Study on the interaction between gliadins and a coumarin as molecular model system of the gliadins-anthocyanidins complexes

Abstract

To clarify the conformational changes of gliadins (Glia) upon complexation with anthocyanidins (in particular cyanidin, Cya), the interaction of Glia with a coumarin derivative (3-ethoxycarbonylcoumarin, 3-EcC), having a benzocondensed structure similar to that of Cya, has been investigated by NMR, IR, and Raman spectroscopy under acidic and neutral conditions. Raman spectra showed that both molecules produce a similar effect on the Glia structure, i.e. an increase in the α-helix conformation and a decrease in β-sheet and β-turns content. In the presence of both molecules, this effect is more marked; the spectroscopic results showed that both Cya and 3-EcC interact with Glia and 3-EcC favors the complex formation with Glia. The results obtained in this study provide new insights into anthocyanidins-Glia interactions and may have relevance to human health, in the field of the attempts to modify gluten proteins to decrease allergen immunoreactivity.

Keywords: Anthocyanidin; Coumarin; DFT calculations; Gliadins; NMR spectroscopy; Raman spectroscopy.