Copigmentation of malvidin-3-O-glucoside with five hydroxybenzoic acids in red wine model solutions: Experimental and theoretical investigations

Copigmentation between malvidin-3- O -glucoside and hydroxycinnamic acids in red wine model solutions: Investigations with experimental and theoretical methods

“…The presence of different substituent groups in the aromatic rings would modify the copigmentation potential. The better copigmentation effect of CA compared to pCA was probably due to the existence of an extra hydroxyl residue at the same aromatic skeleton, which could strengthen the combination between the copigment and pigment through more noncovalent interactions (Boulton, 2001;Malaj et al, 2013;Sun et al, 2010;Zhang et al, 2015). The presence of an additional methoxyl group in hydroxycinnamic acid seems to be more efficient than the presence of a hydroxyl counterpart, like in FA (monomethoxylated hydroxycinnamic acid), which results in a higher contribution to color enhancement than that in CA and pCA (nonmethoxylated ones).…”

“…The formation of intermolecular RCPs and CCPs is indicative of the close contact and π-π interaction, respectively. These two types of interactions are usually classified as van der Waals interactions (Zhang et al, 2015). Therefore, as shown in Table 3, the intermolecular interactions involved in the three copigmentation complexes can be identified.…”

“…But as an exception, (−)-epicatechin had a quasi-planar structure which could reduce the steric hindrance and showed a better effect than its isomer-counterpart, (+)-catechin (Terrier et al, 2009). Hydroxycinnamic acids (Sun, Cao, Bai, Liao, & Hu, 2010), hydroxybenzoic acids (Zhang, Liu, He, Zhou, & Duan, 2015), and hydrolysable tannins (Tuominen, Sinkkonen, Karonen, & Salminen, 2015) were also recognized as important copigments that could enhance and stabilize red wine colors.…”

“…Previous researches also reported that the infrared (IR) vibrational spectra were used to reveal the existence of hydrogen bonds in the copigmentation complex (Dimitric Markovic, Baranac, & Brdaric, 2005). Additionally, the quantum mechanics calculation was employed to study the copigmentation (Di Meo, Sancho Garcia, Dangles, & Trouillas, 2012;Nave et al, 2012), which disclosed the copigmentation mechanism from the micro perspective, including the intermolecular bonding type (Zhang et al, 2015), electron and charge transfer (Ferreira da Silva et al, 2005), copigmentation complex conformation (Sousa et al, 2014), thermodynamic parameters (Teixeira et al, 2013), and others (Kalisz, Oszmiański, Hładyszowski, & Mitek, 2013).…”

The Influence of Prefermentative Addition of Gallic Acid on the Phenolic Composition and Chromatic Characteristics of Cabernet Sauvignon Wines

“…However, other phenolic compounds can also extremely affect the color intensity and stability of red wines during fermentation and aging. Some of these phenolic compounds are called cofactors, known as flavonols, flavan‐3‐ols, hydroxybenzoic acids, and hydroxycinnamic acids in wines, which can interact with anthocyanins in the copigmentation process mainly by the driving forces of hydrogen bonds and van der Waals interaction, enhancing red wine color intensity and stability (Brouillard and others ; Pérez‐Magariño and González‐Manzano ; Zhang and others ). Therefore, phenolic compounds can be considered important factors in improving the color quality of red wines, besides anthocyanins.…”