Macrowine 2021
IVES 9 IVES Conference Series 9 New acylated flavonols identified in the grape skin of Vitis vinifera cv. Tannat and their wines

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

Abstract

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. The assignments were based on their UV-vis and MSn spectral data. Firstly, the MS2 fragmentation pattern of each tentatively identified flavonol glycoside derivative showed a main signal attributable to the expected flavonol aglycone, together with a weak signal corresponding to the intermediate loss of the acyl moiety. The structures of the flavonol aglycones were confirmed by their respective MS3 experiments that matched with those obtained from authentic standards of the three aglycones. In addition, the DAD on-line UV-vis spectra of the suggested flavonol-3-O-(p-coumaroyl)-glucosides closely matched the sum of the respective spectra of the flavonol-3-O-glucoside and that of p-coumaric acid. Interestingly, the presence of these new flavonol derivatives was limited to the minority flavonols. Being acylation a final step in the flavonoid synthesis, our findings suggest a very high specificity of the acyltransferases implied for the flavonol glycoside substrate that in this case would be related to the presence of methoxyl groups in the B ring of the flavonol. The fact that these compounds have been found in Tannat, a Vitis vinifera with scarce cultivation around the world, may indicate that the implied acyltransferases could be little spread among grape varieties. Nevertheless it could be associated to other factors like growth environmental conditions, or to the sensitivity of the analytical technique employed, or others factors, which should be further considered and studied. These results give evidences of new flavonol derivatives in grapes and wines, and expose a case of substrate specificity of the enzymes implied in their synthesis.

Publication date: May 17, 2024

Issue: Macrowine 2016

Type: Poster

Authors

Isidro Hermosín-Gutíerrez*, Diego Piccardo, Gustavo González Neves, Guzmán Favre, Sergio Gómez-Alonso

*Universidad de Castilla-La Mancha

Contact the author

Tags

IVES Conference Series | Macrowine | Macrowine 2016

Citation

Related articles…

Contribution of Piperitone to the mint nuances perceived in the aging bouquet of red Bordeaux wines

During the tasting of a fine, old wine, the aromas generated in the glass are intertwined in an intimate, complex manner, expressing the fragrance of the aging bouquet. This aging bouquet, which develops during bottle storage through a complex transformation process, may result in a broad palette of nuances. Among these, undergrowth, truffle, toasted, spicy, licorice, fresh red- and black-berry fruit and mint descriptors were recently identified as features of its olfactory representation for red Bordeaux wines. Although a targeted chemical approach focusing on volatile sulfur compounds revealed the role played by dimethyl sulfide, 2-furanmethanethiol, and 3-sulfanylhexanol as molecular markers of the typicality of the wine aging bouquet of red Bordeaux wines, its chemical transcription has only partially been elucidated.

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.

WineMetrics: A new approach to unveil the “wine-like aroma” chemical feature

“The Human being has an excellent ability to detect and discriminate odors but typically has great difficulty in identifying specific odorants”(1). Furthermore, “from a cognitive point of view the mechanism used to judge wines is closer to pattern recognition than descriptive analysis.” Therefore, when one wants to reveal the volatile “wine-like feature” pattern recognition techniques are required. Sensomics is one of the most recent “omics”, i.e. a holistic perspective of a complex system, which deals with the description of substances originated from microorganism metabolism that are “active” to human senses (2). Depicting the relevant volatile fraction in wines has been an ongoing task in recent decades to which several research groups have allocated important resources. The most common strategy has been the “target approach” in order to identify the “key odorants” for a given wine varietal.

Identification, quantification and organoleptic impact of « dried fruit » molecular markers in Merlot and Cabernet Sauvignon grapes and in red wines

The aromas found in young Bordeaux red wines made with Merlot and Cabernet Sauvignon suggest a complex mixture of aromas of fresh red fruits such as cherry or blackberry for Merlot, and strawberry or blackcurrant for Cabernet Sauvignon. The aromas of these wines are closely linked with the maturity of the grapes. The climate change that has occurred during the last decade in Bordeaux has induced changes in the ripening conditions of grape berries. It is now widely admitted that over-ripening of the berries during hot and dry summers results in the development of characteristic flavors reminiscent of cooked fruits (fig, prune). The presence of these overriding odors found in both musts and young wines affects the quality and subtlety of the wine flavor and may shorten its shelf life.

Effect of non-Saccharomyces yeast and lactic acid bacteria on selected sensory attributes and polyphenols of Syrah wines

Consumers predominantly use visual, aromatic and texture cues as quality/preference indicators to describe olfactory sensations. In this study, the effect of micro-organism in wine production was investigated using analytical and sensory techniques to achieve relevant analytical characterisation. Selected anthocyanins, flavan-3-ols, flavonols and phenolic acids were quantified in Syrah wines using RP-HPLC-DAD. Standard oenological parameters were also measured. Syrah grape must was fermented with various combinations of Saccharomyces cerevisiae (S. cerevisiae) and non-Saccharomyces (Metschnikowia pulcherrima or Hanseniaspora uvarum) yeasts, which was followed by sequential inoculation of lactic acid bacteria (LAB) (Oenococcus oeni or Lactobacillus plantarum).