Macrowine 2021
IVES 9 IVES Conference Series 9 Flavanol glycosides in grapes and wines : the key missing molecular intermediates in condensed tannin biosynthesis ?

Flavanol glycosides in grapes and wines : the key missing molecular intermediates in condensed tannin biosynthesis ?

Abstract

Polyphenols are present in a wide variety of plants and foods such as tea, cacao and grape1. An important sub-class of these compounds is the flavanols present in grapes and wines as monomers (e.g (+)-catechin or (-)-epicatechin), or polymers also called condensed tannins or proanthocyanidins. They have important antioxidant properties2 but their biosynthesis remains partly unknown. Some recent studies have focused on the role of glycosylated intermediates that are involved in the transport of the monomers and may serve as precursors in the polymerization mechanism3, 4. The global objective of this work is to identify flavanol glycosides in grapes or wines, describe their structure and determine their abundance during grape development and in wine. Material and methods: Chardonnay and Syrah grapes and a Tannat red wine (Tannat, Languedoc, 2015) were used to make polyphenol extracts by using different preparative gel chromatography techniques (HW40S, LH20 and silica gels). The different fractions obtained were analyzed by UPLC-ESI-IT_MS (Waters Acquity, negative scan and targeted mode). Specific molecular ions corresponding to monomeric and dimeric flavanol glycosides were targeted with specific m/z values: 451 (epi) catechin glucoside, 467 epigallocatechin glucoside, 603 epicatechin gallate glucoside and 739 (epi) catechin glucoside dimer. Results: The existence of glycosylated flavan-3-ol monomers in wine and grape seeds have already been reported based on MS/MS experiments.5 Our results confirmed their presence in Tannat wines and grapes but new MS ions corresponding to glycosylated procyanidin dimers (m/z = 739) were also detected. MS/MS specific ions were also found for these dimers like an ion at m/z = 449 (quinone-methide cleavage (QM)) and at m/z = 587 Da (Retro Diels Alder reaction (RDA)). Further work is on the way to elucidate the exact structure of these compounds (hexose nature and position) by NMR. The complete structural elucidation of these glycosylated dimers will help to determine their exact role in proanthocyanidin biosynthesis.

1. Quideau, S., Deffieux, D., Douat-Casassus, C., and Pouysegu, L. (2011), Angew Chem Int Ed Engl 50, 586-621. 2. Antoniolli, A., Fontana, A. R., Piccoli, P., and Rubén, B. (2015), 178, 172–178. 3. Pang Y, C. X., Huhman DV, Ma J, Peel GJ, Yonekura-Sakakibara K, Saito K, Shen G, Sumner LW, Tang Y, Wen J, Yun J, Dixon RA. (2013)., Planta, 139-154. 4. Zhao, J., and Dixon, R. A. (2009), The Plant Cell 21, 2323-2340. 5. Delcambre, A., and Saucier, C. (2012), J Mass Spectrom 47, 727-736. 6. Gu, L., Kelm, M. A., Hammerstone, J. F., Beecher, G., Holden, J., Haytowitz, D., and Prior, R. L. (2003), J Agric Food Chem 51, 7513-7521.

Publication date: May 17, 2024

Issue: Macrowine 2016

Type: Poster

Authors

Cédric Saucier*, Chloé Puech, Emmanuelle Meudec, Jean-Paul Mazauric, Marie Zerbib, Mauve Abelanet, Nancy Terrier, Veronique Cheynier

*Université de Montpellier

Contact the author

Tags

IVES Conference Series | Macrowine | Macrowine 2016

Citation

Related articles…

Bentonite fining in cold wines: prediction tests, reduced efficiency and possibilities to avoid additional fining treatments

Bentonite fining is widely used to prevent protein haze in white wines. Most wineries use laboratory-scale fining trials to define the appropriate amount of bentonite to be used in the cellar. Those pre-tests need to mimic as much as possible the industrial scale fining procedure to determine the exact amount of bentonite necessary for protein stability. Nevertheless it is frequent that, after fining with the recommended amount of bentonite, wines appear still unstable and need an additional fining treatment. It remains a major challenge to understand why the same wine, fined with the same dosage of the same bentonite, achieves stability in the lab, but not in the cellar.

How pressing techniques affect must composition and wine quality of Pinot blanc

This study investigates how the sensory profile of Pinot Blanc is affected from different maceration and pressing techniques. Grapes were sourced from four vineyards in the village Tramin in South Tyrol. For the experiment 200 kg of grapes from each vineyard site were hand picked the day before harvest for the commercial winery took place. Grapes were stored over night at 4°C, homogenized and processed in the experimental winery at Laimburg research centre the day after harvest. Four different pressing techniques were applied in duplicates of 100kg each.

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.

Anti/prooxidant activity of wine polyphenols in reactions of adrenaline auto-oxidation

Adrenaline (epinephrine) belongs to catecholamine class. It is a neurotransmitter and both a hormone which is released by the sympathetic nervous system and adrenal medulla in response to a range of stresses in order to regulate blood pressure, cardiac stimulation, relaxation of smooth muscles and other physiological processes. Adrenaline exhibits an effective antioxidant capacity (1). However, adrenalin is capable to auto-oxidation and in this case it generates toxic reactive oxygen intermediates and adrenochrome. Under in vitro conditions, auto-oxidation of adrenaline occurs in an alkaline medium (2).

Microbial stabilization of wines using innovative coiled UV-C reactor process: impact on chemical and organoleptic proprieties

For several years, numerous studies aimed at limiting the use of SO2 in wines (thermal treatments, pulsed electric fields, microwaves …). Processes must be able to preserve the organoleptic qualities of wines with low energy consumption. In this context, ultraviolet radiations (UV-C), at 254 nm, are well known for their germicidal proprieties. In order to inactivate microorganisms in grape juice and wine without affecting the quality of the product, efficiency of UV-C treatment process should be optimized.