Multispectral fluorescence sensitivity to acidic and polyphenolic changes in Chardonnay wines – The case study of malolactic fermentation

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.

Context and purpose of the study. Fungus-resistant grape varieties (PIWIs) represent a significant advancement toward more environmentally sustainable viticulture.

The phenolic profiles of little known red grape cultivars, namely Garnacho, Moribel and Tinto Fragoso, which are autochthonous from the Spanish region of La Mancha (ca. 600,000 ha of vineyards) have been studied over the consecutive seasons of years 2013 and 2014. The study was separately performed over the skins, the pulp and the seeds, and comprised the following phenolic types: anthocyanins, flavonols, hydroxycinnamic acid derivatives (HCADs), total proanthocyanidins (PAs) and their structural features. The selected grape cultivars belong to the Vine Germplasm Bank created in this region in order to preserve the great diversity of genotypes grown in La Mancha.

3-Mercaptohexanol (3MH) is a volatile thiol occurring in several white and red wines, where it can contribute to fruity attributes. Its content is typically high in wines from certain grape varieties, in particular Sauvignon blanc, where it is considered a varietal marker. The strong nucleophilic character of thiols makes 3MH rather unstable during wine storage, due to the presence of several strong electrophilic species. Among these electrophilics, those arising from the oxidation of flavan3-ols such as catechin and epi-catechin have been indicated as critical for 3MH stability. Accordingly, there is a generalized interest towards the ability of vinification practices to reduce 3MH loss during aging through the management of wine flavan-3-ols content.

Catechins, a subclass of flavonoids widely found in plants and plant-based foods and beverages such as wine and tea, not only exhibit significant antioxidant properties [1], as extensively documented in the literature, but can also inhibit amyloid protein aggregation [2], a key process implicated in the onset of neurodegenerative diseases such as Parkinson’s, Alzheimer’s, and Huntington’s.