Effect of Bridging Atom and Hydroxyl Position on the Antioxidant Capacity of Six Phenolic Schiff Bases

https://doi.org/10.22146/ijc.72379

Abdelhakim Kheniche(1*), Imededdine Kadi(2), Abderrahim Benslama(3), Samiya Rizoug(4), Sarra Bekri(5), Abdenassar Harrar(6)

(1) Laboratory of Inorganic Materials, Faculty of Sciences, University of M’sila, 28000 M’sila, Algeria; Department of Chemistry, Faculty of Sciences, University of M’sila, 28000 M’sila, Algeria
(2) Research Unit in Medicinal Plants (URPM. 3000, Laghouat) Attached to the Research Center of Biotechnology (CRBT. 25000, Constantine)
(3) Department of Biochemistry, Faculty of Sciences, University of M’sila, 28000 M’sila, Algeria
(4) Department of Chemistry, Faculty of Sciences, University of M’sila, 28000 M’sila, Algeria
(5) Department of Chemistry, Faculty of Sciences, University of M’sila, 28000 M’sila, Algeria
(6) Laboratory of Inorganic Materials, Faculty of Sciences, University of M’sila, 28000 M’sila, Algeria
(*) Corresponding Author

Abstract


A series of new phenolic Schiff bases N,N-bis(2,3-dihydroxybenzyl-idene)-4,4’-diphenylmethane (3-DPM), and N,N-bis(2,5-dihydroxybenzylidene)-4,4’-diphenylmethane (5-DPM), for sulfide bridge N,N-bis(2,3-dihydroxybenzyl-idene)-4,4’-diphenyl sulfide (3-DPS), N,N-bis(2,5-dihydroxybenzylidene)-4,4’-diphenyl sulfide (5-DPS), N,N-bis(2,3-dihydroxybenzyl-idene)-4,4’-diphenyl disulfide (3-DPSS), and N,N-bis(2,5-dihydroxybenzylidene)-4,4’-diphenyl disulfide (5-DPSS) were synthesized by condensation of substituted 4,4’-diamino-bis-(4-aminophenyl) methane/sulfide with various substituted aldehydes. The synthesized molecules were characterized by physical data, elemental, IR and 1H-NMR analyses. The antioxidant ability of compounds was determined through the use in vitro assays such as DPPH• scavenging, ABTS, total antioxidant capacity (TAC), hydroxyl radical OH• scavenging, and reducing power capability. The antioxidant activity of the compounds increased slightly after changing the atom bridge and hydroxyl group position. The results showed that the compound 5-DPSS exhibited superior scavenging strength against DPPH (EC50 = 7.10 ± 0.16 μg/mL), whereas 3-DPSS showed the highest activity (EC50 = 1.36 ± 0.08 μg/mL) when inspected by ABTS in relation to butylated hydroxyanisole (BHA) (EC50 = 7.54 ± 0.67). The higher OH• activity was marked by the compound 5-DPS (EC50 = 44.9 ± 3.3 μg/mL) related to BHT at (EC50 = 98.73 ± 0.3 μg/mL). The compounds 5-DPM demonstrated remarkable activity both reducing power (EC50 = 53.2 ± 0.3 μg/mL), and TAC assay (EC50 = 620.0 ± 2.4 μg/mL). These results prove that the modification in hydroxyl group position affect the antioxidant ability of Schiff bases.


Keywords


Schiff bases; free radicals; antioxidant activity; phenolics

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References

[1] Poprac, P., Jomova, K., Simunkova, M., Kollar, V., Rhodes, C.J., and Valko, M., 2017, Targeting free radicals in oxidative stress-related human diseases, Trends Pharmacol. Sci., 38 (7), 592–607.

[2] Archibong, A.E., Rideout, M.L., Harris, K.J., and Ramesh, A., 2018, Oxidative stress in reproductive toxicology, Curr. Opin Toxicol., 7, 95–101.

[3] Hoffmann, M.H., and Griffiths, H.R., 2018, The dual role of Reactive Oxygen Species in autoimmune and inflammatory diseases: Evidence from preclinical models, Free Radical Biol. Med., 125, 62–71.

[4] Phaniendra, A., Jestadi, D.B., and Periyasamy, L., 2015, Free radicals: Properties, sources, targets, and their implication in various diseases, Indian J. Clin. Biochem., 30 (1), 11–26.

[5] Gebicki, J.M., 2016, Oxidative stress, free radicals and protein peroxides, Arch. Biochem. Biophys., 595, 33–39.

[6] McInnis, S.M., Desikan, R., Hancock, J.T., and Hiscock, S.J., 2006, Production of reactive oxygen species and reactive nitrogen species by angiosperm stigmas and pollen: Potential signalling crosstalk?, New Phytol., 172 (2), 221–228.

[7] Hu, S., Yao, G., Wang, Y., Xu, H., Ji, X., He, Y., Zhu, Q., Chen, Z., and Sun, Y., 2014, Transcriptomic changes during the pre-receptive to receptive transition in human endometrium detected by RNA-Seq, J. Clin. Endocrinol. Metab., 99 (12), E2744–E2753.

[8] Goodman, M., Bostick, R.M., Kucuk, O., and Jones, D.P., 2011, Clinical trials of antioxidants as cancer prevention agents: past, present, and future, Free Radicals Biol. Med., 51 (5), 1068–1084.

[9] Khan, N., and Mukhtar, H., 2015, Dietary agents for prevention and treatment of lung cancer, Cancer Lett., 359 (2), 155–164.

[10] Ghasemi, S., and Lorigooini, Z., 2016, A review of significant molecular mechanisms of flavonoids in prevention of prostate cancer, J. Chem. Pharm. Sci., 9 (4), 3388–3394.

[11] Tan, H.W., Mo, H.Y., Lau, A.T., and Xu, Y.M., 2018, Selenium species: Current status and potentials in cancer prevention and therapy, Int. J. Mol. Sci., 20 (1), 75.

[12] Postigo, C., and Barceló, D., 2015, Synthetic organic compounds and their transformation products in groundwater: Occurrence, fate and mitigation, Sci. Total Environ., 503-504, 32–47.

[13] Gobec, M., Tomašič, T., Markovič, T., Mlinarič-Raščan, I., Dolenc, M.S., and Jakopin, Ž., 2015, Antioxidant and anti-inflammatory properties of 1,2,4-oxadiazole analogs of resveratrol, Chem.-Biol. Interact., 240, 200–207.

[14] Alam, M.S., Choi, J.H., and Lee, D.U., 2012, Synthesis of novel Schiff base analogues of 4-amino-1,5-dimethyl-2-phenylpyrazol-3-one and their evaluation for antioxidant and anti-inflammatory activity, Bioorg. Med. Chem., 20 (13), 4103–4108.

[15] Wu, H., Pan, G., Bai, Y., Wang, H., Kong, J., Shi, F., Zhang, Y., and Wang, X., 2014, Preparation, structure, DNA-binding properties, and antioxidant activities of a homodinuclear erbium(III) complex with a pentadentate Schiff base ligand, J. Chem. Res., 38 (4), 211–217.

[16] Poladian, Q., Şahin, O., Karakurt, T., İlhan-Ceylan, B., and Kurt, Y., 2021, A new zinc(II) complex with N2O2-tetradentate Schiff-base derived from pyridoxal-S-methylthiosemicarbazone: Synthesis, characterization, crystal structure, DFT, molecular docking and antioxidant activity studies, Polyhedron, 201, 115164.

[17] Adeleke, A.A., Zamisa, S.J., Islam, M., Olofinsan, K., Salau, V.F., Mocktar, C., and Omondi, B., 2021, Quinoline functionalized Schiff base silver (I) complexes: Interactions with biomolecules and in vitro cytotoxicity, antioxidant and antimicrobial activities, Molecules, 26 (5), 1205.

[18] Shahraki, S., Delarami, H.S., Mansouri-Torshizi, H., and Nouri, H., 2021, Investigation of kinetics and thermodynamics in the interaction process between two pyridine derived Schiff base complexes and catalase, J. Mol. Liq., 334, 116527.

[19] Kheniche, A., Ourari, A., Dakhouche, A., Ghanem, A., Min, W., and Meguellati, K., 2018, Electrochemical and theoretical studies influencing the effect of hydroxyl position of tetraphenolic Schiff bases towards corrosion inhibition of mild steel in 1 M HCl, J. Fundam. Appl. Sci., 10 (3), 209–238.

[20] Benslama, A., Harrar, A., Gul, F., and Demirtas, I., 2017, Phenolic compounds, antioxidant and antibacterial activities of Zizyphus lotus L. leaves extracts, Nat. Prod. J., 7 (4), 316–322.

[21] Sahoo, A.K., Narayanan, N., Sahana, S., Rajan, S.S., and Mukherjee, P.K., 2008, In vitro antioxidant potential of Semecarpus anacardium L., Pharmacologyonline, 3 (3), 27–35.

[22] Benslama, A., and Harrar, A., 2016, Free radicals scavenging activity and reducing power of two Algerian Sahara medicinal plants extracts, Int. J. Herb. Med., 4 (6), 158–161.

[23] Aboseada, H.A., Hassanien, M.M., El-Sayed, I.H., and Saad, E.A., 2021, Schiff base 4-ethyl-1-(pyridin-2-yl) thiosemicarbazide up-regulates the antioxidant status and inhibits the progression of Ehrlich solid tumor in mice, Biochem. Biophys. Res. Commun., 573, 42–47.

[24] Xing, A., Zeng, D., and Chen, Z., 2022, Synthesis, crystal structure and antioxidant activity of butylphenol Schiff bases: Experimental and DFT study, J. Mol. Struct., 1253, 132209.

[25] Daravath, S., Rambabu, A., Ganji, N., Ramesh, G., and Lakshmi, P.V.A., 2022, Spectroscopic, quantum chemical calculations, antioxidant, anticancer, antimicrobial, DNA binding and photo physical properties of bioactive Cu(II) complexes obtained from trifluoromethoxy aniline Schiff bases, J. Mol. Struct., 1249, 131601.

[26] Islam, M.M., Pal, T.K., Paul, S., Uddin, M.N., Sheikh, M.C., Alam, M.A., and Hossen, J., 2022, Computational, Hirshfeld surface, and molecular docking analysis of 2-(((4-methoxyphenyl)imino)methyl)-4-nitrophenol: In-vitro anticancer, antimicrobial, anti-inflammatory, and antioxidant studies, Results Chem., 4, 100331.

[27] Çalışkan, N., Usta, A., Beriş, F.Ş., Baltaş, N., and Çelik, E., 2020, Synthesis, antibacterial and antioxidant activities of some new N substituted azachalcone, Schiff base and pyrazole derivatives, Lett. Org. Chem., 17 (8), 631–638.

[28] Muğlu, H., Yakan, H., Misbah, A.G.A., Çavuş, M.S., and Bakır, T.K., 2021, Synthesis, structure characterization and quantum chemical study on relationship between structure and antioxidant properties of novel Schiff bases bearing (thio)/carbohydrazones, Res. Chem. Intermed., 47 (12), 4985–5005.

[29] Affat, S.S., 2021, Experimental and theoretical studies of new Schiff base as a corrosion inhibitor in acidic media and study antioxidant activity, Iran. J. Chem. Chem. Eng., Article in Press.

[30] Prestiani, A.E., and Purwono, B., 2017, Styrene and azo-styrene based colorimetric sensors for highly selective detection of cyanide, Indones. J. Chem., 17 (2), 238–247.

[31] Güngör, Ö., and Gürkan, P., 2014, Synthesis and characterization of higher amino acid Schiff bases, as monosodium salts and neutral forms. Investigation of the intramolecular hydrogen bonding in all Schiff bases, antibacterial and antifungal activities of neutral forms, J. Mol. Struct., 1074, 62–70.

[32] Maduwanthi, S.D.T., and Marapana, R.A.U.J., 2021, Total phenolics, flavonoids and antioxidant activity following simulated gastro-intestinal digestion and dialysis of banana (Musa acuminata, AAB) as affected by induced ripening agents, Food Chem., 339, 127909.

[33] Irfan, A., Imran, M., Al-Sehemi, A.G., Shah, A.T., Hussien, M., and Mumtaz, M.W., 2021, Exploration of electronic properties, radical scavenging activity and QSAR of oxadiazole derivatives by molecular docking and first-principles approaches, Saudi J. Biol. Sci., 28 (12), 7416–7421.

[34] Abuelizz, H.A., Taie, H.A.A., Bakheit, A.H., Marzouk, M., Abdellatif, M.M., and Al-Salahi, R., 2021, Biological evaluation of 4-(1H-triazol-1-yl) benzoic acid hybrids as antioxidant agents: In vitro screening and DFT study, Appl. Sci., 11 (24), 11642.

[35] Karkar, B., Şahin, S., and Güneş, M.E., 2021, Evaluation of antioxidant properties and determination of phenolic and carotenoid profiles of chestnut bee pollen collected from Turkey, J. Apic. Res., 60 (5), 765–774.

[36] Zheng, Y.Z., Deng, G., and Zhang, Y.C., 2022, Multiple free radical scavenging reactions of flavonoids, Dyes Pigm., 198, 109877.

[37] Enbaraj, E., Dhineshkumar, E., Jeyashri, K., Logeshwari, G., Mohana, V., Manikandan, H., Rajathi, V., Chakkaravarthy, J., Govindaraju, R., and Seenivasan, M., 2021, Novel synthesis, spectral characterisation and DFT calculation of (3,4-bis((E)-(substituted-dichlorobenzylidene)amino) phenyl) (phenyl) methanone derivatives, Mater. Today: Proc., 42, 982–988.

[38] Mar, J.M., da Silva, L.S., Moreira, W.P., Biondo, M.M., Pontes, F.L.D., Campos, F.R., Kinupp, V.F., Campelo, P.H., Sanches, E.A., and Bezerra, J.A., 2021, Edible flowers from Theobroma speciosum: Aqueous extract rich in antioxidant compounds, Food Chem., 356, 129723.

[39] Hong, Y., Wang, Z., Barrow, C.J., Dunshea, F.R., and Suleria, H.A.R., 2021, High-throughput screening and characterization of phenolic compounds in stone fruits waste by LC-ESI-QTOF-MS/MS and their potential antioxidant activities, Antioxidants, 10 (2), 234.

[40] Bendary, E., Francis, R.R., Ali, H.M.G., Sarwat, M.I., and El Hady, S., 2013, Antioxidant and structure–activity relationships (SARs) of some phenolic and anilines compounds, Ann. Agric. Sci., 58 (2), 173–181.

[41] Hernández, J.A., Jiménez, A., Mullineaux, P., and Sevilia, F., 2000, Tolerance of pea (Pisum sativum L.) to long‐term salt stress is associated with induction of antioxidant defences, Plant, Cell Environ., 23 (8), 853–862.

[42] Marc, G., Stana, A., Oniga, S.D., Pîrnău, A., Vlase, L., and Oniga, O., 2019, New phenolic derivatives of thiazolidine-2,4-dione with antioxidant and antiradical properties: Synthesis, characterization, in vitro evaluation, and quantum studies, Molecules, 24 (11), 2060.

[43] Čačić, M., Pavić, V., Molnar, M., Šarkanj, B., and Has-Schön, E., 2014, Design and synthesis of some new 1,3,4-thiadiazines with coumarin moieties and their antioxidative and antifungal activity, Molecules, 19 (1), 1163–1177.

[44] Pele, R., Marc, G., Stana, A., Ionuț, I., Nastasă, C., Tiperciuc, B., Oniga, I., Pîrnău, A., Vlase, L., and Oniga, O., 2022, Synthesis of new phenolic derivatives of quinazolin-4(3H)-one as potential antioxidant agents-In vitro evaluation and quantum studies, Molecules, 27 (8), 2599.

[45] Pedersen, J.Z., Oliveira, C., Incerpi, S., Kumar, V., Fiore, A.M., De Vito, P., Prasad, A.K., Malhotra, S.V., and Saso, L., 2007, Antioxidant activity of 4-methylcoumarins, J. Pharm. Pharmacol., 59 (12), 1721–1728.

[46] Teran, R., Guevara, R., Mora, J., Dobronski, L., Barreiro-Costa, O., Beske, T., Pérez-Barrera, J., Araya-Maturana, R., Rojas-Silva, P., Poveda, A., and Heredia-Moya, J., 2019, Characterization of antimicrobial, antioxidant, and leishmanicidal activities of Schiff base derivatives of 4-aminoantipyrine, Molecules, 24 (15), 2696.

[47] Dawidowicz, A.L., Wianowska, D., and Olszowy, M., 2012, On practical problems in estimation of antioxidant activity of compounds by DPPH method (Problems in estimation of antioxidant activity), Food Chem., 131 (3), 1037–1043.

[48] Farhoosh, R., Johnny, S., Asnaashari, M., Molaahmadibahraseman, N., and Sharif, A., 2016, Structure–antioxidant activity relationships of o-hydroxyl, o-methoxy, and alkyl ester derivatives of p-hydroxybenzoic acid, Food Chem., 194, 128–134.

[49] Martins, A.C., Bukman, L., Vargas, A.M.M., Barizão, É.O., Moraes, J.C.G., Visentainer, J.V., and Almeida, V.C., 2013, The antioxidant activity of teas measured by the FRAP method adapted to the FIA system: Optimising the conditions using the response surface methodology, Food Chem., 138 (1), 574–580.

[50] Prior, R.L., Wu, X., and Schaich, K., 2005, Standardized methods for the determination of antioxidant capacity and phenolics in foods and dietary supplements, J. Agric. Food Chem., 53 (10), 4290–4302.



DOI: https://doi.org/10.22146/ijc.72379

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