Comparison of food antioxidants and iron chelators in two cellular free radical assays: Strong protection by Luteolin

Journal of Agricultural and Food Chemistry

Volumn 62, Issue 33, 2014, Pages 8402-8410

  Hofer, Tim ^a   Jørgensen, Trond Ø ^b   Olsen, Ragnar L ^c  

^a NORWEGIAN INSTITUTE OF PUBLIC HEALTH   (Norway)

^b MabCent SFI ^*  (Norway)

^c UNIVERSITY OF TROMSØ   (Norway)

Author keywords

acetylsalicylic acid (ASA); catechin; curcumin; hydroxytyrosol; resveratrol

Indexed keywords

ANTIOXIDANTS; CHELATION; FLAVONOIDS; IRON COMPOUNDS; LIPIDS; METAL IONS; POLYUNSATURATED FATTY ACIDS; RESVERATROL; AGENTS; CURVE FITTING; FATTY ACIDS; IRON; MOBILE SECURITY; OXIDATION; PIGMENTS;

ACETYLSALICYLIC ACIDS; ANTI-OXIDANT ACTIVITIES; CATECHIN; CELLULAR ANTIOXIDANT ACTIVITIES; CURCUMIN; HYDROXYTYROSOL; INHIBITORY CONCENTRATION; MEMBRANE LIPID PEROXIDATION;

FREE RADICALS;

ANTIOXIDANT; CHELATING AGENT; FREE RADICAL; IRON; LUTEOLIN;

CHEMISTRY; COMPARATIVE STUDY; HEPG2 CELL LINE; HUMAN; LIPID PEROXIDATION; OXIDATION REDUCTION REACTION;

ANTIOXIDANTS; CHELATING AGENTS; FREE RADICALS; HEP G2 CELLS; HUMANS; IRON; LIPID PEROXIDATION; LUTEOLIN; OXIDATION-REDUCTION;

EID: 84906351146     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf5022779     Document Type: Article

References (52)

1. Myhre, O.; Utkilen, H.; Duale, N.; Brunborg, G.; Hofer, T. Metal dyshomeostasis and inflammation in Alzheimer's and Parkinson's diseases: possible impact of environmental exposures Oxid. Med. Cell. Longev. 2013, 2013, 1-19
2. Snodderly, D. M. Evidence for protection against age-related macular degeneration by carotenoids and antioxidant vitamins Am. J. Clin. Nutr. 1995, 62, 1448S-1461S
3. Thome, J.; Zhang, J. J.; Davids, E.; Foley, P.; Weijers, H. G.; Wiesbeck, G. A.; Boning, J.; Riederer, P.; Gerlach, M. Evidence for increased oxidative stress in alcohol-dependent patients provided by quantification of in vivo salicylate hydroxylation products Alcohol.: Clin. Exp. Res. 1997, 21, 82-85
4. Hofer, T.; Marzetti, E.; Xu, J. Z.; Seo, A. Y.; Gulec, S.; Knutson, M. D.; Leeuwenburgh, C.; Dupont-Versteegden, E. E. Increased iron content and RNA oxidative damage in skeletal muscle with aging and disuse atrophy Exp. Gerontol. 2008, 43, 563-570
5. Zhang, R.; Brennan, M. L.; Shen, Z.; MacPherson, J. C.; Schmitt, D.; Molenda, C. E.; Hazen, S. L. Myeloperoxidase functions as a major enzymatic catalyst for initiation of lipid peroxidation at sites of inflammation J. Biol. Chem. 2002, 277, 46116-46122
6. Laguerre, M.; Lecomte, J.; Villeneuve, P. Evaluation of the ability of antioxidants to counteract lipid oxidation: existing methods, new trends and challenges Prog. Lipid Res. 2007, 46, 244-282
7. Rossi, L.; Mazzitelli, S.; Arciello, M.; Capo, C. R.; Rotilio, G. Benefits from dietary polyphenols for brain aging and Alzheimer's disease Neurochem. Res. 2008, 33, 2390-2400
8. Tripoli, E.; Giammanco, M.; Tabacchi, G.; Di Majo, D.; Giammanco, S.; La Guardia, M. The phenolic compounds of olive oil: structure, biological activity and beneficial effects on human health Nutr. Res. Rev. 2005, 18, 98-112
9. Hendrickson, H. P.; Kaufman, A. D.; Lunte, C. E. Electrochemistry of catechol-containing flavonoids J. Pharm. Biomed. 1994, 12, 325-334
10. Manach, C.; Donovan, J. L. Pharmacokinetics and metabolism of dietary flavonoids in humans Free Radical Res. 2004, 38, 771-785
11. Crozier, A.; Jaganath, I. B.; Clifford, M. N. Dietary phenolics: chemistry, bioavailability and effects on health Nat. Prod. Rep. 2009, 26, 1001-1043
12. van Acker, S. A.; van den Berg, D. J.; Tromp, M. N.; Griffioen, D. H.; van Bennekom, W. P.; van der Vijgh, W. J.; Bast, A. Structural aspects of antioxidant activity of flavonoids Free Radical Biol. Med. 1996, 20, 331-342
13. Melidou, M.; Riganakos, K.; Galaris, D. Protection against nuclear DNA damage offered by flavonoids in cells exposed to hydrogen peroxide: the role of iron chelation Free Radical Biol. Med. 2005, 39, 1591-1600
14. Hofer, T.; Olsen, R. L. Cellebasert metode for maling av lipid peroksidasjon og antioksidantaktivitet. Bioingeniøren (Norwegian; archived at www.bioingenioren.no) 2010, 10, 6-12.
15. Hofer, T.; Eriksen, T. E.; Hansen, E.; Varmedal, I.; Jensen, I. J.; Andersen, J. H.; Olsen, R. L. Cellular and chemical assays for discovery of novel antioxidants in marine organisms. In Studies on Experimental Models; Basu, S.; Wiklund, L., Eds.; Springer Science, Humana Press: New York, 2011; p 680.
16. Wolfe, K. L.; Liu, R. H. Cellular antioxidant activity (CAA) assay for assessing antioxidants, foods, and dietary supplements J. Agric. Food Chem. 2007, 55, 8896-8907
17. Song, W.; Derito, C. M.; Liu, M. K.; He, X. J.; Dong, M.; Liu, R. H. Cellular antioxidant activity of common vegetables J. Agric. Food Chem. 2010, 58, 6621-6629
18. Wolfe, K. L.; Kang, X. M.; He, X. J.; Dong, M.; Zhang, Q. Y.; Liu, R. H. Cellular antioxidant activity of common fruits J. Agric. Food Chem. 2008, 56, 8418-8426
19. Mohamed, Y. M. A.; Vik, A.; Hofer, T.; Andersen, J. H.; Hansen, T. V. Polyunsaturated fatty acid-derived chromones exhibiting potent antioxidant activity Chem. Phys. Lipids 2013, 170-171, 41-45
20. Lundholt, B. K.; Scudder, K. M.; Pagliaro, L. A simple technique for reducing edge effect in cell-based assays J. Biomol. Screen. 2003, 8, 566-570
21. Pap, E. H.; Drummen, G. P.; Winter, V. J.; Kooij, T. W.; Rijken, P.; Wirtz, K. W.; Op den Kamp, J. A.; Hage, W. J.; Post, J. A. Ratio-fluorescence microscopy of lipid oxidation in living cells using C11-BODIPY(581/591) FEBS Lett. 1999, 453, 278-282
22. Drummen, G. P.; Gadella, B. M.; Post, J. A.; Brouwers, J. F. Mass spectrometric characterization of the oxidation of the fluorescent lipid peroxidation reporter molecule C11-BODIPY(581/591) Free Radical Biol. Med. 2004, 36, 1635-1644
23. Ma, Y.; de Groot, H.; Liu, Z.; Hider, R. C.; Petrat, F. Chelation and determination of labile iron in primary hepatocytes by pyridinone fluorescent probes Biochem. J. 2006, 395, 49-55
24. Petrat, F.; Rauen, U.; de Groot, H. Determination of the chelatable iron pool of isolated rat hepatocytes by digital fluorescence microscopy using the fluorescent probe, phen green SK Hepatology 1999, 29, 1171-1179
25. Drummen, G. P.; van Liebergen, L. C.; Op den Kamp, J. A.; Post, J. A. C11-BODIPY(581/591), an oxidation-sensitive fluorescent lipid peroxidation probe: (micro)spectroscopic characterization and validation of methodology Free Radical Biol. Med. 2002, 33, 473-490
26. Persson, H. L.; Yu, Z. Q.; Tirosh, O.; Eaton, J. W.; Brunk, U. T. Prevention of oxidant-induced cell death by lysosomotropic iron chelators Free Radical Biol. Med. 2003, 34, 1295-1305
27. Javitt, N. B. Hep-G2 cells as a resource for metabolic studies-lipoprotein, cholesterol, and bile-acids FASEB J. 1990, 4, 161-168
28. Roe, A. L.; Snawder, J. E.; Benson, R. W.; Roberts, D. W.; Casciano, D. A. HepG2 cells-an in vitro model for P450-dependent metabolism of acetaminophen Biochem. Biophys. Res. Commun. 1993, 190, 15-19
29. Huang, M.; Zhang, L.; Mesaros, C.; Zhang, S. H.; Blaha, M. A.; Blair, I. A.; Penning, T. M. Metabolism of a representative oxygenated polycyclic aromatic hydrocarbon (PAH) phenanthrene-9,10-quinone in human hepatoma (HepG2) cells Chem. Res. Toxicol. 2014, 27, 852-863
30. Jetten, M. J. A.; Kleinjans, J. C. S.; Claessen, S. M.; Chesne, C.; van Delft, J. H. M. Baseline and genotoxic compound induced gene expression profiles in HepG2 and HepaRG compared to primary human hepatocytes Toxicol. in Vitro 2013, 27, 2031-2040
31. Kanazawa, K.; Uehara, M.; Yanagitani, H.; Hashimoto, T. Bioavailable flavonoids to suppress the formation of 8-OHdG in HepG2 cells Arch. Biochem. Biophys. 2006, 455, 197-203
32. Gerets, H. H. J.; Tilmant, K.; Gerin, B.; Chanteux, H.; Depelchin, B. O.; Dhalluin, S.; Atienzar, F. A. Characterization of primary human hepatocytes, HepG2 cells, and HepaRG cells at the mRNA level and CYP activity in response to inducers and their predictivity for the detection of human hepatotoxins Cell Biol. Toxicol. 2012, 28, 69-87
33. Wilkening, S.; Stahl, F.; Bader, A. Comparison of primary human hepatocytes and hepatoma cell line HEPG2 with regard to their biotransformation properties Drug. Metab. Dispos. 2003, 31, 1035-1042
34. Fakih, S.; Podinovskaia, M.; Kong, X.; Collins, H. L.; Schaible, U. E.; Hider, R. C. Targeting the lysosome: fluorescent iron(III) chelators to selectively monitor endosomal/lysosomal labile iron pools J. Med. Chem. 2008, 51, 4539-4552
35. 2+ ions: implications for their antioxidant properties Biochem. J. 1998, 330, 1173-1178
36. Taguchi, K.; Shimada, M.; Fujii, S.; Sumi, D.; Pan, X.; Yamano, S.; Nishiyama, T.; Hiratsuka, A.; Yamamoto, M.; Cho, A. K.; Froines, J. R.; Kumagai, Y. Redox cycling of 9,10-phenanthraquinone to cause oxidative stress is terminated through its monoglucuronide conjugation in human pulmonary epithelial A549 cells Free Radical Biol. Med. 2008, 44, 1645-1655
37. Di Mascio, P.; Devasagayam, T. P.; Kaiser, S.; Sies, H. Carotenoids, tocopherols and thiols as biological singlet molecular oxygen quenchers Biochem. Soc. Trans. 1990, 18, 1054-1056
38. El-Agamey, A.; Lowe, G. M.; McGarvey, D. J.; Mortensen, A.; Phillip, D. M.; Truscott, T. G.; Young, A. J. Carotenoid radical chemistry and antioxidant/pro-oxidant properties Arch. Biochem. Biophys. 2004, 430, 37-48
39. Chen, G.; Djuric, Z. Carotenoids are degraded by free radicals but do not affect lipid peroxidation in unilamellar liposomes under different oxygen tensions FEBS Lett. 2001, 505, 151-154
40. Krinsky, N. I. Carotenoids as antioxidants Nutrition 2001, 17, 815-817
41. Miki, W. Biological functions and activities of animal carotenoids Pure Appl. Chem. 1991, 63, 141-146
42. MacDonald, M. L.; Murray, I. V. J.; Axelsen, P. H. Mass spectrometric analysis demonstrates that BODIPY 581/591 C11 overestimates and inhibits oxidative lipid damage Free Radical Biol. Med. 2007, 42, 1392-1397
43. Charkoudian, L. K.; Pham, D. M.; Franz, K. J. A pro-chelator triggered by hydrogen peroxide inhibits iron-promoted hydroxyl radical formation J. Am. Chem. Soc. 2006, 128, 12424-12425
44. Bruin, G. J. M.; Faller, T.; Wiegand, H.; Schweitzer, A.; Nick, H.; Schneider, J.; Boernsen, K. O.; Waldmeier, F. Pharmacokinetics, distribution, metabolism, and excretion of deferasirox and its iron complex in rats Drug. Metab. Dispos. 2008, 36, 2523-2538
45. Shi, X. L.; Ding, M.; Dong, Z. G.; Chen, F.; Ye, J. P.; Wang, S. W.; Leonard, S. S.; Castranova, V.; Vallyathan, V. Antioxidant properties of aspirin: Characterization of the ability of aspirin to inhibit silica-induced lipid peroxidation, DNA damage, NF-κB activation, and TNF-α production Mol. Cell. Biochem. 1999, 199, 93-102
46. 2 J. Chem. Soc., Perkin Trans. 2 2001, 210-213
47. Liang, W. J.; Johnson, D.; Jarvis, S. M. Vitamin C transport systems of mammalian cells Mol. Membr. Biol. 2001, 18, 87-95
48. Balcerczyk, A.; Kruszewski, M.; Bartosz, G. Does the cellular labile iron pool participate in the oxidation of 2′,7′- dichlorodihydrofluorescein? Free Radical Res. 2007, 41, 563-570
49. Lebel, C. P.; Ischiropoulos, H.; Bondy, S. C. Evaluation of the probe 2′,7′-dichlorofluorescin as an indicator of reactive oxygen species formation and oxidative stress Chem. Res. Toxicol. 1992, 5, 227-231
50. Zhou, P.; Li, L. P.; Luo, S. Q.; Jiang, H. D.; Zeng, S. Intestinal absorption of luteolin from peanut hull extract is more efficient than that from individual pure luteolin J. Agric. Food Chem. 2008, 56, 296-300
51. Fecka, I.; Turek, S. Determination of water-soluble polyphenolic compounds in commercial herbal teas from Lamiaceae: peppermint, melissa, and sage J. Agric. Food Chem. 2007, 55, 10908-10917
52. Lu, X. Y.; Sun, D. L.; Chen, Z. J.; Chen, T.; Li, L. P.; Xu, Z. H.; Jiang, H. D.; Zeng, S. Relative contribution of small and large intestine to deglycosylation and absorption of flavonoids from Chrysanthemun morifolium extract J. Agric. Food Chem. 2010, 58, 10661-10667