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Structure-antioxidant capacity relationship of dihydrochalcone compounds in Malus.
- Source :
-
Food Chemistry . Mar2019, Vol. 275, p354-360. 7p. - Publication Year :
- 2019
-
Abstract
- Highlights • Antioxidant capacities of dihydrochalcones were measured using DPPH or ABTS assays. • The 3,4- o -dihydroxyl and 2′-OH were critical for antioxidant activity. • Glycosylation enhanced antioxidant capacity. Abstract The antioxidant capacity (AC) of six dihydrochalcone compounds was evaluated using DPPH and ABTS assays. In water-based solution 3-hydroxyphlorizin exhibited the highest AC among all dihydrochalcones. In acetone and acidic solutions (pH = 2.5 or 2.0), presence of an o -dihydroxyl at the B-ring increased AC, whereas glycosylation at the A-ring decreased AC of dihydrochalcones. By comparing the AC of dihydrochalcones with similar structures, it was found that the o -dihydroxyl at the B-ring and 2′-hydroxyl group at the A-ring were critical for maintaining the AC of dihydrochalcones by promoting hydrogen atom transfer or single electron transfer mechanism. Sequential proton-loss electron transfer commonly occurred during free radical scavenging in water-based solution. Moreover, we report a unique phenomenon in which glycosylation at the 2′-position enhanced the dissociation ability of the 4′-hydroxyl group and increased the AC of dihydrochalcones containing o -dihydroxyl. We speculate that this increase in AC might occur through intramolecular electron transfer. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 03088146
- Volume :
- 275
- Database :
- Academic Search Index
- Journal :
- Food Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 132627680
- Full Text :
- https://doi.org/10.1016/j.foodchem.2018.09.135