Screening for antiradical efficiency of 21 semi-synthetic derivatives of quercetin in a DPPH assay

Milackova, Ivana; Kovacikova, Lucia; Veverka, Miroslav; Gallovic, Ján; Stefek, Milan

doi:10.2478/intox-2013-0003

Abstract

The group of 21 novel semi-synthetic derivatives of quercetin was screened for the antiradical efficiency in a DPPH assay. The initial fast absorbance decrease of DPPH, corresponding to the transfer of the most labile H atoms, was followed by a much slower absorbance decline representing the residual antiradical activity of the antioxidant degradation products. Initial velocity of DPPH decolorization determined for the first 75-s interval was used as a marker of the antiradical activity. Application of the kinetic parameter allowed good discrimination between the polyphenolic compounds studied. The most efficient chloronaphthoquinone derivative (compound Ia) was characterized by antiradical activity higher than that of quercetin and comparable with that of trolox. Under the experimental conditions used, one molecule of Ia was found to quench 2.6±0.1 DPPH radicals.

References

Amić D, Davidović-Amić D, Beslo D, Rastija V, Lucić B, Trinajstić N. (2007). SAR and QSAR of the antioxidant activity of flavonoids. Curr Med Chem 14: 827-845.
Search in Google Scholar
Arts IC, Sesink AL, Faassen-Peters M, Hollman PC. (2004). The type of sugar moiety is a major determinant of the small intestinal uptake and subsequent biliary excretion of dietary quercetin glycosides. Br J Nutr 91: 841-847.
Search in Google Scholar
BischoffSC. (2008). Quercetin: potentials in the prevention and therapy of disease. Curr Opin Clin Nutr Metab Care 11: 733-740.
Search in Google Scholar
Blois MS. (1958). Antioxidant determinations by the use of a stable free radical. Nature 181: 1199-1200.
Search in Google Scholar
Boots AW, Haenen GRMM, Bast A. (2008). Health effects of quercetin: From antioxidant to nutraceutical. Eur J Pharm 585: 325-337.
Search in Google Scholar
Bors W, Heller W, Michel C, Saran M. (1990). Flavonoids as antioxidants. Determination of Radical-Scavanging Efficiences. In Methods in Enzymology (Packer L, Glazer AN, Eds.; Academic Press: San Diego CA) 186: 343-355.
Search in Google Scholar
Bors W, Michel C. (2002). Chemistry of the Antioxidant. Effect of Polyphenols. Ann NY Acad Sci 957: 57-69.
Search in Google Scholar
Butkovic V, Klasinc L, Bors W. (2004). Kinetic Study of Flavonoid Reactions with Stable Radicals. J Agric Food Chem 52: 2816-2820.
Search in Google Scholar
Cao G, Sofic E, Prior RL. (1997). Antioxidant and prooxidant behavior of flavonoids: structure-activity relationships. Free Rad Biol Med 22: 749-760.
Search in Google Scholar
Crozier A, Del Rio D, Clifford MN. (2010). Bioavailability of dietary flavonoids and phenolic compounds. Mol Aspects Med 31: 446-467.
Search in Google Scholar
Golding TB, Griffin JR, Quaterman PC, Slack AJ, Williams GJ. (2001). Analogues or derivatives of quercetin (prodrug). U.S. Patent Application No. 6258840 B1Washington, D.C.: U.S. Patent and Trademark Office.
Search in Google Scholar
Goupy P, Dufour C, Loonis M, Dangles O. (2003). Quantitative kinetic analysis of hydrogen transfer reactions from dietary polyphenols to the DPPH radical. J Agric Food Chem. 51(3): 615-622.
Search in Google Scholar
Harborne JB, ed. (1995). The Flavonoids, Advances in Research Since 1986. Chapman & Hall, London. 378-382.
Search in Google Scholar
Heim KE, Tagliaferro TR, Bobilya DJ. (2002). Flavonoid antioxidants: chemistry, metabolism and structure-activity relationships. J Nutr Biochem 13: 572-584.
Search in Google Scholar
Dimitrić Marković JM, Marković ZS, Pašti IA, Brdarić TP, Popović-Bijelić A, Mojović M. (2012). A joint application of spectroscopic, electrochemical and theoretical approaches in evaluation of the radical scavenging activity of 3-OH flavones and their iron complexes towards different radical species. Dalton Trans. 41(24): 7295-7303.
Search in Google Scholar
Materska M. (2008). Quercetin and its derivatives: chemical structure and bioactivity-Rewiev. Pol J Food Nutr Sci 58: 407-413.
Search in Google Scholar
Nijveldt RJ, van Nood E, van Hoorn DEC, Boelens PG, van Norren K, van Leeuwen PAM. (2001). Flavonoids: a review of probable mechanisms of action and potential applications. Am J Clin Nutr 74: 418.
Search in Google Scholar
Perrier E, Mariotte AM, Boumendje A, Bresson-Rival D. (2001). Flavonoid esters and their use notably in cosmetics. U.S. Patent Application No. 6235294 B1 Washington, D.C.: U.S. Patent and Trademark Office.
Search in Google Scholar
Pietta PG. (2000). Flavonoids as Antioxidants. J Nat Prod 63: 1035.
Search in Google Scholar
Ratty AK, Sunammoto J, Das NP. (1988). Interaction of flavonoids with 1,1-diphenyl-2-picrylhydrazyl free radical, liposomal membranes and soybean lipoxygenase-1. Biochem Pharmacol 37: 989-996.
Search in Google Scholar
Rice-Evans C. (2001). Flavonoid Antioxidants. Curr Med Chem 8: 797.
Search in Google Scholar
Stefek M, Karasu C. (2011). Eye lens in aging and diabetes: effect of quercetin. Rejuvenation Res 14(5): 525-534.
Search in Google Scholar
Veverka M, Gallovič J, Švajdlenka E, Veverkova E, Pronayova N, Milačkova I, Štefek M. (2013). Novel quercetin derivatives: synthesis and screening for antioxidant activity and aldose reductase inhibition. Chem Papers 67(1): 76-83.
Search in Google Scholar
Villano D, Fernandez-Pachon MS, Moya ML, Troncoso AM, Garcia-Parrilla MC. (2007). Radical scavenging ability of polyphenolic compounds towards DPPH free radical. Talanta. 71(1): 230-235.
Search in Google Scholar
Williams RJ, Spencer JP, Rice-Evans C. (2004). Flavonoids: antioxidants or signalling molecules? Free Radic Biol Med 36: 838-849.10.1016/j.freeradbiomed.2004.01.00115019969
Search in Google Scholar

Screening for antiradical efficiency of 21 semi-synthetic derivatives of quercetin in a DPPH assay

Abstract

Paradigm

My account