多酸型α-葡萄糖苷酶抑制剂的抗氧化性能研究

doi:10.6023/A23060276

摘要/Abstract

本研究合成并表征了三类(母体、过渡金属取代的磷钼酸及不同钒个数取代的磷钼酸共11个)Dawson型磷钼酸, 通过对2,2-联氮-二(3-乙基-苯并噻唑-6-磺酸)二铵盐(ABTS)自由基、羟基自由基、1,1-二苯基-2-三硝基苯肼(DPPH)自由基及超氧阴离子自由基的清除效果考察11种化合物的体外抗氧化性能. 通过噻唑蓝(MTT)法检测细胞存活率, 结合体外抗氧化及细胞毒性实验结果, 对H₆[P₂Mo₁₈O₆₂], H₇[P₂Mo₁₇VO₆₂]和H₈[P₂Mo₁₆V₂O₆₂]进行细胞抗氧化研究, 检测其细胞内总抗氧化能力和对细胞超氧化物歧化酶(SOD)活性的影响. 将多酸与α-葡萄糖苷酶进行分子对接, 探究它们之间的相互作用机制. 结果表明11种化合物均具有较好的抗氧化性能. 分子对接结果显示多酸主要通过氢键和范德华力与活性中心的氨基酸残基进行结合. 其中, H₆[P₂Mo₁₈O₆₂], H₈[P₂Mo₁₇Fe(OH₂)O₆₁], H₈[P₂Mo₁₇Ni(OH₂)O₆₁], H₇[P₂Mo₁₇VO₆₂]和H₈[P₂Mo₁₆V₂O₆₂]表现优异, 有望成为兼具α-葡萄糖苷酶抑制效用的抗氧化剂备选材料.

关键词: 多金属氧酸盐, 分子对接, α-葡萄糖苷酶, 抗氧化, 活性氧

Three types of Dawson type phosphomolybdate were synthesized and the in vitro antioxidant properties of the 11 compounds were investigated by the scavenging effect of different concentrations of polyoxometalates (0~50 mg/mL with distilled water and Vitamin C (VC) as positive control, three parallel experiments were set up for each group) on 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) radicals, hydroxyl radicals, 1,1-diphenyl-2-picrylhydrazyl (DPPH) radicals and superoxide anion radicals. The cytotoxicity of the compounds was assayed by methyl thiazolyl tetrazolium (MTT) assay and combined with the results of in vitro antioxidant and cytotoxicity assays, cellular antioxidant studies were performed on H₆[P₂Mo₁₈O₆₂], H₇[P₂Mo₁₇VO₆₂] and H₈[P₂Mo₁₆V₂O₆₂] using HepG2 cells as a model. The total intracellular antioxidant capacity was measured using the ABTS method: 10 μL of the sample/standard solution and 200 μL of the ABTS working solution were mixed in a 96-well plate for 5 min at room temperature, and the absorbance of the sample was measured at 734 nm using a multifunctional enzyme marker. WST-1 assay for cellular superoxide dismutase (SOD) activity: The samples to be tested were diluted to different concentrations and the absorbance values were measured at 450 nm using a multifunctional enzyme marker. The SOD inhibition rate of the sample to be tested was calculated and a sample concentration of 40%~60% inhibition was selected for the experiment. Cellular antioxidant assays showed that H₆[P₂Mo₁₈O₆₂] had a total cellular antioxidant capacity comparable to that of VC at higher concentrations (25 μmol/L and above); it enhanced the activity of cellular superoxide dismutase (SOD) and was more active than VC. We investigated the interaction mechanisms of molecular docking between polyoxometalates and α-glucosidase. The results showed that all 11 compounds had good antioxidant properties, and molecular docking showed that the binding inhibition of the polyoxometalates to the amino acid residues in the active centre was reversible mainly through hydrogen bonding and van der Waals forces, and that the docking fraction was negative and the reaction could proceed spontaneously, but the types of amino acids involved varied. Among them, H₆[P₂Mo₁₈O₆₂], H₈[P₂Mo₁₇Fe(OH₂)O₆₁], H₈[P₂Mo₁₇Ni(OH₂)O₆₁], H₇[P₂Mo₁₇VO₆₂] and H₈[P₂Mo₁₆V₂O₆₂] performed well and could be alternative materials for antioxidants with both α-glucosidase inhibiting effect.

Key words: polyoxometalates, molecular docking, α-glucosidase, antioxidation, reactive oxygen species

引用此文

李瑶, 陈丙年, 罗丹, 雷珊, 王力. 多酸型α-葡萄糖苷酶抑制剂的抗氧化性能研究[J]. 化学学报, 2023, 81(10): 1318-1326.

Yao Li, Bingnian Chen, Dan Luo, Shan Lei, Li Wang. Study on the Antioxidant Properties of Polyoxometalates α-Glucosidase Inhibitors[J]. Acta Chimica Sinica, 2023, 81(10): 1318-1326.

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图/表 6

图1. (a)不同过渡金属取代的Dawson型磷钼酸的ABTS自由基清除能力. (b)不同过渡金属取代的Dawson型磷钼酸的DPPH自由基清除能力. (c)不同过渡金属取代的Dawson型磷钼酸的羟基自由基清除能力. (d)不同钒个数取代的Dawson型磷钼酸的羟基自由基清除能力. (e)不同过渡金属取代的Dawson型磷钼酸的超氧阴离子自由基清除能力. (f)不同钒个数取代的Dawson型磷钼酸的超氧阴离子自由基清除能力

Figure 1. (a) ABTS radical scavenging ability of Dawson type phosphomolybdate with different transition metal substitutions. (b) DPPH radical scavenging ability of Dawson type phosphomolybdate with different transition metal substitutions. (c) Hydroxyl radical scavenging ability of Dawson type phosphomolybdate with different transition metal substitutions. (d) Hydroxyl radical scavenging ability of Dawson type phosphomolybdate with different number of vanadium substitutions. (e) Superoxide anion radical scavenging ability of Dawson type phosphomolybdate with different transition metal substitutions. (f) Superoxide anion radical scavenging ability of Dawson type phosphomolybdate with different number of vanadium substitutions

图2. (a)不同过渡金属取代的Dawson型磷钼酸对HepG2细胞存活率的影响. (b)不同钒个数取代的Dawson型磷钼酸对HepG2细胞存活率的影响.与对照组相比, *表示差异显著(p<0.05), ***表示差异极显著(p<0.001), ****表示差异极显著(p<0.0001)

Figure 2. (a) Effects of different transition metal substitutions of Dawson type phosphomolybdate on the survival rate of HepG2 cells. (b) Effects of Dawson type phosphomolybdate substituted with different amounts of vanadium on the survival rate of HepG2 cells. Compared with the control group, * means significant difference (p<0.05), *** means extremely significant difference (p<0.001), **** means extremely significant difference (p<0.0001)

图3. (a) Dawson型磷钼酸母体的总抗氧化能力. a, b表示不同组间的显著性差异. (b) P2Mo17V、P2Mo16V2的总抗氧化能力. a, b和ab表示不同组间的显著性差异. (c) Dawson型磷钼酸母体的SOD活性. 设对照(溶剂蒸馏水)的酶活性为1.0, 计算P2Mo18处理后细胞SOD的相对活性. a, b, c和ab表示不同组间的显著性差异. (d) P2Mo17V和P2Mo16V2的SOD活性. 设对照(溶剂蒸馏水)的酶活性为1.0, 计算P2Mo17V和P2Mo16V2处理后细胞SOD的相对活性. a, b, c和ab表示不同组间的显著性差异

Figure 3. (a) Total antioxidant capacity of Dawson type phosphomolybdic acid parent. a and b represent significant differences among different groups. (b) Total antioxidant capacity of P2Mo17V and P2Mo16V2. a, b and ab represent significant differences among different groups. (c) SOD activity of Dawson type phosphomolybdate parent. The relative activity of SOD in P2Mo18 treated cells was calculated by setting the enzymatic activity of control (solvent distilled water) as 1.0. a, b, c and ab represent significant differences among different groups. (d) SOD activity of P2Mo17V and P2Mo16V2. The relative activity of SOD in cells treated with P2Mo17V and P2Mo16V2 was calculated by setting the enzymatic activity of control (solvent distilled water) as 1.0. a, b, c and ab represent significant differences among different groups

图4. P2Mo17Fe与α-葡萄糖苷酶活性位点的结合方式

Figure 4. Binding mode of P2Mo17Fe to the active site of α-glucosidase

化合物	氢键和金属键相关氨基酸	氢键数量	对接分数/ (kJ•mol^－1)
P₂Mo₁₇Fe	Arg442, Arg446, Arg315, Arg213, Gln353, Gln279, Asn350, Asp307, Asp215, Asp69, Glu411	17	－122
P₂Mo₁₇Co	Asp215, Asp69, Asp352, Arg442, Arg446, Arg315, Arg213, Gln279, Glu411, Glu277, Tyr72, Tyr316, His315, His112, Asn350	14	－116
P₂Mo₁₇Ni	Asp215, Asp69, Asp352, Arg307, Arg446, Arg315, Arg213, Tyr72, Tyr316, His315, His112, Asn350, Gln353, Gln279	18	－118
P₂Mo₁₇V	Ser240, Asp307, Asp242, Gln279, Tyr158, Arg315, His280	7	－131
P₂Mo₁₆V₂	Phe159, Phe178, Phe303, Val216, Val109, Leu219, Tyr316, Asp215, Asp69, His112, Gln353, Gln279, Gln182, Arg315, Arg213, Arg446	10	－134
P₂Mo₁₄V₄	Glu277, Gln353, Gln279, Asp215, Asp69, Asp352, Arg315, Arg213, Arg446, Asn350	12	－126
P₂Mo₁₃V₅	Asp215, Asp69, Asp307, Glu277, Gln353, Gln279, His351, Arg315, Arg213, Arg446, Asn350	14	－122

表1. P2Mo17Fe, P2Mo17Co, P2Mo17Ni, P2Mo17V, P2Mo16V2, P2Mo14V4和P2Mo13V5与α-葡萄糖苷酶的对接效应

Table 1. Docking effects of P2Mo17Fe, P2Mo17Co, P2Mo17Ni, P2Mo17V, P2Mo16V2, P2Mo14V4, P2Mo13V5 with α-glucosidase

	对照孔	对照空白孔	测定孔	测定空白孔
待测样本/μL	—	—	20	20
蒸馏水/μL	20	20	—	—
酶工作液/μL	20	—	20	—
酶稀释液/μL	—	20	—	20
底物应用液/μL	200	200	200	200

表2. SOD活性检测体系

Table 2. SOD activity detection system

参考文献 60

[1]	Bhatti, J. S.; Sehrawat, A.; Mishra, J.; Sidhu, I. S.; Navik, U.; Khullar, N.; Kumar, S.; Bhatti, G. K.; Reddy, P. H. Free Radic. Biol. Med. 2022, 184, 114. doi: 10.1016/j.freeradbiomed.2022.03.019
[2]	Singh, A.; Kukreti, R.; Saso, L.; Kukreti, S. Molecules 2022, 27, 950. doi: 10.3390/molecules27030950
[3]	Andreadi, A.; Bellia, A.; Di Daniele, N.; Meloni, M.; Lauro, R.; Della-Morte, D.; Lauro, D. Curr. Opin. Pharmacol. 2022, 62, 85. doi: 10.1016/j.coph.2021.11.010
[4]	De Geest, B.; Mishra, M. Antioxidants 2022, 11, 784. doi: 10.3390/antiox11040784
[5]	Yang, J.; Wang, X.; Zhang, C.; Ma, L.; Wei, T.; Zhao, Y.; Peng, X. Food Chem. 2021, 347, 129056. doi: 10.1016/j.foodchem.2021.129056
[6]	Peng, X.; Zhang, G.-W.; Liao, Y.-J.; Gong, D.-M. Food Chem. 2016, 190, 207. doi: 10.1016/j.foodchem.2015.05.088
[7]	Li, H.; Yang, J.-C.; Wang, M.-F.; Ma, X.-Z.; Peng, X. Food Chem. 2023, 420, 136113. doi: 10.1016/j.foodchem.2023.136113
[8]	Cardullo, N.; Muccilli, V.; Pulvirenti, L.; Cornu, A.; Pouysegu, L.; Deffieux, D.; Quideau, S.; Tringali, C. Food Chem. 2020, 313, 126099. doi: 10.1016/j.foodchem.2019.126099
[9]	Wang, X.; Deng, Y.; Xie, P.; Liu, L.; Zhang, C.; Cheng, J.; Zhang, Y.; Liu, Y.; Huang, L.; Jiang, J. Food Chem. 2023, 404, 134481. doi: 10.1016/j.foodchem.2022.134481
[10]	Xu, Y.; Rashwan, A. K.; Ge, Z.; Li, Y.; Ge, H.; Li, J.; Xie, J.; Liu, S.; Fang, J.; Cheng, K.; Chen, W. Food Chem. 2023, 399, 133999. doi: 10.1016/j.foodchem.2022.133999
[11]	Hu, J.-F.; Lai, X.-H.; Wu, X.-D.; Wang, H.-Y.; Weng, N.-H.; Lu, J.; Lyu, M.; Wang, S.-J. Foods 2023, 12, 183. doi: 10.3390/foods12010183
[12]	Tian, T.; Chen, G.; Zhang, H.; Yang, F. Molecules 2021, 26, 4638. doi: 10.3390/molecules26154638
[13]	Dai, T.; Chen, J.; Mcclements, D. J.; Li, T.; Liu, C. Int. J. Biol. Macromol. 2019, 130, 315. doi: 10.1016/j.ijbiomac.2019.02.105
[14]	Chen, X.-Y.; Sun-Waterhouse, D.; Yao, W.-Z.; Li, X.; Zhao, M.-M.; You, L.-J. Food Chem. 2021, 365, 130524. doi: 10.1016/j.foodchem.2021.130524
[15]	Wang, X.-Q.; Wang, W.-J.; Peng, M.-Y.; Zhang, X.-Z. Biomaterials 2021, 266, 120474. doi: 10.1016/j.biomaterials.2020.120474
[16]	Cheung, E. C.; Vousden, K. H. Nat. Rev. Cancer 2022, 22, 280. doi: 10.1038/s41568-021-00435-0
[17]	Murphy, M. P.; Bayir, H.; Belousov, V.; Chang, C. J.; Davies, K. J. A.; Davies, M. J.; Dick, T. P.; Finkel, T.; Forman, H. J.; Janssen-Heininger, Y.; Gems, D.; Kagan, V. E.; Kalyanaraman, B.; Larsson, N.; Milne, G. L.; Nystrom, T.; Poulsen, H. E.; Radi, R.; Van Remmen, H.; Schumacker, P. T.; Thornalley, P. J.; Toyokuni, S.; Winterbourn, C. C.; Yin, H.; Halliwell, B. Nat. Metab. 2022, 4, 651. doi: 10.1038/s42255-022-00591-z
[18]	Juan, C. A.; Perez De La Lastra, J. M.; Plou, F. J.; Perez-Lebena, E. Int. J. Mol. Sci. 2021, 22, 4642. doi: 10.3390/ijms22094642
[19]	Sies, H.; Belousov, V. V.; Chandel, N. S.; Davies, M. J.; Jones, D. P.; Mann, G. E.; Murphy, M. P.; Yamamoto, M.; Winterbourn, C. Nat. Rev. Mol. Cell Biol. 2022, 23, 499. doi: 10.1038/s41580-022-00456-z
[20]	Zhang, C.-Y.; Wang, X.; Du, J.-F.; Gu, Z.-J.; Zhao, Y.-L. Adv. Sci. 2021, 8, 2002797. doi: 10.1002/advs.v8.3
[21]	Kalyane, D.; Choudhary, D.; Polaka, S.; Goykar, H.; Karanwad, T.; Rajpoot, K.; Tekade, R. K. Prog. Mater. Sci. 2022, 130, 100974. doi: 10.1016/j.pmatsci.2022.100974
[22]	Montllor-Albalate, C.; Kim, H.; Thompson, A. E.; Jonke, A. P.; Torres, M. P.; Reddi, A. R. Proc. Natl. Acad. Sci. U. S. A. 2022, 119, e2023328119.
[23]	Hoseinifar, S. H.; Yousefi, S.; Van Doan, H.; Ashouri, G.; Gioacchini, G.; Maradonna, F.; Carnevali, O. Rev. Fish. Sci. Aquac. 2020, 29, 198.
[24]	Lv, R.; Dong, Y.; Bao, Z.; Zhang, S.; Lin, S.; Sun, N. Trends Food Sci. Technol. 2022, 122, 171. doi: 10.1016/j.tifs.2022.02.026
[25]	Rajput, V. D.; Harish; Singh, R. K.; Verma, K. K.; Sharma, L.; Quiroz-Figueroa, F. R.; Meena, M.; Gour, V. S.; Minkina, T.; Sushkova, S.; Mandzhieva, S. Biology-Basel. 2021, 10, 267.
[26]	Kasai, S.; Shimizu, S.; Tatara, Y.; Mimura, J.; Itoh, K. Biomolecules 2020, 10, 320. doi: 10.3390/biom10020320
[27]	Khalil, I.; Yehye, W. A.; Etxeberria, A. E.; Alhadi, A. A.; Dezfooli, S. M.; Julkapli, N. B. M.; Basirun, W. J.; Seyfoddin, A. Antioxidants. 2020, 9, 24. doi: 10.3390/antiox9010024
[28]	Wang, Q.; Cheng, C.-Q.; Zhao, S.; Liu, Q.-Y.; Zhang, Y.-H.; Liu, W.-L.; Zhao, X.-Z.; Zhang, H.; Pu, J.; Zhang, S.; Zhang, H.-G.; Du, Y.; Wei, H. Angew. Chem. Int. Ed. 2022, 61, e202201101.
[29]	Gulcin, I. Arch. Toxicol. 2020, 94, 651. doi: 10.1007/s00204-020-02689-3
[30]	Forman, H. J.; Zhang, H. Nat. Rev. Drug Discov. 2021, 20, 689. doi: 10.1038/s41573-021-00233-1
[31]	Wei, Y. -G. Polyoxometalates 2022, 1, 9140014. doi: 10.26599/POM.2022.9140014
[32]	Zhang, H.-Y.; Zhao, W.; Li, H.-Q.; Zhuang, Q.-H.; Sun, Z.-Q.; Cui, D.-Y.; Chen, X.-J.; Guo, A.; Ji, X.; An, S.; Chen, W.; Song, Y. Polyoxometalates 2022, 1, 9140011. doi: 10.26599/POM.2022.9140011
[33]	Feng, X.-J.; Li, Y.-G.; Zhang, Z.-M.; Wang, E.-B. Acta Chim. Sinica 2013, 71, 1575 (in Chinese). doi: 10.6023/A13060664
	(冯小佳, 李阳光, 张志明, 王恩波, 化学学报, 2013, 71, 1575.)
[34]	Wang, H.-N.; Zhang, A.-G.; Zhang, Z.-T.; Hong, R.; Yue, Q.; Zhao, X.; Lu, Y.; Liu, S.-X. Acta Chim. Sinica 2021, 79, 920 (in Chinese). doi: 10.6023/A21040130
	(王赫男, 张安歌, 张仲田, 洪瑞, 岳倩, 赵雪, 鹿颖, 刘术侠, 化学学报, 2021, 79, 920.)
[35]	Wei, Z.-Y.; Chang, Y.-L.; Yu, H.; Han, S.; Wei, Y.-G. Acta Chim. Sinica 2020, 78, 725 (in Chinese). doi: 10.6023/A20050187
	(魏哲宇, 常亚林, 余焓, 韩生, 魏永革, 化学学报, 2020, 78, 725.)
[36]	Liu, S.-X.; Wang, C.-L.; Yu, M.; Li, Y.-X.; Wang, E.-B. Acta Chim. Sinica 2005, 63, 1069 (in Chinese).
	(刘术侠, 王春玲, 于淼, 李玉新, 王恩波, 化学学报, 2005, 63, 1069.)
[37]	Chen, K.; Dai, G.-Y.; Liu, S.-Q.; Wei, Y.-G. Chin. Chem. Lett. 2023, 34, 107638. doi: 10.1016/j.cclet.2022.06.061
[38]	Li, B.; Wu, L.-X. Polyoxometalates 2023, 2, 9140016. doi: 10.26599/POM.2022.9140016
[39]	Li, J.; Zhang, D.; Chi, Y.; Hu, C. Polyoxometalates 2022, 1, 9140012. doi: 10.26599/POM.2022.9140012
[40]	Xia, Y.; Wei, Y.-G.; Guo, H.-Y. Acta Chim. Sinica 2005, 63, 1931 (in Chinese).
	(夏芸, 魏永革, 郭洪猷, 化学学报, 2005, 63, 1931.)
[41]	Du, D.-Y.; Yan, L.-K.; Su, Z.-M.; Li, S.-L.; Lan, Y.-Q.; Wang, E.-B. Coord. Chem. Rev. 2013, 257, 702. doi: 10.1016/j.ccr.2012.10.004
[42]	Chen, L.; Chen, W.-L.; Wang, X.-L.; Li, Y.-G.; Su, Z.-M.; Wang, E.-B. Chem. Soc. Rev. 2019, 48, 260. doi: 10.1039/C8CS00559A
[43]	Li, N.; Liu, J.; Dong, B.-X; Lan, Y.-Q. Angew. Chem. Int. Ed. 2020, 59, 20779. doi: 10.1002/anie.v59.47
[44]	Wang, Z.-M; Xin, X.; Zhang, M.; Li, Z.; Lv, H.-J; Yang, G.-Y. Sci. China-Chem. 2022, 65, 1515. doi: 10.1007/s11426-022-1276-4
[45]	Bijelic, A.; Aureliano, M.; Rompel, A. Angew. Chem. Int. Ed. 2019, 58, 2980. doi: 10.1002/anie.v58.10
[46]	Aureliano, M.; Gumerova, N. I.; Sciortino, G.; Garribba, E.; Rompel, A.; Crans, D. C. Coord. Chem. Rev. 2021, 447, 214143. doi: 10.1016/j.ccr.2021.214143
[47]	Francese, R.; Civra, A.; Ritta, M.; Donalisio, M.; Argenziano, M.; Cavalli, R.; Mougharbel, A. S.; Kortz, U.; Lembo, D. Antiviral Res. 2019, 163, 29. doi: 10.1016/j.antiviral.2019.01.005
[48]	Chen, X.-S.; Shuai, D.; Jiang, Z.-D.; Yang, H.; Luo, D.; Ni, H.; Wang, L.; Chen, B.-N. Acta Chim. Sinica 2022, 80, 116 (in Chinese). doi: 10.6023/A21110528
	(陈祥松, 帅蝶, 姜泽东, 杨晗, 罗丹, 倪辉, 王力, 陈丙年, 化学学报, 2022, 80, 116.)
[49]	Shuai, D.; Zhao, M.-J.; Chen, B.-N.; Wang, L. Chem. J. Chin. Univ. 2021, 42, 3579 (in Chinese).
	(帅蝶, 赵美娟, 陈丙年, 王力, 高等学校化学学报, 2021, 42, 3579.)
[50]	Lyon, D. K.; Miller, W. K.; Novet, T.; Domaille, P. J.; Evitt, E.; Johnson, D. C.; Finke, R. G. J. Am. Chem. Soc. 1991, 113, 7209. doi: 10.1021/ja00019a018
[51]	Qian, X.-Y.; Tong, X.; Wu, Q.-Y.; He, Z.-Q.; Cao, F.-H.; Yan, W.-F. Dalton Trans. 2012, 41, 9897. doi: 10.1039/c2dt30467h
[52]	Xu, Y.-P.; Yu, H.; Jiang, X.; Shi, J.-J.; Li, B.; Li, L.; Wu, L.-X.; Wang, M. Chin. J. Chem. 2022, 40, 813. doi: 10.1002/cjoc.v40.7
[53]	Re, R.; Pellegrini, N.; Proteggente, A.; Pannala, A.; Yang, M.; Rice-Evans, C. Free Radic. Biol. Med. 1999, 26, 1231. doi: 10.1016/S0891-5849(98)00315-3
[54]	Foh, M. B. K.; Amadou, I.; Foh, B. M.; Kamara, M. T.; Xia, W. Int. J. Mol. Sci. 2010, 11, 1851. doi: 10.3390/ijms11041851
[55]	Zhu, Y.; Qiu, L.; Zhou, J.; Guo, H.; Hu, Y.; Li, Z.; Wang, Q.; Chen, Q.; Liu, B. J. Enzym. Inhib. Med. Chem. 2010, 25, 798. doi: 10.3109/14756360903476398
[56]	Chen, X.-S.; Shuai, D.; Yang, H.; Luo, D.; Wang, L.; Chen, B.-N. Z. Anorg. Allg. Chem. 2022, 648, e202100319.
[57]	Thaipong, K.; Boonprakob, U.; Crosby, K.; Cisneros-Zevallos, L.; Byrne, D. H. J. Food Compos. Anal. 2006, 19, 669. doi: 10.1016/j.jfca.2006.01.003
[58]	Yu, X.; Yang, M.; Dong, J.; Shen, R. J. Food Sci. 2018, 83, 844. doi: 10.1111/jfds.2018.83.issue-3
[59]	Wang, L.-Y.; Ma, M.-T.; Yu, Z.-P.; Du, S.-K. Food Chem. 2021, 352, 129399. doi: 10.1016/j.foodchem.2021.129399
[60]	Huang, S.-Q.; Ding, S.-D.; Fan, L.-P. Int. J. Biol. Macromol. 2012, 50, 1183. doi: 10.1016/j.ijbiomac.2012.03.019