Modification of grape seed and wood tannins to lipophilic antioxidant derivatives

Industrial Crops and Products

Volumn 31, Issue 3, 2010, Pages 509-515

  Poaty, Bouddah ^a   Dumarçay, Stéphane ^a   Gérardin, Philippe ^a   Perrin, Dominique ^a  

^a Ecole Nationale Supérieure des Technologies et Industries du Bois   (France)

Author keywords

Antioxidative activity; Chemical grafting; Lipophilic derivatives; Log P; Plant tannins

Indexed keywords

ALKYL CHAIN; ANTI OXIDATIVE ACTIVITY; ANTIOXIDANT PROPERTIES; CHEMICAL GRAFTING; GRAPE SEEDS; LIPOPHILIC ANTIOXIDANTS; LIPOPHILIC CHARACTER; METHYL LINOLEATE; PARTITION COEFFICIENT; VARIABLE LENGTH;

CHEMICAL MODIFICATION; ESTERS; FATTY ACIDS; FREE RADICALS; HYDROCARBONS; NANOCAPSULES; OXIDATION;

GRAFTING (CHEMICAL);

ANTIOXIDANT; DICOTYLEDON; FATTY ACID; TANNIN; VINE;

QUERCUS MONTANA; SCHINOPSIS BALANSAE; VITACEAE;

ANTIOXIDANT; CHEMICAL COMPOSITION; CHEMICAL MODIFICATION; GRAFTING; OXIDATION; PLANT EXTRACT; WATER;

EID: 77949654155     PISSN: 09266690     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.indcrop.2010.02.003     Document Type: Article

References (20)

1. Chen P., and Du Q. Isolation and purification of a novel long-chain acyl catechin from lipophilic tea polyphenols. Chin. J. Chem. 21 (2003) 979-981
2. Cuvelier M.-E., Richard H., and Berset C. Comparison of the antioxidative activity of some acid-phenols: structure-activity relationship. Biosci. Biotechnol. Biochem. 56 (1992) 324-325
3. De Bruyne T., Pieters L., Deelstra H., and Vlietinck A. Condensed vegetable tannins: biodiversity in structure and biological activities. Biochem. Syst. Ecol. 27 (1999) 445-459
4. De Freitas V.A.P., Glories Y., Bourgeois G., and Vitry C. Characterization of oligomeric and polymeric procyanidins from grape seeds by liquid secondary ion mass spectrometry. Phytochemistry 49 (1998) 1435-1441
5. Diouf P.-N., Merlin A., and Perrin D. Antioxidant properties of wood extracts and colour stability of woods. Ann. Forest Sci. 63 (2006) 525-534
6. Eloualja H., Perrin D., and Martin R. Influence of β-carotene on the induced oxidation of ethyl linoleate. New J. Chem. 19 (1995) 1187-1198
7. Frankel E.N. Antioxidants in lipid foods and their impact on food quality. Food Chem. 57 (1996) 51-55
8. Haslam E. Symmetry and promiscuity in procyanidin biochemistry. Phytochemistry 16 (1977) 1625-1640
9. Haslam E. Plant Polyphenols-Vegetable Tannins Revisited (1989), Cambridge University Press, Cambridge p. 230
10. Jin G., and Yoshioka H. Synthesis of lipophilic poly-lauroy-(+)-catechins and radical-scavenging activity. Biosci. Biotechnol. Biochem. 69 (2005) 440-447
11. Morris S.G., and Riemenschneider R.W. Higher fatty alcohol esters of gallic acid. J. Am. Chem. Soc. 68 (1946) 500-501
12. Noferi M., Masson E., Merlin A., Pizzi A., and Déglise X. Antioxidant characteristics of hydrolysable and polyflavonoid tannins: an ESR kinetic study. J. Appl. Polym. Sci. 63 (1996) 475-482
13. Okuda T., Yoshida T., and Hatano T. Hydrolyzable tannins and related polyphenols. Progr. Chem. Org. Nat. Prod. 66 (1995) 1-117
14. Peng Z., Hayasaka Y., Iland P.G., Sefton M., Høj P., and Waters E.J. Quantitative analysis of polymeric procyanidins (Tannins) from Grape (Vitis vinifera) seeds by reverse phase high-performance liquid chromatography. J. Agric. Food Chem. 49 (2001) 26-31
15. Poaty B., Dumarçay S., and Perrin D. New lipophilic catechin derivatives from an oxa-Pictet-Spengler reaction. Eur. Food Res. Technol. 230 (2009) 111-117
16. Takàcs-Novàk K., and Avdeef A. Interlaboratory study of log P determination by shake-flask and potentiometric methods. J. Pharm. Biomed. Anal. 14 (1996) 1405-1413
17. Van der Kerk G.J.M., Verbeek J.H., and Cleton J.C.F. Preparation of esters of gallic acid with higher primary alcohols. Recl. Trav. Chim. Pays-Bas Belg. 70 (1951) 277-284
18. Weinges K., Kaltenhaüsser W., Marx H.-D., Nader E., Nader F., Perner J., and Seiler D. Proanthocyanidins. X. Procyanidins from fruit. Liebigs Ann. Chem. 711 (1968) 184-204
19. Zhang C.X., Wu H., and Weng X.C. Two novel synthetic antioxidants for deep frying oils. Food Chem. 84 (2004) 219-222
20. Zywicki B., Reemtsma T., and Jekel M. Analysis of commercial vegetable tanning agents by reversed-phase liquid chromatography-electrospray ionization-tandem mass spectrometry and its application to wastewater. J. Chromatogr. A 970 (2002) 191-200