Isolation and structural characterization of new acylated anthocyanin-vinyl-flavanol pigments occurring in aging red wines

• Type: Article in International Scientific Journal
• Date: 2003

Authors

Mateus, N (Author) FCUP; Carvalho, E (Author) Other; Carvalho, ARF (Author) Other; Melo, A (Author) FCUP; Gonzalez Paramas, AM (Author) Other; Santos Buelga, C (Author) Other; Silva, AMS (Author) Other; de Freitas, V (Author) FCUP

Journal

Title: Journal of Agricultural and Food Chemistry

Vol. 51

Pages: 277-282

ISSN: 0021-8561

Publisher: American Chemical Society

Indexing

ISI Web of Knowledge - 95 Citations

Scopus - 104 Citations

Scientific classification

FOS: Agrarian Sciences > Other Agrarian Sciences

Other information

Authenticus ID: P-000-JZ8

DOI: 10.1021/jf020695i

Abstract (EN): Three newly formed pigments were detected and isolated from a 2-year-old Port wine through TSK Toyopearl HW-40(S) gel column chromatography and characterized by UV-visible spectrophotometry, NMR, and mass spectrometry (ESI/MS). H-1 NMR and C-13 NMR data for these pigments obtained using 1D and 2D NMR techniques (COSY, NOESY, gHSQC, and gHMBC) are reported for the first time. The structure of the pigments was found to correspond to the vinyl cycloadducts of malvidin 3-coumaroylglucoside bearing either a procyanidin dimer or a flavanol monomer ((+)-catechin or (-)-epicatechin). Additionally, conformational analysis was performed for one of these newly formed pigment using computer-assisted model building and molecular mechanics. A chemical nomenclature is proposed to unambiguously name this new family of anthocyanin-derived pigments.

Language: English

Type (Professor's evaluation): Scientific

No. of pages: 6