Lipophilized epigallocatechin gallate (EGCG) derivatives as novel antioxidants

Journal of Agricultural and Food Chemistry

Volumn 59, Issue 12, 2011, Pages 6526-6533

  Zhong, Ying ^a   Shahidi, Fereidoon ^a  

^a MEMORIAL UNIVERSITY OF NEWFOUNDLAND   (Canada)

Author keywords

antioxidant; epigallocatechin gallate (EGCG); esterification; lipophilization; polyunsaturated fatty acids (PUFA)

Indexed keywords

1 ,1-DIPHENYL-2-PICRYLHYDRAZYL; ABSORPTION IN VIVO; ANTIOXIDANT; ANTIOXIDANT ACTIVITIES; DOCOSAHEXAENOIC ACID; EICOSAPENTAENOIC ACID; EPIGALLOCATECHIN GALLATE; ESTER DERIVATIVES; GREEN TEA; HEALTH BENEFITS; HPLC-MS; LIPOPHILIC ANTIOXIDANTS; LIPOPHILICITY; LIPOPHILIZATION; OCTANOL-WATER PARTITION COEFFICIENT; POLYPHENOLS; PURIFICATION PROCESS;

AIR POLLUTION CONTROL; ESTERIFICATION; ESTERS; POLYUNSATURATED FATTY ACIDS; STEARIC ACID;

AGENTS;

ANTIOXIDANT; CATECHIN; DRUG DERIVATIVE; EPIGALLOCATECHIN GALLATE; FATTY ACID; PLANT EXTRACT;

ARTICLE; CHEMICAL PHENOMENA; CHEMICAL STRUCTURE; CHEMISTRY; SOLUBILITY; TEA;

ANTIOXIDANTS; CAMELLIA SINENSIS; CATECHIN; FATTY ACIDS; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; MOLECULAR STRUCTURE; PLANT EXTRACTS; SOLUBILITY;

EID: 79959261640     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf201050j     Document Type: Article

References (48)

1. Rietveld, A.; Wiseman, S. Antioxidant effects of tea: evidence from human clinical trials J. Nutr. 2003, 133, 3275-3284
2. Stensvold, I.; Tverdal, A.; Solvoll, K.; Foss, O. P. Tea consumption: relationship to cholesterol, blood pressure, and coronary and total mortality Prev. Med. 1992, 21, 546-663
3. Hamilton-Miller, J. M. T. Anti-carcinogenic properties of tea (Camellia sinensis) J. Med. Microbiol. 2001, 50, 299-302 (Pubitemid 32239014)
4. Graham, H. N. Green tea composition, consumption, and polyphenol chemistry Prev. Med. 1992, 21, 334-350
5. McKay, D. L.; Blumberg, J. B. The role of tea in human health: an update J. Am. Coll. Nutr. 2002, 21, 1-13 (Pubitemid 34123703)
6. Cabrera, C.; Artacho, R; Giménez, R. Beneficial effects of green tea - a review J. Am. Coll. Nutr. 2006, 25, 79-99 (Pubitemid 46939847)
7. Guo, Q.; Zhao, B.; Li, M.; Shen, S.; Xin, W. Studies on protective mechanisms of four components of green tea polyphenols against lipid peroxidation in synaptosome Biochim. Biophys. Acta 1996, 1304, 210-222 (Pubitemid 26426992)
8. Wanasundara, U.; Shahidi, F. Stabilization of seal blubber and menhaden oils with green tea catechins J. Am. Oil Chem. Soc. 1996, 73, 1183-1190 (Pubitemid 126527382)
9. He, Y.; Shahidi, F. Antioxidant activity of green tea and its catechins in a fish meat model system J. Agric. Food Chem. 1997, 45, 4262-4266 (Pubitemid 127491616)
10. Shahidi, F.; Alexander, D. M. Green tea catechins as inhibitors of oxidation of meat lipids J. Food Lipids 1998, 5, 125-133 (Pubitemid 128657213)
11. Kondo, K.; Kurihara, M.; Miyata, N.; Suzuki, T.; Toyoda, M. Mechanistic studies of catechins as antioxidants against radical oxidation Arch. Biochem. Biophys. 1999, 362, 79-86 (Pubitemid 29391653)
12. Lotito, S. B.; Fraga, C. G. Catechins delay lipid oxidation and α-tocopherol and β-carotene depletion following ascorbate depletion in human plasma Proc. Soc. Exp. Biol. Med. 2000, 225, 32
13. Shahidi, F.; Miraliakbari, H. Omega-3 (n-3) fatty acids in health and disease: Part 1 - Cardiovascular disease and cancer J. Med. Food 2004, 7, 387-401 (Pubitemid 40095837)
14. Shahidi, F.; Miraliakbari, H. Omega-3 fatty acids in health and disease: Part 2 - Health effects of omega-3 fatty acids in autoimmune diseases, mental health, and gene expression J. Med. Food 2005, 8, 133-148 (Pubitemid 41008975)
15. Wanasundara, U. N.; Shahidi, F. Concentration of omega-3 polyunsaturated fatty acids of seal blubber oil by urea complexation: optimization of reaction conditions Food Chem. 1999, 65, 41-49 (Pubitemid 29076695)
16. Madhujith, T.; Shahidi, F. Optimization of the extraction of antioxidative constituents of six barley cultivars and their antioxidant properties J. Agric. Food Chem. 2006, 54, 8048-8057 (Pubitemid 44785383)
17. Tanaka, T.; Kusano, R.; Kouno, I. Synthesis and antioxidant activity of novel amphipathic derivatives of tea polyphenol Bioorg. Med. Chem. Lett. 1998, 8, 1801-1806 (Pubitemid 28337996)
18. Lam, W. H.; Kazi, A.; Kuhn, D. J.; Chow, L. M. C.; Chan, A. S. C.; Dou, Q. P.; Chan, T. H. A potential prodrug for a green tea polyphenol proteasome inhibitor: evaluation of the peracetate ester of (-)-epigallocatechin gallate [(-)-EGCG] Bioorg. Med. Chem. 2004, 12, 5587-5593 (Pubitemid 39304058)
19. Volpenhein, R. A. Synthesis of higher polyol fatty acid polyesters using high soap: polyol ratios. U.S. Patent 4518772, 1985.
20. Ferret, M.; Soliveri, J.; Plou, F. J.; Lopez-Cortes, N.; Reyes-Duarte, D.; Christensen, M.; Copa-Patino, J. L.; Ballesteros, A. Synthesis of sugar esters in solvent mixtures by lipases from Thermomyces lanuginosus and Candida antarctica B, and their antimicrobial properties Enzyme Microbial Technol. 2005, 36, 391-398 (Pubitemid 40186832)
21. Ballesteros, A.; Plou, F. J.; Alcalde, M.; Ferrer, M.; García-Arellano, H.; Reyes-Duarte, D.; Ghazi, I. Enzymatic synthesis of sugar esters and oligosaccharides from renewable resources. In Biocatalysts in the Pharmaceutical and Biotechnology Industries; Patel, R., Ed.; CRC Press, Taylor & Francis: Boca Raton, FL, 2007; pp 463-488.
22. Akoh, C. C.; Swanson, B. G. Absorbability and weight gain by mice fed methyl glucoside fatty acid polyesters: potential fat substitutes J. Nutr. Biochem. 1991, 2, 652-655
23. Breeman, R.B.van. Liquid chromatography/mass spectrometry of carotenoids Pure Appl. Chem. 1997, 69, 2061-2066
24. Valcic, S.; Muders, A.; Jacobsen, N. E.; Liebler, D. C.; Timmermann, B. N. Antioxidant chemistry of green tea catechins. Identification of products of the reaction of (-)-epigallocatechin gallate with peroxyl radicals Chem. Res. Toxicol. 1999, 12, 382-386 (Pubitemid 29193915)
25. Islamkov, S. Y.; Karimdzhanov, A. K.; Ismailov, A. I.; Kamaev, F. G.; Sadykov, A. S. PMR spectra of catechins and their derivatives (translation) Khim. Prir. Soedin. 1976, 1, 46-50
26. 13C-Nuclear magnetic resonance spectra of O-acylglucoses: additivity of shift parameters and its application to structure elucidations Chem. Pharm. Bull. 1980, 28, 2065-2074
27. 13C NMR studies on trifluoroacetyl derivatives of 2-acetamido-2-deoxyhexoses Org. Magn. Reson. 1984, 22, 717-719
28. Lambert, J. D.; Sang, S.; Hong, J.; Kwon, S. J.; Lee, M. J.; Ho, C. T.; Yang, C. S. Peracetylation as a means of enhancing in vitro bioactivity and bioavailability of epigallocatechin-3-gallate Drug Metab. Dispos. 2006, 34, 2111-2116 (Pubitemid 44837773)
29. Sabally, K.; Karboune, S.; Yeboah, F. K.; Kermasha, S. Lipase-catalyzed esterification of selected phenolic acids with linolenyl alcohols in organic solvent media Appl. Biochem. Biotechnol. 2005, 127, 17-27 (Pubitemid 41367757)
30. Lee, G. S.; Widjaja, A.; Ju, Y. H. Enzymatic synthesis of cinnamic acid derivatives Biotechnol. Lett. 2006, 28, 581-585
31. Giraldo, L. J. L.; Laguerre, M.; Lecomte, J.; Figueroa-Espinoza, M. C.; Barouh, N.; Baréa, B.; Villeneuve, P. Lipase-catalyzed synthesis of chlorogenate fatty esters in solvent-free media Enzyme Microbial Technol. 2007, 41, 721-726 (Pubitemid 47371025)
32. Lue, B. M.; Karboune, S.; Yeboeah, F. K.; Kermasha, S. Lipase-catalyzed esterification of cinnamic acid and oleyl alcohol in organic solvent media J. Chem. Technol. Biotechnol. 2005, 80, 462-468 (Pubitemid 40443678)
33. Stevenson, D. E.; Parkar, S. G.; Zhang, J.; Stanley, R. A.; Jensen, D. J.; Cooney, J. M. Combinatorial enzymic synthesis for functional testing of phenolic acid esters catalysed by Candida Antarctica lipase B (Novozym 435) Enzyme Microbial Technol. 2007, 40, 1078-1086 (Pubitemid 46371316)
34. Stamatis, H.; Sereti, V.; Kolisis, F. N. Studies on the enzymatic synthesis of lipophilic derivatives of natural antioxidants J. Am. Oil Chem. Soc. 1999, 76, 1505-1510 (Pubitemid 30549865)
35. Aissa, I.; Bouaziz, M.; Ghamgui, H.; Kamoun, A.; Miled, N.; Sayadi, S.; Gargouri, Y. Optimization of lipase-catalyzed synthesis of acetylated tyrosol by response surface methodology J. Agric. Food Chem. 2007, 55, 10298-10305
36. Torres de Pinedo, A.; Penalver, P.; Pérez-Victoria, I.; Rondón, D.; Morales, J. C. Syntheis of new phenolic fatty acid esters and their evaluation as lipophilic antioxidants in an oil matrix Food Chem. 2007, 105, 657-665 (Pubitemid 47053950)
37. Ardhaoui, M.; Falcimaigne, A.; Engasser, J. M.; Oussou, P.; Pauly, G.; Ghoul, M. Enzymatic synthesis of new aromatic and aliphatic esters of flavonoids using Candida antarctica lipase as biocatalyst Biocatal. Biotransform. 2004, 22, 253-259 (Pubitemid 40057503)
38. Kontogianni, A.; Skouridou, V.; Sereti, V.; Stamatis, H.; Kolisis, F. N. Regioselective acylation of flavonoids catalyzed by lipase in low toxicity media Eur. J. Lipid Sci. Technol. 2001, 103, 655-660
39. Lewis, P.; Wähälä, K.; Meng, Q. H.; Adlercreutz, H.; Tikkanen, M. J. Synthesis of antioxidant isoflavone fatty acid esters. Natural antioxidants and anticarcinogens in nutrition, health and disease. In Proceedings of the Second International Conference on Natural Antioxidants and Anticarcionogens in Nutrition, Health and Disease, Helsinki, Finland, June 24-27, 1998.
40. Shimada, Y.; Hirota, Y.; Bada, T.; Sugihara, A.; Moriyama, S.; Tominaga, Y.; Terai, T. Enzymatic syntesis of steryl esters of polyunsaturated fatty acids J. Am. Oil Chem. Soc. 1999, 76, 713-716
41. Hashimoto, T.; Kumazawa, S.; Nanjo, F.; Hara, Y.; Nakayama, T. Interaction of tea catechins with lipid bilayers investigated with liposome systems Biosci., Biotechnol., Biochem. 1999, 63, 2252-2255 (Pubitemid 129549060)
42. Zhu, N.; Wang, M.; Wei, G. J.; Lin, J. K.; Yang, C. S.; Ho, C. T. Identification of reaction products of (-)-epigallocatechin, (-)-epigallocatechin gallate and pyrogallol with 2,2-diphenyl-1-picrylhydrazyl radical Food Chem. 2001, 73, 345-349 (Pubitemid 32396792)
43. Sun, T.; Ho, C. T. Antiradical efficiency of tea components J. Food Lipids 2001, 8, 231-238
44. Xu, J. Z.; Yeung, S. Y. V.; Chang, Q.; Huang, Y.; Chen, Z. Y. Comparison of antioxidant activity and bioavailability of tea epicatechins with their epimers Br. J. Nutr. 2004, 91, 873-881 (Pubitemid 38931451)
45. Chan, E. W. C.; Lim, Y. Y.; Chew, Y. L. Antioxidant activity of Camellia sinensis leaves and tea from a lowland plantation in Malaysia Food Chem. 2007, 102, 1214-1222 (Pubitemid 46178479)
46. Nanjo, F.; Goto, K.; Seto, R.; Suzuki, M.; Sakai, M.; Hara, Y. Scavenging effects of tea catechins and their derivatives on 1,1-diphenyl-2-picrylhydrazyl radical Free Radical Biol. Med. 1996, 21, 895-902 (Pubitemid 26365284)
47. Zhu, N.; Sang, S.; Huang, T. C.; Bai, N.; Yang, C. S.; Ho, C. T. Antioxidant chemistry of green tea catechins: oxidation products of (-)-epigallocatechin gallate and (-)-epigallocatechin with peroxidase J. Food Lipids 2000, 7, 275-282 (Pubitemid 33317320)
48. Caturla, N.; Vera-Samper, E.; Villalain, J.; Mateo, C. R.; Micol, V. The relationship between the antioxidant and the antibacterial properties of galloylated catechins and the structure of phospholipids model membranes Free Radical Biol. Med. 2003, 34, 648-662 (Pubitemid 36288531)