Free Radical Scavenging Properties of Guaiacol Oligomers: A Combined Experimental and Quantum Study of the Guaiacyl-Moiety Role

被引：83

作者：

Anouar, E. ^{[2
]}

Calliste, C. A.

Kosinova, P.

Di Meo, F.

Duroux, J. L.

Champavier, Y. ^{[3
]}

Marakchi, K. ^{[2
]}

Trouillas, P. ^{[1
]}

机构：

[1] Univ Limoges, Biophys Lab, EA 4021, Fac Pharm, F-87025 Limoges, France

[2] Univ Mohammed 5, Chim Theor Lab, Fac Sci, Rabat, Morocco

[3] Univ Limoges, Serv Commun RMN, F-87025 Limoges, France

来源：

JOURNAL OF PHYSICAL CHEMISTRY A | 2009年 / 113卷 / 50期

关键词：

ANTIOXIDANT ACTIVITY; TAXIFOLIN ANTIOXIDANTS; GAS-PHASE; O-H; MECHANISM; HYDROGEN; SPECIFICITY; FLAVONOIDS; REACTIVITY; QUERCETIN;

D O I：

10.1021/jp906285b

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070305 [高分子化学与物理];

摘要：

Natural polyphenols are known to exhibit a lot of different biological properties, including antioxidant activity. For some polyphenols these activities ire attributed to the presence of a guaiacol moiety. In the present paper we focus oil the role of this moiety For this purpose nine different compounds were enzymatically synthesized from guaiacol To elucidate the structure-activity relationship of these polyphenols, DFT-(PCM)B3P86/6-311+G(2d,3pd)//(PCM)B3P86/6-31+G(d,p) Calculations Supported the experimental DPPH free radical scavenging activities. The antioxidant activities were correlated to (i) O-H BDEs (bond dissociation enthalpies), (ii) BDED (BDE of a second H atom abstraction from the phenoxyradicals), (iii) spin density, (iv) HOMO (highest Occupied molecular orbital) distribution, (v) IPs (Ionization potentials), (vi) Delta G and Delta G(#) free energies of HAT (H atom transfer), and (vii) HAT rate constants. BDED appeared to be the most important descriptor to understand file free radical scavenging ability of these compounds.

引用

页码：13881 / 13891

页数：11

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