Radical Scavenging Mechanisms of Phenolic Compounds: A Quantitative Structure-Property Relationship (QSPR) Study

Melanie Platzer, Sandra Kiese, Thorsten Tybussek, Thomas Herfellner, Franziska Schneider, Ute Schweiggert-Weisz, Peter Eisner

Research output: Contribution to journalArticlepeer-review

108 Scopus citations

Abstract

Due to their antioxidant properties, secondary plant metabolites can scavenge free radicals such as reactive oxygen species and protect foods from oxidation processes. Our aim was to study structural influences, like basic structure, number of hydroxyl groups and number of Bors criteria on the outcome of the oxygen radical absorbance capacity (ORAC) assay. Furthermore, similarities and differences to other in vitro antioxidant assays were analyzed by principal component analysis. Our studies confirmed that the antioxidant behavior in the ORAC assay is dominated by the number and types of substituents and not by the Bors criteria, as long as no steric hindrance occurs. For example, morin (MOR) with five hydroxyl groups and two Bors criteria reached an area under the curve of (3.64 ± 0.08) × 105, which was significantly higher than quercetin-7-D-glucoside (QGU7) (P < 0.001), and thus the highest result. Principal component analysis showed different dependencies regarding structural properties of Folin-Ciocalteu (FC)- and 2,2-diphenyl-1-picrylhydrazyl (DPPH)-assays or 2,2'-azino-bis (3-ethylbenzothiazoline-6-sulfonic acid) (ABTS)- and ORAC-assays, respectively. Therefore, we conclude that they are based on different reaction mechanisms. The number of hydroxyl groups showed a stronger influence on the antioxidant activity than the Bors criteria. Due to these differences, the correlation of these rapid tests to specific applications should be validated.

Original languageEnglish
Article number882458
JournalFrontiers in Nutrition
Volume9
DOIs
StatePublished - 4 Apr 2022
Externally publishedYes

Keywords

  • antioxidant effect
  • area under the curve
  • flavonoids
  • phenolic acids
  • structure-activity relationship

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