Quercetin is a natural polyphenol with proven health beneficial activities. In this study 15 new quercetin derivatives were prepared with the aim to enhance their bioavailability. Modification of their physicochemical properties could herewith improve the action in cells. The prepared compounds were tested for their antioxidant and cytotoxic activity. The ability to scavenge free radicals as well as ferric reducing antioxidant power of the new derivatives was not better than that of unmodified quercetin. But for acetylated esters a better cytotoxic activity was found on human cervical cancer cells HeLa than for the initial molecule. The best effect revealed chloronaphtoquinone quercetin (IC50=13.2 μM). For this compound comparable cytotoxic action on non-cancer murine fibroblast cells was detected (IC50=16.5 μM). The obtained results indicate that appropriate lipophilization of the quercetin molecule could improve its cytotoxic action in cells, probably due to its enhanced bioavailability
If the inline PDF is not rendering correctly, you can download the PDF file here.
Baghel SS, Shrivastava N, Baghel RS, Agrawal P, Rajput S. (2012). A review of quercetin: antioxidant and anticancer properties. World J Pharm Pharmaceut Sci 1: 146-160.
Batra P, Sharma AK. (2013). Anti-cancer potential of fl avonoids: recent trends and future perspectives. 3 Biotech in press.
Benzie IF, Strain JJ. (1996). The ferric reducing ability of plasma (FRAP) as a measure of „antioxidant power“: the FRAP assay. Anal Biochem 239: 70-76.
Cárdenas M, Marder M, Blank VC, Roguin LP. (2006). Antitumor activity of some natural fl avonoids and synthetic derivatives on various human and murine cancer cell lines. Bioorg Med Chem 14: 2966-2971.
Chidambara Murthy KN, Kim J, Vikram A, Patil BS. (2012). Diff erential inhibition of human colon cancer cells by structurally similar fl avonoids of citrus. Food Chem 132: 27-34.
Clere N, Faure S, Martinez MC, Andriantsitohaina R. (2011). Anticancer properties of fl avonoids: role in various stages of carcinogenesis. Cardiovasc Hematol Agents Med Chem 9: 62-77.
Delmulle L, Bellahcene A, Dhooge W, Comhaire F, Roelens F, Huvaere K, Heyerick A, Castronovo V, De Keukeleire D. (2006). Anti-proliferative properties of prenylated fl avonoids from hops (Humulus lupulus L.) in human prostate cancer cell lines. Phytomed 13: 732-734.
Diba CS, Pleško I, Hlava P. (2012). Cancer incidence in the Slovak Republic 2007. National Health Information Center, Bratislava.
Filipe P, Silva AMS, Seixas RSGR, Pinto DCGA, Santos A, Patterson LK, Silva JN, Cavaleiro JAS, Freitas JP, Maziere JC, Santus R, Morliere P. (2009). The alkyl chain length of 3-alkyl-3‘,4‘,5,7-tetrahydroxyfl avones modulates eff ective inhibition of oxidative damage in biological systems: Illustration with LDL, red blood cells and human skin keratinocytes. Biochem Pharmacol 77: 957-964.
Genoux E, Nicolle E, Boumendjel A. (2011). Flavonoids as anticancer agents: recent progress and state of the art? Curr Org Chem 15: 2608-2615.
Gibellini L, Pinti M, Nasi M, Montagna JP, De Biasi S, Roat E, Bertoncelli L, Cooper EL, Cossarizza A. (2011). Quercetin and cancer chemoprevention. Evid Based Complement Alternat Med 2011: 1-15.
Jantová S, Matejov P, Theiszová M, Bakoš D. (2010). Biocompatibilty of bioactive glass composite based on Li2O-SiO2-CaO-P2O5-CaF2. Proceedings of The 30th Scientifi c Symposium on Industrial Toxicology 258-264.
Lebeau J, Furman C, Bernier JL, Duriez P, Teissier E, Cotelle N. (2000). Antioxidant properties of di-tert-butylhydroxylated fl avonoids. Free Rad Biol Med 29: 900-912.
Lue BM, Nielsen NS, Jacobsen C, Hellgren L, Guo Z, Xu X. (2010). Antioxidant properties of modifi ed rutin esters by DPPH, reducing power, iron chelation and human low density lipoprotein assays. Food Chem 123: 221-230.
Materska M. (2008). Quercetin and its derivatives: Chemical structure and bioactivity - a review. Pol J Food Nutr Sci 58: 407-413.
Miller AL. (1996). Antioxidant fl avonoids: Structure, function and clinical usage. Altern Med Rev 1: 103-111.
Moheb A, Grondin M, Ibrahim R, Roy R, Sarhan F. (2013). Selective anticancer potential of several methylated phenolic compounds. J Nat Pharm 4: 75-79.
Moghaddam G, Ebrahimi SA, Rahbar-Roshandel N, Foroumadi A. (2012). Antiproliferative activity of fl avonoids: infl uence of sequential methoxylation state of the fl avonoid structure. Phytother Res 26: 1023-1028.
Ou L, Han S, Ding W, Chen Z, Ye Z, Yang H, Zhang G, Lou Y, Chen JZ, Yu Y. (2011). Design, synthesis and 3D-QSAR study of cytotoxic fl avonoid derivatives. Mol Divers 15: 665-675.
Park KD, Lee SG, Kim SU, Sun WS, Cho SJ, Jeong DH. (2004). Anticancer activity of 3-O-acyl and alkyl-(-)-epicatechin derivatives. Bioorg Med Chem Lett 14: 5189-5192.
Salem JH, Chevalot I, Harscoat-Schiavo C, Paris C, Fick M, Humeau C. (2011). Biological activities of fl avonoids from Nitraria retusa (Forssk.) Asch. and their acylated derivatives. Food Chem 124: 486-494.
Veverka M, Gallovič J, Švajdlenka E, Veverková E, Prónayová N, Miláčková I, Štefek M. (2013). Novel quercetin derivatives: synthesis and screening for anti-oxidant activity and aldose reductase inhibition. Chem Pap 67: 76-83.
Viskupičová J, Ondrejovič M, Šturdík E. (2008). Bioavailability and metabolism of fl avonoids. J Food Nutr Res 47: 151-162.
Viskupicova J, Danihelova M, Ondrejovic M, Liptaj T, SturdikE. (2010). Lipophilic rutin derivatives for antioxidant protection of oil-based foods. Food Chem 123: 45-50.
Xiao ZP, Peng ZY, Peng MJ, Yan WB, Ouyang YZ, Zhu HL. (2011). Flavonoids health benefi ts and their molecular mechanism. Mini Rev Med Chem 11: 169-177.
Yen GC, Chen HY. (1995). Antioxidant activity of various tea extracts in relation to their antimutagenicity. J Agric Food Chem 43: 27-32.