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…

Influence of preflowering basal leaf removal on aromatic composition of cv. Tempranillo wine from semiarid climate (Extremadura Western Spain)

Abstract In this work the effects of early leaf removal performed manually at preflowering phenological stage, on the volatile composition of Tempranillo (Vitis vinifera L.) wines were studied. From 2009-2011 vintages 34 wine volatile compounds were identified and quantified by gas chromatography-mass spectrometry (GC-MS) where early leaf removal only modified 25 of them. The total C6 compounds, acetates and volatiles acids (with exception of isobutyric acid) were affected by defoliation, whereas alcohols and esters showed a minor effect. Furthermore the vintage effect also was shown.

Characterization of non-Saccharomyces yeast and its interaction with Saccharomyces cerevisiae with investigation of fermentation kinetics and aromatic composition

[lwp_divi_breadcrumbs home_text="IVES" use_before_icon="on" before_icon="||divi||400" module_id="publication-ariane" _builder_version="4.20.4" _module_preset="default" module_text_align="center" module_font_size="16px" text_orientation="center"...

Some applications come from a method to concentrate proteins

All techniques usually used to assay proteins was not reliable in vegetable extract due to interferences with the components included in extracts like polyphenols, tanins, pectines, aromatics compounds. Absorbance at 280nm, Kjeldhal assay, Biuret and Lowry methods, Acid Bicinchonique technique and Bradford assay give the results depending on the composition of extract, on the presence or not of detergent and on the raw material (Marchal, 1995). Another difficulty in these extracts for the quantification of proteins comes from the large amount of water included in vegetable and the low concentration of proteins. Thus in red wines, proteins are usually not taken into account due to their low concentration (typically below 10 mgL-1) and to the presence of anthocyanis and polyphenols.

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.

Impact of smoke exposure on the chemical composition of grapes

Vineyard exposure to smoke can lead to grapes and wine which exhibit objectionable smoky and ashy aromas and flavours, more commonly known as ‘smoke taint’ [1, 2]. In the last decade, significant bushfires have occurred around the world, including near wine regions in Australia, Canada, South Africa and the USA, as a consequence of the warmer, drier conditions associated with climate change. Considerable research has subsequently been undertaken to determine the chemical, sensory and physiological consequences of grapevine exposure to smoke. The sensory attributes associated with smoke-tainted wine have been linked to the presence of several smoke-derived volatile phenols, such as guaiacols, syringols and cresols [2].