| Theoretical Study on the Antioxidant Activity of Curcumin |
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| 作者姓名： | 孙友敏 王若曦 苑世领 林宪杰 刘成卜 |
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| 作者单位： | [1]InstituteofTheoreticalChemistry,ShandongUniversity,Jinan,Shandong250100,China [2]ShandongPublicSecurityCollege,Jinan,Shandong250014,China |
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| 基金项目： | Project supported by the National Natural Science Foundations of China (Nos. 20373033 and 20303011). |
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| 摘 要： | The computational results for curcumin at the B3LYP/6-31G(d,p) level show that the enol form of curcumin is more stable than the diketo form because of an intramolecular hydrogen bond, which extends the conjugation effect in the enol chain, formed in the enol structure. Cis-diketone form can not be obtained, presumably due to the strong repulsion between the carbonyl dipoles aligned in parallel. According to the phenolic O-H bond dissociation enthalpy, curcumin in its most stable form can be suggested to be a relatively good antioxidant. In order to avoid overcoming H-bond interaction and to improve the antioxidant activity of curcumin, a catechol moiety was incorporated into curcumin for designing a novel antioxidant. It is found that the designed molecule is much more efficient to scavenge radical than curcumin, comparable to vitamin E. Moreover, the ionization potential of the designed molecule is similar to that of curcumin, indicating that the designed molecule can not display the prooxidant effect.
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| 关 键 词： | 姜黄色素 抗氧化活性 密度泛函 氧-氢键离解焓 氢键 电位势 烯醇 |
Theoretical Study on the Antioxidant Activity of Curcumin |
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| SUN,You-MinaWANG,Ruo-Xib YUAN,Shi-Linga LIN,Xian-Jie LIU,Cheng-Bu,a Institute of Theoretical Chemistry,Shandong University,Jinan,Shandong ,China bShandong Public Security College,Jinan,Shandong ,China.Theoretical Study on the Antioxidant Activity of Curcumin[J].Chinese Journal of Chemistry,2004,22(8):827-830. |
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| Authors: | SUN You-MinaWANG Ruo-Xib YUAN Shi-Linga LIN Xian-Jie LIU Cheng-Bu a Institute of Theoretical Chemistry Shandong University Jinan Shandong China bShandong Public Security College Jinan Shandong China |
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| Institution: | SUN,You-MinaWANG,Ruo-Xib YUAN,Shi-Linga LIN,Xian-Jie LIU,Cheng-Bu*,a Institute of Theoretical Chemistry,Shandong University,Jinan,Shandong 250100,China bShandong Public Security College,Jinan,Shandong 250014,China |
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| Abstract: | The computational results for curcumin at the B3LYP/6‐31G(d,p) level show that the enol form of curcumin is more stable than the diketo form because of an intramolecular hydrogen bond, which extends the conjugation effect in the enol chain, formed in the enol structure. Cis‐diketone form can not be obtained, presumably due to the strong repulsion between the carbonyl dipoles aligned h parallel. According to the phenolic O? H bond dissociation enthalpy, curcumin in its most stable form can be suggested to be a relatively good antioxidant. In order to avoid overcoming H‐bond interaction and to improve the antioxidant activity of curcumin, a catechol moiety was incorporated into curcumin for designing a novel antioxidant. It is found that the designed molecule is much more efficient to scavenge radical than curcumin, comparable to vitamin E. Moreover, the ionization potential of the designed molecule is similar to that of curcumin, indicating that the designed molecule can not display the prooxidant effect. |
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| Keywords: | Curcumin density functional theory O?H bond dissociation enthalpy ionization potential antioxidant activity |
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