Coupling reactions between flavylium ions and catechin

Escribano-Bailón, Teresa; Dangles, Olivier; Brouillard, Raymond

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

Cited by 117 publications

(74 citation statements)

References 30 publications

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“…These observations are in agreement with the high pK h values estimated for pigments I and II from investigations on equilibrated solutions. This resistance to hydration may reflect self-association, as suggested earlier by Escribano-Bailon et al (18) for a pigment formed by coupling catechin and a synthetic flavylium ion by a methylmethine linkage. To a lesser degree, selfassociation of Mv3glc could also explain the above-mentioned discrepancies between our results and literature data since a higher pigment concentration was used in our experiments.…”

Section: Resultsmentioning

confidence: 83%

UV−Visible Spectroscopic Investigation of the 8,8-Methylmethine Catechin-malvidin 3-Glucoside Pigments in Aqueous Solution: Structural Transformations and Molecular Complexation with Chlorogenic Acid

Dueñas

Salas

Cheynier

et al. 2005

J. Agric. Food Chem.

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The physicochemical properties of 8,8-methylmethine catechin-malvidin 3-O-glucoside isomers, commonly referred to as catechin-ethyl-malvidin 3-O-glucoside, have been studied in aqueous solutions and compared with those of the parent anthocyanin (malvidin 3-O-glucoside). The hydration and acidity constants (pKh and pKa) of the catechin-ethyl-malvidin 3-O-glucoside pigments and malvidin 3-O-glucoside were determined by UV-visible spectroscopic measurements. The ethyl-linked catechin-malvidin 3-O-glucoside pigments present higher stability toward hydration than the parent anthocyanin. The high resistance of these ethyl-linked pigments toward the hydration is related to the self-association that offers optimal protection from the nucleophilic attack of water. Moreover, the ethyl link may confer to the molecule enough flexibility to undergo intramolecular interaction, further protecting it from hydration and bisulfite discoloration. In the wine pH range (3.2-4.0), due to the low pKa and high pKh values, the ethyl-linked pigments are present as colored forms (flavylium cation and quinonoid bases).

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Section: Resultsmentioning

confidence: 83%

UV−Visible Spectroscopic Investigation of the 8,8-Methylmethine Catechin-malvidin 3-Glucoside Pigments in Aqueous Solution: Structural Transformations and Molecular Complexation with Chlorogenic Acid

Dueñas

Salas

Cheynier

et al. 2005

J. Agric. Food Chem.

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“…The increase of H* value indicated that the yellow hue of the wine was enhanced and the contribution of other pigments which were different from anthocyanins. This might be due to the formation of polymeric pigments resulting from the reaction between the anthocyanin and the flavanol as references (Sommers 1971; Escribano‐Bailón 1996; Pissarra and others 2003). So in the GSKT2‐treated wines the copigmentation and polymer pigment probably happened simultaneously.…”

Section: Resultsmentioning

confidence: 99%

Effect of the Prefermentative Addition of Five Enological Tannins on Anthocyanins and Color in Red Wines

Liu¹,

Liang²,

Wang³

et al. 2013

Journal of Food Science

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The prefermentative application of condensed tannins overall could protect some pigment components from degradation and enhance wine redness. Tannin additives with different origins have different effectiveness. The tannin additive obtained from grape skins, like GSKT2, could produce significant promotion on both redness and yellowness in wine. The prefermentation addition of hydroxylase tannin like FOLT seems not to have a significant effect on wine color.

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“…This is why the "French paradox" has led to a revival of research related to "wine ageing", which is no longer only the process which results in a more delightful wine, but much more the process which may produce the new flavonoids beneficial to human health. Over the past four years several new flavonoid structures, characteristic of red wine have been elucidated [11,12], and it is the aim of this review to give some details on their forming reactions. This field of research is now in full expansion.…”

Section: Introductionmentioning

confidence: 99%

Polyphenols produced during red wine ageing

1997

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Over the past few years, it has been accepted that a moderate red wine consumption is a factor beneficial to human health. Indeed, people of France and Italy, the two major wine-producing European countries, eat a lot of fatty foods but suffer less from fatal heart strokes than people in North-America or in the northern regions of Europe, where wine is not consumed on a regular basis. For a time, ethanol was thought to be the "good" chemical species hiding behind what is known as the "French paradox". Researchers now have turned their investigations towards a family of natural substances called "polyphenols", which are only found in plants and are abundant in grapes. It is well known that these molecules behave as radical scavengers and antioxidants, and it has been demonstrated that they can protect cholesterol in the LDL species from oxidation, a process thought to be at the origin of many fatal heart attacks. However, taken one by one, it remains difficult to demonstrate which are the best polyphenols as far as their antioxidant activities are concerned. The main obstacle in that kind of research is not the design of the chemical and biological tests themselves, but surprisingly enough, the limited access to chemically pure and structurally elucidated polyphenolic compounds. In this article, particular attention will be paid to polyphenols of red wine made from Vitis vinifera cultivars. With respect to the "French paradox", we address the following question: are wine polyphenolic compounds identical to those found in grapes (skin, pulp and seed), or are there biochemical modifications specifically taking place on the native flavonoids when a wine ages? Indeed, structural changes occur during wine conservation, and one of the most studied of those changes concerns red wine colour evolution, called "wine ageing". As a wine ages, it has been demonstrated that the initially present grape pigments slowly turn into new more stable red pigments. That phenomenon goes on for weeks, months and years. Since grape and wine polyphenols are chemically distinct, their antioxidant activities cannot be the same. So, eating grapes might well lead to beneficial effects on human health, due to the variety and sometimes large amounts of their polyphenolic content. However, epidemiological surveys have focused on wines, not on grapes....

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Coupling reactions between flavylium ions and catechin

Cited by 117 publications

References 30 publications

UV−Visible Spectroscopic Investigation of the 8,8-Methylmethine Catechin-malvidin 3-Glucoside Pigments in Aqueous Solution: Structural Transformations and Molecular Complexation with Chlorogenic Acid

UV−Visible Spectroscopic Investigation of the 8,8-Methylmethine Catechin-malvidin 3-Glucoside Pigments in Aqueous Solution: Structural Transformations and Molecular Complexation with Chlorogenic Acid

Effect of the Prefermentative Addition of Five Enological Tannins on Anthocyanins and Color in Red Wines

Polyphenols produced during red wine ageing

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