Macrowine 2021
IVES 9 IVES Conference Series 9 Red wine substituted esters involved in fruity aromatic expression: an enantiomeric approach to understand their sensory impact and their pathway formation

Red wine substituted esters involved in fruity aromatic expression: an enantiomeric approach to understand their sensory impact and their pathway formation

Abstract

Among red wines ethyl esters, those from short hydroxylated and branched-chain aliphatic acids constitute a family with a particular behavior and sensory importance. They have been previously discussed in the literature [1] and recent studies have established that some of them were strongly involved in of red wines’ fruity aroma [2]. As some among them have an asymmetrical carbon atom, it seemed important to separate their different enantiomers to obtain an accurate assessment of their organoleptic impact. Three chiral esters have been identified, presenting alkyl and/or hydroxyle substituants: ethyl 2-hydroxy-4-methylpentanoate, ethyl 2-methylbutanoate, and ethyl 3-hydroxybutanoate. They were present in wines with a single or both enantiomeric forms in various ratios, according to age. On the contrary of most of the ethyl esters, produced during alcoholic fermentation, these esters levels increased gradually over time and then stabilize after about four to five years. For those present under two enantiomeric forms, ratios were modified during ageing. For each ester of this type, the most powerful enantiomer, from an olfactive point of view, was found in relatively small amount at the end of alcoholic fermentation and was then particularly accumulated. The sensorial role of these chiral compounds has been established, revealing their role as natural enhancers of black-berry, red-berry and fresh-fruit aromas. Our data corroborate and specify those of Lytra et al. [2] and Pineau et al. [3] highlighting the impact of substituted esters in fruity expression of red wines. Considering their dynamic evolution of their concentration, these compounds seem to be produced on one hand during alcoholic fermentation by Saccharomyces cerevisiae from amino acids and on the other hand during aging by a chemical esterification from the corresponding substituted acids as previously suggested by Diaz-Maroto et al. [4]. In order to determine the precursors of these esters and to consider synthesis pathways, we have developed a method aimed at quantifying their corresponding substituted acids (2-hydroxy-4-methylpentanoic acid, 2-methylbutanoic acid, and 3-hydroxybutanoic acid) including, if applicable, the enantiomeric forms. Thanks to the quantification of these compounds, the chemical formation of substituted esters during aging as well as the mechanisms of formation of these compounds during alcoholic and malolactic fermentation was described.

References: 1. Guth, H. (1997) J. Agric. Food Chem.45:3027-3032. 2. Lytra, G., Tempere, S., Le Floch, A., de Revel, G., and Barbe, J.-C. (2013) J. Agric. Food Chem. 61:8504-8513. 3. Pineau, B., Barbe, J.-C., Van Leeuwen, C., Dubourdieu, D. (2009) J. Agric. Food Chem. 57:3702-3708. 4. Diaz-Maroto, M.C., Schneider, R., Baumes, R. (2005) J. Agric. Food Chem. 53: 3503-3509.

Publication date: May 17, 2024

Issue: Macrowine 2016

Type: Article

Authors

Georgia Lytra*, Jean-Christophe Barbe, Margaux Cameleyre, Sophie Tempère

*Université de Bordeaux

Contact the author

Tags

IVES Conference Series | Macrowine | Macrowine 2016

Citation

Related articles…

Update knowledge about the presence of condensed tannins in grapes and their contributions to astringency perception

Condensed tannin is a principle group of polyphenol compounds derived from grape, greatly contributing to the bioactivity and the sensory perception of wine. Condensed tannins present as a heterogeneous mixture in nature involving various degrees of both polymerization and galloylation. Even though multiple attempts focusing on fractionation of grape condensed tannins by solid-phase have been conducted over the past decades, few individual tannins have been purified and identified. Hence, our knowledge on grape and wine condensed tannin moleculars has to be limited at the several known monomeric, dimeric and trimeric proanthocyanidins

Fractionation of copper and iron in wine: Assessment of potential macromolecule and sulfur binding agents

Copper and iron are known to substantially impact wine stability through oxidative, reductive or colloidal phenomena. However, the binding of metal ions to different wine components under wine conditions, and the impact of this binding on the ability of the metal ions to induce spoilage processes, is not well understood. This study surveyed a range of red and white wines for an understanding of the variability of broad metal categories within the wines. The techniques utilized included an electrochemical constant current stripping potentiometry technique (ccSP), and solid phase extraction (SPE) fractionation of wine with subsequent analysis of the metal content of each fraction by inductively coupled plasma – optical emission spectroscopy (ICP-OES).

The role of tomato juice serum in malolactic fermentation in wine

Introduction: Malolactic fermentation (MLF) is a common process in winemaking to reduce wine acidity, maintain microbial stability and modify wine aroma. However, successful MLF is often hampered by their sluggish or stuck activity of malolactic bacteria (MLB) which may be caused by nutrient deficiency, especially when MLB are inoculated after alcoholic fermentation (Alexandre et al., 2004; Lerm et al., 2010). Identification and characterization of essential nutrients and growth factors for MLB allows for production of highly efficient nutrient supplements for MLF.

Modulating role of SO2 in white wine protein haze formation

Despite the extensive research performed during the last decades, the multifactorial mechanism responsible for the white wine protein haze formation is not fully characterized. Herein, a new model is proposed, which is based on the experimental identification of sulfur dioxide as a major modulating factor inducing wine protein haze upon heating. As opposed to other reducing agents, such as 2-mercaptoethanol, dithiothreitol and tris(2-carboxyethyl)phosphine hydrochloride (TCEP), the addition of SO2 to must/wine upon heating cleaves intraprotein disulfide bonds, hinders thiol-disulfide exchange during protein interactions and can lead to the formation of novel inter/intraprotein disulfide bonds. Those are eventually responsible for wine protein aggregation which follows a nucleation-growth kinetic model as shown by dynamic light scattering [1].

Defining the mechanisms and impact of winemaking treatments on tannin and polysaccharides in red wine: recent progress in creating diverse styles

Tannin and polysaccharide concentration and composition is important in defining the texture of red wines, but can vary due to factors such as cultivar, region, grape ripeness, viticultural practices and winemaking techniques. However, the concentration and composition of these macromolecules is dependent not only on grape tannin and polysaccharide concentration and composition, but also their extractability and, in the case of polysaccharides, their formation by yeast. Through studies into the influence of grape maturity, winemaking and sensory impacts of red grape polysaccharides, seed and skin tannins, recent research in our laboratory has shown that the processes involved in the extraction of these macromolecules from grapes and their retention in wine are very complex.