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…

Impact of heating must before fermentation on Chardonnay wines

Prefermentation steps of white winemaking are very important for controlling the stability and the sensory attributes of wines. Usually musts are clarified by cold settling to prevent the start of the fermentation, before racking big lees and thus limiting the appearance of vegetable or reduction off flavour while favouring an aromatic expression with low turbidity. Besides, to reach the protein stability, some white wines further require a bentonite fining, sometimes associated with negative effects on the sensory quality. This study aims to know the impact of musts heating after pressing on a Chardonnay wine in northern conditions by comparison with a classic cold racking of the must.

Anthocyanin accumulation and extractability during the maturation of the grapes of three varieties

Anthocyanin accumulation and extractability were studied in Tannat, Cabernet Sauvignon and Merlot grapes produced in the south of Uruguay in two consecutive seasons. Typical cultivation situations employed in the region for each variety were considered. A follow-up was carried out, considering 60 plants per vineyard, and the harvest was determined according to the technological indices of maturity. Samples of grapes were taken in duplicate in each vineyard periodically along grape maturation. The basic composition, polyphenolic potential and anthocyanin extractability were determined. Also, half of grapes were frozen and later peeled; skin extractions over 24 hs with a solution of 12% ethanol and pH 3.2 were carried out. The anthocyanin contents of the extracts obtained were determined by HPLC-DAD. The levels of anthocyanins reached the highest values before technological maturity. Anthocyanin extractability had a decrease during grape maturation.

Characterization of various groups of pyranoanthocyanins in Merlot red wine

In red wines, anthocyanins evolve during the wine-making process and ageing. They react with other compounds (such as vinylphenols, acetaldehyde, pyruvic acid…) to form a stable family of compounds called pyranoanthocyanins. Furthermore, the oxidation process can modify the anthocyanic profile of a red wine. It is also interesting to evaluate the occurrence of the different subclasses of pyranoanthocyanins and to characterize their chemical properties. The first objective of this study is to evaluate the occurrence of the different groups of pyranoanthocyanins in an oxidised Merlot wine by a centrifugal partition chromatography strategy. The second goal is to evaluate their relative impact in red wines from Bordeaux region by measuring their concentrations.

Effect of concentration and competition between different fungicide residues on the adsorption efficiency of activated vegetal fibres for treatment of wine

Vineyards are strongly exposed to fungal diseases, attacks from insects and competition with weeds. Most treatments used on grape vines contain synthetic active substances, which may be transferred to the wine. Such pesticides have a negative image because many active substances are potential health hazards. A specific oenological treatment allowing the reduction of pesticide residues in wine based on activated vegetable fibres (AVF) is under examination by the International Organisation for Vine and Wine. This technique works efficiently and alters the wine only little (Lempereur et al. 2014).

How do different oak treatment affect the sensory composition of Chenin blanc wines over time?

Wooden barrels have been the preferred method for oak maturation for wines, but the use of alternative oak products, such as staves and oak chips have increased in South Africa due to lower production costs. This study investigated the effect of different oak products used during fermentation and ageing on the sensory profile, degree of liking and perceived quality of a South African Chenin blanc wine. The different wine treatments included an unoaked tank control wine, wines matured in 5th fill barrels, wines matured in new barrels from three different cooperages, and wines matured in 5th fill barrels with stave inserts from two different cooperages.