Structure-antioxidant activity relationships of o-hydroxyl, o-methoxy, and alkyl ester derivatives of p-hydroxybenzoic acid

Food Chemistry

Volumn 194, Issue , 2016, Pages 128-134

  Farhoosh, Reza ^a   Johnny, Saeed ^a   Asnaashari, Maryam ^a   Molaahmadibahraseman, Najme ^a   Sharif, Ali ^a  

^a FERDOWSI UNIVERSITY OF MASHHAD   (Iran)

Author keywords

Antioxidant activity; Emulsion; Kilka fish oil; p Hydroxybenzoic acid; Polar paradox theory

Indexed keywords

ANTIOXIDANTS; CHEMICAL COMPOUNDS; EMULSIFICATION; EMULSIONS; ESTERS; FISH; HYDROGEN BONDS;

ANTI-OXIDANT ACTIVITIES; ANTIRADICAL ACTIVITIES; ENVIRONMENTAL CONDITIONS; FISH OIL; INTERFACIAL PROPERTY; INTERMOLECULAR HYDROGEN BONDS; P-HYDROXYBENZOIC ACID; POLAR PARADOX THEORY;

FINANCIAL MARKETS;

4 HYDROXYBENZOIC ACID ESTER; ALPHA TOCOPHEROL; ANTIOXIDANT; CATECHOL; FISH OIL; GALLIC ACID; GALLIC ACID METHYL ESTER; GUAIACOL; HYDROPEROXIDE; PHENOL; PROTOCATECHUIC ACID; PYROGALLOL; SYRINGIC ACID; VANILLIC ACID; WATER OIL CREAM; 4-HYDROXYBENZOIC ACID; HYDROXYBENZOIC ACID DERIVATIVE; HYDROXYL RADICAL; PHENOLIC ACID;

ANTIOXIDANT ACTIVITY; ARTICLE; CHEMICAL REACTION; CONTROLLED STUDY; DPPH RADICAL SCAVENGING ASSAY; HYDROGEN BOND; STRUCTURE ACTIVITY RELATION; CHEMISTRY;

ANTIOXIDANTS; HYDROXYBENZOATES; HYDROXYL RADICAL; PARABENS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84939449760     PISSN: 03088146     EISSN: 18737072     Source Type: Journal    
DOI: 10.1016/j.foodchem.2015.08.003     Document Type: Article

References (31)

1. Y.V. Arkhipeko, and T.G. Sazontova Mechanisms of the cardioprotective effect of a diet enriched with ω-3 polyunsaturated fatty acids Pathophysiology 2 1995 131 140
2. N. Belhaj, E. Arab-Tehrany, and M. Linder Oxidative kinetics of salmon oil in bulk and in nanoemulsion stabilized by marine lecithin Process Biochemistry 45 2010 187 195
3. J.H. Chen, and C.T. Ho Antioxidant activities of caffeic acid and its related hydroxycinnamic acid compounds Journal of Agricultural and Food Chemistry 45 1997 2374 2378
4. Z. Cheng, J. Ren, Y. Li, W. Chang, and Z. Chen Establishment of a quantitative structure-activity relationship model for evaluating and predicting the protective potentials of phenolic antioxidants on lipid peroxidation Journal of Pharmaceutical Sciences 92 2003 475 484
5. L. Cleland, M. James, and S. Proudman The role of fish oils in the treatment of rheumatoid arthritis Drugs 63 2003 845 853
6. P. Cos, M. Calomme, M. Pieters, A.J. Vlietinck, and D. Vanden Berghe Studies in Natural Products Chemistry Atta-Ur-Rahman 22 2000 Elsevier Science Amsterdam 307 341
7. M.I. de Heer, H.-G. Korth, and P. Mulder Poly methoxy phenols in solution: O-H bond dissociation enthalpies, structures, and hydrogen bonding Journal of Organic Chemistry 64 1999 6969 6975
8. R. Farhoosh, and S.Z. Hoseini-Yazdi Shelf-life prediction of olive oils using empirical models developed at low and high temperatures Food Chemistry 141 2013 557 565
9. O.R. Fennema Food Chemistry 1996 Marcel Dekker, Inc New York
10. E.N. Frankel Lipid Oxidation 1998 The Oily Press Ltd West Ferry, Dundee (Scotland)
11. M. Friedman, and H.S. Jurgens Effect of pH on the stability of plant phenolic compounds Journal of Agricultural and Food Chemistry 48 2000 2101 2110
12. M.H. Gorden, F. Paivia-Martins, and M. Almeida Antioxidant activity of hydroxytyrosol acetate compared with that of other olive oil polyphenols Journal of Agricultural and Food Chemistry 49 2001 2480 2485
13. C.-L. Hsieh, G.-C. Yen, and H.-Y. Chen Antioxidant activities of phenolic acids on ultraviolet radiation-induced erythrocyte and low density lipoprotein oxidation Journal of Agricultural and Food Chemistry 53 2005 6151 6155
14. H. Hye-Kyeong, M.A. Della-Fera, J. Lin, and C.A. Baile Docosahexaenoic acid inhibits adipocyte differentiation and induces apoptosis in 3T3-L1 preadipocytes Journal of Nutrition 21 2006 2965 2969
15. J. Kawabata, Y. Okamoto, A. Kodama, T. Makimoto, and T. Kasai Oxidative dimers produced from protocatechuic and gallic esters in the DPPH radical scavenging reaction Journal of Agricultural and Food Chemistry 50 2002 5468 5471
16. H. Kikuzaki, M. Hisamoto, K. Hirose, K. Akiyama, and H. Taniguchi Antioxidant properties of ferulic acd and its related compounds Journal of Agricultural and Food Chemistry 50 2002 2161 2168
17. C.F. Lima, M. Fernandes-Ferreira, and C. Pereira-Wilson Phenolic compounds protect HepG2 cells from oxidative damage: relevance of glutathione levels Life Science 79 2006 2056 2068
18. E.J. Middleton, C. Kandaswami, and T.C. Theoharides The effects of plant flavonoids on mammalian cells: Implications for inflammation, heart disease, and cancer Pharmacological Reviews 52 2000 673 751
19. N. Nenadis, H.-Y. Zhang, and M.Z. Tsimidou Structure-antioxidant activity relationship of ferulic acid derivatives: effect of carbon side chain characteristic groups Journal of Agricultural and Food Chemistry 51 2003 1874 1879
20. J. Pokorny H. Chan, Autoxidation of Unsaturated Lipids 1987 Academic Press London 141 206
21. W.L. Porter Paradoxical behavior of antioxidants in food and biological systems G.M. William, Antioxidants: Chemical, physiological, nutritional and toxicological aspects 1993 Princeton Princeton Scientific 93 122
22. S. Saito, Y. Okamoto, and J. Kawabata Effects of alcoholic solvents on antiradical abilities of protocatechuic acid and its alkyl esters Bioscience, Biotechnology, and Biochemistry 68 2004 1221 1227
23. K. Schwarz, S.-W. Huang, J.B. German, B. Tiersch, J. Hartmann, and E.N. Frankel Activities of antioxidants are affected by colloidal properties of oil-in-water and water-in-oil emulsions and bulk oils Journal of Agricultural and Food Chemistry 48 2000 4874 4882
24. F. Shahidi, and P.K.J.P.D. Wanasundara Phenolic antioxidants Critical Reviews in Food Science and Nutrition. 32 1992 67 103
25. N.C. Shantha, and E.A. Decker Rapid, sensitive, iron-based spectrophotometric methods for determination of peroxide values of food lipids Journal of AOAC International 77 1994 421 424
26. S. Sharina, and S. Jumat Physicochemical characteristics of aji-fish seriola nigrofasciata lipid Malaysian Journal of Analytical Sciences 10 2006 55 58
27. C. Siquet, F. Paiva-Martin, J.F.C. Lima, S. Reis, and F. Borges Antioxidant profile of dihydroxy- and trihydroxyphenolic acids: A structure-activity relationship study Free Radical Research 40 2006 433 442
28. A. Torres de Pinedo, P. Penalver, and J.C. Morales Synthesis and evaluation of new phenolic-based antioxidants: Structure-activity relationship Food Chemistry 103 2007 55 61
29. J. Velasco, M.C. Dobarganes, and G. Marquez-Ruiz Antioxidant activity of phenolic compounds in sunflower oil-in-water emulsion containing sodium caseinate and lactose European Journal of Science and Technology 106 2004 325 333
30. J.S. Wright, E.R. Johnson, and G.A. DiLabio Predicting the activity of phenolic antioxidants: Theoretical method, analysis of substituent effects, and application to major families of antioxidants Journal of the American Oil Chemists' Society 123 2001 1173 1183
31. H.-Y. Zhang, Y.-M. Sun, and X.-L. Wang Substituent effects on O-H bond dissociation enthalpies and ionization potentials of catechols: A DFT study and its implications in the rational design of phenolic antioxidants and elucidation of structure-activity relationships for flavonoid antioxidants Chemistry - A European Journal 9 2003 502 508