Calculation and analysis of interaction between characteristic functional group of persimmon tannin and metal ions

Liu Zhi-Gao; Chen Tao; Hu Chao-Hao; Wang Dian-Hui; Wang Zhong-Min; Li Gui-Yin

doi:10.7498/aps.70.20201947

Abstract

Persimmon tannin has excellent adsorption efficiency of heavy metal ions, and epigallocatechin gallate (EGCG) is the key structural monomer of persimmon tannin to play its active role. In order to analyze the nature of the interaction between persimmon tannin and metal ions, in this paper the density functional theory (DFT) is used to calculate and analyze the interactions between EGCG and metal ions (Ag⁺, Hg²⁺, Cu²⁺, Fe²⁺, In³⁺, Al³⁺, Au³⁺), from the respects of EGCG-metal complex configuration, Mayer bond order, natural population analysis, binding energy, and weak interaction. In this paper, the B3LYP combined with DFT-D3 dispersion correction method is mainly used. For metal atoms, the Lanl2dz basis set is adopted. For H, C and O atoms, the 6-311G (d, p) basis set is adopted for optimizing the structure, and the more accurate 6-311+G (d, p) basis set is selected for calculating the single point energy. At the same time, the study adds the SMD solvation model with water as the solvent. All calculations are done by using the Gaussian 09 package. The method of reduced density gradient function is used to study the weak interactions between EGCG and metal ions. The results of research show that EGCG-Fe²⁺ complex is adsorbed mainly by chelating bond. However, the EGCG adsorbs mainly Ag⁺, Hg²⁺ ions through electrostatic attraction. The configurations of the complexes show that In³⁺, Al³⁺ and Au³⁺ ions with EGCG form unique “luminal structure” metal complexes, so there is not only electrostatic attraction, but also aromatic ring stacking between these three metal ions and D ring 4"O, 5"O. The calculated Mayer bond order indicates that the bond order of the composite bond is formed by Fe²⁺ ion and the EGCG is the largest in the seven metal complexes, and the bond order is formed by In³⁺ ion, and EGCG is smallest. The compound of Cu²⁺ ion and EGCG have chelation, electrostatic attraction and aromatic ring stacking. By observing the binding energy, it can be found that the more charges the metal ions have, the easier the charge transfer will be and the stronger the electrostatic attraction of EGCG may be. These results will provide enlightenment for further studying the mechanism of persimmon tannin's adsorption of metal ions.

Keywords:

Authors and contacts

1.
School of Materials Science and Engineering, Guilin University of Electronic Technology, Guilin 541004, China
2.
School of Electronic Engineering and Automation, Guilin University of Electronic Technology, Guilin 541004, China
3.
School of Life and Environment Sciences, Guilin University of Electronic Technology, Guilin 541004, China

Corresponding author: Wang Zhong-Min, zmwang@guet.edu.cn ; Li Gui-Yin, liguiyin01@guet.edu.cn

Funds: Project supported by the National Natural Science Foundation of China (Grant No. 51961010) and the Guangxi Key Research and Development Program, China (Grant Nos. Guike2018AB38016, GuikeAB18281013, GuikeAB16380278)

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References

[1]	Matheus J R V, Andrade C J D, Miyahira R F, Fai A E C 2020 Food Rev. Int.Google Scholar
[2]	Elhabiri M, Carrer C, Marmolle F, Traboulsi H 2007 Inorg. Chim. Acta 360 353 Google Scholar
[3]	Chen Y M, Wang M K, Huang P M 2006 J. Agric. Food Chem. 54 212 Google Scholar
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[9]	Gurung M, Adhikari B B, Morisada S, Kawakita H, Ohto K, Inoue K, Alam S 2013 Bioresource Technol. 129 108 Google Scholar
[10]	Yi Q, Fan R, Xie F, Zhang Q, Luo Z 2016 J. Taiwan Inst. Chem. Eng. 61 299 Google Scholar
[11]	Li C M, Leverence R, Trombley J D, Xu S, Yang J, Tian Y, Reed J D 2010 J. Agric. Food Chem. 58 9033 Google Scholar
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[16]	Malgorzata B, Pawel P, Giovanni S, Julien B, Vincenzo B 2010 J. Chem. Theory Comput. 6 2115 Google Scholar
[17]	Jonathon W, Matthew G, Jeffrey B N, Martin H 2015 J. Chem. Theory Comput. 11 1481 Google Scholar
[18]	Becke A D 1988 Phys. Rev. A 38 3098 Google Scholar
[19]	Lee C, Yang W, Parr R G 1988 Phys. Rev. B 37 785 Google Scholar
[20]	Bougherara H, Kadri R, Kadri M, Yekhlef M, Boumaza A 2021 J. Mol. Struct. 1223 128855 Google Scholar
[21]	Viji A, Revathi B, Balachandran V, Babiyana S, Narayana B, Salian V V 2020 Chem.l Data Collections 30 100585 Google Scholar
[22]	Goerigk L, Grimme S 2011 Phys. Chem. Chem. Phys. 13 6670 Google Scholar
[23]	Frisch M J, Trucks G W, Schlegel H B, et al. 2009 Gaussian 09 (Rev. A.02). (Gaussian: Inc., Wallingford CT)
[24]	Johnson E R, Kernan S, Mori-Sanchez P, Contreras-Garcia J, Cohen A J, Yang W T 2010 J. Am. Chem. Soc. 132 6498 Google Scholar
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图 1 柿单宁末端结构四种单体结构示意图　(a) 表儿茶素; (b) 表没食子儿茶素; (c) 表儿茶素没食子酸酯; (d) 表没食子儿茶素没食子酸酯

Figure 1. Structures of four monomers in the terminal structure of persimmon tannin: (a) EC; (b) EGC; (c) ECG; (d) EGCG.

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图 2 (a) EGCG结构图; (b) EGCG-金属复合物结构模型图

Figure 2. (a) Structure of EGCG; (b) structure model diagram of EGCG-metal complex.

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图 3 EGCG-金属复合物的几何构型图　(a) EGCG-Ag⁺; (b) EGCG-Hg²⁺; (c) EGCG-Cu²⁺; (d) EGCG-Fe²⁺; (e) EGCG-In³⁺; (f) EGCG-Al³⁺; (g) EGCG-Au³⁺

Figure 3. Geometric diagrams of EGCG-metal complexes: (a) EGCG-Ag⁺; (b) EGCG-Hg²⁺; (c) EGCG-Cu²⁺; (d) EGCG-Fe²⁺; (e) EGCG-In³⁺; (f) EGCG-Al³⁺; (g) EGCG-Au³⁺.

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图 4 EGCG-金属复合物的结合能

Figure 4. Binding energies of EGCG-metal complexes.

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图 5 EGCG-金属复合物的RDG函数等值面图　(a) EGCG-Ag⁺; (b) EGCG-Hg²⁺; (c) EGCG-Cu²⁺; (d) EGCG-Fe²⁺; (e) EGCG-In³⁺; (f) EGCG-Al³⁺; (g) EGCG-Au³⁺

Figure 5. RDG function isosurface diagrams of EGCG-metal complexes: (a) EGCG-Ag⁺; (b) EGCG-Hg²⁺; (c) EGCG-Cu²⁺; (d) EGCG-Fe²⁺; (e) EGCG-In³⁺; (f) EGCG-Al³⁺; (g) EGCG-Au³⁺.

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表 1 EGCG-金属复合物的复合键键长

Table 1. Composite bond lengths of the EGCG-metal complexes.

EGCG-金属复合物	复合键	键长/Å
ECGC-Ag⁺	4"O—Ag	2.363
ECGC-Ag⁺	5"O—Ag	2.302
EGCG-Hg²⁺	4"O—Hg	2.366
EGCG-Hg²⁺	5"O—Hg	2.333
EGCG-Cu²⁺	4"O—Cu	1.941
EGCG-Cu²⁺	5"O—Cu	1.916
EGCG-Fe²⁺	4"O—Fe	1.926
EGCG-Fe²⁺	5"O—Fe	1.893
EGCG-In³⁺	4"O—In	2.929
EGCG-In³⁺	5"O—In	2.683
EGCG-Al³⁺	4"O—Al	2.418
EGCG-Al³⁺	5"O—Al	2.008
EGCG-Au³⁺	4"O—Au	2.979
EGCG-Au³⁺	5"O—Au	2.194

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表 2 EGCG-金属复合物中复合键的Mayer键级

Table 2. The Mayer bond orders of composite bond in the EGCG-metal complexes.

EGCG-金属复合物	复合键	Mayer键级
ECGC-Ag⁺	4"O—Ag	0.3462
ECGC-Ag⁺	5"O—Ag	0.4304
EGCG-Hg²⁺	4"O—Hg	0.3870
EGCG-Hg²⁺	5"O—Hg	0.4697
EGCG-Cu²⁺	4"O—Cu	0.5089
EGCG-Cu²⁺	5"O—Cu	0.5458
EGCG-Fe²⁺	4"O—Fe	0.5940
EGCG-Fe²⁺	5"O—Fe	0.7480
EGCG-In³⁺	4"O—In	0.0742
EGCG-In³⁺	5"O—In	0.1183
EGCG-Al³⁺	4"O—Al	0.1635
EGCG-Al³⁺	5"O—Al	0.3022
EGCG-Au³⁺	4"O—Au	0.1058
EGCG-Au³⁺	5"O—Au	0.4331

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表 3 EGCG-金属复合物中复合原子的自然布居分析

Table 3. Natural population analysis of composite atoms in the EGCG-metal complexes.

EGCG-金属复合物	复合原子	自然电荷分布
ECGC-Ag⁺	Ag	0.7803
	4"O	–0.8837
	5"O	–0.9144
EGCG-Hg²⁺	Hg	1.7086
	4"O	–0.8860
	5"O	–0.9045
EGCG-Cu²⁺	Cu	1.4836
	4"O	–0.8479
	5"O	–0.8421
EGCG-Fe²⁺	Fe	1.4342
	4"O	–0.8121
	5"O	–0.8417
EGCG-In³⁺	In	1.0761
	4"O	–0.5587
	5"O	–0.6041
EGCG-Al³⁺	Al	0.8686
	4"O	–0.5978
	5"O	–0.7942
EGCG-Au³⁺	Au	0.8679
	4"O	–0.5229
	5"O	–0.6244

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[1]	Matheus J R V, Andrade C J D, Miyahira R F, Fai A E C 2020 Food Rev. Int.Google Scholar
[2]	Elhabiri M, Carrer C, Marmolle F, Traboulsi H 2007 Inorg. Chim. Acta 360 353 Google Scholar
[3]	Chen Y M, Wang M K, Huang P M 2006 J. Agric. Food Chem. 54 212 Google Scholar
[4]	Li X J, Wang Z M, Liang H J, Ning J L, Li G Y, Zhou Z D 2017 Environ. Technol. 40 112 Google Scholar
[5]	Wang Z M, Gao M M, Li X J, Ning J L, Zhou Z D, Li G Y 2020 Mater. Sci. Eng., C 108 110196 Google Scholar
[6]	Nakajima A, Sakaguchi T 1993 J. Chem. Technol. Biotechnol. 57 321 Google Scholar
[7]	Gurung M, Adhikari B B, Kawakita H, Ohto K, Inoue K, Alam S 2012 Ind. Eng. Chem. Res. 51 11901 Google Scholar
[8]	Zhou Z D, Liu F L, Huang Y, Wang Z M, Li G Y 2015 Int. J. Biol. Macromol. 77 336 Google Scholar
[9]	Gurung M, Adhikari B B, Morisada S, Kawakita H, Ohto K, Inoue K, Alam S 2013 Bioresource Technol. 129 108 Google Scholar
[10]	Yi Q, Fan R, Xie F, Zhang Q, Luo Z 2016 J. Taiwan Inst. Chem. Eng. 61 299 Google Scholar
[11]	Li C M, Leverence R, Trombley J D, Xu S, Yang J, Tian Y, Reed J D 2010 J. Agric. Food Chem. 58 9033 Google Scholar
[12]	江腾, 马万福, 谢楠, 周平 2011 物理化学学报 27 2291 Google Scholar Jiang T, Ma W F, Xie N, Zhou P 2011 Acta Phys-Chim. Sin. 27 2291 Google Scholar
[13]	王晓巍, 蒋刚, 杜际广 2011 物理化学学报 27 309 Google Scholar Wang X W, Jiang G, Du J G 2011 Acta Phys.-Chim. Sin. 27 309 Google Scholar
[14]	Kohn W, Sham L J 1965 Phys. Rev. 140 A1133 Google Scholar
[15]	Becke A D 1993 J. Chem. Phys. 98 5648 Google Scholar
[16]	Malgorzata B, Pawel P, Giovanni S, Julien B, Vincenzo B 2010 J. Chem. Theory Comput. 6 2115 Google Scholar
[17]	Jonathon W, Matthew G, Jeffrey B N, Martin H 2015 J. Chem. Theory Comput. 11 1481 Google Scholar
[18]	Becke A D 1988 Phys. Rev. A 38 3098 Google Scholar
[19]	Lee C, Yang W, Parr R G 1988 Phys. Rev. B 37 785 Google Scholar
[20]	Bougherara H, Kadri R, Kadri M, Yekhlef M, Boumaza A 2021 J. Mol. Struct. 1223 128855 Google Scholar
[21]	Viji A, Revathi B, Balachandran V, Babiyana S, Narayana B, Salian V V 2020 Chem.l Data Collections 30 100585 Google Scholar
[22]	Goerigk L, Grimme S 2011 Phys. Chem. Chem. Phys. 13 6670 Google Scholar
[23]	Frisch M J, Trucks G W, Schlegel H B, et al. 2009 Gaussian 09 (Rev. A.02). (Gaussian: Inc., Wallingford CT)
[24]	Johnson E R, Kernan S, Mori-Sanchez P, Contreras-Garcia J, Cohen A J, Yang W T 2010 J. Am. Chem. Soc. 132 6498 Google Scholar
[25]	施斌, 袁荔, 唐天宇, 陆利敏, 赵先豪, 魏晓楠, 唐延林 2021 物理学报 70 053102 Google Scholar Shi B, Yuan L, Tang T Y, Lu L M, Zhao X H, W X N, Tang Y L 2021 Acta Phys. Sin. 70 053102 Google Scholar
[26]	Navarro R E, Santacruz H, Inoue M 2005 J. Inorg. Biochem. 99 584 Google Scholar
[27]	Inoue M B, Inoue M, Fernando Q, Valcic S, Timmermann B N 2002 J. Inorg. Biochem. 88 7 Google Scholar
[28]	Esparza I, Salinas I, Santamaria C, Garcia-Mina J M, Fernandez J M 2005 Anal. Chim. Acta 543 267 Google Scholar
[29]	Lu T, Chen F W 2013 J. Phys. Chem. A. 117 3100 Google Scholar
[30]	卢天, 陈飞武 2012 物理化学学报 28 1 Google Scholar Lu T, Chen F W 2012 Acta Phys.-Chim. Sin. 28 1 Google Scholar
[31]	Lu T, Chen F W 2012 J. Comput. Chem. 33 580 Google Scholar
[32]	Humphrey W, Dalke A, Schulten K 1996 J. Mol. Graphics. 14 33 Google Scholar

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