A Brief Review of Phenolic Antioxidant and their Biological Activity
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Abstract
Antioxidant compounds are considered essential materials because they prevent or reduce free radical side chain reactions, which cause much damage. It is widely acknowledged that these damages are a major contributing factor to numerous diseases. Phenolic antioxidants are considered one of the most important antioxidant species. There is ample evidence that the antioxidant substances found in fruits and vegetables can prevent various diseases such as cancer, heart disease, diabetes, and cataracts. The food and pharmaceutical industries also make extensive use of it. Additionally, quite several phenolic medicinal compounds for anticancer, anti-inflammatory, anti-necrotic, hepato-protective, and neuroprotective purposes possess antioxidant abilities. The synthetic phenolic compounds exhibited remarkable antioxidant capacity in addition to various biological activities. These facts prompted the researchers to focus on newly synthesized phenolic compound derivatives and explore their biological activities, particularly those containing heterocyclics in their molecular structures. The biological activities of heterocyclic compounds are widely recognized.
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References
Shacter, E. Quantification and Significance of Protein Oxidation in Biological Samples. Drug Metabolism Reviews 2000, 32(3-4), 307-326. https://doi.org/10.1081/DMR-100102336.
Valko, M.; Leibfritz, D.; Moncol, J.; Cronin, M. T.; Mazur, M.; Telser, J. Free Radicals and Antioxidants in Normal Physiological Functions and Human Disease. The International Journal of Biochemistry & Cell Biology 2007, 39(1), 44-84. https://doi.org/10.1016/j.biocel.2006.07.001.
Silpak, B.; Rintu, D.; Ena Ray, B. Role of Free Radicals in Human Inflammatory Diseases. AIMS Biophysics 2017, 4(4), 596-614. https://doi.org/10.3934/biophy.2017.4.596.
Khan, F.; Garg, V. K.; Singh, A. K.; Kumar, T. Role of Free Radicals and Certain Antioxidants in the Management of Huntington’s Disease: A Review. Journal of Analytical and Pharmaceutical Research 2018, 7(4), 386-392. https://doi.org/10.15406/japlr.2018.07.00256.
Grigalius, I.; Petrikaite, V. Relationship between Antioxidant and Anticancer Activity of Trihydroxyflavones. Molecules (Basel, Switzerland) 2017, 22(12), 2169.
https://doi.org/10.3390/molecules22122169.
Flora, S.J. Structural, Chemical and Biological Aspects of Antioxidants for Strategies Against Metal and Metalloid Exposure. Oxidative Medicine and Cellular Longevity 2009, 2(4), 191-206.
https://doi.org/10.4161/oxim.2.4.9112.
Shakir, R.M. Synthesis and Antioxidant Ability of Some 4-(((4-(5-(Aryl)-1,3,4-Oxadiazol-2-Yl) Benzyl)Oxy)Methyl)-2,6-Dimethoxyphenol. Oriental Journal of Chemistry 2016, 32(5), 2611-2619.
http://dx.doi.org/10.13005/ojc/320533.
Mustapha, A. Influence of Steric Hindrance on the Antioxidant Activity of Some Schiff Base Ligands And Their Copper(II) Complexes. Oriental Journal of Chemistry 2014, 30, 1529-1534.
http://dx.doi.org/10.13005/ojc/300410.
Ostrea, J.E.M.; Cepeda, E.E.; Fleury, C.A.; Balun, J.E. Red Cell Membrane Lipid Peroxidation and Hemolysis Secondary to Phototherapy. Acta Paediatrica Scandinavica 1985, 74(3), 378-381.
https://doi.org/10.1111/j.1651-2227.1985.tb10987.x
Wright, J.S.; Johnson, E.R.; DiLabio, G.A. Predicting the Activity of Phenolic Antioxidants: Theoretical Method, Analysis of Substituent Effects, and Application to Major Families of Antioxidants. Journal of the American Chemical Society 2001, 123(6), 1173-1183. https://doi.org/10.1021/ja002455u.
Chifei Wu, T-A.Y.; Nakamoto, Y.; Ishida, Sh-I.; Kubota, S.; Nitta, K.H. Organic Hybrid of Chlorinated Polyethylene and Hindered Phenol. II. Influence of the Chemical Structure of Small Molecules on Viscoelastic Properties. Journal of Polymer Science Part B: Polymer Physics 2000, 38(11), 1496–1503. https://doi.org/10.1002/(SICI)1099-0488(20000601)38:11.
Moore, G.G.S.K. 2,6-Di-Tert-Butyl-4-(2'-Thenoyl)Phenol(R-830): A Novel Nonsteroidal Anti-Inflammatory Agent with Antioxidant Properties. Agents Actions 1982, 12(5-6), 674-683. https://doi.org/10.1007/BF01965078.
Shirota, H.C.K.; Ono, H.; Yamamoto, H.; Kobayashi, S.; Terato, K.; Ikuta, H.; Yamatsu, I.; Katayama, K. Pharmacological Properties of the Novel Non-Steroidal Antiinflammatory Agent N-Methoxy-3-(3,5-Di-Tert-Butyl-4-Hydroxybenzylidene)Pyrrolidin-2 -One. Arzneimittelforschung 1987, 37(8), 930-936. PMID: 3499909.
Hidaka, T.H.K.; Yamashita, T.; Watanabe, K.; Hiramatsu, Y.; Fujimura, H. Analgesic and Anti-Inflammatory Activities in Rats of Alpha-(3,5-Di-T-Butyl-4-Hydroxybenzylidene)-Gamma-Butyrolactone (KME-4), and its Intestinal Damage. The Journal of Pharmacy and Pharmacology 1986, 38(10), 748-753. https://doi.org/10.1111/j.2042-7158.1986.tb04483.x.
Cheemanapalli, S.; Palaniappan, C.; Mahesh, Y.; Iyyappan, Y.; Yarrappagaari, S.; Kanagaraj, S. In Vitro and in Silico Perspectives to Explain Anticancer Activity of a Novel Syringic Acid Analog ((4-(1H-1, 3-Benzodiazol-2-Yl)-2, 6-Dimethoxy Phenol)) Through Apoptosis Activation and Nfkb Inhibition In K562 Leukemia Cells. Computers in Biology and Medicine 2023, 152, 106349. https://doi.org/10.1016/j.compbiomed.2022.106349.
Tatipamula, V.B.; Kukavica, B. Phenolic Compounds As Antidiabetic, Anti-Inflammatory, and Anticancer Agents and Improvement of their Bioavailability by Liposomes. Cell Biochemistry and Function 2021, 39(8), 926-944. https://doi.org/10.1002/cbf.3667.
Grewal, A.S.; Sharma, N.; Singh, S.; Arora, S. Molecular Docking Studies of Phenolic Compounds from Syzygium cumini with Multiple Targets of Type 2 Diabetes. Journal of Pharmaceutical Technology. Research and Management 2018, 6(2), 125-133.https://doi.org/10.15415/jptrm.2018.62009.
Zulfiqar, S.; Haroon, M.; Baig, M.W.; Tariq, M.; Ahmad, Z.; Tahir, M.N.; Akhtar, T. Synthesis, Crystal Structure, Anti-Cancer, Anti-Inflammatory Anti-Oxidant and Quantum Chemical Studies of 4-(Pyrrolidine-2,5 Dione 1-Yl)Phenol. King Fahd University of Petroleum and Minerals 2021, 1224, 129267. https://doi.org/10.1016/j.molstruc.2020.129267.
Mariswamy, V.H.; Bindya, S.; Costa, R.A.; Prasad, S.K.; Shivamallu, C.; Begum, S.M.; Veerapur, R.; Syed, A.; Kollur, S.P. 2-Methoxy-5-(6-Methoxypyridin-3-Yl-Imino-Methyl)Phenol and its Transition Metal Complexes as Potent Antibacterial Agents: Synthesis, Characterization, Theoretical Investigations and Biological Evaluation. Results in Chemistry 2021, 3, 100120.
https://doi.org/10.1016/j.rechem.2021.100120.
Jiang, Y.; Su, L.; Liao, Y.; Shen, Y.; Gao, H.; Zhang, Y.; Wang, R.; Mao, Z. Synthesis And Antifungal Evaluation of Phenol-Derived Bis(Indolyl)Methanes Combined with FLC Against Candida Albicans. Bioorganic and Medicinal Chemistry Letters 2022, 58, 128525.
https://doi.org/10.1016/j.bmcl.2022.128525.
Halabi, M.F.; Shakir, R.M.; Bardi, D.A.; Al-Wajeeh, N.S.; Ablat, A.; Hassandarvish, P.; Hajrezaie, M.; Norazit, A.; Abdulla, M.A. Gastroprotective Activity of Ethyl-4-[(3,5-Di-Tert-Butyl-2-Hydroxybenzylidene) Amino]Benzoate Against Ethanol-Induced Gastric Mucosal Ulcer in Rats. PLOS One 2014, 9(5), e95908. https://doi.org/10.1371/journal.pone.0095908.
Ye, X,Z.W.; Li, Y.; Sun, Y.; Zhang, Y.; Ji, H.; Lai, Y. Darbufelone, a Novel Anti-Inflammatory Drug, Induces Growth Inhibition of Lung Cancer Cells Both in Vitro and in Vivo. Cancer Chemotherapy and Pharmacology 2010, 66(2), 277-285. https://doi.org/10.1007/s00280-009-1161-z.
Shakir, R.M.; Ariffin, A.; Abdulla, M.A. Synthesis of New 2,5-Di-Substituted 1,3,4-Oxadiazoles Bearing 2,6-Di-Tert-Butylphenol Moieties and Evaluation of their Antioxidant Activity. Molecules (Basel, Switzerland) 2014, 19(3), 3436-3449. https://doi.org/10.3390/molecules19033436.
Saoud, S.A.; Ali, K.F.; Shakir, R.M. Relationship between the Structure of Newly Synthesized Derivatives of 1,3,4-Oxadiazole Containing 2-Methylphenol and their Antioxidant and Antibacterial Activities. Oriental Journal of Chemistry 2017, 33(4), 1781-1798.http://dx.doi.org/10.13005/ojc/330423.
Skakir, R.M.; Jasim, H.S.; Saoud, S.A.; Hussain, D.F.; Ali, K.F. Synthesis, Antioxidant, Antibacterial and Docking Structure of New Dihydro-Pyrimidine Derivatives Containing Multi Phenol. Journal of Pharmaceutical Negative Results 2022, 13(2), 57-68.
https://doi.org/10.47750/pnr.2022.13.02.009.
Shakir, R.M.; Jasim, H.S.; Hussain, D.F. Synthesis, Antioxidant Activity and Molecular Docking Study of 1,2,4-Triazole and their Corresponding Fused Rings Containing 2-Methylphenol. International Journal of Drug Delivery Technology 2021, 11(2), 501-5011. https://doi.org/10.25258/ijddt.11.2.47.
Artunc, T.; Menzek, A.; Taslimi, P.; Gulcin, I.; Kazaz, C.; Sahin, E. Synthesis and Antioxidant Activities of Phenol Derivatives from 1,6-Bis(Dimethoxyphenyl)Hexane-1,6-Dione. Bioorganic Chemistry 2020, 100, 103884. https://doi.org/10.1016/j.bioorg.2020.103884.
Marc, G.; Stana, A.; Oniga, S. D.; Pîrnău, A.; Vlase, L.; Oniga, O. New Phenolic Derivatives of Thiazolidine-2,4-dione with Antioxidant and Antiradical Properties: Synthesis, Characterization, In Vitro Evaluation, and Quantum Studies. Molecules (Basel, Switzerland) 2019, 24(11), 2060. https://doi.org/10.3390/molecules24112060.
Gerasimova, E.L.; Gazizullina, E. R.; Borisova, M.V.; Igdisanova, D.I.; Nikiforov, E.A.; Moseev, T. D.; Varaksin, M.V.; Chupakhin, O.N.; Charushin, V.N.; Ivanova, A.V. Design and Antioxidant Properties of Bifunctional 2H-Imidazole-Derived Phenolic Compounds-A New Family of Effective Inhibitors for Oxidative Stress-Associated Destructive Processes. Molecules (Basel, Switzerland) 2021, 26(21), 6534. https://doi.org/10.3390/molecules26216534.
Costantino, L.; Parenti, C.; Di Bella, M.; Zanoli, P.; Baraldi, M. Anti-Inflammatory Activity of Newly Synthesized 2,6-Bis-(1,1-Dimethylethyl)Phenol Derivatives. Pharmacological Research 1993, 27(4), 349-358. https://doi.org/10.1006/phrs.1993.1034.