TY - JOUR
T1 - Radical Scavenging Mechanisms of Phenolic Compounds
T2 - A Quantitative Structure-Property Relationship (QSPR) Study
AU - Platzer, Melanie
AU - Kiese, Sandra
AU - Tybussek, Thorsten
AU - Herfellner, Thomas
AU - Schneider, Franziska
AU - Schweiggert-Weisz, Ute
AU - Eisner, Peter
N1 - Publisher Copyright:
Copyright © 2022 Platzer, Kiese, Tybussek, Herfellner, Schneider, Schweiggert-Weisz and Eisner.
PY - 2022/4/4
Y1 - 2022/4/4
N2 - 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.
AB - 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.
KW - antioxidant effect
KW - area under the curve
KW - flavonoids
KW - phenolic acids
KW - structure-activity relationship
UR - http://www.scopus.com/inward/record.url?scp=85128556411&partnerID=8YFLogxK
U2 - 10.3389/fnut.2022.882458
DO - 10.3389/fnut.2022.882458
M3 - Article
AN - SCOPUS:85128556411
SN - 2296-861X
VL - 9
JO - Frontiers in Nutrition
JF - Frontiers in Nutrition
M1 - 882458
ER -