Macrowine 2021
IVES 9 IVES Conference Series 9 Characterization of various groups of pyranoanthocyanins in Merlot red wine

Characterization of various groups of pyranoanthocyanins in Merlot red wine

Abstract

In red wines, anthocyanins evolve during the wine-making process and ageing. They react with other compounds (such as vinylphenols, acetaldehyde, pyruvic acid…) to form a stable family of compounds called pyranoanthocyanins. Furthermore, the oxidation process can modify the anthocyanic profile of a red wine. It is also interesting to evaluate the occurrence of the different subclasses of pyranoanthocyanins and to characterize their chemical properties. The first objective of this study is to evaluate the occurrence of the different groups of pyranoanthocyanins in an oxidised Merlot wine by a centrifugal partition chromatography strategy. The second goal is to evaluate their relative impact in red wines from Bordeaux region by measuring their concentrations. Centrifugal partition chromatography (CPC), as the key purification technique, is commonly used in phytochemistry to separate natural substances. Based on the partition of compounds in a non-miscible liquid-liquid system, it provides many advantages. On one hand, the fractionation is applied on a significant quantity of product, in a short period of time, and thus leads to high purification yield. On the other hand, the selectivity of the solvent system provides efficiency for separating molecules from each other. The red wine used in this study was an oxidized sample from Merlot. It was also fractionated with a gradient elution solvent system. Each obtained fraction from CPC was submitted to HPLC-ESI in order to group the same UV and visible profiles. The pigments were also distributed in 8 blocks and the wash fraction, which were finally analysed with a UHPLC-ESI/Q-ToF strategy. Attention was first focused on blocks 1 and 2. The study of their anthocyanic profile by UHPLC-ESI/Q-ToF revealed the occurrence of various adducts depending on the polarity. Some pyranomalvidin-3-O-coumaroylglucoside adducts, and pyranomalvidin3-O-glucoside with a procyanidin dimer were detected in block 1, and pyranomalvidin-3-O-glucoside-4-vinyl(epi)catechin or acetylglucoside-4-vinyl(epi)catechin were found in block 2. HPLC at the preparative scale allowed separating and collecting each pigment in order to determine and validate their molecular structure by nuclear magnetic resonance (NMR). With the aim to complete this study, further investigation will determine the chemical properties of these molecules. Finally, a first evaluation of their concentrations in a few red wines from Bordeaux region
(oxidized or not) will determine a kinetic pattern of the pigments and their relative importance as markers of wine ageing. Furthermore, CPC which is used in this study is an appropriate anthocyanin fractionation and purification technique at the preparative scale towards the complexity of the red wine sample.

Publication date: May 17, 2024

Issue: Macrowine 2016

Type: Poster

Authors

Pierre-Louis Teissedre*, Cindy Quaglieri, Michael Jourdes, Pierre Waffo-Téguo, Tristan Richard

*ISVV- Université de Bordeaux

Contact the author

Tags

IVES Conference Series | Macrowine | Macrowine 2016

Citation

Related articles…

Attractiveness and sweetness of red wines: Synergies between American oak barrels and mannoproteins

In partnership with a Bordeaux property wanting to improve the quality of its second wine, the effects of two factors, American oak barrels and mannoproteins were studied. Their impact on the attractiveness and sweetness of wines were characterized during two successive vintages (2012 and 2013). Vinification took place with a homogeneous batch of Cabernet Sauvignon. The wine was then divided up into various groups of five barrels of French and American oak, new or reused. Analyses of volatile and non-volatile wood compounds were undertaken at four months and eight months of wood ageing, by LC-MS and GC-MS.

Cytochrome P450 CYP71BE5 from grapevine (Vitis vinifera) catalyzes the formation of the spicy aroma compound, (-)-rotundone

(-)-Rotundone, an oxygenated sesquiterpene, is a potent odorant molecule with a characteristic spicy aroma existing in various plants including grapes1. It is considered as a significant compound notably in wines and grapes because of its low sensory threshold (16 ng L-1 in red wine, 8 ng L-1 in water) and aroma properties. (-)-Rotundone was first identified in red wine made from the grape cultivar Syrah (regionally called Shiraz) in Australia1, and then it was found in several grape varieties such as Duras, Grüner Veltliner, Schioppettino and Vespolina from Europe2, 3. Several environmental factors affecting the accumulation of (-)-Rotundone during the grape maturation, were reported such as ambient temperature4, soil properties and topography5, soil moisture from irrigation and light exposure in the bunch zone by leaf removal2.

Effect of intra‐vineyard ripeness variation on the efficiency of commercial enzymes on berry cell wall deconstruction under winemaking conditions

Intra-vineyard variation grape berry ripening occurs within bunches, between bunches on the same vine and between vines. Although it is assumed that such variation also occurs at the grape berry cell wall level, no study to data has investigated in any depth. Here we have used a intra-vineyard panel design to investigate pooled bunches from six vines (per panel) in the context of a winemaking scenario. The dissected vineyard was harvested by separate panels, where each panel was then subjected to a standard winemaking procedure with or without the addition of three different enzyme preparations for maceration.

Metabolomics of grape polyphenols as a consequence of post-harvest drying: on-plant dehydration vs warehouse withering

A method of suspect screening analysis to study grape metabolomics, was developed [1]. By performing ultra-high performance liquid chromatography (UHPLC) – high-resolution mass spectrometry (HRMS) analysis of the grape extract, averaging 320-450 putative grape compounds are identified which include mainly polyphenols. Identification of metabolites is performed by a new HRMS-database of putative grape and wine compounds expressly constructed (GrapeMetabolomics) which currently includes around 1,100 entries.

Glutathione content evolution during spontaneous alcoholic fermentations of Sangiovese grapes

Glutathione is a tripeptide (γ-Glu-Cys-Gly), which can occur in grapes, in must and in wine prevalently in the reduced form as well as in the oxidized form as glutathione disulfide. The importance of the reduced form of glutathione lies in its antioxidant activity. In must, it limits browning by reducing o-quinones produced by polyphenol oxidase activity on hydroxycinnamic acids; in wine, it exerts a protective effect on various aromatic compounds. Glutathione concentration in wine is lower than in grape juice and variable as it depends on several factors, ranging from the native content of grapes to winemaking technique.