The minor structural difference between the antioxidants quercetin and 4'O-methylquercetin has a major impact on their selective thiol toxicity

International Journal of Molecular Sciences

Volumn 15, Issue 5, 2014, Pages 7475-7484

  Lemmens, Kristien J A ^a   Vrolijk, Misha F ^a   Bouwman, Freek G ^a   van Der Vijgh, Wim J F ^a   Bast, Aalt ^a   Haenen, Guido R M M ^a  

^a MAASTRICHT UNIVERSITY   (Netherlands)

Author keywords

Antioxidant; Creatine kinase; Quercetin; Tamarixetin; Thiol reactivity

Indexed keywords

ASCORBIC ACID; CREATINE KINASE; NICOTINAMIDE ADENINE DINUCLEOTIDE; QUERCETIN; QUERCETIN 4 METHYL ETHER; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE; THIOL; UNCLASSIFIED DRUG; ANTIOXIDANT; DISACCHARIDE; TAMARIXETIN; THIOL DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; ENZYME ACTIVITY; MATRIX ASSISTED LASER DESORPTION IONIZATION TIME OF FLIGHT MASS SPECTROMETRY; TOXICITY; ANALOGS AND DERIVATIVES; ANTAGONISTS AND INHIBITORS; CHEMISTRY; METABOLISM; OXIDATION REDUCTION REACTION;

ANTIOXIDANTS; CREATINE KINASE; DISACCHARIDES; MODELS, MOLECULAR; OXIDATION-REDUCTION; QUERCETIN; SULFHYDRYL COMPOUNDS;

EID: 84899739989     PISSN: 16616596     EISSN: 14220067     Source Type: Journal    
DOI: 10.3390/ijms15057475     Document Type: Article

References (18)

1. Willcox, J. K.; Ash, S. L.; Catignani, G. L. Antioxidants and prevention of chronic disease. Crit. Rev. Food Sci. Nutr. 2004, 44, 275-295.
2. Halliwell, B. Antioxidants in human health and disease. Ann. Rev. Nutr. 1996, 16, 33-50.
3. Bjelakovic, G.; Nikolova, D.; Gluud, C. Antioxidant supplements and mortality. Curr. Opin. Clin. Nutr. Metabo. Care 2014, 17, 40-44.
4. Boots, A. W.; Haenen, G. R.; den Hartog, G. J.; Bast, A. Oxidative damage shifts from lipid peroxidation to thiol arylation by catechol-containing antioxidants. Biochim. Biophys. Acta 2002, 1583, 279-284.
5. Ito, S.; Kato, T.; Fujita, K. Covalent binding of catechols to proteins through the sulphydryl group. Biochem. Pharmacol. 1988, 37, 1707-1710.
6. Reddy, S.; Jones, A. D.; Cross, C. E.; Wong, P. S.; van der Vliet, A. Inactivation of creatine kinase by S-glutathionylation of the active-site cysteine residue. Biochem. J. 2000, 347, 821-827.
7. Brevik, A.; Rasmussen, S. E.; Drevon, C. A.; Andersen, L. F. Urinary excretion of flavonoids reflects even small changes in the dietary intake of fruits and vegetables. Cancer Epidemiol. Biomark. Prev. 2004, 13, 843-849.
8. Spencer, J. P.; Kuhnle, G. G.; Williams, R. J.; Rice-Evans, C. Intracellular metabolism and bioactivity of quercetin and its in vivo metabolites. Biochem. J. 2003, 372, 173-181.
9. Bast, A.; Haenen, G. R. Ten misconceptions about antioxidants. Trends Pharmacol. Sci. 2013, 34, 430-436.
10. 2+ release by rat liver mitochondria. Arch. Biochem. Biophys. 1988, 267, 539-550.
11. Kalyanaraman, B.; Premovic, P. I.; Sealy, R. C. Semiquinone anion radicals from addition of amino acids, peptides, and proteins to quinones derived from oxidation of catechols and catecholamines. An ESR spin stabilization study. J. Biol. Chem. 1987, 262, 11080-11087.
12. O'Brien, P. J. Molecular mechanisms of quinone cytotoxicity. Chem. Biol. Interact 1991, 80, 1-41.
13. Boots, A. W.; Li, H.; Schins, R. P.; Duffin, R.; Heemskerk, J. W.; Bast, A.; Haenen, G. R. The quercetin paradox. Toxicol. Appl. Pharmacol. 2007, 222, 89-96.
14. Jacobs, H.; Moalin, M.; Bast, A.; van der Vijgh, W. J.; Haenen, G. R. An essential difference between the flavonoids monoHER and quercetin in their interplay with the endogenous antioxidant network. PLoS One 2010, 5, e13880.
15. Zhao, T. J.; Liu, Y.; Chen, Z.; Yan, Y. B.; Zhou, H. M. The evolution from asparagine or threonine to cysteine in position 146 contributes to generation of a more efficient and stable form of muscle creatine kinase in higher vertebrates. Int. J. Biochem. Cell Biol. 2006, 38, 1614-1623.
16. Pearson, R. G. Hard and soft acids and bases. J. Am. Chem. Soc. 1963, 85, 3533-3539.
17. Moalin, M.; van Strijdonck, G. P.; Bast, A.; Haenen, G. R. Competition between ascorbate and glutathione for the oxidized form of methylated quercetin metabolites and analogues: tamarixetin, 4'O-methylquercetin, has the lowest thiol reactivity. J. Agric. Food Chem. 2012, 60, 9292-9297.
18. Bast, A.; Haenen, G. R. The toxicity of antioxidants and their metabolites. Environ. Toxicol. Pharmacol. 2002, 11, 251-258.