Free radical scavenging potency of ellagic acid and its derivatives in multiple H
Antioxidant activity
Density functional theory
Ellagic acid
Ellagic acid derivatives
Multiple H(+)/e(‒) processes
Journal
Phytochemistry
ISSN: 1873-3700
Titre abrégé: Phytochemistry
Pays: England
ID NLM: 0151434
Informations de publication
Date de publication:
Dec 2020
Dec 2020
Historique:
received:
10
06
2020
revised:
16
07
2020
accepted:
07
09
2020
pubmed:
21
9
2020
medline:
24
11
2020
entrez:
20
9
2020
Statut:
ppublish
Résumé
The reaction energetics of the multiple free radical scavenging mechanisms of ellagic acid and its derivatives were studied by DFT method. Ellagic acid and its derivatives that bear catechol or guaiacyl moieties can proceed multiple free radical scavenging processes. Intramolecular hydrogen-bonds were found in the most stable geometries of the investigated compounds and can influence the antioxidant activity of the related groups and hydrogen atom/proton loss sequence. The stronger hydrogen-bond, the weaker antioxidant activity of the hydrogen atom/proton-donating group. The preferred mechanisms vary among different phases. All of the investigated compounds prefer to trap free radicals by multiple HAT mechanisms in gas and benzene phases. The second HAT reaction preferably occurs in the same catechol or guaiacyl unit of the first HAT group with the formation of stable quinone or benzodioxole. The catechol and guaiacyl moieties not only retain high free radical scavenging ability of the parent compounds but even show increased potency for the second and fourth H
Identifiants
pubmed: 32950773
pii: S0031-9422(20)30698-1
doi: 10.1016/j.phytochem.2020.112517
pii:
doi:
Substances chimiques
Antioxidants
0
Free Radical Scavengers
0
Free Radicals
0
Protons
0
Ellagic Acid
19YRN3ZS9P
Hydrogen
7YNJ3PO35Z
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
112517Informations de copyright
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