Glutathione and the antioxidant potential of binary mixtures with flavonoids: Synergisms and antagonisms

Molecules

Volumn 18, Issue 8, 2013, Pages 8858-8872

  Pereira, Renato B ^a   Sousa, Carla ^a   Costa, Andreia ^a   Andrade, Paula B ^a   Valentão, Patrícia ^a  

^a UNIVERSITY OF PORTO   (Portugal)

Author keywords

Antagonism; Antioxidant activity; Flavonoids; Glutathione; Synergism

Indexed keywords

ANTIOXIDANT; FLAVONOID; GLUTATHIONE; MYRICETIN; PHENOL DERIVATIVE; SCAVENGER;

ANTAGONISTS AND INHIBITORS; CHEMISTRY; OXIDATIVE STRESS; STRUCTURE ACTIVITY RELATION; ARTICLE; DRUG ANTAGONISM;

ANTIOXIDANTS; FLAVONOIDS; FREE RADICAL SCAVENGERS; GLUTATHIONE; OXIDATIVE STRESS; PHENOLS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84883181278     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules18088858     Document Type: Article

References (39)

1. Thomas, J.A.; Poland, B.; Honzatko, R. Protein sulfhydryls and their role in the antioxidant function of protein S-thiolation. Arch. Biochem. Biophys. 1995, 319, 1-9.
2. Huang, K.P.; Huang, F.L. Glutathionylation of proteins by glutathione disulfide S-oxide. Biochem. Pharmacol. 2002, 64, 1049-1056.
3. Hayes, J.D.; Pulford, D.J. The glutathione S-transferase supergene family: Regulation of GST and the contribution of the isoenzymes to cancer chemoprotection and drug resistance. Crit. Rev. Biochem. Mol. Biol. 1995, 30, 445-600.
4. Wild, A.C.; Mulcahy, R.T. Regulation of γ-glutamylcysteine synthetase subunit gene expression: Insights into transcriptional control of antioxidant defenses. Free Radic. Res. 2000, 32, 281-301.
5. Rice-Evans, C.A.; Miller, N.J.; Bolwell, P.G.; Bramley, P.M.; Pridham, J.B. The relative antioxidant activities of plant-derived polyphenolic flavonoids. Free Radic. Res. 1995, 22, 375-383.
6. Rice-Evans, C.A.; Miller, N.J.; Paganga, G. Structure-antioxidant activity relationships of flavonoids and phenolic acids. Free Radic. Biol. Med. 1996, 20, 933-956.
7. Milella, L.; Caruso, M.; Galgano, F.; Favati, F.; Padula, M.C.; Martelli, G. Role of the cultivar in choosing Clementine fruits with a high level of health-promoting compounds. J. Agric. Food Chem. 2011, 59, 5293-5298.
8. Walle, T. Absorption and metabolism of flavonoids. Free Radic. Biol. Med. 2004, 36, 829-837.
9. Gaikwad, P.; Barik, A.; Priyadarsini, K.I.; Rao, B.S.M. Antioxidant activities of phenols in different solvents using DPPH assay. Res. Chem. Intermed. 2010, 36, 1065-1072.
10. Beecher, C.W.W. Cancer preventive properties of varieties of Brassica oleracea - A review. Am. J. Clin. Nutr. 1994, 59, 1166S-1170S.
11. Van Poppel, G.; Verhoeven, D.T.H.; Verhagen, H.; Goldbohm, R.A. Brassica vegetables and cancer prevention - Epidemiology and mechanisms. Adv. Nutr. Cancer 1999, 2, 159-168.
12. Millic, B.L.; Diljas, S.M.; Canadanovic-Brunet, J.M. Antioxidative activity of phenolic compounds on the metal-ion breakdown of lipid peroxidation system. Food Chem. 1998, 61, 443-447.
13. Karadag, A.; Ozcelik, B.; Saner, S. Review of methods to determine antioxidant capacities. Food Anal. Methods 2009, 2, 41-60.
14. Menezes, J.C.; Kamat, S.P.; Cavaleiro, J.A.; Gaspar, A.; Garrido, J.; Borges, F. Synthesis and antioxidant activity of long chain alkyl hydroxycinnamates. Eur. J. Med. Chem. 2011, 46, 773-777.
15. Arnao, M.B. Some methodological problems in the determination of antioxidant activity using chromogen radicals: A practical case. Trends Food Sci. Technol. 2000, 11, 419-421.
16. ̇+ method: Influence of sample dilution and time. Talanta 2004, 64, 501-509.
17. Marais, J.P.J.; Deavours, B.; Dixon, R.A.; Ferreira, D. The Stereochemistry of Flavonoids. In The Science of Flavonoids; Grotewold, E., Ed.; Springer Press: New York, NY, USA, 2007; pp. 1-35.
18. Boots, A.W.; Kubben, N.; Haenen, G.R.; Bast, A. Oxidized quercetin reacts with thiols rather than with ascorbate: Implication for quercetin supplementation. Biochem. Biophys. Res. Commun. 2003, 308, 560-565.
19. Kessler, M.; Ubeaud, G.; Jung, L. Anti- and pro-oxidant activity of rutin and quercetin derivatives. J. Pharm. Pharmacol. 2003, 55, 131-142.
20. Yao, L.H.; Jiang, Y.M.; Shi, J.; Tomás-Barberán, F.A.; Datta, N.; Singanusong, R.; Chen, S.S. Flavonoids in food and their health benefits. Plant Foods Hum. Nutr. 2004, 59, 113-122.
21. Heimann, W.; Reiff, F. Beziehung zwischen chemischer konstitution und antioxygener wirkung bei flavonolen (In German). Fette Seifen Anstr-Mittel. 1953, 55, 451-458.
22. Bors, W.; Heller, W.; Michel, C.; Saran, M. Flavonoids as antioxidants: Determination of radical scavenging efficiencies. Methods Enzymol. 1990, 186, 343-355.
23. ̇-. Free Radic. Biol. Med. 1991, 11, 1-8.
24. Rastija, V.; Medić-Sarić, M. QSAR study of antioxidant activity of wine polyphenols. Eur. J. Med. Chem. 2009, 44, 400-408.
25. Harborne, J.B.; Mabry, T.J.; Mabry, H. The Flavonoids; Chapman and Hall: London, UK, 1975.
26. Burda, S.; Oleszek, W. Antioxidant and antiradical activities of flavonoids. J. Agric. Food Chem. 2001, 49, 2774-2779.
27. Ratty, A.K.; Das, N.P. Effects of flavonoids on nonenzymatic lipid peroxidation: Structure-activity relationship. Biochem. Med. Metab. Biol. 1988, 39, 69-79.
28. Matthiesen, L.; Malterud, K.E.; Sund, R.B. Hydrogen bond formation as basis for radical scavenging activity: A structure-activity study of C-methylated dihydrochalcones from Myrica gale and structurally related acetophenones. Free Radic. Biol. Med. 1997, 2, 307-311.
29. Wu, M.J.; Huang, C.L.; Lian, T.W.; Kou, M.C.; Wang, L. Antioxidant activity of Glossogyne tenuifolia. J. Agric. Food Chem. 2005, 53, 6305-6312.
30. Chou, T.C.; Talalay, P. Quantitative analysis of dose-effect relationships: The combined effects of multiple drugs or enzyme inhibitors. Adv. Enzyme Regul. 1984, 22, 27-55.
31. Webb, J.L. Effect of More than One Inhibitor. In Enzyme and Metabolic Inhibitors; Academic Press: New York, NY, USA and London, UK, 1963; Volume 1, pp. 66-79, 488-512.
32. Awad, H.M.; Boersma, M.G.; Boeren, S.; van Bladeren, P.J.; Vervoort, J.; Rietjens, I.M. The regioselectivity of glutathione adduct formation with flavonoid quinone/quinone methides is pH-dependent. Chem. Res. Toxicol. 2002, 15, 343-351.
33. Hodnick, W.F.; Kung, F.S.; Roettger, W.J.; Bohmont, C.W.; Pardini, R.S. Inhibition of mitochondrial respiration and production of toxic oxygen radicals by flavonoids: A structure-activity study. Biochem. Pharmacol. 1986, 35, 2345-2357.
34. Frey-Schroder, G.; Barz, W. Isolation and characterization of flavonol converting enzymes from Mentha piperita plants and from Mentha arvensis cell suspension cultures. Z. Naturforsch. 1979, 34C, 200-209.
35. Dangles, O.; Fargeix, G.; Dufour, C. One-electron oxidation of quercetin derivatives in protic and non protic media. J. Chem. Soc. Perkin Trans. 1999, 2, 1387-1395.
36. Van der Woude, H.; Boersma, M.G.; Alink, G.M.; Vervoort, J.; Rietjens, I.M. Consequences of quercetin methylation for its covalent glutathione and DNA adduct formation. Chem. Biol. Interact. 2006, 160, 193-203.
37. Awad, H.M.; Boersma, M.G.; Boeren, S.; van Bladeren, P.J.; Vervoort, J.; Rietjens, I.M.C.M. Structure-activity study on the quinone/quinone methide chemistry of flavonoids. Chem. Res. Toxicol. 2001, 14, 398-408.
38. Moridani, M.Y.; Scobie, H.; Salehi, P.; O'Brien, P.J. Catechin metabolism: Glutathione conjugate formation catalyzed by tyrosinase, peroxidase, and cytochrome p450. Chem. Res. Toxicol. 2001, 14, 841-848.
39. ̇, superoxide radical, hydroxyl radical and hypochlorous acid. Food Chem. 2006, 98, 416-425.