Please use this identifier to cite or link to this item:
https://hdl.handle.net/10216/92043
Author(s): | Jingren R He Joana Oliveira Artur M S Silva Nuno Mateus Victor De Freitas |
Title: | Oxovitisins: A New Class of Neutral Pyranone-anthocyanin Derivatives in Red Wines |
Issue Date: | 2010 |
Abstract: | A new class of stable yellowish pigments with similar unique spectral features, displaying only a pronounced broad band around 370 nm in the UV-vis spectrum, was detected in an aged Port wine fraction obtained by a combination of chromatography on TSK Toyopearl HW-40(s) and Polyamide resins. These compounds were identified by liquid chromatography-diode array detector/electrospray ionization mass spectrometry (LC-DAD/ESI/MS) and shown to be direct oxidative derivatives of carboxy-pyranoanthocyanins (vitisins A) by synthesis experiments performed in a wine model solution. Their structures were fully characterized by MS and NMR spectroscopy ((1)H, gCOSY, gHSQC, and gHMBC) and found to correspond to alpha-pyranone-anthocyanins (lactone or pyran-2-one-anthocyanins). Their formation involves first the nucleophilic attack of water into the positively charged C-10 position of vitisins, followed by decarboxylation, oxidation, and dehydration steps, yielding a new and neutral pyranone structure. The occurrence of these novel pigments in aged wines points to a new pathway involving anthocyanin secondary products (vitisins A) as precursors of new pigments in subsequent stages of wine aging that may contribute to its color evolution. |
Subject: | Outras ciências agrárias Other Agrarian Sciences |
Scientific areas: | Ciências agrárias::Outras ciências agrárias Agrarian Sciences::Other Agrarian Sciences |
URI: | https://repositorio-aberto.up.pt/handle/10216/92043 |
Document Type: | Artigo em Revista Científica Internacional |
Rights: | restrictedAccess |
Appears in Collections: | FCUP - Artigo em Revista Científica Internacional |
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49210.pdf Restricted Access | 1.05 MB | Adobe PDF | Request a copy from the Author(s) |
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