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Enzymatic synthesis of oligoesculin: structure and biological activities characterizations

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Abstract

The oligomerization of esculin, catalyzed by the laccase from Trametes versicolor, was realized in an attempt to improve the properties of this glycosidic coumarin. MALDI-TOF analyses showed a degree of oligomerization up to 9, whereas NMR spectra revealed the formation of C–C and C–O bridges, which involve both the phenolic and the glucosidic part of the coumarin. The solubility of oligomers is 189-fold higher than esculin’s solubility. Moreover, antioxidant properties of oligomers were correlated with their mass; the more the mass, the more the xanthine oxidase inhibitory activity and the radical scavenging activity are important. These experimental results were completed by in silico structural investigations, which suggested the preferential formation of C8–C8 linkages between esculin units during the oligomerization reaction.

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Authors and Affiliations

  1. Laboratoire d’Ingénierie des Biomolécules, Ecole Nationale Supérieure d’Agronomie et des Industries Alimentaires, Institut National Polytechnique de Lorraine ENSAIA-INPL, 54505, Vandoeuvre les Nancy, France

    Julie Anthoni, Catherine Humeau, Latifa Chebil, Jean-Marc Engasser & Mohamed Ghoul

  2. Laboratório de Estudos Estruturais Moleculares (LEEM), Instituto de Química, Universidade de Brasília, Campus Darcy Ribeiro, C.P. 4478, Brasília, 70904-970, DF, Brazil

    Elaine Rose Maia

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  1. Julie Anthoni
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  2. Catherine Humeau
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  3. Elaine Rose Maia
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  4. Latifa Chebil
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  5. Jean-Marc Engasser
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  6. Mohamed Ghoul
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Correspondence to Mohamed Ghoul.

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Anthoni, J., Humeau, C., Maia, E.R. et al. Enzymatic synthesis of oligoesculin: structure and biological activities characterizations. Eur Food Res Technol 231, 571–579 (2010). https://doi.org/10.1007/s00217-010-1298-3

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  • DOI: https://doi.org/10.1007/s00217-010-1298-3

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