Major Flavonoids in Grape Seeds and Skins: Antioxidant Capacity of Catechin, Epicatechin, and Gallic Acid

Journal of Agricultural and Food Chemistry

Volumn 52, Issue 2, 2004, Pages 255-260

  Yilmaz, Yusuf ^a   Toledo, Romeo T ^a  

^a UNIVERSITY OF GEORGIA   (United States)

Author keywords

Antioxidant; Antioxidant capacity; Catechin; Chardonnay; Epicatechin; Gallic acid; Galvinoxyl; Grape seed; Grape skin; Merlot; Muscadine; ORAC

Indexed keywords

ANTIOXIDANT; CATECHIN; ELLAGIC ACID; EPICATECHIN; FLAVONOID; FLAVONOL; GALLIC ACID; GALLOCATECHIN; PEROXY RADICAL; PHENOL; PROCYANIDIN; RESVERATROL; PERHYDROXYL RADICAL; PEROXIDE; PLANT EXTRACT; SCAVENGER;

ANTIOXIDANT ACTIVITY; ARTICLE; DIET SUPPLEMENTATION; DRY MASS; FOOD ANALYSIS; GRAPE; PHYTOCHEMISTRY; PLANT SEED; WINE; CHEMISTRY; FRUIT; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY;

VITACEAE; VITIS; VITIS ROTUNDIFOLIA; VITIS SP.; VITIS VINIFERA;

ANTIOXIDANTS; CATECHIN; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; FREE RADICAL SCAVENGERS; FRUIT; GALLIC ACID; PEROXIDES; PLANT EXTRACTS; SEEDS; VITIS;

EID: 1542289825     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf030117h     Document Type: Article

References (42)

1. Palma, M.; Taylor, L. R. Extraction of polyphenolic compounds from grape seeds with near critical carbon dioxide. J. Chromatogr. A 1999, 849, 117-124.
2. Souquet, J.; Cheynier, V.; Brossaud, F.; Moutounet, M. Polymeric proanthocyanidins from grape skins. Phytochemistry 1996, 43, 509-512.
3. Lotito, S. B.; Fraga, C. G. (+)-Catechin prevents human plasma oxidation. Free Radical Biol. Med. 1997, 24 (3), 435-441.
4. Moini, H.; Guo, Q.; Packer, L. Xanthine oxidase and xanthine dehydrogenase inhibition by the procyanidin-rich French maritime pine bark extract, Pycnogenol: a protein binding effect. Adv. Exp. Med. Biol. 2002, 505, 141-149.
5. Scott, B. C.; Butler, J.; Halliwell, B.; Aruoma, O. I. Evaluation of the antioxidant actions of ferulic acid and catechins. Free Radical Res. Commun. 1993, 19 (4), 241-253.
6. Bors, W.; Michel, C. Antioxidant capacity of flavanols and gallate esters: pulse radiolysis studies. Free Radical Biol. Med. 1999, 27 (11/12), 1413-1426.
7. Fukumoto, L. R.; Mazza, G. Assessing antioxidant and prooxidant activities of phenolic compounds. J. Agric. Food Chem. 2000, 48, 3597-3604.
8. Morel, I.; Lescoat, G.; Cogrel, P.; Sergent, O.; Pasdeloup, N.; Brissot, P.; Cillard, P.; Cillard, J. Antioxidant and iron chelating activities of the flavonoids catechin, quercetin and diosmetin on iron-loaded rat hepatocyte cultures. Biochem. Pharmacol. 1993, 45 (1), 13-19.
9. Liu, Z. Q.; Ma, L. P.; Zhou, B.; Yang, L.; Liu, Z. L. Antioxidative effects of green tea polyphenols on free radical initiated and photosensitized peroxidation of human low-density lipoprotein. Chem. Phys. Lipids 2000, 106, 53-63.
10. Nakao, M.; Takio, S.; Ono, K. Alkyl peroxyl radical-scavenging activity of catechins. Phytochemistry 1998, 49, 2379-2382.
11. Sanchez-Moreno, C.; Larrauri, J. A.; Saura-Calixto, F. Free radical scavenging capacity and inhibition of lipid oxidation of wines, grape juices and related polyphenolic constituents. Food Res. Int. 1999, 32, 407-412.
12. Gunckel, S.; Santander, P.; Cordano, G.; Ferreira, J.; Munoz, S.; Nunez-Vergara, L. J.; Squella, J. A. Antioxidant activity of gallates: an electrochemical study in aqueous media. Chem.-Biol. Interact. 1998, 114, 45-59.
13. Shukla, Y. N.; Srivastava, A.; Kumar, S.; Kumar, S. Phytotoxic and antimicrobial constituents of Argyreia speciosa and Oenothera biennis. J. Ethnopharmacol. 1999, 67, 241-245.
14. Sato, M.; Bagchi, D.; Tosaki, A.; Das, D. K. Grape seed proanthocyanidin reduces cardiomyocyte apoptosis by inhibiting ischemia/reperfusion-induced activation of JNK-1 and C-JUN. Free Radical Biol. Med. 2001, 31 (6), 729-737.
15. Tebib, K.; Rouanet, J. M.; Besancon, P. Antioxidant effects of dietary polymeric grape seed tannins in tissues of rats fed a high cholesterol-vitamin E-deficient diet. Food Chem. 1997, 59, 135-141.
16. Bouhamidi, R.; Prevost, V.; Nouvelot, A. High protection by grape seed proanthocyanidins (GSPC) of polyunsaturated fatty acids against UV-C induced peroxidation. Life Sci. 1998, 321, 31-38.
17. Bagchi, D.; Garg, A.; Krohn, R. L.; Bagchi, M.; Bagchi, D. J.; Balmoori, J.; Stohs, S. J. Protective effects of grape seed proanthocyanidins and selected antioxidants against TPA-induced hepatic and brain lipid peroxidation and DNA fragmentation, and peritoneal macrophage activation in mice. Gen. Pharmacol. 1998, 30, 771-776.
18. Sato, M.; Maulik, G.; Ray, P. S.; Bagchi, D.; Das, D. K. Cardioprotective effects of grape seed proanthocyanidin against ischemic reperfusion injury. J. Mol. Cell. Cardiol. 1999, 31, 1289-1297.
19. Yamakoshi, J.; Kataoka, S.; Koga, T.; Ariga, T. Proanthocyanidin-rich extract from grape seeds attenuates the development of aortic atherosclerosis in cholesterol-fed rabbits. Atherosclerosis 1999, 142, 139-149.
20. Saito, M.; Hosoyama, H.; Ariga, T.; Kataoka, S.; Yamaji, N. Antiulcer activity of grape seed extract and procyanidins. J. Agric. Food Chem. 1998, 46, 1460-1464.
21. 2+, common signals for apoptosis induced by gallic acid. Biochem. Pharmacol. 1998, 55, 1973-1998.
22. Joshi, S. S.; Kuszynski, C. A.; Bagchi, M.; Bagchi, D. Chemopreventive effects of grape seed proanthocyanidin extract on Chang liver cells. Toxicology 2000, 155, 83-90.
23. Tebib, K.; Besancon, P.; Rouanet, J. Effects of dietary grape seed tannins on rat cecal fermentation and colonic bacterial enzymes. Nutr. Res. 1996, 16 (1), 105-110.
24. Chung, K. T.; Lu, Z.; Chou, M. W. Mechanism of inhibition of tannic acid and related compounds on the growth of intestinal bacteria. Food Chem. Toxicol. 1998, 36, 1053-1060.
25. Ursini, F.; Rapuzzi, I.; Toniolo, R.; Tubaro, F.; Bontempelli, G. Characterization of antioxidant effect of procyanidins. Methods Enzymol. 2001, 335, 338-350.
26. Bravo, L. Polyphenols: chemistry, dietary sources. Metabolism, and nutritional significance. Nutr. Rev. 1998, 56, 317-333.
27. Skibola, C.; Smith, M. T. Potential health impacts of excessive flavonoid intake. Free Radical Biol. Med. 2000, 29, 375-383.
28. Bentivegna, S. S.; Whitney, K. M. Subchronic 3-mo oral toxicity study of grape seed and grape skin extract. Food Chem. Toxicol. 2002, 40, 1731-1743.
29. Cao, G.; Prior, R. Measurement of oxygen radical absorbance capacity in biological samples. Methods Enzymol. 1999, 299, 50-63.
30. Shi, H.; Noguchi, N.; Niki, E. Galvinoxyl method for standardizing electron and proton donation activity. Methods Enzymol. 2001, 335, 157-166.
31. SAS Institute. SAS User's Guide: Statistics, version 6.4; SAS Institute: Cary, NC, 1990.
32. Fuleki, T.; Ricardo da Silva, J. M. Catechin and procyanidin composition of seeds from grape cultivars grown in Ontario. J. Agric. Food Chem. 1997, 45, 1156-1160.
33. Escribano-Bailon, T.; Gutierrez-Fernandez, Y.; Rivas-Gonzalo, J. C. R.; Santos-Buelga, C. Characterization of procyanidins of Vitis vinifera variety Tinta del Pais grape seeds. J. Agric. Food Chem. 1992, 40, 1794-1799.
34. Oszmianski, J.; Sapis, J. C. Fractionation and identification of some low molecular weight grape seed phenolics. J. Agric. Food Chem. 1989, 37, 1293-1297.
35. Revilla, E.; Ryan, J. M. Analysis of several phenolic compounds with potential antioxidant properties in grape extracts and wines by high-performance liquid chromatography-photodiode array detection without sample preparation. J. Chromatogr. A 2000, 881, 461-469.
36. Santos-Buelga, C.; Francia-Aricha, E. M.; Escribano-Bailon, T. M. Comparative flavan-3-ol composition of seeds from different grape varieties. Food Chem. 1995, 53, 197-201.
37. Santos-Buelga, C.; Francia-Aricha, E. M.; Escribano-Bailon, M. T. Comparative flavan-3-ol of seeds from different grape varieties. Food Chem. 1995, 53, 197-301.
38. Ector, B. J.; Magee, J. B.; Hegwood, C. P.; Coign, M. J. Resveratrol concentration in muscadine berries, juice, pomace, purees, seeds and wines. Am. J. Enol. Vitic. 1996, 47, 57-62.
39. Cuendet, M.; Potterat, O.; Salvi, A.; Testa, B.; Hostettmann, K. A stilbene and dihydrochalcones with radical scavenging activities from Loiseleuria procumbens. Phytochemistry 2000, 54, 871-874.
40. Tadolini, B.; Juliano, C.; Piu, L.; Franconi, F.; Cabrini, L. Resveratrol inhibition of lipid peroxidation. Free Radical Res. 2000, 33, 105-114.
41. Torel, J.; Cillard, J.; Cillard, P. Antioxidant activity of flavonoids and reactivity with peroxyl radical. Phytochemistry 1986, 25, 383-385.
42. Guo, C.; Cao, G.; Sofic, E.; Prior, R. L. High-performance liquid chromatography coupled with coulometric array detection of electroactive components in fruits and vegetables: relationship to oxygen radical absorbance capacity. J. Agric. Food Chem. 1997, 45, 1787-1796.