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…

Molecular cloning and characterization of UDP-glucose: furaneol glucosyltransferase gene from Japanese

2,5-Dimethyl-4-hydroxy-3(2H)-furanone (furaneol) is an important aroma compound in fruits, such as pineapple and strawberry, and is reported to contribute to the strawberry-like note in some wines. Several grapevine species are used in winemaking, and furaneol is one of the characteristic aroma compounds in wines made from American grape (Vitis labrusca) and its hybrid grape, similar to methyl anthranilate. Muscat Bailey A is a hybrid grape variety [V. labrusca (Bailey) x V. vinifera (Muscat Hamburg)], and its wine is one of the most popular in Japan. The inclusion of Muscat Bailey A in the ‘International List of Vine and Varieties and their Synonyms’ managed by the ‘International Organisation of Vine and Wine (OIV)’ in 2013 has further fueled its popularity among winemakers and researchers worldwide.

The commercial yeast strain as a significant source of variance for tyrosol and hydroxytyrosol in white wine

Tyrosol (TYR) and hydroxytyrosol (HYT) are bioactive phenols present in olive oil and wine, basic elements of the Mediterranean diet. TYR is reported in the literature for its interesting antioxidant, cardioprotective and anti-inflammatory properties. In wine, its concentration can reach values as high as about 40 mg/L
[Pour Nikfardjam et al. 2007] but, more frequently, this phenol – derived from yeast metabolism of tyrosine during fermentation – is present at lower levels, generally higher in red wines compared to whites. HYT was measured for the first time by Di Tommaso et al. [1998] in Italian wines – with maximum values of 4.20 mg/L and 1.92 mg/L for red and white wines, respectively – while definitely lower concentrations have been found later in Greek samples.

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.

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).

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].