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…

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.

Effects of post-fermentative cold maceration on chemical and sensory characteristics of Syrah, Cabernet Franc and Montepulciano wines

Astringency sensation decreases slowly during the aging of red wine. Complex reactions of condensation and precipitation of wine polyphenols are involved in this phenomenon. Wine composition and conditions of aging, such as temperature and oxygen availability, strongly influence evolution of the phenol matrix. Recently, a Post-Fermentative cold Maceration (PFM) technique was tested with the aim of accelerating reactions leading to the reduction of astringency and exploiting chemical compounds not extracted from the solid parts of grapes during the previous traditional maceration phase. To this purpose, an innovative maceration system was engineered and used to perform PFM trials on marc derived from vinification of different varieties of red grapes.

Interest and impact of PVP/PVI (Polyvinylpyrrolidone/ Polyvinylimidazole) on winemaking and final quality of wines

Céline Sparrow a, Christophe Morge a, a SOFRALAB SAS, 79, av. A.A. Thévenet – CS 11031 – 51530 Magenta, France Consumers’ health and security force authorities to limit, in wine as in others food industry products, the concentration in « dangerous » molecules. Therefore the legal limit in heavy metals keeps on decreasing. As per proof EU regulation just decrease the stain concentration in wine from 0,2 to 0,15 mg/l. Certain changes , such as sodium arsenite treatment in vines, disappearance of brass in wineries to the benefit of stainless steel, limit even more the concentration of heavy metals in wines. But the use of copper derivates in vines treatments is difficult to replace. In the case of wine and its elaboration, the problem is even more complex. Indeed, regulation forces the wine producers to control the concentration of certain heavy metals in final wines.

Development and validation of a standardized oxidation assay for the accurate measurement of the ability of different wines to form “de novo” oxidation-related aldehydes

From the standpoint of wine aroma oxidation there are two effects observed: aroma degradation of oxygen sensitive compounds (polyfunctional mercaptans) and the appearance of new substances with high aromatic power (acetaldehyde, methional, phenylacetaldehyde, sotolon, alkenals, isobutanal and 2, 3-metylbutanals) (1-5). According to our experience, Strecker aldehydes are compounds with highest sensory relevance in the oxidative degradation of many wines (5-7).

New biological tools to control and secure malolactic fermentation in high pH wines

Originally, the role of the malolactic fermentation (MLF) was simply to improve the microbial stability of wine via biological deacidification. However, there is an accumulation of evidence to support the fact that lactic acid bacteria (LAB) also contribute positively to the taste and aroma of wine. Many different LAB enter into grape juice and wine from the surface of grape berries, cluster stems, vine leaves, soil and winery equipment. Due to the highly selective environment of juices and wine, only a few types of LAB are able to grow.