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…

Impact of GoLo technology on the aroma profile of red and white wines after total and partial dealcoholisation

Wine dealcoholisation has been practised since the early 1900s and has gained importance due to climate change
and shifting consumer preferences for lower-alcohol beverages. Rising temperatures are accelerating grape
ripening, increasing sugar content and, consequently, raising the alcohol strength of wines.

Read More

Convergence and divergence in chemical and sensory profiles of disease-resistant and Vitis vinifera white wines from South Tyrol: addressing strategies for market adoption

This study investigates the chemical and sensory profiles of white wines produced from disease-resistant hybrid grape cultivars (DRHGCs) compared to traditional Vitis vinifera L. cultivars in South Tyrol, Italy.

Read More

Sensory and consumer perceptions, and consumption barriers of low and no-alcohol wines in Trentino/Alto Adige

The growing demand for non-alcoholic beverages, driven by health-conscious consumers and shifting social norms, has positioned dealcoholized wines as a promising alternative in the global beverage industry (Akhtar et al., 2025, in press; Kakroo, 2024).

Read More

How sensory quality of wines can be accessed as a trait in MAS grape vine breeding

In the context of the global crises of global warming, biodiversity and pollution, current agricultural practices need to be reconsidered.

Read More

IMPACT OF CLIMATIC CONDITIONS ON THE SEASONING QUALITY OF OAK WOOD FOR OENOLOGICAL USE (QUERCUS PETRAEA)

For coopers, seasoning and toasting are considered crucial steps in barrel making during which the oak wood develops specific organoleptic properties. Seasoning, carried out in the open air, allows reducing the moisture content of the staves to between 14 and 18% (compared to 70 to 90% after splitting) while modulating the intrinsic composition of the oak wood. Toasting consists of applying different degrees of heat to a barrel for a specific period of time. As the temperature increases, oak wood produces a wide range of chemical compounds through thermal degradation of its intrinsic composition.

Read More