A theoretical study of the structure-radical scavenging activity of trans-resveratrol analogues and cis-resveratrol in gas phase and water environment
A theoretical study of the structure-radical scavenging activity of trans-resveratrol analogues and cis-resveratrol in gas phase and water environment
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DOI：
10.1016/j.ejmech.2009.11.044
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发表时间：
2010-03-01
影响因子：
6.7
通讯作者：
Molski, Marcin
中科院分区：
文献类型：
--
作者：
Mikulski, Damian;Gorniak, Rafal;Molski, Marcin
采用密度泛函理论（DFT）方法研究了反式白藜芦醇（TR）、顺式白藜芦醇（CR）、反式-4，4 '-二羟基二苯乙烯（TRs）的结构与抗氧化活性之间的关系（trans-4，4'-DHS），trans-3，4-dihydroxystilbene（trans-3，4，-DHS），trans-3，4，4'-trihydroxystilbene（反式-3，4，4 '-THS）、反式-3，4，5-三羟基二苯乙烯（反式-3，4，5-THS）和α，β-二氢-3，4'，5-三羟基二苯乙烯（α，β-二氢-3，4 '，5-THS）在气相和水环境中。我们已经表明，所考虑的化合物的反式立体异构体的抗氧化活性与其苯氧基自由基有关，其显示平面和半醌构象，允许通过整个反式二苯乙烯骨架的未成对电子离域。计算结果表明，反式-3，4-DHS、反式-3，4，4 ′-THS、反式-3，4，5-THS和反式-4，4 ′-DHS的抗氧化活性高于TR，而α，β-二氢-3，4 ′，5-THS和CR的抗氧化活性低于TR。我们证明了所有化合物在气相中的供氢能力都比在水介质中的高，因为它们对供电子非常敏感。结果表明，在这两种环境中，氢转移清除自由基的机制比单电子转移更可取。它们与确认所考虑化合物的特定生物活性的实验一致。(C)2009年Elsevier Masson SAS。All rights reserved.
Quantum calculations based on the density functional theory (DFT) have been employed to study the relation between the structure and antioxidant activity of trans-resveratrol (TR), cis-resveratrol (CR), trans-4,4'-dihydroxystilbene (trans-4,4'-DHS), trans-3,4-dihydroxystilbene (trans-3,4,-DHS), trans-3,4,4'-trihydroxystilbene (trans-3,4,4'-THS), trans-3,4,5-trihydroxystilbene (trans-3,4,5-THS) and alpha,beta-dihydro-3,4',5-trihydroxystilbene (alpha,beta-dihydro-3,4',5-THS) in the gas phase and water environment. We have shown that the antioxiclant activity of trans-stereoisomers of the compounds considered is related to their phenoxy radicals showing a planar and semiquinone conformation that allows delocalization of the Unpaired electron through the whole trans-stilbene skeleton. The calculations have revealed that trans-3,4-DHS, trans-3,4,4'-THS, trans-3,4,5-THS and trans-4,4'-DHS exhibit higher antioxiclant activity than TR, while alpha,beta-dihydro-3,4',5-THS and CR are less efficient antioxidants than TR. We have proved that all compounds have higher ability to donate hydrogen atom in the gas phase than in the presence of water medium in which they are very sensitive to electron donation. The results obtained demonstrate that the H-transfer mechanism for scavenging of the free radicals is more preferable than the single-electron transfer in both types of environment. They are consistent with the experiments confirming the specific biological activity of the compounds considered. (C) 2009 Elsevier Masson SAS. All rights reserved.