Role of galloylation and polymerization in cytoprotective effects of polyphenolic fractions against hydrogen peroxide insult

Journal of Agricultural and Food Chemistry

Volumn 59, Issue 5, 2011, Pages 2113-2119

  Mitjans, Montserrat ^a   Ugartondo, Vanessa ^a   Martínez, Verónica ^a   Touriño, Sonia ^b   Torres, Josep L ^b   Vinardell, M Pilar ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

^b INSTITUTE OF ADVANCED CHEMISTRY OF CATALONIA IQAC CSIC   (Spain)

Author keywords

antioxidant; chemoprevention; grape pomace; pine bark; toxicity; witch hazel bark

Indexed keywords

ANTIOXIDANT; CHEMOPREVENTION; GRAPE POMACE; PINE BARK; WITCH HAZEL BARK;

AGRICULTURE; BYPRODUCTS; CELL CULTURE; CYTOTOXICITY; HYDROGEN; HYDROGEN PEROXIDE; OXIDATION; PHENOLS; POLYMERIZATION; POLYMERS;

FRUITS;

FLAVONOID; GALLIC ACID; HYDROGEN PEROXIDE; PHENOL DERIVATIVE; POLYPHENOLS;

ANIMAL; ARTICLE; BARK; CELL STRAIN 3T3; CHEMISTRY; DRUG EFFECT; FRUIT; GRAPE; HAMAMELIS; HEMOLYSIS; HUMAN; LIPID PEROXIDATION; MOUSE; OXIDATION REDUCTION REACTION; OXIDATIVE STRESS; PINE; PLANT; POLYMERIZATION; STRUCTURE ACTIVITY RELATION;

3T3 CELLS; ANIMALS; FLAVONOIDS; FRUIT; GALLIC ACID; HAMAMELIS; HEMOLYSIS; HUMANS; HYDROGEN PEROXIDE; LIPID PEROXIDATION; MICE; OXIDATION-REDUCTION; OXIDATIVE STRESS; PHENOLS; PINUS; PLANT BARK; PLANTS; POLYMERIZATION; STRUCTURE-ACTIVITY RELATIONSHIP; VITIS;

HAMAMELIS; HAMAMELIS VIRGINIANA; VITACEAE;

EID: 79952163177     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf1025532     Document Type: Article

References (34)

1. Park, Y. H.; Han, D. W.; Suh, H.; Ryu, G. H.; Hyon, S. H.; Cho, B. K.; Park, J. C. Protective effects of green tea polyphenol against reactive oxigen species-induced oxidative stress in cultured rat calvarial osteoblast Cell Biol. Toxicol. 2003, 19, 325-337 (Pubitemid 38002152)
2. Lee, K. J.; Jeong, H. G. Protective effects of kahweol and cafestol against hydrogen peroxideinduced oxidative stress and DNA damage Toxicol. Lett. 2007, 173, 80-87 (Pubitemid 47371047)
3. Harrison, D. G.; Gongora, M. C. Oxidative stress and hypertension Med. Clin. N. Am. 2009, 93, 621-635
4. Visconti, R.; Grieco, D. New insights on oxidative stress in cáncer Curr. Opin. Drug Discovery Dev. 2009, 12, 240-245
5. Amin, A. R.; Kucuk, O.; Khuri, F. R.; Shin, D. M. Perspectives for cancer prevention with natural compounds J Clin. Oncol. 2009, 27, 2712-2725
6. Khan, N.; Afaq, F.; Mukhtar, H. Cancer chemoprevention through dietary antioxidants: propress and promise Antioxid. Redox Signal. 2008, 10, 475-510
7. Manach, C.; Scalbert, A.; Morand, C.; Rémésy, C.; Jiménez, L. Polyphenols: food sources and bioavailability Am. J. Clin. Nutr. 2004, 79, 727-747 (Pubitemid 41103873)
8. Arlorio, M.; Bottini, C.; Travaglia, F.; Locatelli, M.; Bordiga, M.; Coïsson, J. D.; Martelli, A.; Tessitore, L. Protective activity of Theobroma cacao L. phenolic extract on AML12 and MLP29 liver cells by preventing apoptosis and inducing autophagy J. Agric. Food Chem. 2009, 57, 10612-10618
9. Torres, J. L.; Bobet, R. J. 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, 4627-4634 (Pubitemid 32988696)
10. Rüweler, M.; Anker, A.; Gülden, M.; Maser, E.; Seibert, H. Inhibition of peroxide-induced radical generation by plant polyphenols in C6 astroglioma cells Toxicol. in Vitro 2008, 22, 1377-1381
11. Torres, J. L.; Varela, B.; García, M. T.; Carilla, J.; Matito, C.; Centelles, J. J.; Cascante, M.; Sort, X.; Bobet, R. J. 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, 7548-7555 (Pubitemid 35453715)
12. Touriño, S.; Selga, A.; Jiménez, A.; Juliá, L.; Lozano, C.; Lizárraga, D.; Cascante, M.; Torres, J. L. 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. 2005, 53, 4728-4735 (Pubitemid 40937589)
13. Ugartondo, V.; Mitjans, M.; Touriño, S.; Torres, J. L.; Vinardell, M. P. Comparative antioxidant and cytototoxic effect of procyanidin fractions from grape and pine Chem. Res. Toxicol. 2007, 20, 1543-1548 (Pubitemid 350057225)
14. Touriño, S.; Lizárraga, D.; Carreras, A.; Lorenzo, S.; Ugartondo, V.; Mitjans, M.; Vinardell, M. P.; Juliá, L.; Cascante, M.; Torres, J. L. Highly galloylated tannin fractions from witch hazel (Hamamelis virginiana) bark: electron transfer capacity, In vitro antioxidant activity and effects on skin related cells Chem. Res. Toxicol. 2008, 21, 696-704 (Pubitemid 351498045)
15. Grinberg, L. N.; Newmark, H.; Kitrossky, N.; Rahamim, E.; Chevion, M.; Rachmilewitz, E. A. Protective effects of tea polyphenols against oxidative damage to red blood cells Biochem. Pharmacol. 1997, 54, 973-978 (Pubitemid 27475235)
16. 2-induced oxidative stress J. Agric. Food Chem. 2009, 57, 4459-4465
17. Bukowska, B.; Kowalska, S. Phenol and catechol induce prehemolytic and hemolytic changes in human erythrocytes Toxicol. Lett. 2004, 152, 73-84 (Pubitemid 39030789)
18. Stocks, J.; Dormandy, T. L. The autooxidation of human red cell lipids induced by hydrogen peroxide Br. J. Hamaetol. 1971, 20, 95-111
19. Srour, M. A.; Bilto, Y. Y.; Juma, M. Evaluation of different methods used to measure malonyldialdehyde in human erythrocytes Clin. Hemorheol. Microcirc. 2000, 23, 23-30 (Pubitemid 32047489)
20. Borenfreund, E.; Puerner, J. A. Toxicity determined in vitro by morphological alterations and neutral red absorption Toxicol. Lett. 1985, 24, 119-124 (Pubitemid 15103513)
21. Riddell, R. J.; Clothier, R. H.; Ball, M. An evaluation of three in vitro cytotoxicity assays Food Chem. Toxicol. 1986, 24, 469-471 (Pubitemid 17183981)
22. Zou, C. G.; Agar, N. S.; Jones, G. L. Oxidative insult to human red blood cells induced by free radical initiator AAPH and its inhibition by a commercial antioxidant mixture Life Sci. 2001, 69, 75-86 (Pubitemid 32523936)
23. Vestraeten, S. V.; Oteiza, P. I.; Fraga, C. G. Membrane effects of cocoa procyanidins in liposomes and Jurkat T cells Biol. Res. 2004, 37, 293-300 (Pubitemid 39328269)
24. Ajila, C. M.; Prasada Rao, U. J. S. Protection against hydrogen peroxide induced oxidative damage in rat erythrocytes by Mangifera indica L. peel extract Food Chem. Toxicol. 2008, 46, 303-309 (Pubitemid 350235775)
25. Pazos, M.; Torres, J. L.; Andersen, M. L.; Skibsted, L. H.; Medina, I. Galloylated polyphenols efficiently reduce r-tocopherol radicals in a phospholipid model system composed of sodium dodecyl sulfate (SDS) micelles J. Agric. Food Chem. 2009, 57, 5042-5048
26. Plumb, G. W.; De Pascual-Teresa, S.; Santos-Buelga, C.; Cheynier, V.; Williamson, G. Antioxidant properties of catechins and proanthocyanidins: effect of polymerization, galloylation and glycosylation Free Radical Res. 1998, 29, 351-358 (Pubitemid 29027455)
27. Liegibel, U. M.; Abrahamse, S. L.; Pool-Zobel, B. L.; Rechkemmer, G. Application of confocal laser scanning microscopy to detect oxidative stress in human colon cells Free Radical Res. 2000, 32, 535-547 (Pubitemid 30241356)
28. Llópiz, N.; Puiggròs, F.; Céspedes, E.; Arola, L.; Ardévol, A.; Bladé, C.; Salvadó, M. J. Antigenotoxic effect of grape seed procyanidin extract in Fao cells submitted to oxidative stress J. Agric. Food Chem. 2004, 52, 1083-1087
29. Roig, R.; Cascón, E.; Arola, L; Bladé, C.; Salvadó, M. J. Procyanidins protect Fao cells against hydrogen peroxide-induced oxidative stress Biochim. Biophys. Acta 2002, 1572, 25-30 (Pubitemid 35223052)
30. Iglesias, J.; Pazos, M.; Lois, S.; Medina, I. Contribution of galloylation and polymerization to the antioxidant activity of polyphenols in fish lipid systems J. Agric. Food Chem. 2010, 58, 7423-7431
31. Pazos, M.; Iglesias, J.; Maestre, R.; Medina, I. Structure-activity relationships of polyphenols to prevent lipid oxidation in pelagic fish muscle J. Agric. Food Chem. 2010, 58, 11067-11074
32. Lizárraga, D.; Lozano, C.; Briedé, J. J.; Van Delft, J. H.; Touriño, S.; Centelles, J. J.; Torres, J. L.; Cascante, M. The importance of polymerization and galloylation for the antiproliferative properties of procyanidin-rich natural extracts FEBS J. 2007, 274, 4802-4811 (Pubitemid 47353134)
33. Fan, P.; Lou, H. Effects of polyphenols from grape seeds on oxidative damage to cellular DNA Mol. Cell. Biochem. 2004, 267, 67-74 (Pubitemid 39562386)
34. Halliwell, B. The wanderings of a free radical Free Radical Biol. Med. 2009, 46, 531-542