Identification and structural characterization of a novel -catechin-caffeic acid adduct present in wines

• Type: Article in International Scientific Journal
• Date: 2024

Authors

Azevedo, J (Author) Other; Joana Oliveira (Author) FCUP; Cruz, L (Author) Other; Mateus, N (Author) Other; Victor de Freitas (Author) FCUP

Journal

Title: Food Chemistry

Vol. 442

ISSN: 0308-8146

Publisher: Elsevier

Indexing

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Other information

Authenticus ID: P-00Z-SM1

DOI: 10.1016/j.foodchem.2024.138480

Abstract (EN): A new compound with a molecular ion mass of m/z 467 in the negative ion mode was found to occur in a white wine aged 30 months in bottle. In this latter, fragment ions compatible with the loss of a carboxylic acid (-44 a.m. u.), a caffeic acid unit (-178 a.m.u.), and a Retro-Diels Alder (-152 a.m.u.) were observed. The present work reports the synthesis of a (+)-catechin-caffeic acid adduct resulting from the condensation reaction between caffeic acid and (+)-catechin. The structural characterization by NMR showed that this adduct is formed by the linkage between carbon 8 at ring A from (+)-catechin and carbon 9 from caffeic acid. In addition, the similarity in the HPLC retention time and UV-Visible spectra of the synthesized compound with the one detected in white wine and the bottling experiments, confirms the presence of this novel (+)-catechin-derived compound in those matrices.

Language: English

Type (Professor's evaluation): Scientific

No. of pages: 7