Efficient One Pot Extraction and Depolymerization of Grape (Vitis vinifera) Pomace Procyanidins for the Preparation of Antioxidant Thio-Conjugates

Journal of Agricultural and Food Chemistry

Volumn 52, Issue 3, 2004, Pages 467-473

  Selga, Ariadna ^a   Sort, Xavier ^b   Bobet, Raül ^b   Torres, Josep Lluís ^a  

^a DEPARTMENT OF ENVIRONMENTAL CHEMISTRY   (Spain)

^b Miguel Torres SA   (Spain)

Author keywords

Antioxidants; Catechins; Flavanols; Free radical scavenging; Grape; Polyphenols; Procyanidins; Vitis vinifera

Indexed keywords

ACETIC ACID; ANTIOXIDANT; CATECHIN; FLAVONOID; MERCAPTAMINE; PHENOL DERIVATIVE; PLANT EXTRACT; POLYMER; POLYPHENOL; POLYPHENOLS; PROCYANIDIN; PROCYANIDIN DERIVATIVE; THIOL DERIVATIVE; WATER;

ARTICLE; CATION EXCHANGE; CHEMICAL MODIFICATION; CHEMISTRY; COMPARATIVE STUDY; DEPOLYMERIZATION; EXTRACTION; FRUIT; GRAPE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ION EXCHANGE CHROMATOGRAPHY; ISOLATION AND PURIFICATION; NONHUMAN; PURIFICATION; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY;

VITIS; VITIS SP.; VITIS VINIFERA;

EID: 0842306418     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf035048l     Document Type: Article

References (35)

1. Domínguez, H.; Torres, J. L.; Núñez, M. J. Antioxidant phenolics as food additives from agricultural wastes. Polyphénols Actualités 2001, 21, 26-30.
2. Torres, J. L. High value-added products from byproducts and wastes. Electron. J. Environ. Agric. Food Chem. 2003, 2.
3. Packer, L.; Rimbach, G.; Virgili, F. Antioxidant activity and biologic properties of a procyanidin-rich extract from pine (Pinus maritima) bark, pycnogenol. Free Radical Biol. Med. 1999, 27, 704-724.
4. Liao, S. S.; Kao, Y. H.; Hiipakka, R. A. Green tea: biochemical and biological basis for health benefits. In Vitamins and Hormones. Advances in Research and Applications; Litwack, G., Ed.; Academic Press Inc.: San Diego, 2001; pp 1-94.
5. Wren, A. F.; Cleary, M.; Frantz, C.; Melton, S.; Norris, L. 90-day oral toxicity study of a grape seed extract (IH636) in rats. J. Agric. Food Chem. 2002, 50, 2180-2192.
6. Vinson, J. A.; Mandarano, M. A.; Shuta, D. L.; Bagchi, M.; Bagchi, D. Beneficial effects of a novel IH636 grape seed proanthocyanidin extract and a niacin-bound chromium in a hamster atherosclerosis model. Mol. Cell. Biochem. 2002, 240, 99-103.
7. Ray, S.; Bagchi, D.; Lim, P. M.; Bagchi, M.; Gross, S. M.; Kothari, S. C.; Preuss, H. G.; Stohs, S. J. Acute and long-term safety evaluation of a novel IH636 grape seed proanthocyanidin extract. Res. Commun. Mol. Pathol. Pharmacol. 2001, 109, 165-197.
8. Yamakoshi, J.; Saito, M.; Kataoka, S.; Kikuchi, M. Safety evaluation of proanthocyanidin-rich extract from grape seeds. Food Chem. Toxicol. 2002, 40, 599-607.
9. Rohdewald, P. A review of the French maritime pine bark extract (Pycnogenol (R)), a herbal medication with a diverse clinical pharmacology. Int. J. Clin. Pharmacol. Ther. 2002, 40, 158-168.
10. Ahmad, N.; Mukhtar, H. Green tea polyphenols and cancer: Biologic mechanisms and practical implications. Nutr. Rev. 1999, 57, 78-83.
11. Yang, C. S.; Chung, J. Y.; Yang, G. Y.; Chhabra, S. K.; Lee, M. J. Tea and tea polyphenols in cancer prevention. J. Nutr. 2000, 130, 472S-478S.
12. Zandi, P.; Gordon, M. H. Antioxidant activity of extracts from old tea leaves. J. Agric. Food Chem. 1999, 64, 285-288.
13. Levites, Y.; Amit, T.; Youdim, M. B. H.; Mandel, S. Involvement of protein kinase C activation and cell survival/cell cycle genes in green tea polyphenol (-)-epigallocatechin 3-gallate neuroprotective action. J. Biol. Chem. 2002, 277, 30574-30580.
14. Ferreira, D.; Slade, D. Oligomeric proanthocyanidins: naturally occurring O-heterocycles. Nat. Prod. Rep. 2002, 19, 517-541.
15. Torres, J. L.; Bobet, R. 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. 2001, 49, 4627-4634.
16. Torres, J. L.; Lozano, C.; Juliá, L.; Sánchez-Baeza, F. J. ; Anglada, J. M.; Centelles, J. J.; Cascante, M. Cysteinyl-flavan-3-ol conjugates from grape procyanidins. Antioxidant and antiproliferative properties. Bioorg. Med. Chem. 2002, 10, 2497-2509.
17. Selga, A.; Lozano, C.; Cascante, M.; Núñez, M. J.; Haro, I. ; Carilla, J.; Busquets, M. A.; Mitjans, M.; Vinardell, P.; Sort, X.; Bobet, R. ; Constantí, C.; Torres, J. L. Recovery of antioxidants from byproducts and wastes through the formation of novel bio-based conjugates. Polyphenols Communications 2002. XXI International Conference on Polyphenols.; El Hadrami, I., Ed.; El Watanya: Marrakech, Morocco 2002; Vol. 2, pp 379-380.
18. Rigaud, J.; Pérez-Ilzarbe, J.; Ricardo da Silva, J. M.; Cheynier, V. Micro method for identification of proanthocyanidin using thiolysis monitored by high-performance liquid chromatography. J. Chromatogr. 1991, 540, 401-405.
19. Prieur, C.; Rigaud, J.; Cheynier, V.; Moutounet, M. Oligomeric and polymeric procyanidins from grape seeds. Phytochemistry 1994, 36, 781-784.
20. Torres, J. L.; Selga, A. Procyanidin size and composition by thiolysis with cysteamine hydrochloride and chromatography. Chromatographia 2003, 57, 441-445.
21. Blois, M. S. Antioxidant determinations by the use of stable free radical. Nature 1958, 181, 1199-1200.
22. Brand-Williams, W.; Cuvelier, M. E.; Berset, C. Use of a free radical method to evaluate antioxidant activity. Lebensm.-Wiss. Technol. 1995, 28, 25-30.
23. Souquet, J.-M.; Cheynier, V.; Brossaud, F.; Moutounet, M. Polymeric proanthocyanidins from grape skins. Phytochemistry 1996, 43, 509-512.
24. Souquet, J. M.; Labarbe, B.; LeGuerneve, C.; Cheynier, V.; Moutounet, M. Phenolic composition of grape stems. J. Agric. Food Chem. 2000, 48, 1076-1080.
25. Torres, J. L.; Varela, B.; García, M. T.; Carilla, J.; Matito, C. ; Centelles, J. J.; Cascante, C.; 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, 7548-7555.
26. Plumb, G. W.; Price, K. R.; Rhodes, M. J. C.; Williamson, G. Antioxidant properties of the major polyphenolic compounds in broccoli. Free Radical Res. 1997, 27, 429-435.
27. Saint-Cricq de Gaulejac, N.; Provost, C.; Vivas, N. Comparative study of polyphenol scavenging activities assessed by different methods. J. Agric. Food Chem. 1999, 47, 425-431.
28. 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 the inhibitory action. Free Radical Biol. Med. 1999, 27, 855-863.
29. Bors, W.; Michel, C.; Stettmaier, K. Electron paramagnetic resonance studies of radical species of proanthocyanidins and gallate esters. Arch. Biochem. Biophys. 2000, 374, 347-355.
30. Tanaka, T.; Takahashi, R.; Kouno, I.; Nonaka, G.-I. Chemical evidence for the de-astringency (insolubilization of tannins) of persimmon fruit. J. Chem. Soc., Perkin Trans. 1 1994, 3013-3022.
31. Torres, J. L.; Lozano, C. Chromatographic characterisation of proanthocyanidins after thiolysis with cysteamine. Chromatographia 2001, 54, 523-526.
32. Sears, K. D.; Casebier, R. L. Cleavage of proanthocyanidins with thioglycolic acid. Chem. Commun. 1968, 1437-1438.
33. Dangles, O.; Fargeix, G.; Dufour, C. Antioxidant properties of anthocyanins and tannins: a mechanistic investigation with catechin and the 3′,4′,7-trihydroxyflavylium ion. J. Chem. Soc., Perkin Trans. 2 2000, 1653-1666.
34. Kennedy, J. A.; Jones, G. P. Analysis of proanthocyanidin cleavage products following acid-catalysis in the presence of excess phloroglucinol. J. Agric. Food Chem. 2001, 49, 1740-1746.
35. Lozano, C.; Cascante, M.; Torres, J. L. Cation-exchange micropreparative separation of galloylated and nongalloylated sulphur conjugated catechins. J. Chromatogr. A 2002, 973, 229-234.