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…

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"...

Comprehensive exploration of wine aroma-related compounds as promoted by alternative vinification procedures in case of Zelen (Vitis vinifera L.) grapes processing

Not only vintner’s decisions in the vineyard, but also winemaker’s choices of technology approaches in the cellar play a significant role in the final wine style and quality. Whereas traditional technologies within chosen terroir are quite well explored and thus somehow predictable, there is no proper knowledge available on possible outcomes in case of implementing novel, alternative winemaking strategies. To reveal their effects on wine aroma compounds and sensory characteristics, two alternative strategies
(cryoextraction or addition of whole grape berries during last stages of fermentation) were compared to classical Vipava valley winemaking approach as normally used for an autochthonous variety Zelen. After separate vinification and bottling, all the experimental wines were subjected to semiquantitative metabolic profiling of volatile compounds (VOCs) by means of GC/MS and were then also sensorialy evaluated by pre-trained panel.

Interaction between the enzymes of central carbon metabolism and anthocyanin biosynthesis during grape berry development

Primary and secondary metabolites are major components of grape quality and wine typicity. Their accumulation is interconnected through a complex metabolic network, which is still not well understood. This study aims to investigate how the enzymes of central carbon metabolism interact with anthocyanin biosynthesis during grape berry development: does the accumulation of anthocyanins, which represents a non-negligible diversion of carbon metabolic fluxes, require reprogramming of central enzymes or is it controlled downstream of central metabolism? To this end, 23 enzymes involved in central carbon metabolism pathways have been analyzed in the berries of 3 grape cultivars, which have close genetic background but distinct temporal dynamics of anthocyanin accumulation.

Using combinations of recombinant pectinases to elucidate the deconstruction of the polysaccharide‐rich grape cell wall during winemaking

The effectiveness of enzyme-mediated maceration processes in red winemaking relies on a clear picture of the target (berry cell wall structure) to achieve the optimum combination of specific enzymes to be used. However, we lack the information on both essential factors of the reaction (i.e. specific activities in commercial enzyme preparation and the cell wall structure of berry tissue). In this study, the different combinations of pure recombinant enzymes and the recently validated high throughput cell wall profiling tools were applied to extend our knowledge on the grape berry cell wall polymeric deconstruction during the winemaking following a combinatorial enzyme treatment design.

Microbial stabilization of wines using innovative coiled UV-C reactor process: impact on chemical and organoleptic proprieties

For several years, numerous studies aimed at limiting the use of SO2 in wines (thermal treatments, pulsed electric fields, microwaves …). Processes must be able to preserve the organoleptic qualities of wines with low energy consumption. In this context, ultraviolet radiations (UV-C), at 254 nm, are well known for their germicidal proprieties. In order to inactivate microorganisms in grape juice and wine without affecting the quality of the product, efficiency of UV-C treatment process should be optimized.