THE INFLUENCE OF THE HOST-GUEST INTERACTION ON THE OXIDATION OF NATURAL FLAVONOID DYES

被引:9
作者
Ramesova, Sarka [1 ]
Sokolova, Romana [1 ]
Degano, Ilaria [2 ]
Hromadova, Magdalena [1 ]
Gal, Miroslav [1 ]
Kolivoska, Viliam [1 ]
Colombini, Maria Perla [2 ]
机构
[1] Acad Sci Czech Republic, J Heyrovsky Inst Phys Chem, Vvi, CR-18223 Prague, Czech Republic
[2] Univ Pisa, Dept Chem & Ind Chem, I-56100 Pisa, Italy
关键词
Oxidation; Inclusion complexes; Protection against oxidation; Flavonoids; Cyclic voltammetry; Natural products; BETA-CYCLODEXTRIN; ELECTROCHEMICAL OXIDATION; INCLUSION COMPLEXES; AQUEOUS-SOLUTION; QUERCETIN; 7-HYDROXYFLAVONE; FLUORESCENCE; DEGRADATION; ANTIOXIDANT; LUTEOLIN;
D O I
10.1135/cccc2011106
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The influence of the molecular cavity protection on degradation processes of bioorganic compounds quercetin and luteolin used as the original dyes in old tapestries was studied. The degradation processes were studied by electrochemical methods in aqueous media. The products of the exhaustive electrolysis were separated and identified by GC-MS analysis. Cyclic voltammetry characteristics indicate that the inclusion complex is formed. The inclusion affects the redox potentials of both oxidation waves related to the different dissociation forms of the flavonoid molecule. It was shown that decomposition products formed by the oxidation of quercetin are stabilized in the cavity of beta-cyclodextrin, including the main oxidation product 2(3',4'-dihydroxybenzoyl)-2,4,6-trihydroxybenzofuran-3(2H)-one. The formation of the 1: 1 inclusion complex of luteolin with beta-cyclodextrin is supported by the enhancement of fluorescence intensity. In the case of quercetin, a decrease of fluorescence intensity occurs when 1: 1 inclusion complex with beta-cyclodextrin is formed.
引用
收藏
页码:1651 / 1667
页数:17
相关论文
共 39 条
[1]   Studies on the interactions between some flavonols and cyclodextrins [J].
Bergonzi, Maria Camilla ;
Bilia, Anna Rita ;
Di Bari, Lorenzo ;
Mazzi, Giovanni ;
Vincieri, Franco Francesco .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2007, 17 (21) :5744-5748
[2]   Flavonol-serum albumin complexation. Two-electron oxidation of flavonols and their complexes with serum albumin [J].
Dangles, O ;
Dufour, C ;
Bret, S .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1999, (04) :737-744
[3]  
DELAPENA AM, 1993, J INCLUS PHENOM MOL, V15, P131
[4]   Flavonoids: Old and new aspects of a class of natural therapeutic drugs [J].
Di Carlo, G ;
Mascolo, N ;
Izzo, AA ;
Capasso, F .
LIFE SCIENCES, 1999, 65 (04) :337-353
[5]  
Eckschlager K., 1991, CHEMOMETRIE
[6]   COMPLEXING BEHAVIOR OF RUTIN AND QUERCETIN [J].
ESCANDAR, GM ;
SALA, LF .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1991, 69 (12) :1994-2001
[7]   Comparison of beta-cyclodextrin effect on polyphenol oxidation catalyzed by purified polyphenol oxidase from different sources [J].
Fayad, N ;
Marchal, L ;
Billaud, C ;
Nicolas, J .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 1997, 45 (07) :2442-2446
[8]   Peroxidative metabolism of apigenin and naringenin versus luteolin and quercetin: Glutathione oxidation and conjugation [J].
Galati, G ;
Moridani, MY ;
Chan, TS ;
O'Brien, PJ .
FREE RADICAL BIOLOGY AND MEDICINE, 2001, 30 (04) :370-382
[9]   ELECTROCHEMISTRY OF CATECHOL-CONTAINING FLAVONOIDS [J].
HENDRICKSON, HP ;
KAUFMAN, AD ;
LUNTE, CE .
JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS, 1994, 12 (03) :325-334
[10]  
Heyrovsky J., 1962, ZAKLADY POLAROGRAFIE, P111