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…

Oligosaccharides in red wines: could their structure and composition be influenced by the grape-growing

Oligosaccharides have only recently been characterized in wine, and the information on composition and content is still limited. In wine, these molecules are mainly natural byproducts of the degradation of grape berry cell wall polysaccharides. Wine oligosaccharides present several physicochemical properties, being one relevant factor linked to the astringency perception of wines (1,2). A terroir can be defined as a grouping of homogeneous environmental units based on the typicality of the products obtained. This notion is particularly associated with wine, being the climate and the soil two of the major elements of terroir concept.

Improving the phenolic composition of cv tempranillo wines by blending grapes of different ripening state

The aim of this work was to reduce the alcohol content of Tempranillo wine. Tempranillo wines were produced by grapes harvested at different ripening dates (August 11 which was 21 oBrix and September 28 with 25 oBrix). At the second date, the Tempranillo wines were elaborated as follows: grapes were destemmed, crushed and collected into 50 L stainless-steel vats. Before preferementative maceration in cold, 50 % (M1) and 70 % (M2) of the must have been replaced by the same percentage of must from the first harvest. In addition, a control wine (C) was performed with only grapes from the second harvest.

Cover crops influence on soil N availability and grapevine N status, and its relationship with biogenic

The type of soil management, tillage versus cover crops, can modify the soil microbial activity, which causes the mineralization of organic N to NO3–N and, therefore, may change the soil NO3–N availability in vineyard. The soil NO3–N availability could influence the grapevine nutritional status and the grape amino acid composition. Amino acids are precursors of biogenic amines, compounds mainly formed during the malolactic fermentation. Biogenic amines have negative effects on consumer health and on the wine organoleptic quality. The objective was to study if the effect of conventional tillage and two different cover crops (leguminous versus gramineous) on grapevine N status, could relate to the wine biogenic amines composition.

Reduction of herbaceous aromas by wine lactic acid bacteria mediated degradation of volatile aldehydes

Consumers typically prefer wines with floral and fruity aromas over those presenting green-pepper, vegetal or herbaceous notes. Pyrazines have been identified as causatives for herbaceous notes in wines, especially Bordeaux reds. However, pyrazines are not universally responsible for herbaceousness, and several other wine volatile compounds are known to produce distinct vegetal/herbaceous aromas in wines. Specifically, volatile aldehydes elicit sensations of herbaceousness or grassiness and have been described in wines well above their perception thresholds.

Identification of green, aggressive and hard character of wines by a chemo-sensory directed methodology

With climate change, it is progressively more often to obtain grapes with an acceptable content in sugars or acids but with immature tannins described as green, aggressive or hard (noted as GAH onwards). During winemaking, the oenologist has to make decisions related to the elaboration of such grapes based mainly on empirical experience, given the lack of objective criteria to this concern. An increase in the chemical and sensory knowledge of immature tannins would allow managing this GAH character of grapes with the maximum possible efficiency during winemaking processes. The present work aims at isolating and identifying the group of compounds responsible for the GAH character present in wines.