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…

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.

Characterization of Glycosidically Bound Aroma Compounds of País cv. grapes of different Chilean zones

País grape has been estimated to arrive to Chile almost 500 years ago, being the first strain grown in this country. Traditionally, this grape has been used to mix with other varieties, to produce poor quality wines, but today is beginning to be used in the production of high quality wines. However, very little is known about the chemical characteristics of this variety. The aroma is one of the most important quality attributes of wine. Volatile compounds of this beverage may come from the grape (varietal aromas), from the fermentation process, from the ageing. The aromatic compounds are found in the grape in two forms: as free volatile compounds and as non-volatile compounds. The last ones, are aroma precursors present mainly as glycoconjugates formed by a sugar and an aglycone…

Partial dealcoholisation of red wine by reverse osmosis-evaporative perstraction: impact on wine composition

Around the world, the alcohol content of wine has been steadily increasing; partly as a consequence of climate change, but also due to improvements in viticultural management practices and winemaking techniques [1,2]. Concurrently, market demand for wines with lower alcohol levels has increased as consumers seek to reduce alcohol intake for social and/or health reasons [3]. As such, there is increasing demand for both innovative methods that allow winemakers to produce ‘reduced alcohol wines’ (RAW) and a better understanding of the impact of such methods on the composition of RAW. This study therefore aimed to investigate compositional changes in two red wines resulting from partial alcohol removal following treatment by one such method, involving a combination of reverse osmosis and evaporative perstraction (RO-EP).

Characterization of commercial enological tannins and its effect on human saliva diffusion

Commercial oenological tannins (TECs) are widely used in the wine industry. TECs are rich in condensed tannins, hydrolyzable tannins or a mixture of both. Wine grapes are a important source of proanthocyanidins or condensed tannins while oak wood possess a high concentration of hydrolyzable tannins (Obreque-Slier et al., 2009). TECs contribute with the antioxidant capacity of wine, catalyze oxide-reduction reactions and participate in the removal of sulfur compounds and metals.

Comparison of fortified, sfursat and passito winemaking techniques for the enhancement of the oenological potential of the black grape cultivar Moscato nero d’Acqui (Vitis vinifera L.)

One of the key factors of the economical development of viticulture and wine industry in specific limited areas is the exploitation of ancient, local grape varieties. Therefore, in recent years the growing interest to rediscover minor varieties, previously cultivated, has promoted many studies. With this regard, the focus of this study was the Vitis vinifera L. cultivar Moscato nero d’Acqui, nowadays found only in old vineyards in the Acqui zone (North-West Italy). In particular, the aims of this work were: i) to investigate secondary metabolites profile of the grapes, and ii) to evaluate the attitude to the production of special wines.