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- Title
Antioxidant Structure–Activity Relationship Analysis of Five Dihydrochalcones.
- Authors
Li, Xican; Chen, Ban; Xie, Hong; He, Yuhua; Zhong, Dewei; Chen, Dongfeng
- Abstract
The study determined the comparative antioxidant capacities of five similar dihydrochalcones: phloretin, phloridzin, trilobatin, neohesperidin dihydrochalcone, and naringin dihydrochalcone. In the ferric-reducing antioxidant power (FRAP) assay, the antioxidant activities of pairs of dihydrochalcones had the following relationship: phloretin > phloridzin, phloretin > trilobatin, trilobatin > phloridzin, trilobatin > naringin dihydrochalcone, and neohesperidin dihydrochalcone > naringin dihydrochalcone. Similar relative antioxidant levels were also obtained from 1,1-diphenyl-2-picryl-hydrazl radical (DPPH•)-scavenging, 2,2′-azino-bis(3-ethylbenzo-thiazoline-6-sulfonic acid) (ABTS•+)-scavenging, and superoxide radical (•O2−)-scavenging assays. Using ultra-performance liquid chromatography coupled with electrospray ionization quadrupole time-of-flight tandem mass spectrometry (UPLC−ESI−Q−TOF−MS/MS) analysis for the reaction products with DPPH•, phloretin, phloridzin, and trilobatin were found to yield both dihydrochalcone-DPPH adduct and dihydrochalcone-dihydrochalcone dimer, whereas naringin dihydrochalcone gave a naringin dihydrochalcone-DPPH adduct, and neohesperidin dihydrochalcone gave a dimer. In conclusion, the five dihydrochalcones may undergo redox-based reactions (especially electron transfer (ET) and hydrogen atom transfer (HAT)), as well as radical adduct formation, to exert their antioxidant action. Methoxylation at the <italic>ortho</italic>-OH enhances the ET and HAT potential possibly via p-π conjugation, whereas the glycosylation of the –OH group not only reduces the ET and HAT potential but also hinders the ability of radical adduct formation. The 2′,6′-di-OH moiety in dihydrochalcone possesses higher ET and HAT activities than the 2′,4′-di-OH moiety because of its resonance with the adjacent keto group.
- Subjects
DIHYDROCHALCONES; ANTIOXIDANTS; CHINESE medicine; PHLORETIN; HEPATOTOXICOLOGY; ANTIBACTERIAL agents
- Publication
Molecules, 2018, Vol 23, Issue 5, p1162
- ISSN
1420-3049
- Publication type
Article
- DOI
10.3390/molecules23051162