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…

Evaluating South African Chenin blanc wine styles using an LC-MS screening method

Sorting Chenin blanc is one of the most important white wine cultivars in South Africa. It has received a lot of attention and accolades in the past years and more research than ever is dedicated to this versatile cultivar. According to the Chenin blanc association of South Africa, there are three recognized dry wine styles, Fresh and Fruity (FF), Rich and Ripe Unwooded
(RRU), and Rich and Ripe Wooded (RRW). They are traditionally established with the aid of expert sensory evaluation, but the cost and the (subjective) human factor are aspects to be taken into account. A more objective and possibly robust way of assessing and attributing these styles can be the use of chemical analysis.

Phenolic profiles of minor red grape cultivars autochthonous from the Spanish region of La Mancha

The phenolic profiles of little known red grape cultivars, namely Garnacho, Moribel and Tinto Fragoso, which are autochthonous from the Spanish region of La Mancha (ca. 600,000 ha of vineyards) have been studied over the consecutive seasons of years 2013 and 2014. The study was separately performed over the skins, the pulp and the seeds, and comprised the following phenolic types: anthocyanins, flavonols, hydroxycinnamic acid derivatives (HCADs), total proanthocyanidins (PAs) and their structural features. The selected grape cultivars belong to the Vine Germplasm Bank created in this region in order to preserve the great diversity of genotypes grown in La Mancha.

The effect of Nitrogen and Sulphur foliar applications in hot climates

ine nitrogen deficiency can negatively influence the aroma profile and ageing potential of white wines. Canopy management can alter vine microclimate, affect the nitrogen availability and influence the response of leaf senescence. Increasing the nitrogen availability to vines can increase the Yeast Assimilable Nitrogen (YAN) levels in harvested fruit and wine. Studies show that foliar nitrogen and sulphur applications at véraison, on low YAN Sauvignon blanc grapes have an effect on the level of amino acids (Jreij et al. 2009) and on S-containing compounds such as glutathione and thiols (Lacroux et al. 2008), which in turn can influence the formation of major volatiles and the aroma profile of the wine.

Efficiency of alternative chemical and physical treatments in reducing Brettanomyces Bruxellensis from oak wood

Oak barrels form an integral part of wine production, especially that of high quality wines. However, due to its porosity, wood presents an ecological niche for microbial proliferation and is highly susceptible to microbial spoilage which could cause considerable economic losses. Brettanomyces bruxellensis, the most commonly encountered microorganism responsible for spoilage during barrel ageing, can remain in barrels after barrel sanitation to contaminate new batches of wine after refilling. Therefore, effective sanitation treatments are of utmost importance to prevent recurring wine spoilage.

Proteomic and activity characterization of exocellular laccases from three Botrytis cinerea strains

Botrytis cinerea is a fungus that causes common infection in grapes and other fruits. In winemaking, its presence can be both considered desirable in the case of noble rot infection or undesirable when grey rot is developed. This fungus produces an extracellular enzyme known as laccase which is able to cause oxidation of phenolic compounds present in must and wine, causing most of the times a decrease in its quality and problems during the winemaking process [1]. Material and methods: Three B. cinerea strains (B0510, VA612 and RM344) were selected and grown in a liquid medium adapted from one previously described [2]. The enzyme was isolated by tangential ultrafiltration of the culture medium using a QuixStand system equipped with a 30 KDa filtration membrane.