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…

Study of the volatil profile of minority white varieties

The genetic material preservation is a priority issue in winemaking research. The recovery of minority grape varieties can control the genetic erosion, contributing also to preserve wine typical characteristics. In D.O.Ca. Rioja (Spain) the number of grown white varieties has been very limited, representing Viura the 91% of the cultivated white grape area in 2005, while the others, Garnacha Blanca and Malvasía riojana, hardly were grown. For this reason, a recovery and characterization study of plant material was carried out in this region. In 2008, the results obtained allowed the authorization of three minority white varieties: Tempranillo Blanco, Maturana Blanca and Turruntés.

Metabolomics comparison of non-Saccharomyces yeasts in Sauvignon blanc and Shiraz

Saccharomyces cerevisiae (SC) is the main driver of alcoholic fermentation however, in wine, non-Saccharomyces species can have a powerful effect on aroma and flavor formation. This study aimed to compare untargeted volatile compound profiles from SPME-GC×GC-TOF-MS of Sauvignon blanc and Shiraz wine inoculated with six different non-Saccharomyces yeasts followed by SC. Torulaspora delbrueckii (TD), Lachancea thermotolerans (LT), Pichia kluyveri (PK) and Metschnikowia pulcherrima (MP) were commercial starter strains, while Candida zemplinina (CZ) and Kazachstania aerobia (KA), were isolated from wine grape environments. Each fermentation produced a distinct chemical profile that was unique for both grape musts. The SC-monoculture and CZ-SC sequential fermentations were the most distinctly different in the Sauvignon blanc while the LT-SC sequential fermentations were the most different from the control in the Shiraz fermentations.

Effect of supplementation with inactive yeast during alcoholic fermentation in base wine for sparkling

INTRODUCTION: Foam stability of sparkling wines is significantly favored by the presence of surface active agents such as proteins and polysaccharides [1]. For that reason, the renowned sparkling wines are aged after the second fermentation in contact with the lees for several months (even years). Thereby wines are enriched in these macromolecules due to yeast autolysis. Since this practice is slow and costly, winemakers are seeking for alternative procedures to increase their concentration in base wines. In that sense, the supplementation with inactive yeast during alcoholic fermentation has been proposed [2]. The aim of this study was to determine whether this new strategy is really useful for enriching base wines in macromolecules and for improving foam properties of the base wines.

New acylated flavonols identified in the grape skin of Vitis vinifera cv. Tannat and their wines

Flavonols are a class of flavonoid compounds derived from plant secondary metabolism. There they play different roles like antioxidants, internal regulators and UV screenings. In red wines, flavonols have increasingly received consideration by part of scientific and winemakers according their properties began to arise known. Among these stand out wine colour stabilization and their value as bioactive compounds. In this work the complete series of the acetylated and p-coumaroylated derivatives of the 3-O-glycosides of methoxylated flavonols, namely isorhamnetin, laricitrin and syringetin, have been identified in grapes and their respective wines from Vitis vinifera cv. Tannat.

Attractiveness and sweetness of red wines: Synergies between American oak barrels and mannoproteins

In partnership with a Bordeaux property wanting to improve the quality of its second wine, the effects of two factors, American oak barrels and mannoproteins were studied. Their impact on the attractiveness and sweetness of wines were characterized during two successive vintages (2012 and 2013). Vinification took place with a homogeneous batch of Cabernet Sauvignon. The wine was then divided up into various groups of five barrels of French and American oak, new or reused. Analyses of volatile and non-volatile wood compounds were undertaken at four months and eight months of wood ageing, by LC-MS and GC-MS.