基于实验和密度泛函理论研究EGCG与Zn(II)的相互作用

doi:10.3866/PKU.WHXB20111005

物理化学学报 >> 2011, Vol. 27 >> Issue (10): 2291-2296.doi: 10.3866/PKU.WHXB20111005

基于实验和密度泛函理论研究EGCG与Zn(II)的相互作用

江腾, 马万福, 谢楠, 周平

复旦大学高分子科学系, 聚合物分子工程教育部重点实验室, 上海 200433

收稿日期:2011-05-30 修回日期:2011-07-04 发布日期:2011-09-27
通讯作者: 周平 E-mail:pingzhou@fudan.edu.cn
基金资助:
国家自然科学基金(10475017, 20673022, 21074025)及复旦大学本科生学术研究计划(08007)资助项目

Study on the Interaction of EGCG with Zn(II) Based on Experiments and Density Functional Theory

JIANG Teng, MA Wan-Fu, XIE Nan, ZHOU Ping

Key Laboratory of Molecular Engineering of Polymers, Ministry of Education, Department of Macromolecular Science, Fudan University, Shanghai 200433, P. R. China

Received:2011-05-30 Revised:2011-07-04 Published:2011-09-27
Contact: ZHOU Ping E-mail:pingzhou@fudan.edu.cn
Supported by:
The project was supported by the National Natural Science Foundation of China (10475017, 20673022, 21074025) and Fudan's Undergraduate Research Opportunities Program, China (08007).

摘要/Abstract

摘要： 用紫外-可见(UV-Vis)吸收光谱和¹H核磁共振(NMR)谱研究了茶多酚类衍生物表没食子儿茶素没食子酸酯(EGCG)与Zn(II)离子的相互作用, 并用密度泛函理论(DFT)计算了EGCG与Zn(II)离子络合前后的空间结构及其紫外和核磁共振谱. 实验与理论研究结果表明: EGCG主要构象是其芳香B环以e 键(平伏键)及芳香D环以a 键(直立键)形式共同与C环链接. EGCG通过其芳香D环上酚羟基与Zn(II)离子相互作用, 生成稳定的Zn(II)与EGCG摩尔比为1:1的Zn(II)-EGCG四面体络合物.

关键词: 密度泛函理论, 络合物, 表没食子儿茶素没食子酸酯, Zn(II)

Abstract: The interaction between the tea polyphenols derivative (-)-epigallocatechin-3-gallate (EGCG) and Zn(II) was investigated by ultraviolet visible (UV-Vis) spectroscopy and liquid-state ¹H nuclear magnetic resonance (NMR). In addition, density functional theory (DFT)-based UV and chemical shifts were calculated to view insight into the complex structure and property. The main conformer of EGCG is an aromatic B-ring in an e-bond (equatorial bond) and an aromatic D-ring in an a-bond (axial bond) and these are linked to the C-ring. In addition, the Zn(II) ion can coordinate with the phenolic hydroxyl groups in the D-ring and form a steady tetrahedral Zn(II)-EGCG complex in a 1:1 molar ratio.

Key words: Density functional theory, Complex, (-)-Epigallocatechin-3-gallate, Zn(II)

MSC2000:

O641

江腾, 马万福, 谢楠, 周平. 基于实验和密度泛函理论研究EGCG与Zn(II)的相互作用[J]. 物理化学学报, 2011, 27(10): 2291-2296.

JIANG Teng, MA Wan-Fu, XIE Nan, ZHOU Ping. Study on the Interaction of EGCG with Zn(II) Based on Experiments and Density Functional Theory[J]. Acta Phys. -Chim. Sin., 2011, 27(10): 2291-2296.

参考文献

(1) Selkoe, D. J. Physiol. Rev. 2001, 81, 741.
(2) Gupta, V. B.; Anitha, S.; Hegde, M. L.; Zecca, L.; Garruto, R. M.; Ravid, R.; Shankar, S. K.; Stein, R.; Shanmugavelu, P.; Rao, K. S. J. Cell. Mol. Life Sci. 2005, 62, 143.

(3) Barrow, C. J.; Zagorski, M. G. Science 1991, 253, 179.

(4) Etcheberrigaray, R.; Ito, E.; Kim, C. S.; Alkon, D. L. Science 1994, 264, 276.

(5) Masters, C. L.; Simms, G.;Weinman, N. A.; Multhaup, G.; Mcdonald, B. L.; Beyreuther, K. Proc. Natl. Acad. Sci. U. S. A. 1985, 82, 4245.

(6) Multhaup, G.; Schlicksupp, A.; Hesse, L.; Beher, D.; Ruppert, T.; Masters, C. L.; Beyreuther, K. Science 1996, 271, 1406.

(7) Kawahara, M.; Muramoto, K.; Kobayashi, K.; Mori, H.; Kuroda, Y. Biochem. Biophys. Res. Commun. 1994, 198, 531
(8) Lovell, M. A.; Robertson, J. D.; Teesdale,W. J.; Campbell, J. L.; Markesbery,W. R. J. Neurol. Sci. 1998, 158, 47.

(9) Mantyh, P.W.; Ghilardi, J. R.; Rogers, S.; Demaster, E.; Allen, C. J.; Stimson, E. R.; Maggio, J. E. J. Neurochem. 1993, 61, 1171.

(10) Cuajungco, M. P.; Faget, K. Y. Brain Res. Rev. 2003, 41, 44.

(11) Yang, D. S.; McLaurin, J.; Qin, K. F.;Westaway, D.; Fraser, P. E. Eur. J. Biochem. 2000, 267, 6692.
(12) Domingo, J. L. J. Alzheimers Dis. 2006, 10, 331.
(13) Rodriguez-Rodriguez, C.; de Groot, N. S.; Rimola, A.; Alvarez- Larena, A.; Lloveras, V.; Vidal-Gancedo, J.; Ventura, S.; Vendrell, J.; Sodupe, M.; Gonzalez-Duarte, P. J. Am. Chem. Soc. 2009, 131, 1436.

(14) Hindo, S. S.; Mancino, A. M.; Braymer, J. J.; Liu, Y. H.; Vivekanandan, S.; Ramamoorthy, A.; Lim, M. H. J. Am. Chem. Soc. 2009, 131, 16663.

(15) Zatta, P.; Tognon, G.; Carampin, P. J. Pineal. Res. 2003, 35, 98.

(16) Yoon, I.; Lee, K. H.; Cho, J. S. Arch. Pharmacal Res. 2004, 27, 454.

(17) Baum, L.; Ng, A. J. Alzheimers Dis. 2004, 6, 367.
(18) Tan, E. K.; Tan, C.; Fook-Chong, S. M. C.; Lum, S. Y.; Chai, A.; Chung, H.; Shen, H.; Zhao, Y.; Teoh, M. L.; Yih, Y.; Pavanni, R.; Chandran, V. R.;Wong, M. C. J. Neurol. Sci. 2003, 216, 163.

(19) Orgogozo, J. M.; Dartigues, J. F.; Lafont, S.; Letenneur, L.; Commenges, D.; Salamon, R.; Renaud, S.; Breteler, M. Rev. Neurol-France 1997, 153, 185.
(20) Rechner, A. R.; Kuhnle, G.; Bremner, P.; Hubbard, G. P.; Moore, K. P.; Rice-Evans, C. A. Free Radical Biol. Med. 2002, 33, 220.

(21) Abd El Mohsen, M. M.; Kuhnle, G.; Rechner, A. R.; Schroeter, H.; Rose, S.; Jenner, P.; Rice-Evans, C. A. Free Radical Biol. Med. 2002, 33, 1693.

(22) Khokhar, S.; Magnusdottir, S. G. M. J. Agric. Food Chem. 2002, 50, 565.

(23) Nanjo, F.; Mori, M.; Goto, K.; Hara, Y. Biosci. Biotechnol. Biochem. 1999, 63, 1621.

(24) Pannala, A.; RiceEvans, C. A.; Halliwell, B.; Singh, S. Biochem. Biophys. Res. Commun. 1997, 232, 164.

(25) Nanjo, F.; Goto, K.; Seto, R.; Suzuki, M.; Sakai, M.; Hara, Y. Free Radical Biol. Med. 1996, 21, 895.

(26) Elhabiri, M.; Carrer, C.; Marmolle, F.; Traboulsi, H. Inorg. Chim Acta. 2007, 360, 353.

(27) Inoue, M. B.; Inoue, M.; Fernando, Q.; Valcic, S.; Timmermann, B. N. J. Inorg. Biochem. 2002, 88, 7.

(28) Chen, Y. M.;Wang, M. K.; Huang, P. M. J. Agric. Food Chem. 2006, 54, 212.

(29) Zaveri, N. T. Life Sci. 2006, 78, 2073.

(30) Weinreb, O.; Mandel, S.; Amit, T.; Youdim, M. B. H. J. Nutr. Biochem. 2004, 15, 506.

(31) Bodini, M. E.; del Valle, M. A.; Tapia, R.; Leighton, F.; Berrios, P. Polyhedron 2001, 20, 1005.

(32) Frisch, M. J.; Trucks, G.W.; Schlegel, H. B.; et al. Gaussian 03, Revision B.05; Gaussian, Inc.:Wallingford, CT, 2004.
(33) Becke, A. D. J. Chem. Phys. 1993, 98, 5648.

(34) Lee, C. T.; Yang,W. T.; Parr, R. G. Phys. Rev. B 1988, 37, 785.

(35) Zhou, P.; Li, G. Y.; Shao, Z. Z.; Pan, X. Y.; Yu, T. Y. J. Phys. Chem. B 2001, 105, 12469.

(36) Crescenzi, O.; Pavone, M.; De Angelis, F.; Barone, V. J. Phys. Chem. B 2005, 109, 445.

(37) Preat, J.; Jacquemin, D.;Wathelet, V.; Andre, J. M.; Perpete, E. A. J. Phys. Chem. A 2006, 110, 8144.

(38) Chen, H. J.; Xie, S. A.; Zhang,W. Inorganic and Analytical Chemistry. Science Press: Beijiang. 2002; p 400.
[陈虹锦, 谢少艾, 张卫. 无机与分析化学. 北京: 科学出版社, 2002; p 400.]
(39) Xue, S. Organic Structure Analysis. Press of University of Science and Technology of China: Hefei, 2005; p 342.
[薛松. 有机结构分析. 合肥: 中国科学技术大学出版社, 2005; p 342.]

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基于实验和密度泛函理论研究EGCG与Zn(II)的相互作用

Study on the Interaction of EGCG with Zn(II) Based on Experiments and Density Functional Theory

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