Convenient and highly efficient adsorption of diosmetin from lemon peel by magnetic surface molecularly imprinted polymers

doi:10.1016/j.jmst.2024.06.001

Abstract

Abstract: As a typical bioflavonoid, diosmetin is desirable in the field of natural medicine, healthy food, and cosmetics by anti-cancer, antibacterial, antioxidant, estrogen-like and anti-inflammatory activities, and it comes from a wide range of sources in traditional Chinese medicine like spider fragrance, spearmint and chrysanthemum, as well as in Citrus fruit. However, traditional analytical methods such as silica gel column chromatography face multiple challenges in the selective extraction of diosmetin from biological materials and traditional Chinese medicinal materials. Therefore, it is urgent to develop a new type of absorbent with high efficiency, recyclability and good specificity to diosmetin. In this investigation, a magnetic surface molecularly imprinted polymer (labeled as Diosmetin/SMIPs) was synthesized employing magnetic nanoparticles as the carrier and 4-vinylpyridinyl (4-VP) as the functional monomer by surface imprinting technology. The functional monomer was screened by the binding energy (ΔE) between functional monomers and template molecules via computational simulation. The Diosmetin/SMIPs had a high level of specific recognition and adsorption capability towards diosmetin with a 20.25 mg g^-1 adsorption capacity and an imprinting factor (IF) of 2.28. Additionally, it demonstrated excellent regeneration performance with 8 adsorption/desorption cycles. In addition, 91.20 %-94.16 % of spiked diosmetin was recovered from the lemon peel samples. The strategy of constructing Diosmetin/SMIPs based on computational simulation can effectively enhance the specific adsorption performance of diosmetin. Meanwhile, Diosmetin/SMIPs synthesized by imprinting polymerization showed excellent anti-interference and reusability, and realized efficient targeted extraction of diosmetin from lemon peel samples. The results of this investigation provide a promising adsorbent for selective enrichment of diosmetin from Citrus fruit and complicated materials.

Key words: Diosmetin, Selective extraction, Magnetic molecularly imprinted polymer, Lemon peel

Dongliang Xie, Yi Kuang, Bingnan Yuan, Yunlong Zhang, Chenyu Ye, Yuyi Guo, Hua Qiu, Juanna Ren, Saud O. Alshammari, Qamar A. Alshammari, Zeinhom M. El-Bahy, Kui Zhao, Zhanhu Guo, Qingqing Rao, Shengxiang Yang. Convenient and highly efficient adsorption of diosmetin from lemon peel by magnetic surface molecularly imprinted polymers[J]. J. Mater. Sci. Technol., 2025, 211: 159-170.

References

[1] A. Bahukhandi, K. Joshi, P. Kewlani, D.C. Tiwari, A.K. Jugran, I.D. Bhatt, Plant Physiol. Biochem. 200(2023) 107751.
[2] B.N. Silva, V. Cadavez, C. Caleja, E. Pereira, R.C. Calhelha, M. Añibarro-Ortega, T. Finimundy, M. Kostić, M. Soković, J.A. Teixeira, L. Barros, U. Gonzales-Barron, Foods 12 (2023) 947.
[3] L. Chen, J. Sun, Z. Pan, Y. Lu, Z. Wang, L. Yang, G. Sun, Molecules. 28(2023) 579.
[4] T. Chatzimitakos, V. Athanasiadis, K. Kotsou, E. Bozinou, S.I. Lalas, Antioxidants 12 (2023) 1605.
[5] R. Bodoira, M. Cecilia Cittadini, A. Velez, Y. Rossi, M. Montenegro, M. Martínez, D. Maestri, Food Chem. 381(2022) 132250.
[6] Z. Peng, S. Tian, H. Li, L. Zhu, Z. Zhao, G. Zheng, Q. Wen, H. Tian, D. Yang, Food Hydrocoll. 136(2023) 108237.
[7] Q. Sun, S. Hu, Z. Lou, J. Gao, Biomed. Pharmacother. 161(2023) 114469.
[8] L. Zhao, L. Jin, B. Yang, Life Sci. 331(2023) 122060.
[9] H. Ding, H. Ding, P. Mu, X. Lu, Z. Xu, Chem. Biol. Interact. 370(2023) 110311.
[10] L. Pan, F. Feng, J. Wu, L. Li, H. Xu, L. Yang, K. Xu, C. Wang, Food Function 12 (2021) 12036-12046.
[11] C. Yu, J. Shan, Z. Fu, H. Ju, X. Chen, G. Xu, Y. Liu, H. Li, Y. Wu, Foods. 12(2023) 2861.
[12] M. Wójciak, M. Feldo, G. Borowski, T. Kubrak, B.J. Płachno, I. Sowa, Molecules 27 (2022) 8232.
[13] B. Xie, D. Pan, H. Liu, M. Liu, X. Shi, X. Chu, J. Lu, M. Zhu, B. Xia, J. Wu, Mol. Nutr. Food Res. 65 (2021) 210 0 070.
[14] M.J. Alqahtani, W.A. Negm, H.M. Saad, E.A. Salem, I.A. Hussein, H.A. Ibrahim, Biomed. Pharmacother. 165(2023) 115095.
[15] Z. Li, T. Zhao, M. Shi, Y. Wei, X. Huang, J. Shen, X. Zhang, Z. Xie, P. Huang, K. Yuan, Front. Nutr. 10(2023) 1139558.
[16] Y. Yan, X. Liu, J. Gao, Y. Wu, Y. Li, Molecules 25 (2020) 192.
[17] J. Hu, W. Ma, N. Li, K.J. Wang, J. Mex. Chem.Soc. 61(2017) 282-289.
[18] M.M. Victor, J.M. David, M.V.M.Cortez, J.L. Leite, G.S.B.da Silva, Waste BioMass Valorization. 12(2021) 313-320.
[19] M.S. Sammani, S. Clavijo, L. Portugal, R. Suárez, H. Seddik, V. Cerdà, Talanta 167 (2017) 695-702.
[20] S. Wang, Y. Han, J. Chen, L. Bai, H. Yan, H. Liu, Instrum. Sci. Technol. 51(2023) 222-239.
[21] M.A. Shenashen, M.Y. Emran, A. El Sabagh, M.M. Selim, A. Elmarakbi, S.A.El-Safty, Prog. Mater. Sci. 124(2022) 100866.
[22] A. Plaskova, J. Mlcek, Front. Nutr. 10(2023) 1118761.
[23] H. Qin, H. Liu, Y. Liu, S. Di, Y. Bao, Y. Zhai, S. Zhu, Trac-Trends Anal. Chem. 164(2023) 117112.
[24] P. Górnaś, G. Baškirovs, A. Siger, Molecules 27 (2022) 6560.
[25] J. Xiong, Q. Hu, J. Wu, Z. Jia, S. Ge, Y. Cao, J. Zhou, Y. Wang, J. Yan, L. Xie, X. Chai, L. Zhang, G. Du, S. Wang, K. Xu, Adv. Compos. Hybrid Mater. 6(2023) 99.
[26] Z. Ding, Z. Tian, X. Ji, H. Dai, C. Si, Adv. Compos. Hybrid Mater. 5(2022) 2138-2153.
[27] F. Yao, W. Zhang, D. Hu, S. Li, X. Kong, S. Uemura, T. Kusunose, Q. Feng, Adv. Compos. Hybrid Mater. 6(2023) 2.
[28] R. Kaur, R. Goyat, J. Singh, A. Umar, V. Chaudhry, S. Akbar, Eng. Sci. 21(2023) 771.
[29] R. Das, B.K. Binay.K.Dutta, ES Energy Environ. 22(2023) 1015.
[30] C. Sungsook, T.R. Srinophakun, Eng. Sci. 28(2024) 1045.
[31] K. Hou, X. Xu, Y. Xiang, X. Chen, S.S. Lam, M. Naushad, C. Sonne, S. Ge, Adv. Compos. Hybrid Mater. 6(2023) 77.
[32] Q. Wu, L. Gao, M. Huang, G.A.M.Mersal, M.M. Ibrahim, Z.M. El-Bahy, X.Shi, Q. Jiang, Adv. Compos. Hybrid Mater. 5(2022) 1044-1053.
[33] X. Xie, H. Gao, X. Luo, Y. Zhang, Z. Qin, H. Ji, Adv. Compos. Hybrid Mater. 5(2022) 2772-2786.
[34] A.H. Naeini, M.R. Kalaee, O. Moradi, R. Khajavi, M. Abdouss, Adv. Compos. Hybrid Mater. 5(2022) 335-349.
[35] H. Zhang, Z. Wang, Y. Zhao, W. Cui, X. Zhang, S. Wang, E.D. Walter, M.J. Sassi, C.I. Pearce, S.B. Clark, K.M. Rosso, Eng. Sci. 24(2023) 896.
[36] M. Cheng, C. Yao, Y. Su, J. Liu, L. Xu, J. Bu, H. Wang, S. Hou, Eng. Sci. 18(2022) 299-307.
[37] Z. Yang, J. Wang, T. Shah, P. Liu, M. Ahmad, Q. Zhang, B. Zhang, Talanta 224 (2021) 121760.
[38] Y. Wu, Y. Zhang, J. Qian, X. Xin, S. Hu, S. Zhang, J. Wei, R. Soc.Open Sci. 4(2017) 170905.
[39] Q. Zhang, Q. Sun, R. Wang, Y. Chi, B. Shi, ACS Appl. Mater. Interfaces 15 (2023) 18516-18527.
[40] X. Wei, D. Huang, D. Pei, B. Liu, D. Di, Micropor. Mesopor. Mater. 348(2023) 112333.
[41] A.M. Aljeboree, A.B. Mahdi, W.K.Y. Albahadly, S.E. Izzat, M.M.R.A.L. Kubaisy, F.M. Abid, A.K.O. Aldulaimi, A.F. Alkaim, Eng. Sci. 20(2022) 321-329.
[42] W.D.P.Rengga, N.A.C.Imani, N. Wijayati, T. Tohiran, W.H. Cahyati, D. Saputra, Eng. Sci. 23(2023) 873.
[43] T. Wang, Y. Lyu, Z. Yang, H. Cheng, Q. Zhang, B. Zhang, Ind. Eng. Chem. Res. 62(2023) 9290-9301.
[44] X. Li, J. Zhou, L. Tian, Y. Wang, B. Zhang, H. Zhang, Q. Zhang, Sens. Actuator B-Chem. 241(2017) 413-421.
[45] X.Z. Dong, B.L. Zhang, Q.Y. Zhang, Indian J. Chem. Technol. 29(2022) 678-687.
[46] W. Gang, L.I.U.Genqi, Z. Lingli, W.Yue, L.I.U. Lisha, Chem. J. Chin. Univ. Chin. 44(2023) 20220757.
[47] Y. Shao, Y. Zhu, R. Zheng, P. Wang, Z. Zhao, J. An, Adv. Compos. Hybrid Mater. 5(2022) 3104-3116.
[48] J.Y. He, Q. Li, H.X. Xu, Q.Y. Zheng, Q.H. Zhang, L.D. Zhou, C.Z. Wang, C.S. Yuan, Trac-Trends Anal. Chem. 162(2023) 117033.
[49] M. Tang, J. Wan, Y. Wang, G. Ye, Z. Yan, Y. Ma, J. Sun, Appl. Catal. B-Environ. 334(2023) 122852.
[50] B. Tse Sum Bui, A.Mier, K. Haupt, Small. 19(2023) 2206453.
[51] M. Wei, X. Yan, S. Liu, Y. Liu, J. Mater. Sci. 53(2018) 4 897-4 912.
[52] J. Peng, F. Deng, H. Shi, Z. Wang, X. Li, J. Zou, X. Luo, Appl. Catal. B-Environ. 340(2024) 123179.
[53] A.I. Bărăian, B.C. Iacob, A.E. Bodoki, E. Bodoki, Int. J. Mol. Sci. 23(2022) 14071.
[54] T. Wen, Q. Nie, L. Han, Z. Gong, D. Li, Q. Ma, Z. Wang, W. He, L. Wen, H. Peng, Food Chem. 387(2022) 132905.
[55] S.I. Kaya, A. Cetinkaya, S.A. Ozkan, Trends Environ. Anal. Chem. 37(2023) e00193.
[56] J. Miao, A. Liu, L. Wu, M. Yu, W. Wei, S. Liu, Anal. Chim. Acta1095 (2020) 82-92.
[57] Y. Kuang, Y. Xia, X. Wang, Q. Rao, S. Yang, Front. Chem. 10(2022) 862777.
[58] K. Banan, F. Ghorbani-Bidkorbeh, H. Afsharara, D. Hatamabadi, B. Landi, R. Keçili, B. Sellergren, Anal. Chim. Acta1198 (2022) 339548.
[59] Y. Zhang, Z. Ma, K. Ruan, J. Gu, Nano Res. 15(2022) 5601-5609.
[60] L. Wang, H. Qiu, C. Liang, P. Song, Y. Han, Y. Han, J. Gu, J. Kong, D. Pan, Z. Guo, Carbon 141 (2019) 506-514.
[61] Y. Wu, K. Huang, X. Weng, R. Wang, P. Du, J. Liu, S. Lin, K. Huang, H. Yang, M. Lei, Adv. Compos. Hybrid Mater. 5(2022) 71-82.
[62] H. Cheng, L. Xing, Y. Zuo, Y. Pan, M. Huang, A. Alhadhrami, M.M. Ibrahim, Z.M.El-Bahy, C.Liu, C. Shen, X. Liu, Adv. Compos. Hybrid Mater. 5(2022) 755-765.
[63] X. Tang, L. Manamanchaiyaporn, Eng. Sci. (2024), doi: 10.30919/es1135.
[64] W. Yu, Z. Wang, J. Lin, Y. Xiao, L. Zhu, J. Huang, A. Pereira, Z. Guo, Y. Min, Eng. Sci. 30(2024) 1113.
[65] R.B.J.Chandra, B. Shivamurthy, S.B.B. Gowda, M.S. Kumar, Eng. Sci. 21(2023) 777.
[66] H. Wang, W. Feng, D. Liu, G. Zhang, Y. Liua, J. Wang, L. Zou, Eng. Sci. 22(2023) 809.
[67] M.B. Khanvilkar, A.K. Nikumbh, R.A. Pawar, N.J. Karale, P.A. Nagwade, D.V. Nighot, G.S. Gugale, M.D. Sangale, S.B. Misal, S.P. Panchgalle, Eng. Sci. 22(2023) 850.
[68] L. Ji, X. Shen, R. Zhao, C. Hu, X. Zhao, Y. Li, J. Zhang, W. Chen, Y. Chen, J. Daoud, X. Zhang, Eng. Sci. 19(2022) 136-143.
[69] M.S. Gadwal, J. Kaur, S.F. Shaikh, P.E. Lokh, V.L. Mathe, S.D. Sartale, H.M. Pathan, Copper Substrate&nbsp, ES Mater. Manuf. 18(2022) 1-9.
[70] Y. Wang, X. Gao, C. Lin, L. Shi, X. Li, G. Wu, J. Alloy. Compd. 785(2019) 765-773.
[71] T. Gao, H. Rong, K.H. Mahmoud, J. Ruan, S.M.El-Bahy, A.A. Faheim, Y. Li, M. Huang, M.A. Nassan, R. Zhao, Adv. Compos. Hybrid Mater. 5(2022) 1158-1167.
[72] C. Wang, H. Gao, D. Liang, S. Liu, H. Zhang, H. Guan, Y. Wu, Y. Zhang, Adv. Compos. Hybrid Mater. 5(2022) 2906-2920.
[73] Z. Yang, K. Yang, Y. Cui, T. Shah, M. Ahmad, Q. Zhang, B. Zhang, J. Mater. Sci.Technol. 74(2021) 203-215.
[74] Y. Kuang, W. Chen, Z. Chen, Y. Xia, Q. Rao, S. Yang, Food Chem. 405(2023) 134993.
[75] W. Li, A. Liang, Z. Lu, Y. Xie, Eng. Proceed. 49(2023) 1.
[76] F. Nie, C. Li, N. Ahmad, Z. Yuan, Y. Tan, Y. Xu, C. Zhao, ACS Appl, Polym. Mater. 4(2022) 9294-9304.
[77] B. Wang, Y. Kuang, M. Li, X. Wang, X. Zhang, Q. Rao, B. Yuan, S. Yang, Adv. Compos. Hybrid Mater. 6(2023) 196.
[78] N. Sieffert, G. Wipff, Dalton Trans. 44(2015) 2623-2638.
[79] W.W. Deng, X.P. Mei, Z.J. Cheng, X. Tian, J.N. Hu, C.R. Zang, B. Sun, J. Wu, Y. Deng, R.A. Ghiladi, Food Chem. 405(2023) 134817.
[80] T. Fan, D. Pan, H. Zhang, Ind. Eng. Chem. Res. 50(2011) 9009-9018.
[81] L. Lin, H. Zhao, Y. Dong, B. Yang, M. Zhao, Food Chem. 130(2012) 417-424.
[82] T. Lu, F. Chen, J. Comput. Chem. 33(2012) 580-592.
[83] Z. Jia, J. Liu, Z. Gao, C. Zhang, G. Wu, Adv. Funct. Mater. (2024) 2405523, doi: 10.1002/adfm.202405523.
[84] Y. Shi, B. Liang, H. Gao, R. Zhao, Q. Dong, T. Li, Y. Ma, W. Gao, J. Zhang, J. Gu, S. Melhi, M. Shalash, Z.M. El-Bahy, Z. Guo, Carbon 227 (2024) 119244.
[85] Y. Yi, C. Zhao, H.L. Shindume, J. Ren, L. Chen, H. Hou, M.M. Ibrahim, Z.M.El-Bahy, Z.Guo, Z. Zhao, J. Gu, Colloid Surf, A-Physicochem. Eng. Asp. 694(2024) 134149.
[86] Y. Long, Z. Zhang, K. Sun, C. Wang, N. Zeng, B. Gao, X. Tang, X. Qi, R. Fan, Adv. Compos. Hybrid Mater. 6(2023) 173.
[87] S. Zhang, Z. Jia, B. Cheng, Z. Zhao, F. Lu, G. Wu, Adv. Compos. Hybrid Mater. 5(2022) 2440-2460.
[88] C. Xiong, Q. Xiong, M. Zhao, B. Wang, L. Dai, Y. Ni, Adv. Compos. Hybrid Mater. 6(2023) 205.
[89] Z. Gao, D. Lan, X. Ren, Z. Jia, G. Wu, Compos. Commun. 48(2024) 101922.
[90] X. Chen, Z. Jia, A. Feng, B. Wang, X. Tong, C. Zhang, G. Wu, J. Colloid Interface Sci. 553(2019) 465-474.
[91] S. Zhang, W. Li, H. Wu, J. Jiao, Adv. Compos. Hybrid Mater. 6(2023) 154.
[92] D. Skoda, J. Vilcakova, R.S. Yadav, B. Hanulikova, T. Capkova, M. Jurca, M. Urbanek, P. Machac, L. Simonikova, J. Antos, I. Kuritka, Adv. Compos. Hybrid Mater. 6(2023) 113.
[93] M.X. Sun, W.Q. Cao, P.Y. Zhu, Z.M. Xiong, C.C. Chen, J.C. Shu, W.H. Huang, F. Wu, Adv. Compos. Hybrid Mater. 6(2023) 54.
[94] Z. Jia, B. Wang, A. Feng, J. Liu, M. Zhang, Z. Huang, G. Wu, J. Alloy. Compd. 799(2019) 216-223.
[95] Z. Zhang, Z. Li, Y. Zhao, X. Bi, Z. Zhang, Z. Long, Z. Liu, L. Zhang, W. Cai, Y. Liu, R. Fan, Adv. Compos. Hybrid Mater. 5(2022) 3176-3189.
[96] N. Wu, B. Zhao, Y. Lian, S. Liu, Y. Xian, J. Gu, G. Wu, Carbon 226 (2024) 119215.
[97] S. Zhang, D. Lan, J. Zheng, J. Kong, J. Gu, A. Feng, Z. Jia, G. Wu, Carbon 221 (2024) 118925.
[98] Q. Zhang, D. Lan, S. Deng, J. Gu, Y. Wang, J. Ren, G. Wu, Z. Jia, Carbon 226 (2024) 119233.
[99] M. Kloster, A.A.d. Almeida, D.Muraca, N.E. Marcovich, M.A. Mosiewicki, Eng. Sci. 22(2023) 851.
[100] A.Q. Malik, H. Singh, A. Kumar, R. Aepuru, D. Kumar, T.u.G. Mir, Q.u. Ain, A.A. Bhat, A. Mubayi, ES Energy Environ. 19(2023) 744.
[101] S. Balsure, V. More, S. Kadam, R. Kadam, A. Kadam, Eng. Sci. 21(2023) 774.
[102] H. Yao, S. Wang, M. Lei, K. Bi, Eng. Sci. 16(2021) 301-307.
[103] X. Chen, D. Lan, L. Zhou, Z. Zeng, Y. Liu, S. Du, Z. Zou, G. Wu, Ceram. Int. 50(2024) 24549-24557.
[104] L. Yu, D. Lan, Z. Guo, A. Feng, G. Wu, Z. Jia, X. Feng, P. Yin, J. Mater. Sci.Technol. 189(2024) 155-165.