Macrowine 2021

A mechanistic investigation of H/D scrambling processes in flavonoids

Abstract

Several classes of flavonoids, such as anthocyanins, flavonols, flavanols and flavones, undergo a slow H/D exchange on aromatic ring A, leading to full deuteration at positions C(6) and C(8). Within the flavanol class, H-C(6) and H-C(8) of catechin and epicatechin are slowly exchanged in D2O to the corresponding deuterated analogues; even quercetin, a relevant flavonol representative, shows the same behaviour in a D2O/DMSOd6 1:1 solution. Detailed kinetic measurements of these H/D scrambling processes are here reported by exploiting the time-dependent changes of their peak areas in the 1H-NMR spectra taken at different temperatures. A unifying reaction mechanism is also proposed based on our detailed kinetic observations, even taking into account pH and solvent effects. Molecular modelling and QM calculations were also carried out to shed more light on several molecular details of the proposed mechanism.

DOI:

Publication date: September 16, 2021

Issue: Macrowine 2021

Type: Article

Authors

Graziano Guella

Biorganic Chemistry Lab/Dept. of Physics/University of Trento,Federico Bonaldo1, Fulvio Mattivi2, Daniele Catorci*, &, Panagiotis Arapitsas3, Graziano Guella1, * 1  Bioorganic Chemistry Laboratory, Department of Physics, University of Trento, Trento, Italy; 2 Department of Cellular, Computational and Integrative Biology – CIBIO and C3A, University of Trento, Trento, Italy; 3 Department of Food Quality and Nutrition, Research and Innovation Centre, Fondazione Edmund Mach (FEM), San Michele all’Adige, Italy; * D. Catorci passed away on June 27th, 2020

Contact the author

Keywords

flavonoids; chemistry of polyphenols; h/d isotopic scrambling; reaction mechanism

Citation

Related articles…

Isolation of indigenous yeast strains from the Purcari and Trifești wine centers in the Republic of Moldova and evaluation of their impact on the quality of dry red wines

In the conducted research, 30 yeast strains from red grape varieties were isolated from the Purcari wine center, and 28 yeast strains from red grape varieties were isolated from the Trifești wine center in the Republic of Moldova.

Read More

PROFILING OF LIPIDS IN WINES FROM MONOCULTURE FERMENTATION WITH INDIGENOUS METSCHNIKOWIA YEAST SPECIES

Lipids are a diverse group of organic compounds essential for living systems. They are vital compounds for yeast which makes them an important modulator of yeast metabolism in alcoholic fermentation. This study presents a comprehensive lipidome analysis of wine samples from the Vitis vinifera L., Maraština. The fermentation trails were set up in monoculture with different indigenous yeast strains selected from a collection of native yeasts established at the Institute for Adriatic Crops and Karst Reclamation in 2021, previously isolated from Croatian Maraština grapes: Metschnikowia pulcherrima, Metshnikowia sinensis/shanxiensis , and Metschnikowia chyrsoperlae.

Read More

Impact of red blotch disease on Cabernet Sauvignon and Merlot grape and wine composition and wine sensory attributes

Grapevine Red Blotch disease (RB) is a recently discovered disease that has become a major concern for the viticulture and winemaking industry in California, USA. The causal
agent, Grapevine Red Blotch Virus (GRBV) was identified in 2011 and its presence was confirmed in several states in the US, in Canada, and in Switzerland. It has been demonstrated that RB compromised the regulation of ripening by suppressing specific ripening events, altering the expression patterns of transcription factors and causing hormonal imbalances in Zinfandel.

Read More

Mapping terroirs at the reconnaissance level, by matching soil, geology, morphology, land cover and climate databases with viticultural and oenological results from experimental vineyards

This work was aimed at setting up a methodology to define and map the «Unités Terroir de Reconnaissance» (UTR), combining environmental information stored in a Soil Information System with experimental data coming from benchmark vineyards of Sangiovese vine.

Read More

Application of remote and proximal sensors for precision vineyard management in Valpolicella

The integration of sensor systems in viticulture is significantly improving vineyard management by enabling faster, comprehensive crop data collection across the entire vineyard, supporting more informed viticultural decision-making, and as a result promoting sustainability.

Read More