Decomposition of Flavonols in the Presence of Saliva

Abstract

In this study, the LC-MS/MS was applied to explore the stability of four common dietary flavonols, kaempferol, quercetin, isorhamnetin, and myricetin, in the presence of hydrogen peroxide and saliva. In addition, the influence of saliva on the representative quercetin glycosides, rutin, quercitrin, hyperoside, and spiraeoside was examined. Our study showed that, regardless of the oxidative agent used, flavonols stability decreases with increasing B-ring substitution. The decomposition of analyzed compounds was based on their splitting by the opening the heterocyclic C-ring and realizing more simple aromatic compounds. The dead-end products corresponded to different benzoic acid derivatives derived from B-ring. Kaempferol, quercetin, isorhamnetin, and myricetin were transformed into 4-hydroxybeznoic acid, protocatechuic acid, vanillic acid, and gallic acid, respectively. Additionally, for quercetin and myricetin, two intermediate depsides and 2,4,6-trihydroxybenzoic acid derived from A-ring were detected. All analyzed glycosides were resistant to hydrolysis in the presence of saliva. Based on our data, saliva was proven to be a next oxidative agent which leads to the formation of corresponding phenolic acids. Hence, studies on flavonols’ metabolism should take into consideration that the flavonols decomposition starts in the oral cavity; hence, in subsequent parts of the human digestive tract, they could be present not in their parent form but as phenolic acids. Further analyses of the influence of saliva on flavonols glycosides need to be performed due to the possible interindividual fluctuations.

Keywords

• flavonols
• H₂O₂
• saliva
• metabolism
• oxidation
• LC-MS/MS