Two phenolic diterpenes as antioxidants

被引：0

作者：

Cao, H ^{[1
]}

Li, TH

Li, C

Pan, XL

Song, ZR

Xie, XG

机构：

[1] Yunnan Univ, Modern Biol Res Ctr, Kunming 650091, Peoples R China

[2] Yuxi Coll, Dept Chem, Chongqing 402168, Peoples R China

来源：

CHINESE JOURNAL OF STRUCTURAL CHEMISTRY | 2005年 / 24卷 / 02期

关键词：

rosmanol; carnosbl; DFT; antioxidant properties;

D O I：

暂无

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A DFT study was carried out to investigate the structure-activity relationship of rosmanol and camosol. The geometry, HOMO and LUMO of parent molecules, O-H bond dissociation energy (BDE), and distribution of. impaired electron obtained by B3LYP/6-31G* were used to elucidate the antioxidant properties of the two compounds. The results proved the intramolecular hydrogen bond and:delocalization of the unpaired electron to be the important factors affecting the stability of phenoxyl free radical generated after the H-Astraction.

引用

页码：219 / 225

页数：7

共 22 条

[1] ASSESSMENT OF THE IMPORTANCE OF CHANGES IN GROUND-STATE ENERGIES ON THE BOND-DISSOCIATION ENTHALPIES OF THE O-H BONDS IN PHENOLS AND THE S-H BONDS IN THIOPHENOLS [J].

BORDWELL, FG ;

ZHANG, XM ;

SATISH, AV ;

CHENG, JP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (15) :6605-6610

[2] AUTOXIDATION OF BIOLOGICAL MOLECULES .1. THE ANTIOXIDANT ACTIVITY OF VITAMIN-E AND RELATED CHAIN-BREAKING PHENOLIC ANTIOXIDANTS INVITRO [J].

BURTON, GW ;

INGOLD, KU .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (21) :6472-6477

[3]

BURTON GW, 1980, J AM CHEM SOC, V102, P7792

[4] Density functional theory calculations for resveratrol [J].

Cao, H ;

Pan, XL ;

Li, C ;

Zhou, C ;

Deng, FY ;

Li, TH .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2003, 13 (11) :1869-1871

[5] Antioxidant activity of a rosemary extract and its constituents, carnosic acid, carnosol, and rosmarinic acid, in bulk oil and oil-in-water emulsion [J].

Frankel, EN ;

Huang, SW ;

Aeschbach, R ;

Prior, E .

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 1996, 44 (01) :131-135

[6]

FRISH MJ, 2002, GAUSSIAN98 REVISION

[7] INHIBITION OF LIPID-PEROXIDATION AND SUPEROXIDE GENERATION BY DITERPENOIDS FROM ROSMARINUS-OFFICINALIS [J].

HARAGUCHI, H ;

SAITO, T ;

OKAMURA, N ;

YAGI, A .

PLANTA MEDICA, 1995, 61 (04) :333-336

[8] Gas-phase acidities of some neutral Bronsted superacids: A DFT and ab initio study [J].

Koppel, IA ;

Burk, P ;

Koppel, I ;

Leito, I ;

Sonoda, T ;

Mishima, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (21) :5114-5124

[9]

LALIA M, 1993, PHYTOCHEMISTRY, V34, P1493

[10] KINETIC-BEHAVIOR AND THERMOCHEMICAL PROPERTIES OF PHENOXY RADICALS [J].

MAHONEY, LR ;

DAROOGE, MA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (16) :4722-4731

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