Chemical evidence for the synergistic effect of a cysteinyl thiol on the antioxidant activity of caffeic and dihydrocaffeic esters

Food Chemistry

Volumn 138, Issue 2-3, 2013, Pages 1483-1492

  Fujimoto, Aya ^a   Inai, Miyuki ^a   Masuda, Toshiya ^a  

^a UNIVERSITY OF TOKUSHIMA   (Japan)

Author keywords

Antioxidant activity; Caffeic acid; Cysteinyl thiol; Dihydrocaffeic acid; Synergism

Indexed keywords

ANALYTICAL RESULTS; ANTI-OXIDANT ACTIVITIES; ANTI-OXIDATION; CAFFEIC ACIDS; CHEMICAL EVIDENCES; CYSTEINYL THIOL; INDUCTION PERIODS; INHIBITION RATE; LIPID OXIDATION; LIQUID CHROMATOGRAPHY-MASS SPECTROMETRY; SYNERGISM; SYNERGISTIC EFFECT;

HIGH PERFORMANCE LIQUID CHROMATOGRAPHY;

CHROMATOGRAPHY;

ANTIOXIDANT; CAFFEIC ACID; CAFFEIC ACID METHYL ESTER; CYSTEINYL THIOL; METHYL DIHYDROCAFFEATE; THIOL; UNCLASSIFIED DRUG;

ANTIOXIDANT ACTIVITY; ARTICLE; DRUG POTENTIATION; LIPID OXIDATION;

ANTIOXIDANTS; CAFFEIC ACIDS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; ESTERS; MASS SPECTROMETRY; SULFHYDRYL COMPOUNDS;

EID: 84873723226     PISSN: 03088146     EISSN: 18737072     Source Type: Journal    
DOI: 10.1016/j.foodchem.2012.11.073     Document Type: Article

References (43)

1. H.M. Awad, M.G. Boersma, S. Boeren, P.J. van Bladeren, J. Vervoort, and I.M.C.M. Rietjens The regioselectivity of glutathione adduct formation with flavonoid quinone/quinone methides is pH-dependent Chemical Research in Toxicology 15 2002 343 351
2. +) with amino acids, kinetics and mechanism Canadian Journal of Chemistry 78 2000 1052 1059
3. L.R.C. Barclay, S.J. Locke, and J.M. MacNeil The autoxidation of unsaturated lipids in micelles. Synergism of inhibitors vitamins C and E Canadian Journal of Chemistry 61 1983 1288 1290
4. D. Bassil, D.P. Makris, and P. Kefalas Oxidation of caffeic acid in the presence of l-cysteine: Isolation of 2-S-cysteinylcaffeic acid and evaluation of its antioxidant properties Food Research International 38 2005 395 402
5. 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
6. J.J.L. Cilliers, and V.L. Singleton Caffeic acid autoxidation and effects of thiols Journal of Agricultural and Food Chemistry 38 1990 1789 1796
7. R.J. Elias, D.J. McClements, and E.A. Decker Antioxidant activity of cysteine, tryptophan, and methionine residues in continuous phase β-lactoglobulin in oil-in-water emulsions Journal of Agricultural and Food Chemistry 53 2005 10248 10253
8. E.N. Frankel Lipid oxidation 2nd ed. 2005 The Oily Press Bridgwater (Chaper 9)
9. A. Fujimoto, and T. Masuda Chemical interaction between polyphenol and a cysteinyl thiol under radical oxidation conditions Journal of Agricultural and Food Chemistry 60 2012 5142 5151
10. A. Fujimoto, and T. Masuda Antioxidation mechanism of rosmarinic acid, identification of an unstable quinone derivative by the addition of odourless thiol Food Chemistry 132 2012 901 906
11. A. Fujimoto, Y. Shingai, M. Nakamura, T. Maekawa, Y. Sone, and T. Masuda A novel ring-expanded product with enhanced tyrosinase inhibitory activity from classical Fe-catalyzed oxidation of rosmarinic acid, a potent antioxidative Lamiaceae polyphenol Bioorganic & Medicinal Chemistry Letters 20 2010 7393 7396
12. S. Fujisawa, and Y. Kadoma Anti- and pro-oxidant effects of oxidized quercetin, curcumin or curcumin-related compounds with thiols or ascorbate as measured by the induction period method In Vitro 20 2006 39 44
13. N. Güngör, M. Özyürek, K. Gülçü, and S.D.Ç.R. Apak Comparative evaluation of antioxidant capacities of thiol-based antioxidants measured by different in vitro methods Talanta 83 2011 1650 1658
14. C. Hansch, A. Leo, and R.W. Taft A survey of Hammett substituent constants and resonance and field parameters Chemical Reviews 91 1991 165 195
15. Y. Kadoma, and S. Fujisawa A comparative study of the radical-scavenging activity of the phenol carboxylic acids caffeic acid, p-coumaric acid, chlorogenic acid and ferulic acid, with or without 2-mercaptoethanol, a thiol, using the induction period method Molecules 13 2008 2488 2499
16. L.R. Mahoney Antioxidants Angewante Chemie International Edition 8 1969 547 555
17. J. Malmström, M. Jonsson, I.A. Cotgreave, L. Hammarström, M. Sjödin, and L. Engman The antioxidant profile of 2,3-dihydrobenzo[b]furan- 5-ol and its 1-thio, 1-seleno, and 1-telluro analogues Journal of the American Chemical Society 123 2001 3434 3440
18. K. Maruyama, and M. Okubo Yuuki Kouzo (Organic Structure) 1983 Maruzen Tokyo (Chapter 4)
19. T. Masuda, Y. Inaba, T. Maekawa, Y. Takeda, H. Tamura, and H. Yamaguchi Recovery mechanism of the antioxidant activity from carnosic acid quinone, an oxidized sage and rosmary antioxidant Journal of Agricultural and Food Chemistry 50 2002 5863 5869
20. T. Masuda, Y. Inaba, T. Maekawa, Y. Takeda, H. Yamaguchi, and K. Nakamoto Simple detection method of powerful antiradical compounds in the raw extract of plants and its application for the identification of antiradical plant constituents Journal of Agricultural and Food Chemistry 51 2003 1831 1838
21. T. Masuda, T. Kirikihira, and Y. Takeda Recovery of antioxidant activity from carnosol quinone: Antioxidants obtained from a water-promoted conversion of carnosol quinone Journal of Agricultural and Food Chemistry 53 2005 6831 6834
22. T. Masuda, K. Yamada, J. Akiyama, T. Someya, Y. Odaka, and Y. Takeda Antioxidation mechanism studies of caffeic acid: Identification of antioxidation products of methyl caffeate from lipid oxidation Journal of Agricultural and Food Chemistry 56 2008 5947 5952
23. T. Masuda, J. Akiyama, A. Fujimoto, S. Yamaguchi, T. Maekawa, and Y. Sone Antioxidation reaction mechanism studies of phenolic lignans, identification of antioxidation products of secoisolariciresinol from lipid oxidation Food Chemistry 123 2010 442 450
24. J.-H. Moon, and J. Terao Antioxidant activity of caffeic acid and dihydrocaffeic acid in lard and human low-density lipoprotein Journal of Agricultural and Food Chemistry 46 1998 5062 5065
25. K. Mukai, S. Ito, and H. Morimoto Stopped-flow kinetic study of vitamin E regeneration reaction with biological hydroquinones (Reduced forms of ubiquinone, vitamin K, and tocophenol quinone) in solution Journal of Biological Chemistry 267 1992 22277 22281
26. E. Niki, T. Saito, A. Kawakami, and Y. Kamiya Inhibition of oxidation of methyl linoleate in solution by vitamin E and vitamin C Journal of Biological Chemistry 259 1984 4177 4182
27. M. Nikolantonaki, M. Jourdes, K. Shinoda, P.-L. Teissedre, S. Quideau, and P. Darriet Identification of adducts between an odoriferous volatile thiol and oxidized grape phenolic compounds: Kinetic study of adduct formation under chemical and enzymatic oxidation conditions Journal of Agricultural and Food Chemistry 60 2012 2647 2656
28. M. Nikolantonaki, and A.L. Waterhouse A method to quantify quinone reaction rates with wine relevant nucleophiles: A key to the understanding of oxidative loss of varietal thiols Journal of Agricultural and Food Chemistry 60 2012 8484 8491
29. K. Okada, S. Nagai, and E. Bansho Antioxidative activities of cysteine derivatives and cysteine-containing dipeptides and their synergism with antioxidants in the autoxidation of linoleic acid Eisei Kagaku 26 1980 1 7
30. S. Rohn, H.M. Rawel, and J. Kroll Antioxidant activity of protein-bound quercetin Journal of Agricultural and Food Chemistry 52 2004 4725 4729
31. M.L. Sagrista, A.F. Garcia, M.A.D. Madariaga, and M. Mora Antioxidant and pro-oxidant effect of the thiolic compounds N-acetyl-l-cysteine and glutathione against free radical-induced lipid peroxidation Free Radical Research 36 2002 329 340
32. S. Saito, and J. Kawabata Synergistic effects of thiols and amines on antiradical efficiency of protocatechuic acid Journal of Agricultural and Food Chemistry 52 2004 8163 8168
33. T. Sato, and H. Kise Structural effect of phenol derivatives on antioxidant properties for an ester lubricant Journal of Japan Oil Chemists' Society 37 1988 166 170
34. F. Shahidi, and M. Naczk Phenolics in Food and Nutraceuticals 2004 CRC Press Boca Raton (Chapter 3)
35. H. Sies Polyphenols and health: Update and prospective Archives of Biochemistry and Biophysics 501 2010 2 5
36. R.M. Silverstein, G.C. Bassler, and T.C. Morrill Spectrometric identification of organic compounds 5th ed. 1992 Tokyo Kagaku Dojin Tokyo (Chapter 7)
37. H. Takahashi, K. Matsumoto, M. Ueda, Y. Miyake, and Y. Fukuyama Biomimetic syntheses of neurotophic americanol A and isoamericanol A by horseradish peroxidase (HRP) catalysed oxidative coupling Heterocycles 56 2002 245 256
38. M.J. Taylor, and T. Richardson Antioxidant activity of cysteine and protein sulfhydryls in a linoleate emulsion oxidized by hemoglobin Journal of Food Science 45 1980 1223 1230
39. H. Tazaki, D. Taguchi, T. Hayashida, and K. Nabeta Stable isotope-labeling studies on the oxidative coupling of caffeic acid via o-quinone Bioscience, Biotechnology, and Biochemistry 65 2001 2613 2621
40. S.A.B.E. Van Acker, L.M.H. Koymans, and A. Bast Molecular pharmacology of vitamin E: Structural aspects of antioxidant activity Free Radical Biology & Medicine 15 1993 311 328
41. D.D.M. Wayner, and D.R. Arnold Substituent effects on benzyl radical hyperfine coupling constants. Part 2. The effect of sulphur substituents Canadian Journal of Chemistry 62 1984 1164 1169
42. Y. Yukawa, Y. Tsuno, and M. Sawada Resonance effect in Hammett relationship. IV. Linear free energy relationship based on the normal substituent constants Bulletin of the Chemical Society of Japan 39 1966 2274 2286
43. H.A. Zahalka, B. Robillard, L. Hughes, J. Lusztyk, G.W. Burton, and E.G. Janzen Antioxidant activity of 1-thio-α-tocopherol and related compounds. EPR, ENDOR, and UV-visible absorption spectra of some of the derived phenoxyl radicals Journal of Organic Chemistry 53 1988 3739 3745