Antioxidant Structure–Activity Relationship Analysis of Five Dihydrochalcones
AbstractThe 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 ortho-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. View Full-Text
- Supplementary File 1:
ZIP-Document (ZIP, 1360 KB)
Share & Cite This Article
Li, X.; Chen, B.; Xie, H.; He, Y.; Zhong, D.; Chen, D. Antioxidant Structure–Activity Relationship Analysis of Five Dihydrochalcones. Molecules 2018, 23, 1162.
Li X, Chen B, Xie H, He Y, Zhong D, Chen D. Antioxidant Structure–Activity Relationship Analysis of Five Dihydrochalcones. Molecules. 2018; 23(5):1162.Chicago/Turabian Style
Li, Xican; Chen, Ban; Xie, Hong; He, Yuhua; Zhong, Dewei; Chen, Dongfeng. 2018. "Antioxidant Structure–Activity Relationship Analysis of Five Dihydrochalcones." Molecules 23, no. 5: 1162.
Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.