Macrowine 2021
IVES 9 IVES Conference Series 9 Influence of toasting oak wood on ellagitannin structures

Influence of toasting oak wood on ellagitannin structures

Abstract

Ellagitannins (ETs) have been reported to be the main phenolic compounds found in oak wood. These compounds, belonging to the hydrolysable tannin class of polyphenols, are esters of hexahydroxydiphenic acid (HHDP) and a polyol, usually glucose or quinic acid. They own their name to their capacity to be hydrolysed and liberate ellagic acid and they have an impact on astringency and bitterness sensation, which is strongly dependant on their structure. The toasting phase is particularly crucial in barrels fabrication and influences wood composition. Burning the inner oak wood barrels surface with an open fire inducing severe changes in ellagitannins structures and compositions. Up to now thermal ellagitannin products or the reaction mechanisms underlying the ellagitannin degradation are not well searched, thus the goal of the present study is to research oak wood ellagitannin changes during toasting. For this purpose a purification protocol was established, 100 mg ellagitannins crude extract was fractionated on Toyopearl TSK HW-40 (F) gel from Tosoh Corp, ellagitannins were eluted in the acetone/water fraction. This fraction was fractionated for two times on a C-18 column. The final fraction containing only the eight principal ellagitannins was dry-heated in a lab oven for 60 min at 220 °C. After cooling, it was further fractionated on C-18 column and separated by means of preparative HPLC before being injected in UPLC/TOF-MS. Reduction process is occuring during toasting whereas oxydation can occur without heating; Thus vescalagin, is reduced into deoxyvescalagin whereas castalagin oxidation form is presented before and after toasting. Additionally to deoxyvescalagin, other ellagitannin derivatives which showed [M-H]-ion peak at m/z 1055.0631, 1041.0792, 1011.0756 and 971.0456 were produced by the toasting and identified for the first time. LC-MS/MS analyses gave strong evidence that decarboxylations as well as ellagic acid loss are the key steps in ellagitanin thermal degradation.

Publication date: May 17, 2024

Issue: Macrowine 2016

Type: Poster

Authors

Kleopatra Chira*, Michael Jourdes, Pierre Louis Teissedre

*Institut des sciences de la vigne et du vin

Contact the author

Tags

IVES Conference Series | Macrowine | Macrowine 2016

Citation

Related articles…

Influence of methyl jasmonate foliar application to vineyard on grape volatile composition over three consecutive vintages

An alternative to improve grape quality is the application to the vineyard of elicitors. Although these compounds were first used to increase resistance of plants against pathogens, it has been found that they are also able to induce mechanisms involved in the synthesis of phenolic compounds and some amino acids. However, researches about the influence of elicitors on grape volatile composition are scarcely. Therefore, the aim of this work was to study the influence of methyl jasmonate (MeJ) foliar application on grape aroma composition over three consecutive vintages. MeJ was applied to Tempranillo grapevines at a concentration of 10 mM in 2013, 2014, and 2015 years. Control plants were sprayed with water.

Effect of the winemaking technology on the phenolic compounds, foam parameters in sparklig wines

Contribution Sparkling wines elaborated following the traditional method undergo a second fermentation in closed bottles of base wines, followed by aging of wines with lees for at least 9 months. Most of the sparkling wines elaborated are white and rosé ones, although the production of red ones is highly increasing. One of the initial problems in red sparkling wine processing is to obtain suitable base wines that should have moderate alcohol content and astringency and adequate color intensity; which is difficult to obtain when grapes must be harvested at low phenolic and industrial maturity stage. The low phenolic maturity degree in the red grapes makes essential to choose an adequate winemaking methodology to obtain the base wines because the extracted polyphenols will vary according the winemaking technique: carbonic maceration or destemmed-crushed grapes.

Light-struck taste in white wine: enological approach for its prevention

Light-struck taste is a defect prevalent in white wines bottled in clear glass light-exposed for a considerable amount of time leading to a loss of color and appearance of sulfur-like odors. The reaction involves riboflavin (RF), a highly photosensitive compound that undergoes to intermolecular photoreduction by the uptake of two electron equivalents from an external donor, the methionine. The reaction includes different steps forming methional which is extremely unstable and decomposes to methane thiol and acrolein. The reaction of two molecules of methane thiol yields dimethyl disulfide. Methane thiol is highly volatile, has a low perception threshold (2 to 10 µg/L in wine) and confers aroma-like rotten eggs or cabbage.

Reaction Mechanisms of Copper and Iron with Hydrogen Sulfide and Thiols in Model Wine

Fermentation derived sulfidic off-odors due to hydrogen sulfide (H2S) and low molecular weight thiols are commonly encountered in wine production and removed by Cu(II) fining. However, the mechanism underlying Cu(II) fining remains poorly understood, and generally results in increased Cu concentration that lead to deleterious reactions in finished wine. The present study describes a mechanistic investigation of the iron and copper mediated reaction of H2S, cysteine, 3-sulfanylhexan-1-ol, and 6-sulfanylhexan-1-ol with oxygen. The concentrations of H2S, thiols, oxygen, and acetaldehyde were monitored over time. It was found that Cu(II) was rapidly reduced by both H2S and thiols to Cu(I).

Influence of SO2 and Zinc on the formation of volatile aldehydes during alcoholic fermentation

Laboratório de Análisis del Aroma y Enologia (LAAE). Department of Analytical Chemistry, Faculty of Sciences, Universidad de Zaragoza, 50009, Zaragoza, Spain, During alcoholic fermentation, fusel (or Strecker) aldehydes are intermediates in the amino acid catabolism to form fusel alcohols following the Ehrlich Pathway (1). One of the main enzymes involved in this pathway is Alcohol Dehydrogenase (ADH), whose activity is highly strain dependent and determines the rate of conversion of aldehydes into fusel alcohols (2). This enzyme has a Zn2+ catalytic binding site, which suggests that the must Zn2+ levels will most likely influence the rate of reduction of aldehydes into alcohols. On the other hand, SO2 is commonly used in winemaking for its antiseptic and antioxidant properties.