New compounds obtained by enzymatic oxidation of phloridzin |
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Authors: | Christine Le Guernevé Jean-François Drilleau |
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Institution: | a INRA UMR Sciences pour l’Oenologie, 2 place Viala 34060 Montpellier Cedex 02, France b INRA Unité de Recherches Cidricoles, Domaine de la Motte BP 35327, 35653 Le Rheu Cedex, France c Coopérative Elle & Vire, Département Ingrédients Bioactifs, BP 2, 50890 Condé sur Vire, France |
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Abstract: | Oxidation of phloridzin was studied in a model system in the presence of apple polyphenol oxidase. In addition to 3-hydroxy phloridzin, two major oxidation products were purified by reversed phase HPLC at the semi-preparative scale. Their structures were elucidated by UV, ESI-MSn and NMR spectroscopies. The first compound was a colourless product, whose novel structure strongly differs from its precursor showing a biphenyl moiety and a propionic acid chain. The second product was an oxidised form of the first one and corresponded to a stable yellow pigment with two isomeric forms. A mechanism of formation of these products, which implied successive oxidation and nucleophilic addition steps was proposed. |
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Keywords: | Phloridzin Dihydrochalcone Apple Polyphenol oxidase Oxidation products Browning |
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