2,558
Views
18
CrossRef citations to date
0
Altmetric
Articles

Computational and experimental validation of antioxidant properties of synthesized bioactive ferulic acid derivatives

ORCID Icon, , , , , & show all
Pages 86-98 | Received 17 Aug 2017, Accepted 09 Feb 2018, Published online: 18 Apr 2018

References

  • Yogeeta, S.; Hanamuntra, R.; Gnanapragasam, A.; Subramanian, S.; Rajakannu, S.; Devaki, T. Attenuation of Abnormalities in the Lipid Metabolism during Experimental Myocardial Infarction Induced by Isoproterenol in Rats: Beneficial Effects of Ferulic Acid and Ascorbic Acid. Basic and Clinical Pharmacology and Toxicology. 2006, 98(5), 467–472. DOI: 10.1111/j.1742-7843.2006.pto_335.x.
  • Rice-Evans, C.; Miller, N.; Paganga, G. Antioxidant Properties of Phenolic Compounds. Trends Plant Science. 1997, 2(4), 152–159. DOI: 10.1016/S1360-1385(97)01018-2.
  • Cui, C.; Wang, Z.; Du, X.; Wang, L.; Yu, S.; Liu, X.; Li, Z.; Zhao, W. Synthesis and Antiviral Activity of Hydrogenated Ferulic Acid Derivatives. Journal of Chemistry. 2013, 2013, 1–5, Article ID 269434. DOI: 10.1155/2013/269434.
  • Paiva, L.; Goldbeck, R.; Santos, W.; Squina, F. Ferulic Acid and Derivatives: Molecules with Potential Application in the Pharmaceutical Field. Braz. Journal of Pharmaceutical Sciences. 2013, 49(3), 395–411. DOI: 10.1590/S1984-82502013000300002.
  • Sultana, R.;. Ferulic Acid Ethyl Ester as a Potential Therapy for Neurodegenerative Disorders. Biochimica et Biophysica Acta. 2012, 1822, 748–752. DOI: 10.1016/j.bbadis.2011.10.015.
  • Srinivasan, M.; Sudheer, A. R.; Menon, V. P. Ferulic Acid: Therapeutic Potential through Its Antioxidant Property. Journal of Clinical Biochemitry and Nutritoin. 2007, 40(2), 92–100. DOI: 10.3164/jcbn.40.92.
  • Kanasaki, J.; Aksenova, M.; Stoyanova, A.; Butterfield, D. A. Ferulic Acid Antioxidant Protection against Hydroxyl and Peroxy Radical Oxidation in Synaptosomal and Neuronal Cell Culture Systems in Vitro: Structure Activity Studies. Journal of Nutritional Biochemistry. 2002, 13, 273–281. DOI: 10.1016/S0955-2863(01)00215-7.
  • Hosoda, A.; Ozaki, Y.; Kashiwada, A.; Mutoh, M.; Wakabayashi, K.; Mizuno, K.; Nomura, E.; Taniguchi, H. Syntheses of Ferulic Acid Derivatives and Their Suppressive Effects on Cyclooxygenase-2 Promoter Activity. Bioorganic and Medicinal Chemistry. 2002, 10(4), 1189–1196. DOI: 10.1016/S0968-0896(01)00386-8.
  • Anselmi, C.; Bernardi, F.; Centini, M.; Gaggelli, E.; Gaggelli, N.; Valensin, D.; Valensin, G. Interaction of Ferulic Acid Derivatives with Human Erythrocytes Monitored by Pulse Field Gradient NMR Diffusion and NMR Relaxation Studies. Chemistry and Physics of Lipids. 2005, 134(2), 109–117. DOI: 10.1016/j.chemphyslip.2004.12.005.
  • Rakotondramanana, D.L.A.; Delomenèd, M.; Baltas, M.; Duran, H.; Bedos-Belval, F.; Rasoanaivo, P.; Negre-Salvayre, A.; Gornitzka, H. Synthesis of Ferulic Ester Dimers, Functionalisation and Biological Evaluation as Potential Antiatherogenic and Antiplasmodial Agents. Bioorganic and Medicinal Chemistry. 2007, 15(18), 6018–6026. DOI: 10.1016/j.bmc.2007.06.047.
  • Chigorimbo-Murefu, N. T. L.; Riva, S.; Burton, S. G. Lipase-Catalysed Synthesis of Esters of Ferulic Acid with Natural Compounds and Evaluation of Their Antioxidant Properties. Journal of Molecular Catalalysis B: Enzymatic. 2009, 56(4), 277–282. DOI: 10.1016/j.molcatb.2008.05.017.
  • Kalgutkar, A. S.; Marrnet, A. B.; Crews, B. C. Ester and Amide Derivatives of the Nonsteroidal Antiinflammatory Drug, Indomethacin, as Selective Cyclooxygenase-2 Inhibitors. Journal of Medicinal Chemistry. 2000, 43(15), 2860–2870. DOI: 10.1021/jm000004e.
  • Wang, F.; Lu, W.; Zhang, T.; Dong, J.; Gao, H.; Li, P.; Wang, S.; Zhang, J. Development of Novel Ferulic Acid Derivatives as Potent Histone Deacetylase Inhibitors. Bioorganic and Medicinal Chemistry. 2013, 21(22), 6973–6980. DOI: 10.1016/j.bmc.2013.09.021.
  • Fang, X.; Shima, M.; Kadota, M.; Tsuno, T.; Adachi, S. Suppressive Effect of Alkyl Ferulate on the Oxidation of Linoleic Acid. Bioscience Biotechnology and Biochemistry. 2006, 70, 457–461. DOI: 10.1271/bbb.70.457.
  • Stamatis, H.; Sereti, V.; Kolisis, F. N. Enzymatic Systematic Systhesis of Hydrophilic and Hydrophobic Derivatives of Natural Phenolic Acids in Organic Media. Journal of Molecular Catalalysis B: Enzymatic. 2001, 11, 323–328. DOI: 10.1016/S1381-1177(00)00016-3.
  • Li, W.; Li, N.; Tang, Y.; Li, B.; Lu, L.; Zhang, X.; Fu, H.; Duan, J. Biological Activity Evaluation and Structure-Activity Relationships Analysis of Ferulic Acid and Caffeic Acid Derivatives for Anticancer. Bioorganic and Medicinal Chemistry. Letters. 2012, 22, 6085–6088. DOI: 10.1016/j.bmcl.2012.08.038.
  • Balakrishnan, S.; Menon, V. P.; Manoharan, S. Ferulic Acid Inhibits 7,12-dimethylbenz[α]anthracene-induced Hamster Buccal Pouch Carcinogenesis. Journal of Medicinal Food. 2008, 11(4), 693–700. DOI: 10.1089/jmf.2007.0103.
  • Kwon, E. Y.; Do, G. M.; Cho, Y. Y.; Park, Y. B.; Jeon, S. M.; Choi, M. S. Anti-Atherogenic Property of Ferulic Acid in Apolipoprotein E-Deficient Mice Fed Western Diet: Comparison with Clofibrate. Food and Chemical Toxicology. 2010, 48(8–9), 2298–2303. DOI: 10.1016/j.fct.2010.05.063.
  • Lin, X. F.; Min, W.; Luo, D. Anticarcinogenic Effect of Ferulic Acid on ultraviolet-B Irradiated Human Keratinocyte HaCaT Cells. Journal of Medicinal Plant Research. 2010, 4(16), 1686–1694.
  • Shanmugam, H.; Doble, M. Combination of Ferulic Acid and Antibiotics as Effective Antibacterial Agents. Planta Medica. 2010, 76(12), 1191. DOI: 10.1055/s-0030-1264292.
  • Ou, L.; Kong, L. Y.; Zhang, X. M.; Niwa, M. Oxidation of Ferulic Acid by Momordica Charantia Peroxidase and Related Anti-Inflammation Activity Changes. Biological and Pharmaceutical Bulletin. 2003, 26(11), 1511–1516. DOI: 10.1248/bpb.26.1511.
  • Tetsuka, T.; Baier, L. D.; Morrison, A. R. Antioxidants Inhibit Interleukin-1-Induced Cyclooxygenase and Nitric-Oxide Synthase Expression in Rat Mesangial Cells: Evidence for Post-Transcriptional Regulation. Journal of Biological Chemistry. 1996, 271(20), 11689–11693. DOI: 10.1074/jbc.271.20.11689.
  • Nazare, A.; Faria, C.; Chiari, B.; Petronio, M.; Regasini, L.; Silva, D.; Correa, M.; Isaac, V.; Fonseca, L.; Ximenes, V. Ethyl Ferulate, a Component with anti-Inflammatory Properties for Emulsion-Based Creams. Molecules. 2014, 19, 8124–8139. DOI: 10.3390/molecules19068124.
  • Kumar, A.; Kanwar, S. Synthesis of Ethyl Ferulate in Organic Medium Using Celite-Immobilized Lipase. Bioresource Technology. 2011, 102(3), 2162–2167. DOI: 10.1016/j.biortech.2010.10.027.
  • Karamac, M.; Bucinski, A.; Pegg, R.; Amarowicz, R. Antioxidant and Antiradical Activity of Ferulates. Czech Journal of Food Sciences. 2005, 23(2), 64–68. DOI: 10.17221/3373-CJFS.
  • Sorensen, A.; Lyneborg, K.; Villeneuve, P.; Jacobsen, C. Alkyl Chain Length Impacts the Anti-Oxidative Effect of Lipophilized Ferulic Acid in Fish Oil Enriched Milk. Journal of Functional Foods. 2014, 18, 959–967. DOI: 10.1016/j.jff.2014.04.008.
  • Luo, X. D.; Basile, M. J.; Kennelly, E. J. Polyphenolic Antioxidants from the Fruits of Chrysophyllum Cainito L. [Star Apple]. Journal Of Agriculture and Food Chemistry. 2002, 50(6), 1379–1382. DOI: 10.1021/jf011178n.
  • Meeprom, A.; Sompong, W.; Chan, C.; Adisakwattana, S. Isoferulic Acid, a New Anti-Glycation Agent, Inhibits Fructose- and Glucose-Mediated Protein Glycation in Vitro. Molecules. 2013, 18, 6439–6454. DOI: 10.3390/molecules18066439.
  • Benzie, F. F.; Strain, J. J. Ferric Reducing/Antioxidant Power Assay: Direct Measure of Total Antioxidant Activity of Biological Fluids and Modified Version for Simultaneous Measurement of Total Antioxidant Power and Ascorbic Acid Concentration. Methods in Enzymology. 1999, 299, 15–23.
  • Devi, G. K.; Manivannan, K.; Thirumaran, G.; Rajathi, F. A. A.; Anantharaman, P. In Vitro Antioxidant Activities of Selected Seaweeds from Southeast Coast of India. Asian Pacific Journal of Tropical Medicine. 2011, 4, 205–211. DOI: 10.1016/S1995-7645(11)60070-9.
  • Ilavarasan, R.; Mallika, M.; Venkataraman, S. Antiinflammatory and Antioxidant Activities of Cassia fistula Linn. Bark Extracts. African Journal of Traditional Complementary and Alternative Medicines. 2005, 2(1), 70–85.
  • Lee, M. J.; Maliakal, P.; Chen, L.; Meng, X.; Bondoc, F. Y.; Prabhu, S.; Lambert, G.; Mohr, S.; Yang, C. S. Pharmacokinetics of Tea and [+] -Epigallocatechin-3-Gallate by Humans: Formation of Different Metabolites and Individual Variability. Cancer Epidermiology Biomarker Prevention. 2002, 11, 1025–1032.
  • Saha, M. R.; Hasan, S. M. R.; Akter, R.; Hossain, M. M.; Alam, M. S.; Alam, M. A.; Mazumder, M. E. H. In Vitro Free Radical Scavenging Activity of Methanol Extract of the Leaves of Mimusops Elengi Linn. Banglandesh Journal of Veterinary Medicine. 2008, 6, 197–202.
  • Malomo, S. O.; Ore, A.; Yakubu, M. T. In Vitro and in Vivo Antioxidant Activity of the Aqueous Extract of Celosia argentea Leaves. Indian Journal of Pharmacology. 2011, 43(3), 278–285. DOI: 10.4103/0253-7613.81519.
  • Ohkawa, H.; Ohishi, N.; Yagi, K. Assay for Lipid Peroxides in Animal Tissues by Thiobarbituric Acid Reaction. Analytical Biochemistry. 1979, 95, 351–358. DOI: 10.1016/0003-2697(79)90738-3.
  • Accelrys Software Inc. Discovery Studio Modeling Environment, Release 3.5; Accelrys Software Inc, San Diego, 2012.
  • Jones, G.; Willett, P.; Glen, R. C.; Leach, R.; Taylor, R. Development and Validation of a Genetic Algorithm for Flexible Docking. Journal of Molecular Biology. 1997, 267, 727–748. DOI: 10.1006/jmbi.1996.0897.
  • Psotová, J.; Lasovský, J.; Vičar, J. Metal-Chelating Properties, Electrochemical Behavior, Scavenging and Cytoprotective Activities of Six Natural Phenolics. Biomedical Papers. 2003, 147(2), 147–153. DOI: 10.5507/bp.2003.020.
  • Ogiwara, T.; Satoh, K.; Kadoma, Y.; Murakami, Y.; Unten, S.; Atsumi, T.; Sakagami, H.; Fujisawa, S. Radical Scavenging Activity and Cytotoxicity of Ferulic Acid. Anticancer Research. 2002, 22(5), 2711–2717.
  • Naik, G. H.; Priyadarsini, K. I.; Satav, J. G.; Banavalikar, M. M.; Sohoni, D. P.; Biyani, M. K.; Mohan, H. Comparative Antioxidant Activity of Individual Herbal Components Used in Ayurvedic Medicine. Phytochemistry. 2003, 63, 97–104. DOI: 10.1016/S0031-9422(02)00754-9.