Pyranoanthocyanin Derived Pigments in Wine: Structure and Formation during Winemaking

Abstract

In recent years many studies have been carried out on new pigments derived from anthocyanins that appear in wine during processing and aging. This paper aims to summarize the latest research on these compounds, focusing on the structure and the formation process. The main pyranoanthocyanins are formed from the reaction between the anthocyanins and some metabolites released during the yeast fermentation: carboxypyranoanthocyanins or type A vitisins, formed upon the reaction between the enol form of the pyruvic acid and the anthocyanins; type B vitisins, formed by the cycloaddition of an acetaldehyde molecule on an anthocyanin; methylpyranoanthocyanins, resulted from the reaction between acetone and anthocyanins; pinotins resulted from the covalent reaction between the hydroxycinnamic acids and anthocyanins; and finally flavanyl-pyranoanthocyanins. On the other hand, the second generation of compounds has also been reviewed, where the initial compound is a pyranoanthocyanin. This family includes oxovitisins, vinylpyranoanthocyanins, pyranoanthocyanins linked through a butadienylidene bridge, and pyranoanthocyanin dimers.

Finding Sensory Profilers Amongst Red Wine Composition: A Novel Nationwide Approach

“…In terms of color expression, isolated anthocyanins range from red with a purple tint at pH 1 to purple at pH 4 to blue at pH 7, but ethyl-linked anthocyaninflavanol compounds, when predominant, show greater color stability and leading orange tonalities. Another recent review confirms that late compounds are responsible for a gradual change of the red-purple color towards orange hues, because these adducts have a more reddish-orange color than their anthocyanin counterparts (Marquez et al, 2013). The results of the present study showed that it was possible to differentiate PGI red wines by their Color Tonality (Figure 2a, 2b, 2c and 2d) but analytical support has yet to be confirmed, despite some cited aligned literature.…”

“…The phenolic composition of wines is conditioned by the grape variety and by other factors that affect the berry development, such as soil, geographical location and weather conditions (Monagas et al, 2005). Phenolic compounds in red wines include both non-colored compounds (i.e., flavan-3-ols, flavonols, phenolic acids, stilbenes), potentially colored anthocyanins and anthocyanin derivatives (Boulton 2001;Alcalde-Eon et al, 2006;Dopico-García et al, 2008;Marquez et al, 2013). Flavanol oligomers and polymers are also called condensed tannins or proanthocyanidins.…”

Bioactive Compounds of Chamber-Dried Blueberries at Controlled Temperature and Wines Obtained from Them

“…This fact could be due to, on the one hand, the adsorption of anthocyanin by the cell membranes of yeast; as the time of contact with yeasts increases, a reduction of these compounds occurs in the juice [25]. Furthermore, condensation reactions occur between the monomeric anthocyanins and some yeast metabolites resulting in new compounds called pyranoanthocyanins [27] or condensation reactions with other phenolic compounds such as flavonols and flavans [28].…”

From vine to wine: photophysics of a pyranoflavylium analog of red wine pyranoanthocyanins

“…However, during the ageing of red wines, the anthocyanins are slowly degraded or transformed by condensation with yeast metabolites or copigments into a variety of more complex pigment molecules whose colors are much more pH-stable and, in addition, much less susceptible to bleaching by sulfite [8,[12][13][14][15][16]. Of particular Scheme 1: The pH-dependent anthocyanin multiequilibria [1][2][3], illustrated with malvidin 3-O-glucoside.…”

“…Unauthenticated Download Date | 6/7/19 6:45 AM importance for the color of mature wines are the pyranoanthocyanins, which differ from the anthocyanins by the presence of an additional pyran ring bridging between the 4-carbon and the 5-hydroxy group of the anthocyanin precursor [13][14][15], as shown in Scheme 2 for the transformation of malvidin 3-O-glucoside into a corresponding pyranoanthocyanin related to Vitisin B (R = H) found in mature red wine.…”