High-performance liquid chromatography/electrospray ionization mass spectrometric characterization of new products formed by the reaction between flavanols and malvidin 3-glucoside in the presence of acetaldehyde

• Type: Article in International Scientific Journal
• Date: 2007

Authors

Sun, BS (Author) Other; Reis Santos, CPR (Author) Other; Leandro, MC (Author) Other; Victor de Freitas (Author) FCUP; Spranger, MI (Author) Other

Journal

Title: Rapid Communications in Mass Spectrometry

Vol. 21

Pages: 2227-2236

ISSN: 0951-4198

Publisher: Wiley-Blackwell

Indexing

ISI Web of Knowledge - 17 Citations

Scopus - 16 Citations

Other information

Authenticus ID: P-004-EHJ

DOI: 10.1002/rcm.3082

Abstract (EN): Monomer and polymer flavan-3-ols and anthocyanins are the two major groups of phenolic compounds in red wine and one of the most important reactions during red wine ageing is the condensation reaction, either direct or indirect, between these two classes of compounds. In this work, the reaction of (+)-catechin, (-)-epicatechin and dimer procyanidin B(2) with malvidin 3-glucoside, in the presence of acetaldehyde, was carried out in wine model solutions at pH 1.7 and 3.2. Identification of the reaction products was carried out by high-performance liquid chromatography/electrospray ionization mass spectrometry (HPLC/ESI-MS) and MS(n) analysis. Various reaction products were detected. The structures of three condensation products - malvidin-3-glucoside-ethyl-(epi)catechin-1 ''-hydroxyethyl, malvidin-3-glucoside-ethyl-dimer-vinyl and malvidin3-glucoside-ethyl-dimer-1 ''-hydroxyethyl - were identified in a model solution for the first time. Moreover, in the reaction solution containing dimer B(2) at pH 3.2, monomer epicatechin, trimer and tetramer procyanidins were also detected indicating that, under these conditions, dimer procyanidins can either be hydrolyzed to monomers or polymerized to higher oligomer or polymers. Copyright (C) 2007 John Wiley & Sons, Ltd.

Language: English

Type (Professor's evaluation): Scientific

No. of pages: 10