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 influence of soil management practices on functional traits and biodiversity of weed communities in Swiss vineyards

Green cover in vine rows provides many ecological services, but can also negatively impact the crop, depending on the weed species. The composition of a vineyard weed community is influenced by many parameters. Ensuring an evolution of the vine row flora into a desired direction is therefore very complex. A key step towards this goal is to know which factors influence the establishment of the weed community and which types of communities are best suited for vineyards. In this study, we analysed the weed communities of several vineyards in the Lake Geneva region (379 botanical surveys on 117 plots), with the aim to highlight the links between soil management practices (chemical and mechanical weeding, mowing, mulching roll) and phytosociological profiles, biodiversity and selected functional traits (growth forms, life strategies, root depth). T

Technological possibilities of grape marc cell walls as wine fining agent. Effect on wine phenolic composition

Fining is a technique that is used to remove unwanted wine components that affect clarification, astringency, color, bitterness, and aroma. Fining involves the addition of adsorptive or reactive material in order to reduce or eliminate the presence of certain less desirable wine components and to ensure that a wine remains in a particular stable state for a given period of time Recently concerns have been raised about the addition of animal proteins, such as gelatin, to wine due to the disease known as bovine spongiform encephalopathy (Mad Cow disease). Although the origin of gelatins has been moved to porcine, winemakers are asking for substitute products with properties and application protocols similar to the traditional animal-derived ones, making the use of plant-derived proteins in fining a practically viable possibility. As a consequence, various fining agents derived from plants have been proposed, including proteins from cereals, legumes, and potato.

Glutathione content evolution during spontaneous alcoholic fermentations of Sangiovese grapes

Glutathione is a tripeptide (γ-Glu-Cys-Gly), which can occur in grapes, in must and in wine prevalently in the reduced form as well as in the oxidized form as glutathione disulfide. The importance of the reduced form of glutathione lies in its antioxidant activity. In must, it limits browning by reducing o-quinones produced by polyphenol oxidase activity on hydroxycinnamic acids; in wine, it exerts a protective effect on various aromatic compounds. Glutathione concentration in wine is lower than in grape juice and variable as it depends on several factors, ranging from the native content of grapes to winemaking technique.

Estimation of chemical age of red wines with the use of Fourier transform infrared spectroscopy (FT-IR) and chemometrics

The color of a red wine is one of the most important parameters of its quality, giving much information on its status, such as the grape variety used or the winemaking style. As the result of a complex equilibrium between different forms of anthocyanins and polymerization reactions which occur over the course of time, color can also serve as an indication of a wines’ age. For this purpose the “chemical age” i and ii indexes have been introduced by Somers in 1977. The chemical age index i measures the color absorbance after the addition of acetaldehyde while chemical index ii provides an indication of how much of the total red pigments are resistant to SO2 bleaching.

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.