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Formation of anthocyanin-flavanol adducts in model solutions [An article from: Analytica Chimica Acta]


by M. Duenas, H. Fulcrand, V. Cheynier

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Studio: Elsevier
Binding: Digital
Publication Date: December 04, 2008
Publisher: Elsevier


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Product Description
This digital document is a journal article from Analytica Chimica Acta, published by Elsevier in . The article is delivered in HTML format and is available in your Amazon.com Media Library immediately after purchase. You can view it with any web browser.

Description:
The mechanism of direct reactions between malvidin 3-O-glucoside (Mv3glc) and a flavanol monomer, (-)-epicatechin, was studied in model solutions in the pH range 2.0-6.0. The direct reactions are strongly related to pH. The rate of Mv3glc and epicatechin disappearance increased with pH. Nucleophilic addition of epicatechin onto the flavylium form of Mv3glc took place at all pH values. At pH 2.0, the resulting intermediate flavene yielded a colourless Mv3glc-epicatechin adduct with an A-type linkage. In the range pH 3.2-6.0, two new products with UV-vis spectra characteristic of those of xanthylium ions and mass signals at m/z 633 and 453, respectively, in the positive ion mode were detected. These products are postulated to be degradation products of the flavylium form of Mv3glc-epicatechin arising from the intermediate flavene. Moreover, above pH 4.0, oxidation of epicatechin promoted the formation of new pigments detected at m/z 781, in the positive ion mode. These ions were attributed to epicatechin-Mv3glc adducts formed by addition of Mv3glc onto the epicatechin o-quinone as the loss of a 138amu fragment indicated a biphenyl or biphenyl-ether linkage between the flavanol B-ring and the anthocyanin A-ring.
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