Comparative antioxidant and cytotoxic effect of procyanidin fractions from grape and pine

Chemical Research in Toxicology

Volumn 20, Issue 10, 2007, Pages 1543-1548

  Ugartondo, Vanessa ^a   Mitjans, Montserrat ^a   Touriño, Sonia ^b   Torres, Josep Lluis ^b   Vinardell, María Pilar ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

^b DEPARTMENT OF ENVIRONMENTAL CHEMISTRY   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

2,2' AZOBIS(2 AMIDINOPROPANE); FLAVONOID; PLANT EXTRACT; PROCYANIDIN DERIVATIVE; PROCYANIDOL OLIGOMER; PROCYANIDOL OLIGOMER IVG; PROCYANIDOL OLIGOMER IVP; PROCYANIDOL OLIGOMER OWG; PROCYANIDOL OLIGOMER OWP; PROCYANIDOL OLIGOMER VIIIG; PROCYANIDOL OLIGOMER VIIIP; PROCYANIDOL OLIGOMER XIG; PROCYANIDOL OLIGOMER XIP; UNCLASSIFIED DRUG;

ANIMAL CELL; ANTIOXIDANT ACTIVITY; ARTICLE; BIOLOGICAL ACTIVITY; CELL FUNCTION; COMPARATIVE STUDY; CONCENTRATION RESPONSE; CONTROLLED STUDY; CYTOTOXICITY; FIBROBLAST; GRAPE; HEMOLYSIS; HUMAN; HUMAN CELL; KERATINOCYTE; MOUSE; NONHUMAN; PINE; SAFETY; STRUCTURE ACTIVITY RELATION;

3T3 CELLS; AMIDINES; ANIMALS; ANTIOXIDANTS; BIFLAVONOIDS; CATECHIN; CELL LINE, TRANSFORMED; CELL PROLIFERATION; CELL SURVIVAL; CHEMICAL FRACTIONATION; ERYTHROCYTES; FIBROBLASTS; FLAVONOIDS; HEMOLYSIS; HUMANS; KERATINOCYTES; MICE; PHENOLS; PINUS; PLANT BARK; PLANT EXTRACTS; PROANTHOCYANIDINS; STRUCTURE-ACTIVITY RELATIONSHIP; VITIS;

VITACEAE;

EID: 35848940716     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx700253y     Document Type: Article

References (38)

1. Laufenberg, G., Kunz, B., and Nystroem, M. (2003) Transformation of vegetable waste into value added products: (A) the upgrading concept; (B) practical implementations. Bioresour. Technol. 87, 167-198.
2. Tones, J. L., Selga, A., and Cascante, M. (2003) Bioactive products from by-products and wastes. Electron. J. Environ. Agric. Food. Chem. 2, 211-214.
3. Rice-Evans, C. (2001) Flavonoid antioxidants. Curr. Med. Chem. 8, 797-807.
4. Packer, L., Rimbach, G., and Virgili, F. (1999) Antioxidant activity and biologic properties of a procyanidin-rich extract from pine (Pinus maritima) bark, pycnogenol. Free Radical Biol. Med. 27, 704-724.
5. Hara-Kudo, Y., Yamasaki, A., Sasaki, M., Okubo, T., Minai, Y., Haga, M., Kondo, K., and Sugita-Konishi, Y. (2005) Antibacterial action on pathogenic bacterial spore by green tea catechins. J. Sci. Food Agric. 85, 2354-2361.
6. Toda, M., Okubo, S., Hiyoshi, R., and Shimamura, T. (1989) The Bactericidal Activity of Tea and Coffee. Lett. Appl. Microbiol. 8, 123-125.
7. Hayakawa, S., Kimura, T., Saeki, K., Koyama, Y., Aoyagi, Y., Noro, T., Nakamura, Y., and Isemura, M. (2001) Apoptosis-inducing activity of high molecular weight fractions of tea extracts. Biosci. Biotechnol. Biochem. 65, 459-462.
8. Ruf, J. C. (1999) Wine and polyphenols related to platelet aggregation and atherothrombosis. Drugs Exp. Clin. Res. 25, 125-131.
9. Katiyar, S. K., and Mukhtar, H. (1997) Tea antioxidants in cancer chemoprevention. J. Cell Biochem. Suppl. 27, 59-67.
10. Middlenton, E, Jr., Kandaswami, C., and Theoharis, C. (2000) The effects of plant flavonoids on mammalian cells: implications for inflammation, heart disease, and cancer. Pharmacol. Rev. 52, 673-751.
11. Medina, I., Lois, S., Lizarraga, D., Pazos, M., Touriño, S., Cascante, M., and Torres, J. L. (2006) Functional fatty fish supplemented with grape procyanidins. Antioxidant and proapoptotic properties on colon cell lines. J. Agric. Food Chem. 54, 3598-3603.
12. Torres, J. L., and Bobet, R. (2001) New flavanol derivatives from grape (Vitis vinifera) byproducts. Antioxidant aminoethylthio-flavan-3-ol conjugates from a polymeric waste fraction used as a source of flavanols. J. Agric. Food Chem. 49, 4627-4634.
13. Torres, J. L., Varela, B., García, M. T., Carilla, J., Matito, C., Centelles, J. J., Cascante, M., Sort, X., and Bobet, R. (2002) Valorization of grape (Vitis vinifera) byproducts. Antioxidant and biological properties of polyphenols fractions differing in procyanidin composition and flavonol content. J. Agric. Food. Chem. 50, 7548-7555.
14. Touriño, S., Selga, A., Jiménez, A., Julià, L., Lozano, C., Lizarraga, D., Cascante, M., and Torres, J. L. (2005) Procyanidin fractions from Pine (Pinus pinaster) bark: radical scavenging power in solution, antioxidant activity in emulsion, and antiproliferative effect in melanoma cells. J. Agric. Food Chem. 53, 4728-4735.
15. Selga, A., Sort, X., Bobet, R., and Torres, J. L. (2004) Efficient one pot extraction and depolymerization of grape (Vitis vinifera) pomace procyanidins for the preparation of antioxidant thio-conjugates. J. Agric. Food Chem. 52, 467-473.
16. Pazos, M., Lois, S., Torres, J. L., and Medina, I. (2006) Inhibition of hemoglobin- and iron-promoted oxidation in fish microsomes by natural phenolics. J. Agric. Food. Chem. 54, 4417-4423.
17. Miki, M., Tamai, H., Mino, M., Yamamoto, Y., and Niké, E. (1987) Free radical chain oxidation of rar red blood cells by molecular oxygen and its inhibition by α-toxopherol. Arch. Biochem. Biophys. 258, 373-80.
18. Babich, H., Krupka, M. E., Nissim, H. A., and Zuckerbraun, H. L. (2005) Differential in vitro cytotoxicity of (-)-epicatechin gallate (ECG) to cancer and normal cells from the human oral cavity. Toxicol. In Vitro, 19, 231-42.
19. Borenfreund, E. P. J. A. (1983) Rapid colorimetric assay to cellular . growth and survival: Application to proliferation and cytotoxicity | assay. Toxicol. Lett. 24, 119-124.
20. Riddell, R. J., Clothier, R. H., and Balls, M. (1986) An evaluation of ] three in vitro cytotoxicity assays. Food Chem. Toxicol. 24, 469-471.
21. Vuorela, S., Kreander, K., Karonen, M., Nieminem, R., Hämäläinen, j M., Galkin, A., Laitinen, L., Salminen, J., Moilanen, E., Pihlaja, K., Vuorela, H., Vuorela, P., and Heinonen, M. (2005) Preclinical evaluation of rapeseed, raspberry, and pine bark phenolics for health related effects. J. Agric. Food Chem. 53, 5922-5931.
22. Mitjans, M., Del Campo, J., Abajo, C., Martinez, V., Selga, A., Lozano, C., Torres, J. L., and Vinardell, M. P. (2004) Immunomodulatory activity of a new family of antioxidants obtained from grape polyphenols. J. Agric. Food Chem. 52, 7297-7299.
23. Kitawa, S., Sakamoto, H., and Tano, H. (2004) Inhibitory effects of flavonoids on free-radical-induced hemolysis and their oxidative effects on hemoglobin. Chem. Pharm. Bull. 52, 999-1001.
24. Plumb, G. W., De Pascual-Teresa, S., Santos-Buelga, C., Cheynier, V., and Williamson, G. (1998) Antioxidant properties of catechins and proanthocyanidins: effect of polymerisation, galloylation and glycosylation. Free Radical Res. 29, 351-358.
25. Sroka, Z. (2005) Antioxidative and antiradical properties of plant phenolics. Z. Naturforsch., C: Biosci. 60, 833-843.
26. Torres, J. L., Lozano, C., Julià, L., Sánchez, F. J., Anglada, J., Centelles, J. J., and Cascante, M. (2002) Cysteiniyl-flavan-3-ol conjugates from grape procyanidins. Antioxidant and antiproliferative properties. Bioorg. Med. Chem. 10, 2497-2509.
27. Simao, A., Suzukawa, A., Casado, M. F., Oliveira, R., Guarnier, F., and Cecchini, R. (2006) Genistein abrogates pre-hemolytic and oxidative stress damage induced by 2,2′-azobis(amidinopropane). Life Sci. 78, 1202-1210.
28. Caturla, N., Vera-Samper, E., Villalaín, J., Mateo, C., and Micol, V. (2003) The relationship between the antioxidant and the antibacterial preperties of galloylated catechins and the structure of phospholipid model membranes. Free Radical Biol. Med. 34, 648-662.
29. Erlejman, A.G., Verstraeten, S. V., Fraga, C. G., and Oteiza, P. I. (2004) The interaction of flavonoids with membranes: Potential determination of flavonoid antioxidant effects. Free Radical Res. 38, 1311-1320.
30. Na, H. K., and Surh, Y. J. (2006) Intracellular signaling network as a prime chemopreventive target of (-)-epigallocatechin gallate. Mol. Nutr. Food Res. 50, 152-159.
31. Tan, X. H., Hu, D. R., Li, S. R., Han, Y., Zhanc, Y. L., and Zhou, D. Y. (2000) Differences of four cathechins in cell cycle arrest and induction of apoptosis in LoVo cells. Cancer Lett. 158, 1-6.
32. Matito, C., Mastorakou, F., Centelles, J. J., Torres, J. L., and Cascante, M. (2003) Antiproliferative effect of antioxidant polyphenols from grape in murine Hepa-1c1c7. Eur. J. Nutr. 42, 43-49.
33. Dai, F., Miao, Q., Zhou, B., Yang, L., and Liu, Z. (2006) Protective effects of flavonols and theirglycosides against free radical-induced oxidative hemolysis of red blood cells. Life Sci. 78, 2488-2493.
34. Ugartondo, V., Mitjans, M., Lozano, C., Torres, J. L., and Vinardell, M. P. (2006) Comparative study of the cytotoxicity induced by antioxidant epicatechin conjugates obtained from grape. J. Agric. Food Chem. 54, 6945-6950.
35. Benavides, T., Mitjans, M., Martínez, V., Clapés, P., Infante, M. R., Clothier, R. H., and Vinardell, M. P. (2004) Assessment of primary eye and skin irritants by in vitro cytotoxicity and phototoxicity models: an in vitro approach of nex arginine-based surfactants-induced irritation. Toxicology 197, 229-237.
36. Clothier, R., Willshaw, A., and Cox, H. (1999) The use of human keratynocytes in the EU/COLIPA international in vitro phototoxicity test validation study and the ECVAM/COLIPA study on UV filter chemicals. ATLA. Altern. Lab. Anim. 27, 247-259.
37. Schmidt, M., Schmitz, H. J., Baumgart, A., Guédon, D., Netsch, M. I., Kreuter, M. H., Schmidlin, C. B., and Schrenk, D. (2005) Toxicity of green tea extracts and their constituents in rat hepatocytes in primary culture. Food Chem. Toxicol, 43, 307-314.
38. Lozano, C., Torres, J., Julià, L., Jiménez, A., Centelles, J. J., and Cascante, M. (2005) Effect of new antioxidant cysteinyl-flavanol conjugates on skin cancer cells. FEBS Lett. 579, 4219-4225.