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NMR and molecular fluorescence spectroscopic study of the structure and thermodynamic parameters of EGCG/β-cyclodextrin inclusion complexes with potential antioxidant activity

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Abstract

The present study is focused on the characterization of the interaction between (−)-epigallocatechingallate (EGCG) and cyclodextrins like β-cyclodextrin (βCD), heptakis(2,6 di-O-methyl)-β-cyclodextrin (DMβCD), and hydroxypropyl-β-cyclodextrin (HPβCD) in aqueous solution. These inclusion complexes previously demonstrated improvements in the antioxidant activity respect to free EGCG. The structural evidence obtained by 2D-ROESY and selective 1D-ROESY experiments was rationalized by autodock studies and indicates that all the complexes have similar inclusion geometries, but the difference resides on the exposition degree of the antioxidant rings of EGCG, such as pyrogallol and galloyl groups. The thermodynamic study allowed estimating that the inclusion process is entalpically driven for the derivatized cyclodextrins complexes and entropically driven for βCD complexes due to the predominance of hydrophobic interactions with EGCG.

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Acknowledgments

This work was supported by CONICYT Project 24091025 and FONDECYT Project 11080038. Christian Folch-Cano gratefully acknowledges the contribution of CONICYT-CHILE for a Ph.D. fellowship. J. Guerrero gratefully acknowledges the contribution of MECESUP-0007 for an NMR spectrometer.

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Authors and Affiliations

  1. Departamento Química Analítica e Inorgánica, Facultad de Ciencias Químicas y Farmacéuticas, Universidad de Chile, Santiago, Chile

    Christian Folch-Cano & Claudio Olea-Azar

  2. Departamento de Ciencias del Ambiente, Facultad de Química y Biología, Universidad de Santiago de Chile, Santiago, Chile

    Juan Guerrero

  3. Laboratorio de Antioxidantes, Instituto de Nutrición y Tecnología de los Alimentos, Universidad de Chile, Santiago, Chile

    Christian Folch-Cano & Hernán Speisky

  4. Departamento Química Orgánica y Fisicoquímica, Facultad de Ciencias Químicas y Farmacéuticas, Universidad de Chile, Santiago, Chile

    Carolina Jullian

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  1. Christian Folch-Cano
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  2. Juan Guerrero
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  3. Hernán Speisky
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  4. Carolina Jullian
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  5. Claudio Olea-Azar
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Correspondence to Carolina Jullian.

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Folch-Cano, C., Guerrero, J., Speisky, H. et al. NMR and molecular fluorescence spectroscopic study of the structure and thermodynamic parameters of EGCG/β-cyclodextrin inclusion complexes with potential antioxidant activity. J Incl Phenom Macrocycl Chem 78, 287–298 (2014). https://doi.org/10.1007/s10847-013-0297-y

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  • DOI: https://doi.org/10.1007/s10847-013-0297-y

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