科研之友
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摘要
A computational analysis of UV filtering and radical scavenging capacity of a flavanone, Eriodictyol has been performed under DFT-B3LYP/6-31 + G (d, p). Eriodictyol is nontoxic and nonirritant bitter masker commonly used in the wine industry. It has been reported that the flavanones were widely acceptable for photoprotection due to its potential UV filtering and radical scavenging capacity. This study provides theoretical evidence that the eriodictyol has an absorbance in the UV-A and UV-B region of the electromagnetic spectrum and therefore can be used as a potential UV filter in sunscreen lotions and other cosmetic products. The major transitions in the UV-Visible spectrum of Eriodictyol are between HOMO and HOMO-1 with LUMO level and are well explained by NBO-NLMO tool in G09 software. In addition to this, Eriodictyol is a potent antioxidant than that of the most commonly studied Quercetin. The most active site in the compound is 3' position and is confirmed by NPA, NBO and pKa value analysis. The lowest energy conformer of Eriodictyol contains a Hydrogen bond between carbonyl oxygen (O2) and H30. This is confirmed by the highest value of interaction energy between lone pairs of O2 and sigma* of O3- H30. Both the two lone pairs of O2 interacts with the sigma* of O3- H30. This decreases the bond order of 5-OH and at the same time it restricts the hydrogen transfer from this position to form a radical. Similarly, the lone pair of O5 (3' position) interacts with H33 resulting in the low bond order value and consequently less favorable for radical formation. These results indicate that the BDE values follow the order 3' < 4' < 7 < 5. Thus the title compound can be used for photo protection due to its potential UV filtering and radical scavenging capacity.
- 出版日期2018-8
