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…

A multivariate approach using attenuated total reflectance mid-infrared spectroscopy to measure the surface mannoproteins and β-glucans of yeast cell walls during wine fermentations

Yeast cells possess a cell wall comprising primarily glycoproteins, mannans, and glucan polymers. Several yeast phenotypes relevant for fermentation, wine processing, and wine quality are correlated with cell wall properties. To investigate the effect of wine fermentation on cell wall composition, a study was performed using mid-infrared (MIR) spectroscopy coupled with multivariate methods (i.e., PCA and OPLS-DA). A total of 40 yeast strains were evaluated, including Saccharomyces strains (laboratory and industrial) and non-Saccharomyces species. Cells were fermented in both synthetic MS300 and Chardonnay grape must to stationery phase, processed, and scanned in the MIR spectrum.

Contribution of Piperitone to the mint nuances perceived in the aging bouquet of red Bordeaux wines

During the tasting of a fine, old wine, the aromas generated in the glass are intertwined in an intimate, complex manner, expressing the fragrance of the aging bouquet. This aging bouquet, which develops during bottle storage through a complex transformation process, may result in a broad palette of nuances. Among these, undergrowth, truffle, toasted, spicy, licorice, fresh red- and black-berry fruit and mint descriptors were recently identified as features of its olfactory representation for red Bordeaux wines. Although a targeted chemical approach focusing on volatile sulfur compounds revealed the role played by dimethyl sulfide, 2-furanmethanethiol, and 3-sulfanylhexanol as molecular markers of the typicality of the wine aging bouquet of red Bordeaux wines, its chemical transcription has only partially been elucidated.

Microbial life in the grapevine: what can we expect from the leaf microbiome?

The above-ground parts of plants, which constitute the phyllosphere, have long been considered devoid of bacteria and fungi, at least in their internal tissues and microbial presence there was long considered a sign of disease. However, recent studies have shown that plants harbour complex bacterial communities, the so-called “microbiome”[1]. We are only beginning to unravel the origin of these bacterial plant inhabitants, their community structure and their roles, which in analogy to the gut microbiome, are likely to be of essential nature. Among their multifaceted metabolic possibilities, bacteria have been recently demonstrated to emit a wide range of volatile organic compounds (VOCs), which can greatly impact the growth and development of both the plant and its disease-causing agents.

Correlations between sensory characteristics and colloidal content in dry white wines

Must clarification is an important step occurring just after grape extraction in the elaboration of white wine, consisting in a solid-liquid separation. Traditionally, low must turbidity, around 50-150 NTU, is generally reached in white winemaking in order to prevent reductive aromas and facilitating alcoholic fermentation. Alternatively, a higher turbidity (300 NTU or above) can be sought for reasons such as a better expression of grapes identity (terroir), or for getting a must matrix that could supposedly lead to wines having greater ageing potential.

Fingerprinting the origin of rosé wines with a new high throughput polyphenomics method

Wine is a widely consumed alcoholic beverage with a high commercial value. More specifically, the worldwide consumption of rosé wine has increased by 20% since 2002[1]. But because of its high commercial value, it can become a subject of fraud, and authenticity control is necessarily required. More than one hundred polyphenols have been recently quantified in various rosé wines [2]. They are key components defining color, taste and quality of wines. Their amount and composition depend on many different factors such as grape variety, winemaking and age of the wine. In this study, the influence of geographic origin of some rosé French wines was investigated. An original and very fast UPLC-QTOF-MS method was developed and used to predict the geographic origin authenticity of rosé wines.