INNOVATIVE SYNTHESIS OF ZINC AND SELENIUM COMPLEXES WITH GALLIC ACID: EXPLORING THEIR ANTIOXIDANT POTENTIAL
Abstract
Polyphenols are naturally occurring compounds found largely in fruits, vegetables, cereals and beverages. Fruits like grapes, apple, pear, cherries and berries contain up to 200–300 mg polyphenols per 100 grams fresh weight. Among these compounds, gallic acid, (GA), a trihydroxybenzoic acid, stands out for its selective cytotoxicity against various tumor cell lines. This study focuses on the synthesis and analysis of a new complex of Zn(II) with GA, but also Se(IV) with gallic acid, exploring its comparative antioxidant potential. Materials and methods: The complex, synthesized in a 1:2 molar ratio of GA to zinc acetate dihydrate, respectively sodium selenite pentahydrate, showed various promising therapeutic roles in vitro. GA and zinc both possess antioxidant properties, and their coordination in the complex increases these attributes depending on the concentration. Results: GA, known for its powerful antioxidant effects, outperforms popular antioxidants like ascorbic acid in various tests. The study evaluates the ability of GA to remove reactive species, showing its superior efficiency. In addition, GA and its ester derivatives demonstrate protective effects against lipid peroxidation, a important process in cellular damage. Conclusions: The synthesized Zn(II) complex, with its structure-activity relationship suggesting Zn(O4) coordination, opens avenues for understanding its antioxidant potential. Overall, this research reveals the multifaceted pharmacological potential of GA and its complexes, providing insights into their antioxidant effects.
References
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28. Inoue M, Sakaguchi N, Isuzugawa K, Tani H, Ogihara Y. Role of reactive oxygen species in gallic acid-induced apoptosis. Biological and Pharmaceutical Bulletin 2000; 23(10): 1153-1157.
29. Tsai CL, Chiu YM, Ho TY, et al. Gallic acid induces apoptosis in human gastric adenocarcinoma cells. Anticancer Research 2018; 38(4): 2057-2067.
30. Liu Z, Li D, Yu L, Niu F. Gallic acid as a cancer-selective agent induces apoptosis in pancreatic cancer cells. Chemotherapy 2012; 58(3): 185-194.
31. Pauli GF, Godecke T, Jaki BU, Lankin DC. Quantitative 1H NMR. Development and potential of an analytical method: an update. Journal of Natural Products 2012; 75(4): 834-851.
32. Yuan Y, Song Y, Jing W, Wang Y, Yang X, Liu D. Simultaneous determination of caffeine, gallic acid, theanine, (−)-epigallocatechin and (−)-epigallocatechin-3-gallate in green tea using quantitative 1 H-NMR spectroscopy. Analytical Methods 2014; 6(3): 907-914.
33. Can M, Bulut E, Özacar M. Synthesis and characterization of gallic acid resin and its interaction with palladium (II), rhodium (III) chloro complexes. Industrial & Engineering Chemistry Research 2012; 51(17): 6052-6063.
34. Hu JS, Yao XQ, Zhang MD, Qin L, Li YZ, et al. Syntheses, structures, and characteristics of four new metal–organic frameworks based on flexible tetrapyridines and aromatic polycarboxylate acids. Crystal Growth & Design 2012;12(7): 3426-3435.
35. Yesufu HB, Musa SA, Mohammed GT, Fugu MB. Synthesis, characterization and antioxidant proper-ties of metal (II) complexes of gallic acid and quercetin. Int J Res Innov Appl Sci 2020; 5: 226-231.
36. Singh TA, Sharma A, Tejwan N, Ghosh N, Das J, Sil PC. A state-of-the-art review on the synthesis, antibacterial, antioxidant, antidiabetic and tissue regeneration activities of zinc oxide nanoparticles. Advances in Colloid and Interface Science 2021; 295: 102495.
37. Variya BC, Bakrania AK, Patel SS. Antidiabetic potential of gallic acid from Emblica officinalis: Improved glucose transporters and insulin sensitivity through PPAR-γ and Akt signaling. Phytomedi-cine 2020; 73: 152906.
38. Amoussa AM, Sanni A, Lagnika L. Antioxidant activity and total phenolic, flavonoid and flavonol contents of the bark extracts of Acacia ataxacantha. Journal of Pharmacognosy and Phytochemistry 2015; 4(2): 172-178.
39. Mishra K, Ojha H, Chaudhury NK. Estimation of antiradical properties of antioxidants using DPPH assay: A critical review and results. Food Chemistry 2012; 130(4): 1036-1043.
40. Sirivibulkovit K, Nouanthavong S, Sameenoi Y. Based DPPH assay for antioxidant activity analysis. Analytical sciences 2018; 34(7): 795-800.
41. El-Megharbel SM, Hamza RZ. Synthesis, spectroscopic characterizations, conductometric titration and investigation of potent antioxidant activities of gallic acid complexes with Ca (II), Cu (II), Zn (III), Cr (III) and Se (IV) metal ions. Journal of Molecular Liquids 2022; 358: 119196.
42. Motloung DM, Mashele SS, Matowane GR, et al. Synthesis, characterization, antidiabetic and antiox-idative evaluation of a novel Zn (II)-gallic acid complex with multi-facet activity. Journal of Pharmacy and Pharmacology 2020; 72(10): 1412-1426.
43. Abdelwahed A, Bouhlel I, Skandrani I, et al. Study of antimutagenic and antioxidant activities of gallic acid and 1, 2, 3, 4, 6-pentagalloylglucose from Pistacia lentiscus: Confirmation by microarray expression profiling. Chemico-Biological Interactions 2007; 165(1): 1-13.
44. Nenadis N, Lazaridou O, Tsimidou MZ. Use of reference compounds in antioxidant activity assess-ment. Journal of Agricultural and Food Chemistry 2007; 55(14): 5452-5460.
45. Cho YS, Kim SK, Ahn CB, Je JY. Preparation, characterization, and antioxidant properties of gallic acid-grafted-chitosans. Carbohydrate Polymers 2011; 83(4): 1617-1622.
46. Mainzen Prince PS, Kumar MR, Selvakumari CJ. Effects of gallic acid on brain lipid peroxide and lipid metabolism in streptozotocin‐induced diabetic Wistar rats. Journal of Biochemical and Molecular Toxicology 2011; 25(2): 101-107.
47. Fimognari C. Antitumor Effects of anthocyanins: focus on apoptosis. In: Natural compounds as in-ducers of cell death: volume 1. Dordrecht: Springer Netherlands, 2012, 49-68.
2. Choubey S, Varughese LR, Kumar V, Beniwal V. Medicinal importance of gallic acid and its ester derivatives: a patent review. Pharmaceutical patent analyst 2015;4(4):305-15.
3. Chitiala RD, Burlec AF, Nistor A, Caba IC, Mircea C, Hancianu M, Cioanca O. Chemical assessment and biologic potential of a special Lespedeza capitata extract. Med Surg J 2023; 127(3): 474-479.
4. Nani E, Hancianu M, Iancu C, Corciova A, Cioanca O, Stan C, Mircea C. Antioxidant and enzyme inhibitory effects of Morus sp. extracts. Med Surg J 2022; 126(4): 593-604.
5. Ionita R, Postu PA, Beppe GJ, Mihasan M, Petre BA, Hancianu M, Cioanca O, Hritcu L. Cognitive-enhancing and antioxidant activities of the aqueous extract from Markhamia tomentosa (Benth.) K. Schum. stem bark in a rat model of scopolamine. Behavioral and Brain Functions 2017; 13: 1-3.
6. Yen GC, Duh PD, Tsai HL. Antioxidant and pro-oxidant properties of ascorbic acid and gallic acid. Food Chemistry 2002;79(3): 307-13.
7. Naksuriya O, Okonogi S. Comparison and combination effects on antioxidant power of curcumin with gallic acid, ascorbic acid, and xanthone. Drug Discoveries & Therapeutics 2015; 9(2): 136-141.
8. Aruoma OI, Murcia A, Butler J, Halliwell B. Evaluation of the antioxidant and prooxidant actions of gallic acid and its derivatives. Journal of Agricultural and Food Chemistry 1993; 41(11):1880-1885.
9. Lu Z, Nie G, Belton PS, Tang H, Zhao B. Structure–activity relationship analysis of antioxidant ability and neuroprotective effect of gallic acid derivatives. Neurochemistry International 2006;48(4): 263-274.
10. Lungu II, Marin-Batîr D, Panainte A, Mircea C, Tuchiluș C, et al. Catechin-zinc-complex: synthesis, characterization and biological activity assessment. Farmacia 2023; 71(4): 755-763.
11. Lone SH, Rehman SU, Bhat KA. Synthesis of gallic-acid-1-phenyl-1H-[1, 2, 3] triazol-4-yl methyl esters as effective antioxidants. Drug Research 2017; 11(02): 111-118.
12. Bai J, Zhang Y, Tang C, et al. Gallic acid: Pharmacological activities and molecular mechanisms involved in inflammation-related diseases. Biomedicine & Pharmacotherapy 2021; 133: 110985.
13. Adefegha SA, Oboh G, Ejakpovi II, Oyeleye SI. Antioxidant and antidiabetic effects of gallic and protocatechuic acids: a structure–function perspective. Comparative Clinical Pathology 2015; 24: 1579-85.
14. Al-Salih RM. Clinical experimental evidence: synergistic effect of gallic acid and tannic acid as antidiabetic and antioxidant agents. Thi-Qar Med J 2010; 4(4): 109-119.
15. Punithavathi VR, Prince PS, Kumar R, Selvakumari J. Antihyperglycaemic, antilipid peroxidative and antioxidant effects of gallic acid on streptozotocin induced diabetic Wistar rats. European Journal of Pharmacology 2011; 650(1): 465-471.
16. Kahkeshani N, Farzaei F, Fotouhi M, et al. Pharmacological effects of gallic acid in health and diseases: A mechanistic review. Iranian Journal of Basic Medical Sciences 2019; 22(3): 225.
17. Abbas M, Saeed F, Anjum FM, et al. Natural polyphenols: An overview. International Journal of Food Properties 2017; 20(8): 1689-1699.
18. Ahuja I, Kissen R, Bones AM. Phytoalexins in defense against pathogens. Trends in Plant Science 2012; 17(2): 73-90.
19. Subramanian AP, John AA, Vellayappan MV, et al. Gallic acid: prospects and molecular mechanisms of its anticancer activity. Rsc Advances 2015; 5(45): 35608-35621.
20. Jiang Y, Pei J, Zheng Y, Miao YJ, Duan BZ, Huang LF. Gallic acid: a potential anti-cancer agent. Chinese Journal of Integrative Medicine. 2022;28(7):661-671.
21. Zhao J, Khan IA, Fronczek FR. Gallic acid. Acta Crystallographica Section E: Structure Reports Online 2011; 67(2): o316-317.
22. Badhani B, Sharma N, Kakkar R. Gallic acid: A versatile antioxidant with promising therapeutic and industrial applications. Rsc Advances 2015; 5(35): 27540-27557.
23. Saini AK, Zahiruddin S, Newton KG, et al. Validation and standardization of gallic acid and ellagic acid in Quercus infectoria, Terminalia chebula, and Pistacia integerrima. Journal of AOAC International 2023; 106(5): 1305-1312.
24. Sanz M, Cadahia E, Esteruelas E, et al. Phenolic compounds in chestnut (Castanea sativa Mill.) heartwood. Effect of toasting at cooperage. Journal of Agricultural and Food Chemistry 2010; 58(17): 9631-9640.
25. Locatelli C, Filippin-Monteiro FB, Centa A, Creczinsky-Pasa TB. Antioxidant, antitumoral and anti-inflammatory activities of gallic acid. Handbook on Gallic Acid: Natural Occurrences, Antioxidant Properties and Health Implications, (4th Edition). Nova Publishers. 2013; 1-23.
26. Kaur R, Arora S, Thukral AK. A report on antimutagenic and antioxidant activities of gallic acid. Journal of Pharmacognosy and Phytochemistry 2015; 3(5): 173-178.
27. BenSaad LA, Kim KH, Quah CC, Kim WR, Shahimi M. Anti-inflammatory potential of ellagic acid, gallic acid and punicalagin A&B isolated from Punica granatum. BMC Complementary and Alternative Medicine 2017; 17: 1-10.
28. Inoue M, Sakaguchi N, Isuzugawa K, Tani H, Ogihara Y. Role of reactive oxygen species in gallic acid-induced apoptosis. Biological and Pharmaceutical Bulletin 2000; 23(10): 1153-1157.
29. Tsai CL, Chiu YM, Ho TY, et al. Gallic acid induces apoptosis in human gastric adenocarcinoma cells. Anticancer Research 2018; 38(4): 2057-2067.
30. Liu Z, Li D, Yu L, Niu F. Gallic acid as a cancer-selective agent induces apoptosis in pancreatic cancer cells. Chemotherapy 2012; 58(3): 185-194.
31. Pauli GF, Godecke T, Jaki BU, Lankin DC. Quantitative 1H NMR. Development and potential of an analytical method: an update. Journal of Natural Products 2012; 75(4): 834-851.
32. Yuan Y, Song Y, Jing W, Wang Y, Yang X, Liu D. Simultaneous determination of caffeine, gallic acid, theanine, (−)-epigallocatechin and (−)-epigallocatechin-3-gallate in green tea using quantitative 1 H-NMR spectroscopy. Analytical Methods 2014; 6(3): 907-914.
33. Can M, Bulut E, Özacar M. Synthesis and characterization of gallic acid resin and its interaction with palladium (II), rhodium (III) chloro complexes. Industrial & Engineering Chemistry Research 2012; 51(17): 6052-6063.
34. Hu JS, Yao XQ, Zhang MD, Qin L, Li YZ, et al. Syntheses, structures, and characteristics of four new metal–organic frameworks based on flexible tetrapyridines and aromatic polycarboxylate acids. Crystal Growth & Design 2012;12(7): 3426-3435.
35. Yesufu HB, Musa SA, Mohammed GT, Fugu MB. Synthesis, characterization and antioxidant proper-ties of metal (II) complexes of gallic acid and quercetin. Int J Res Innov Appl Sci 2020; 5: 226-231.
36. Singh TA, Sharma A, Tejwan N, Ghosh N, Das J, Sil PC. A state-of-the-art review on the synthesis, antibacterial, antioxidant, antidiabetic and tissue regeneration activities of zinc oxide nanoparticles. Advances in Colloid and Interface Science 2021; 295: 102495.
37. Variya BC, Bakrania AK, Patel SS. Antidiabetic potential of gallic acid from Emblica officinalis: Improved glucose transporters and insulin sensitivity through PPAR-γ and Akt signaling. Phytomedi-cine 2020; 73: 152906.
38. Amoussa AM, Sanni A, Lagnika L. Antioxidant activity and total phenolic, flavonoid and flavonol contents of the bark extracts of Acacia ataxacantha. Journal of Pharmacognosy and Phytochemistry 2015; 4(2): 172-178.
39. Mishra K, Ojha H, Chaudhury NK. Estimation of antiradical properties of antioxidants using DPPH assay: A critical review and results. Food Chemistry 2012; 130(4): 1036-1043.
40. Sirivibulkovit K, Nouanthavong S, Sameenoi Y. Based DPPH assay for antioxidant activity analysis. Analytical sciences 2018; 34(7): 795-800.
41. El-Megharbel SM, Hamza RZ. Synthesis, spectroscopic characterizations, conductometric titration and investigation of potent antioxidant activities of gallic acid complexes with Ca (II), Cu (II), Zn (III), Cr (III) and Se (IV) metal ions. Journal of Molecular Liquids 2022; 358: 119196.
42. Motloung DM, Mashele SS, Matowane GR, et al. Synthesis, characterization, antidiabetic and antiox-idative evaluation of a novel Zn (II)-gallic acid complex with multi-facet activity. Journal of Pharmacy and Pharmacology 2020; 72(10): 1412-1426.
43. Abdelwahed A, Bouhlel I, Skandrani I, et al. Study of antimutagenic and antioxidant activities of gallic acid and 1, 2, 3, 4, 6-pentagalloylglucose from Pistacia lentiscus: Confirmation by microarray expression profiling. Chemico-Biological Interactions 2007; 165(1): 1-13.
44. Nenadis N, Lazaridou O, Tsimidou MZ. Use of reference compounds in antioxidant activity assess-ment. Journal of Agricultural and Food Chemistry 2007; 55(14): 5452-5460.
45. Cho YS, Kim SK, Ahn CB, Je JY. Preparation, characterization, and antioxidant properties of gallic acid-grafted-chitosans. Carbohydrate Polymers 2011; 83(4): 1617-1622.
46. Mainzen Prince PS, Kumar MR, Selvakumari CJ. Effects of gallic acid on brain lipid peroxide and lipid metabolism in streptozotocin‐induced diabetic Wistar rats. Journal of Biochemical and Molecular Toxicology 2011; 25(2): 101-107.
47. Fimognari C. Antitumor Effects of anthocyanins: focus on apoptosis. In: Natural compounds as in-ducers of cell death: volume 1. Dordrecht: Springer Netherlands, 2012, 49-68.
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