Journal
PHYTOCHEMISTRY
Volume 179, Issue -, Pages -Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.phytochem.2020.112393
Keywords
Dihydrochalcones; C-Glycosylation; Radical scavenging activity; Antioxidative mechanism; Density functional theory
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Funding
- Science and Technology Project of Xuzhou [KC18048]
- Foundation for High-Level Talent in Six Areas of Jiangsu Province [2016-YY-038]
- Innovative Practice Training Program for Students of Jiangsu Higher Education Institutions [201910313072Y]
- Priority Academic Program Development of Jiangsu Higher Education Institutions
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Dihydrochalcones (DHCs), an important subgroup of flavonoids, have recently received much attention due to their diverse biological activities. In contrast to their O-glycosides, understanding of the antioxidant property and mechanism of DHC C-glycosides remains limited. Herein, the free radical scavenging activity and mechanism of two representative C-glycosyl DHCs, aspalathin (ASP) and nothofagin (NOT) as well as their aglycones, 3-hydroxyphloretin (HPHL) and phloretin (PHL) were evaluated using the density functional theory (DFT) calculations. The results revealed the crucial role of sugar moiety on the conformation and the activity. The o-dihydroxyl in the B-ring and the 2',6'-dihydroxyacetophenone moiety were found significant in determining the activity. Our results showed that hydrogen atom transfer (HAT) is the dominant mechanism for radical-trapping in the gas and benzene phases, while the sequential proton loss electron transfer (SPLET) is more preferable in the polar environments. Also, the results revealed the feasibility of the double HAT and double SPLET as well as the SPLHAT mechanisms, which provide alternative pathways to trap radical for the studied DHCs. These results could deepen the understanding of the antiradical activity and mechanism of DHCs, which will facilitate the design of novel efficient antioxidants.
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