DFT insights into the structure, reactivity and radical scavenging activity of cycloartocarpesin

Daily increase in the number of patients suffering from illnesses due to reactive species has induced the permanent discovery and study of antioxidant compounds. The structure, reactivity, and antioxidant activity (AOA) of a phenolic compound named cycloartocarpesin (CAP), evaluated at DFT/B3LYP/6‐3...

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Bibliographic Details
Published in:Journal of physical organic chemistry 2021-09, Vol.34 (9), p.n/a
Main Authors: Tamafo Fouegue, Aymard Didier, Tedongmo, Hilaire, Abdoul Ntieche, Rahman, Ghogomu, Julius Numbonui
Format: Article
Language:English
Subjects:
antioxidant activity
Antioxidants
cycloartocarpesin
DFT
Electron transfer
Electronic spectra
Hydrogen bonds
Phenols
Scavenging
UV‐filtration properties
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Summary:Daily increase in the number of patients suffering from illnesses due to reactive species has induced the permanent discovery and study of antioxidant compounds. The structure, reactivity, and antioxidant activity (AOA) of a phenolic compound named cycloartocarpesin (CAP), evaluated at DFT/B3LYP/6‐31 + G(d,p) level, is reported herein in the gas, pentyl ethanoate, and water phases. Bader topological analysis revealed that two of the three O‐H groups of CAP are involved in hydrogen bonds while the average local ionization energy (ALIE) and appropriate Fukui functions showed that electrons in the near vicinity of C7, C10, and C12 are the least tightly held and can easily be attacked by radicals. Analysis of the transition state of the reaction between CAP and HOO• radical shows that the proton coupled electron transfer process is not favored. Moreover, analyses of electronic spectra calculated at TD‐DFT/B3LYP/6‐31 + G(d,p) has interestingly demonstrate the ability of CAP to filtrate UVA, UVB, and UVC, thus exhibiting a photo‐protective activity. DFT/B3LYP/6‐31+G(d,p) and DFT/M052x/6‐31+G(d,p) methods revealed that cycloartocarpesin (CAP) in neutral and anionic forms can scavenge the HOO• radical in physiological conditions. Moreover, CAP is found to filtrate all types of UV radiations, making it a promising candidate for cosmetic industry.
ISSN:0894-3230
1099-1395
DOI:10.1002/poc.4245