Home
Resources
Publications
Antioxidant Structure⁻Activity Relationship Analysis of Five Dihydrochalcones

Antioxidant Structure⁻Activity Relationship Analysis of Five Dihydrochalcones

Xican Li, Ban Chen, Hong Xie, Yuhua He, Dewei Zhong, Dongfeng Chen

Molecules. 2018 May 12;23(5):1162.

PMID: 29757201

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 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.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP18916171	Naringin dihydrochalcone		18916-17-1	Price

As a specialist in analytical chemical Products, Alfa Chemistry offers consumers a wealth of raw materials and a full range of technologies and services.

QUICK LINKS

HEADQUARTERS

Tel:

Fax:

Email: