyanins, Catechin, Copigmentation, Flavylium ions, Red wine pigments, Self-association, Tannins",

author = "Teresa Escribano-Bail{\'o}n and Olivier Dangles and Raymond Brouillard",

year = "1996",

doi = "10.1016/0031-9422(95)00811-X",

language = "English",

volume = "41",

pages = "1583--1592",

journal = "Phytochemistry",

issn = "0031-9422",

publisher = "Elsevier Ltd",

number = "6",

}

TY - JOUR

T1 - Coupling reactions between flavylium ions and catechin

AU - Escribano-Bailón, Teresa

AU - Dangles, Olivier

AU - Brouillard, Raymond

PY - 1996

Y1 - 1996

N2 - 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.

AB - 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.

KW - Acetaldehyde

KW - Anthocyanins

KW - Catechin

KW - Copigmentation

KW - Flavylium ions

KW - Red wine pigments

KW - Self-association

KW - Tannins

UR - https://www.scopus.com/pages/publications/0030064874

U2 - 10.1016/0031-9422(95)00811-X

DO - 10.1016/0031-9422(95)00811-X

M3 - Article

AN - SCOPUS:0030064874

SN - 0031-9422

VL - 41

SP - 1583

EP - 1592

JO - Phytochemistry

JF - Phytochemistry

IS - 6

ER -

Coupling reactions between flavylium ions and catechin

Abstract

Keywords

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