Comparative study of the cytotoxicity induced by antioxidant epicatechin conjugates obtained from grape

Journal of Agricultural and Food Chemistry

Volumn 54, Issue 18, 2006, Pages 6945-6950

  Ugartondo, Vanessa ^a   Mitjans, Montserrat ^a   Lozano, Carles ^b   Torres, Josep Lluis ^b   Vinardell, Maria Pilar ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

^b DEPARTMENT OF ENVIRONMENTAL CHEMISTRY   (Spain)

Author keywords

Antioxidants; Catechins; Cytotoxicity; Grapes; Polyphenols

Indexed keywords

ANTIOXIDANT; CATECHIN; FLAVONOL DERIVATIVE;

ANIMAL; ARTICLE; CELL DEATH; CELL LINE; CELL STRAIN 3T3; CHEMISTRY; COMPARATIVE STUDY; DRUG EFFECT; FIBROBLAST; FRUIT; GRAPE; HUMAN; KERATINOCYTE; MOUSE; STRUCTURE ACTIVITY RELATION;

3T3 CELLS; ANIMALS; ANTIOXIDANTS; CATECHIN; CELL DEATH; CELL LINE, TRANSFORMED; FIBROBLASTS; FLAVONOLS; FRUIT; HUMANS; KERATINOCYTES; MICE; STRUCTURE-ACTIVITY RELATIONSHIP; VITIS;

VITACEAE; VITIS SP.;

EID: 33748904916     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf061356i     Document Type: Article

References (38)

1. Kanupriya; Prasad, D.; Sai Ram, M.; Kumar, R.; Sawhney, R. C.; Sharma, S. K.; Ilavazhagan, G.; Kumar, D.; Banerjee, P. K. Cytoprotective and antioxidant activity of Rhodiola imbricata against tert-butyl hydroperoxide induced oxidative injury in U-937 human macrophages. Mol. Cell. Biochem. 2005, 275 (1-2), 1-6.
2. Kitagawa, S.; Sakamoto, H.; Tano, H. Inhibitory Effects of Flavonoids on Free Radical-Induced Hemolysis and Their Oxidative Effects on Hemoglobin. Chem. Pharm. Bull. 2004, 52 (8), 999-1001.
3. Puiggròs, F.; Llópiz, N.; Ardévol, A.; Bladé, C.; Arola, L. I.; Salvadó, M. J. Grape Seed Procyanidins Prevent Oxidative Injuty by Modulating the Expression of Antioxidant Enzyme Systems. J. Agric. Food Chem. 2005, 53, 6080-6.
4. Manach, C.; Scalbert, A.; Morand, C. Polyphenols: Food sources and bioavailability. Am. J. Clin. Nutr. 2004, 79, 727-47.
5. Torres, J.; Varela, B.; García, M. T.; Carilla, J.; Matito, C.; Centelles, J. J.; Cascante, M.; Sort, X.; Bobet, R. Valorization of Grape (Vitis vinifera) Byproducts. Antioxidant and Biological Properties of Polyphenolic Fractions Differing in Procyanidin Composition and Flavonol Content. J. Agric. Food Chem. 2002, 50, 7548-55.
6. Selga, A.; Sort, X.; Bobet, R.; Torres, J. L. Efficient One Pot Extraction and Depolymerization of Grape (Vitis vinifera) Pomace Procyanidins for the Preparation of Antioxidant Thio-Conjugates. J. Agric. Food Chem. 2004, 52, 467-73.
7. Torres, J. L.; Lozano, C.; Julià, L.; Sánchez, F. J.; Anglada, J.; Centelles, J. J.; Cascante, M. Cysteinyl-flavan-3-ol conjugates from grape procyanidins. Antioxidant and antiproliferative properties. Bioorg. Med. Chem. 2002, 10, 2497-509.
8. Mitjans, M.; Martínez, V.; Del Campo, J.; Abajo, C.; Lozano, C.; Torres, J. L.; Vinardell, M. P. Novel epicatechin derivatives with antioxidant activity modulate interleukin-1β release in lipopolysaccharide-stimulated human blood. Bioorg. Med. Chem. Lett. 2004, 14, 5031-4.
9. Lozano, C.; Torres, J.; Julià, L., Jiménez, A.; Centelles, J. J.; Cascante, M. Effect of new antioxidant cysteinyl-flavanol conjugates on skin cancer cells. FEBS Lett. 2005, 579, 4219-25.
10. Yang, C. S.; Landau, J. M.; Huang, M. T.; Newmark, H. L. Inhibition of carcinogenesis by dietary polyphenolic compounds. Annu. Rev. Nutr. 2001, 21, 381-406.
11. Soares, V. C.; Varanda, E. A.; Raddi, M. S. In vitro basal and metabolism-mediated cytotoxicity of flavonoids. Food Chem. Toxicol. 2006, 44, 835-8.
12. Popiolkiewicz, J.; Polkowski, K.; Skierski, J. S.; Mazurek, A. P. In vitro toxicity evaluation in the development of new anticancer drugs: Genistein glycosides. Cancer Lett. 2005, 229, 67-75.
13. Glei, M.; Matuschek, M.; Steiner, C.; Böhm, V.; Persin, C.; Pool-Zobel, B. L. Initial in vitro toxicity testing of functional foods rich in catechins and anthocyanins in human cells. Toxicol. in Vitro 2003, 17, 723-9.
14. Torres, J. L.; Bobet, R. New flavanol-derivatives from grape (Vitis vinifera) byproducts. Antioxidant aminoethylthiol-flavan-3-ol conjugates from a polymeric waste fraction used as a source of flavanols. J. Agric. Food Chem. 2001, 49, 4627-34.
15. Miki, M.; Tamai, H.; Mino, M.; Yamamoto, Y.; Niké, E. Free radical chain oxidation of rat red blood cells by molecular oxygen and its inhibition by α-toxopherol. Arch. Biochem. Biophys. 1987, 258, 373-80.
16. Babich, H.; Krupka, M. E.; Nissim, H. A.; Zuckerbraun, H. L. Differential in vitro cytotoxicity of (-)-epicathechin gallate (ECG) to cancer and normal cells from the human oral cavity. Toxicol. in Vitro 2005, 19, 231-42.
17. Borenfreund, E. P. J. A. Rapad colorimetric assay to cellular growth and survival: Application to proliferation and cytotoxicity assay. Toxicol. Lett. 1983, 24, 119-24.
18. Riddell, R. J.; Clothier, R. H.; Ball, M. An evaluation of three in vitro cytotoxicity assays. Food Chem. Toxicol. 1986, 24 (6/7), 469-71.
19. Sánchez, L.; Mitjans, M.; Infante, M. R.; Vinardell, M. P. Assessment of the Potential Skin Irritation of Lysine-Derivative Anionic Surfactants Using Mouse Fibroblast and Human Keratinocytes as an Alternative to Animal Testing. Pharmacol. Res. 2004, 21, 1637-41.
20. Kondo, K.; Kurihara, M.; Miyata, N.; Suzuki, T.; Toyoda, M. Mechanistic studies of catechins as antioxidants against radical oxidation. Arch. Biochem. Biophys. 1999, 362, 79-86.
21. Sagristá, M. L. L.; García, A.; Madariaga, M. A.; Mora, M. Antioxidant and pro-oxidant effect of thiolic compounds N-acetyl-L-cysteine and glutathione against free radical-induced lipid peroxidation. Free Radical Res. 2002, 36 (3), 329-40.
22. Sroka, Z. Antioxidative and antiradical properties of plant phenolics. Z. Naturforsch., C 2005, 60 (11-12), 833-43.
23. Kondo, K.; Kurihara, M.; Miyata, N.; Suzuki, T.; Toyoda, M. Scavenging mechanisms of (-)-epigallocatechin gallate and (-)-epicatechin gallate on peroxyl radicals and formation of superoxide during inhibitory action. Free Radical Biol. Med. 1999, 27, 855-63.
24. Bors, W.; Michel, C.; Stettmaier, K. Electron paramagnetic resonance studies of radical species of proanthocyanidins and gallate esters. Arch. Biochem. Biophys. 2000, 374, 347-55.
25. Lozano, C.; Julia, L.; Jimenez, A.; Touriño, S.; Centelles, J. J.; Cascante, M.; Torres, J. L. Electron-transfer capacity of catechin derivatives and influence on the cell cycle and apoptosis in HT29 cells. FEBS Lett. 2006, 273 (11), 2475-86.
26. Carmichael, J. Current Issues in Cancer: Cancer chemotherapy: Identifying novel anticancer drugs. BMJ [Br. Med. J.] 1994, 308, 1288-90.
27. Clothier, R.; Willshaw, A.; Cox, H. The use of human keratinocytes in the EU/COLIPA international in vitro phototoxicity test validation study and the ECVAM/COLIPA study on UV filter chemicals. ATLA, Altern. Lab. Anim. 1999, 27, 247-59.
28. Spielmann, H.; Balls, M.; Dupuis, J.; Pape, W. J.; Pechovitch, G.; de Silva, O.; Holzhütter, H. G.; Clothier, R.; Desolle, P.; Gerberick, F.; Liebsch, M.; Lovell, W. W.; Maurer, T.; Pfannenbecker, U.; Potthast, J. M.; Csato, M.; Sladowski, D.; Steiling, W.; Brantom, P. The international EU/COLIPA in vitro phototoxicity validation study results of phase II (blind trial). Part I: The 3T3 NRU phototoxicity test. Toxicol. in Vitro 1998, 12, 305-27.
29. Galati, G.; Lin, A.; Sultan, A. M.; O'Brien, P. J. Cellular and in vivo hepatotoxicity caused by green tea phenolic acids and catechins. Free Radical Biol. Med. 2006, 40, 570-80.
30. Schmidt, M.; Schmitz, H. J.; Baumgart, A.; Guédon, D.; Netsch, M. I.; Kreuter, M. H.; Schmidlin, C. B.; Schrenk, D. Toxicity of green tea extracts and their constituents in rat hepatocytes in primary culture. Food Chem. Toxicol. 2005, 43, 307-14.
31. Mohmmad-Abdul, H.; Butterfield, D. A. Protection against amyloid β-peptide (1-42)-induced loss of phospholipids asymmetry in synaptosomal membranes by tricyclodecan-9-xanthogenate (D609) and ferulic acid ethyl ester: Implications for Alzheimer's disease. Biochim. Biophys. Acta 2005, 1741, 140-8.
32. Kikukaki, H.; Hisamoto, M.; Hirose, K.; Akiyama, K.; Taniguchi, H. Antioxidant properties of ferulic acic and its related compounds. J. Agric. Food Chem. 2002, 50, 2161-8.
33. Sultana, R.; Ravagna, A.; Mohmmad-Abdul, H.; Calíbrese, V.; Butterfield, D. A. Ferulic acid ethyl ester protects neurons against amyloid β-peptide(1-42)-induced oxidative stress and neurotoxicity: Relationship to antioxidant activity. J. Neurochem. 2005, 92, 749-58.
34. Chalas, J.; Claise, C.; Edeas, M.; Messaoudi, C.; Vergnes, L.; Abella, A.; Lindenbaum, A. Effect of ethyl esterification of phenolic acids on low-density lipoprotein oxidation. Biomed. Pharmacother. 2001, 55, 54-60.
35. Mitjans, M.; Del Campo, J.; Abajo, C.; Martinez, V.; Selga, A.; Lozano, C.; Torres, J. L.; Vinardell, M. P. Immunomodulatory Activity of a New Family of Antioxidants Obtained from Grape Polyphenols. J. Agric. Food Chem. 2004, 52, 7297-9.
36. Chen, Z. P.; Schell, J. B.; Ho, C. T.; Chen, Y. Green tea epigallocatechin gallate shows a pronounced growth inhibitory effect on cancerous cells but not on their normal counterparts. Cancer Lett. 1997, 129, 173-9.
37. Chen, C.; Shen, G.; Hebbar, V.; Hu, R.; Owuor, E. D.; Kong, A. N. T. Epigallocatechin-3-gallate-induced stress signals in HT-29 human colon adenocarcinoma cells. Carcinogenesis 2003, 24, 1369-78.
38. Yamamoto, T. J.; Lewis, J.; Wahata, D.; Dickinson, B.; Singh, W. B.; Bollarg, E.; Ueta, T.; Osaki, T.; Athar, M.; Shuster, G.; Hsu, S. Roles of catalase and hydrogen peroxide in green tea polyphenols-induced chemopreventive effects. J. Pharmacol. Exp. Ther. 2004, 308, 317-23.