A new class of blue anthocyanin-derived pigments isolated from red wines

被引：164
作者：
Mateus, N
Silva, AMS
Rivas-Gonzalo, JC
Santos-Buelga, C
De Freitas, V
机构：
[1] Univ Porto, Fac Ciencias, Dept Quim, Ctr Invest Quim, P-4169007 Oporto, Portugal
[2] Univ Aveiro, Dept Quim, P-3810193 Aveiro, Portugal
[3] Univ Salamanca, Fac Farm, Unidad Nutr & Bromatol, E-37007 Salamanca, Spain
来源：
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY | 2003年 / 51卷 / 07期
关键词：
pyranoanthocyanin; flavanols; red wine; aging; blue color;
D O I：
10.1021/jf020943a
中图分类号：
S [农业科学];
学科分类号：
09 ;
摘要：
Two newly formed anthocyanin-derived pigments that revealed unique spectroscopic features, showing maximum absorption in their UV-vis spectra at 575 nm, were isolated by TSK Toyopearl HW-40 (S) gel column chromatography and semipreparative HPLC from an aged Port red wine. Further characterization by ESI/MS and NMR (H-1, gCOSY) showed them to belong to a new class of pigments described here for the first time, the structure of which consisted of a pyranoanthocyanin moiety linked to a flavanol by a vinyl bridge. The extended conjugation of the is electrons throughout all the pigment molecule is likely to confer a higher stability on it and is probably the origin of the intense blue color. The formation of these pigments was found to arise from the reaction between anthocyanin-pyruvic acid adducts and vinyl-flavanol adducts.
引用
收藏
页码：1919 / 1923
页数：5
相关论文
共 32 条
[1]   Effect of oxygenation on polyphenol changes occurring in the course of wine-making [J].
Atanasova, V ;
Fulcrand, H ;
Cheynier, W ;
Moutounet, M .
ANALYTICA CHIMICA ACTA, 2002, 458 (01) :15-27
[2]  
BAKKER J, 1993, VITIS, V32, P111
[3]   Isolation, identification, and characterization of new color-stable anthocyanins occurring in some red wines [J].
Bakker, J ;
Timberlake, CF .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 1997, 45 (01) :35-43
[4]   Identification of an anthocyanin occurring in some red wines [J].
Bakker, J ;
Bridle, P ;
Honda, T ;
Kuwano, H ;
Saito, N ;
Terahara, N ;
Timberlake, CF .
PHYTOCHEMISTRY, 1997, 44 (07) :1375-1382
[5]  
CameiradosSantos PJ, 1996, J SCI FOOD AGR, V70, P204, DOI 10.1002/(SICI)1097-0010(199602)70:2<204::AID-JSFA484>3.3.CO
[6]  
2-6
[7]   Studies on the acetaldehyde-induced condensation of (-)-epicatechin and malvidin 3-O-glucoside in a model solution system [J].
Es-Safi, NE ;
Fulcrand, H ;
Cheynier, V ;
Moutounet, M .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 1999, 47 (05) :2096-2102
[8]   Structure of a new xanthylium salt derivative [J].
Es-Safi, NE ;
Le Guernevé, C ;
Labarbe, B ;
Fulcrand, H ;
Cheynier, V ;
Moutounet, M .
TETRAHEDRON LETTERS, 1999, 40 (32) :5869-5872
[9]   Color and stability of pigments derived from the acetaldehyde-mediated condensation between malvidin 3-O-glucoside and (+)-catechin [J].
Escribano-Bailón, T ;
Alvarez-García, M ;
Rivas-Gonzalo, JC ;
Heredia, FJ ;
Santos-Buelga, C .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2001, 49 (03) :1213-1217
[10]   PLANT PROANTHOCYANIDINS .3. CONFORMATIONAL AND CONFIGURATIONAL STUDIES OF NATURAL PROCYANIDINS [J].
FLETCHER, AC ;
PORTER, LJ ;
HASLAM, E ;
GUPTA, RK .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1977, (14) :1628-1637
1234