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

• Published in: Monatshefte 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
• Language: English
• 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
• ISSN: 0026-9247; 1434-4475
• DOI: 10.1007/s00706-016-1737-3

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.
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