First insights into the binding mechanism and colour effect of the interaction of grape seed 11S globulin with malvidin 3-O-glucoside by fluorescence spectroscopy, differential colorimetry and molecular modelling

Francisco Chamizo-González; Ignacio García Estévez; Belén Gordillo; Elvira Manjón; M T Escribano-Bailón; Francisco J Heredia; M Lourdes González-Miret

doi:10.1016/j.foodchem.2023.135591

First insights into the binding mechanism and colour effect of the interaction of grape seed 11S globulin with malvidin 3-O-glucoside by fluorescence spectroscopy, differential colorimetry and molecular modelling

Food Chem. 2023 Jul 1:413:135591. doi: 10.1016/j.foodchem.2023.135591. Epub 2023 Jan 31.

Authors

Francisco Chamizo-González¹, Ignacio García Estévez², Belén Gordillo³, Elvira Manjón⁴, M T Escribano-Bailón⁵, Francisco J Heredia⁶, M Lourdes González-Miret⁷

Affiliations

¹ Food Colour & Quality Lab., Área de Nutrición y Bromatología, Facultad de Farmacia, Universidad de Sevilla, 41012 Sevilla, Spain. Electronic address: fchamizo@us.es.
² Grupo de Investigación en Polifenoles, Facultad de Farmacia, Universidad de Salamanca, Campus Miguel de Unamuno, E 37007 Salamanca, Spain. Electronic address: igarest@usal.es.
³ Food Colour & Quality Lab., Área de Nutrición y Bromatología, Facultad de Farmacia, Universidad de Sevilla, 41012 Sevilla, Spain. Electronic address: bgordillo@us.es.
⁴ Grupo de Investigación en Polifenoles, Facultad de Farmacia, Universidad de Salamanca, Campus Miguel de Unamuno, E 37007 Salamanca, Spain. Electronic address: elvira87@usal.es.
⁵ Grupo de Investigación en Polifenoles, Facultad de Farmacia, Universidad de Salamanca, Campus Miguel de Unamuno, E 37007 Salamanca, Spain. Electronic address: escriban@usal.es.
⁶ Food Colour & Quality Lab., Área de Nutrición y Bromatología, Facultad de Farmacia, Universidad de Sevilla, 41012 Sevilla, Spain. Electronic address: heredia@us.es.
⁷ Food Colour & Quality Lab., Área de Nutrición y Bromatología, Facultad de Farmacia, Universidad de Sevilla, 41012 Sevilla, Spain. Electronic address: miret@us.es.

PMID: 36764161
DOI: 10.1016/j.foodchem.2023.135591

Abstract

Recently, the search for alternative proteins endogenous to grapes to be used as wine colour protecting agents became an important research trend. In this study, the molecular interaction between the grape seed 11S globulin from winemaking by-product and malvidin-3-O-glucoside was investigated by fluorescence, differential colorimetry and molecular modelling. Fluorescence studies revealed the formation of grape seed protein- pigment complex whose K_S was 8.5 × 10⁴ M^-1 and binding sites, n = 1.3. Malvidin-3-O-glucoside showed darker and more vivid bluish colour of in the presence of 11S globulin, suggesting the flavylium cation protection in a hydrophobic region of the protein. Docking analysis and molecular dynamics simulation indicated that malvidin-3-O-glucoside interacts mainly with the acidic subunit (40 kDa) of the 11S globulin monomer (60 kDa). An average of two hydrogen bonds and Van der Wall forces were the main interaction forces found for the protein-pigment complex, whose stability was confirmed by root-means-square deviation.

Keywords: Colour; Fluorescence quenching; Grape seed 11S globulin; Guided docking; Malvidin3-O-glucoside; Winemaking by-product.

MeSH terms

Anthocyanins / analysis
Color
Colorimetry
Globulins*
Glucosides / chemistry
Seeds / chemistry
Spectrometry, Fluorescence
Vitis* / chemistry
Wine* / analysis

Substances

Anthocyanins
Globulins
Glucosides
malvidin
oenin