On the difference in decomposition of taxifolin and luteolin vs. fisetin and quercetin in aqueous media

The decomposition of flavonols quercetin and fisetin, flavone luteolin and flavanone taxifolin was studied in slightly alkaline solution under ambient conditions. The study was based on spectrophotometry and high-pressure liquid chromatography. Products formed by atmospheric oxygen oxidation and hyd...

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Bibliographic Details
Published inMonatshefte für Chemie Vol. 147; no. 8; pp. 1375 - 1383
Main Authors Sokolová, Romana, Ramešová, Šárka, Kocábová, Jana, Kolivoška, Viliam, Degano, Ilaria, Pitzalis, Emanuela
Format Journal Article
LanguageEnglish
Published Vienna Springer Vienna 01.08.2016
Subjects
Analytical Chemistry
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
Inorganic Chemistry
Organic Chemistry
Original Paper
Physical Chemistry
Theoretical and Computational Chemistry
Fisetin
Taxifolin
Luteolin
Oxidation mechanism
Quercetin
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Summary:The decomposition of flavonols quercetin and fisetin, flavone luteolin and flavanone taxifolin was studied in slightly alkaline solution under ambient conditions. The study was based on spectrophotometry and high-pressure liquid chromatography. Products formed by atmospheric oxygen oxidation and hydrolysis were identified by HPLC–DAD and HPLC–ESI-MS/MS. Only small differences in the chemical structure of flavonoids resulted in extremely variable oxidation pathways and products. Oxidation of flavonols led to the formation of both a benzofuranone derivative and several open structures. On the contrary, the benzofuranone derivative was not found as a product of taxifolin and luteolin oxidative decomposition. These compounds were oxidized to their hydroxylated derivatives and typical open structures. Quercetin was not identified as a possible oxidation product of taxifolin. Graphical Abstract
ISSN:0026-9247
1434-4475
DOI:10.1007/s00706-016-1737-3