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…

Influence of social interaction levels on panel effectiveness in developing wine sensory profiles using consensus method

The development of sensory profiles is crucial for quality control and innovation in the wine industry. If quantitative descriptive analysis is the most commonly used method for establishing sensory profiles due to its robustness, it presents significant limitations.

Read More

Gamma-ray spectrometry In Burgundy vineyard for high resolution soil mapping

Aim: A soil mapping methodology based on gamma-ray spectrometry and soil sampling has been applied for the first time in Burgundy. The purpose of this innovative high-resolution mapping is to delimit soil areas, to define elementary units of soil for terroir characterization and vineyard management. The added value of this integrated approach is a continuous geophysical mapping of the soil with an investigation depth of 60cm.

Read More

High resolution remote sensing for mapping intra-block vine vigour heterogeneity

In vineyard management, the block is considered today as the technical work unit. However, considerable variability can exist inside a block with regard to physiological parameters, such as vigour, particularly because of soil heterogeneity. To represent this variability spatially, many measurements have to be taken, which is costly in both time and money. High resolution remote sensing appears to be an efficient tool for mapping intra-block heterogeneity.

Read More

Maturità fenolica e cellulare come metodo di valutazione dell’interazione vitigno-ambiente: il caso del Cabernet-Sauvignon

ln the current work, phenolic and cellular maturation curves were used to assess the degree of adaptation of the cultivar Cabernet sauvignon to the sites under esamination. Five wine­-producing zones with different pedoclimatic characteristics and latitudes were considered (Marche, Toscana, Emilia, Friuli and Slovenia).

Read More

SO2 consumption in white wine oxidation: approaches to low input vinifications based on rapid electrochemical analyses and predictive enology

Oxidative stability is a critical factor in maintaining wine quality during its shelf-life. SO₂ is commonly added to wine due to its strong antioxidant activity, although there is a general push to reduce SO₂ use in vinification.

Read More