Nanoencapsulation enhances epigallocatechin-3-gallate stability and its antiatherogenic bioactivities in macrophages

Journal of Agricultural and Food Chemistry

Volumn 61, Issue 38, 2013, Pages 9200-9209

  Zhang, Jia ^a   Nie, Shufang ^a   Wang, Shu ^a  

^a TEXAS TECH UNIVERSITY   (United States)

Author keywords

atherosclerosis; EGCG; macrophage; nanostructured lipid carriers; stability; uptake

Indexed keywords

ATHEROSCLEROSIS; ATHEROSCLEROTIC LESIONS; CHOLESTEROL CONTENT; EGCG; EPIGALLOCATECHIN-3-GALLATE; NANO-ENCAPSULATION; NANOSTRUCTURED LIPID CARRIERS; UPTAKE;

CHITOSAN; CONVERGENCE OF NUMERICAL METHODS;

MACROPHAGES;

CARDIOVASCULAR AGENT; CATECHIN; CCL2 PROTEIN, HUMAN; CHOLESTEROL; DRUG DERIVATIVE; EPIGALLOCATECHIN GALLATE; MONOCYTE CHEMOTACTIC PROTEIN 1; NANOPARTICLE; PLANT EXTRACT;

ARTICLE; ATHEROSCLEROSIS; CAMELLIA SINENSIS; CELL LINE; CHEMISTRY; DRUG EFFECT; DRUG FORMULATION; DRUG STABILITY; GENETICS; HUMAN; MACROPHAGE; METABOLISM;

ATHEROSCLEROSIS; CAMELLIA SINENSIS; CARDIOVASCULAR AGENTS; CATECHIN; CELL LINE; CHEMOKINE CCL2; CHOLESTEROL; DRUG COMPOUNDING; DRUG STABILITY; HUMANS; MACROPHAGES; NANOPARTICLES; PLANT EXTRACTS;

EID: 84884870666     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf4023004     Document Type: Article

References (50)

1. Wang, S.; Noh, S. K.; Koo, S. I. Green tea catechins inhibit pancreatic phospholipase A(2) and intestinal absorption of lipids in ovariectomized rats J. Nutr. Biochem. 2006, 17 (7) 492-498
2. Basu, A.; Lucas, E. A. Mechanisms and effects of green tea on cardiovascular health Nutr. Rev. 2007, 65 (8 Part 1) 361-375
3. Ananingsih, V. K.; Sharma, A.; Zhou, W. B. Green tea catechins during food processing and storage: a review on stability and detection Food Res. Int. 2013, 50, 469-479
4. Stangl, V.; Dreger, H.; Stangl, K.; Lorenz, M. Molecular targets of tea polyphenols in the cardiovascular system Cardiovasc. Res. 2007, 73 (2) 348-358
5. The World Health Organization Report 2007-Cardiovascular Diseases, 2006.
6. Go, A. S.; Mozaffarian, D.; Roger, V. L.; Benjamin, E. J.; Berry, J. D.; Borden, W. B.; Bravata, D. M.; Dai, S.; Ford, E. S.; Fox, C. S.; Franco, S.; Fullerton, H. J.; Gillespie, C.; Hailpern, S. M.; Heit, J. A.; Howard, V. J.; Huffman, M. D.; Kissela, B. M.; Kittner, S. J.; Lackland, D. T.; Lichtman, J. H.; Lisabeth, L. D.; Magid, D.; Marcus, G. M.; Marelli, A.; Matchar, D. B.; McGuire, D. K.; Mohler, E. R.; Moy, C. S.; Mussolino, M. E.; Nichol, G.; Paynter, N. P.; Schreiner, P. J.; Sorlie, P. D.; Stein, J.; Turan, T. N.; Virani, S. S.; Wong, N. D.; Woo, D.; Turner, M. B. Heart disease and stroke statistics-2013 update: a report from the American Heart Association Circulation 2013, 127 (1) e6-e245
7. Martinovic, I.; Abegunewardene, N.; Seul, M.; Vosseler, M.; Horstick, G.; Buerke, M.; Darius, H.; Lindemann, S. Elevated monocyte chemoattractant protein-1 serum levels in patients at risk for coronary artery disease Circ. J. 2005, 69 (12) 1484-1489
8. Ross, R.; Harker, L. Hyperlipidemia and atherosclerosis Science 1976, 193 (4258) 1094-1100
9. Guyton, J. R.; Klemp, K. F. Development of the lipid-rich core in human atherosclerosis Arterioscler. Thromb. Vasc. Biol. 1996, 16 (1) 4-11
10. Cuccioloni, M.; Mozzicafreddo, M.; Spina, M.; Tran, C. N.; Falconi, M.; Eleuteri, A. M.; Angeletti, M. Epigallocatechin-3-gallate potently inhibits the in vitro activity of hydroxy-3-methyl-glutaryl-CoA reductase J. Lipid Res. 2011, 52 (5) 897-907
11. Hong, M. H.; Kim, M. H.; Chang, H. J.; Kim, N. H.; Shin, B. A.; Ahn, B. W.; Jung, Y. D. (-)-Epigallocatechin-3-gallate inhibits monocyte chemotactic protein-1 expression in endothelial cells via blocking NF-κB signaling Life Sci. 2007, 80 (21) 1957-1965
12. Joo, S. Y.; Song, Y. A.; Park, Y. L.; Myung, E.; Chung, C. Y.; Park, K. J.; Cho, S. B.; Lee, W. S.; Kim, H. S.; Rew, J. S.; Kim, N. S.; Joo, Y. E. Epigallocatechin-3-gallate inhibits LPS-induced NF-κB and MAPK signaling pathways in bone marrow-derived macrophages Gut Liver 2012, 6 (2) 188-196
13. Melgarejo, E.; Medina, M. A.; Sanchez-Jimenez, F.; Urdiales, J. L. Epigallocatechin gallate reduces human monocyte mobility and adhesion in vitro Br. J. Pharmacol. 2009, 158 (7) 1705-1712
14. Chyu, K. Y.; Babbidge, S. M.; Zhao, X.; Dandillaya, R.; Rietveld, A. G.; Yano, J.; Dimayuga, P.; Cercek, B.; Shah, P. K. Differential effects of green tea-derived catechin on developing versus established atherosclerosis in apolipoprotein E-null mice Circulation 2004, 109 (20) 2448-2453
15. Wolfram, S. Effects of green tea and EGCG on cardiovascular and metabolic health J Am Coll Nutr 2007, 26 (4) 373S-388S
16. Arab, L.; Liu, W.; Elashoff, D. Green and black tea consumption and risk of stroke: a meta-analysis Stroke 2009, 40 (5) 1786-1792
17. Chen, L.; Lee, M. J.; Li, H.; Yang, C. S. Absorption, distribution, elimination of tea polyphenols in rats Drug Metab. Dispos. 1997, 25 (9) 1045-1050
18. Warden, B. A.; Smith, L. S.; Beecher, G. R.; Balentine, D. A.; Clevidence, B. A. Catechins are bioavailable in men and women drinking black tea throughout the day J. Nutr. 2001, 131 (6) 1731-1737
19. Lee, M. J.; Maliakal, P.; Chen, L.; Meng, X.; Bondoc, F. Y.; Prabhu, S.; Lambert, G.; Mohr, S.; Yang, C. S. Pharmacokinetics of tea catechins after ingestion of green tea and (-)-epigallocatechin-3-gallate by humans: formation of different metabolites and individual variability Cancer Epidemiol. Biomarkers Prev. 2002, 11 (10 Part 1) 1025-1032
20. Lambert, J. D.; Yang, C. S. Mechanisms of cancer prevention by tea constituents J. Nutr. 2003, 133 (10) 3262S-3267S
21. Hong, J.; Lu, H.; Meng, X.; Ryu, J. H.; Hara, Y.; Yang, C. S. Stability, cellular uptake, biotransformation, and efflux of tea polyphenol (-)-epigallocatechin-3-gallate in HT-29 human colon adenocarcinoma cells Cancer Res. 2002, 62 (24) 7241-7246
22. Lu, H.; Meng, X.; Yang, C. S. Enzymology of methylation of tea catechins and inhibition of catechol- O -methyltransferase by (-)-epigallocatechin gallate Drug Metab. Dispos. 2003, 31 (5) 572-579
23. Vaidyanathan, J. B.; Walle, T. Glucuronidation and sulfation of the tea flavonoid (-)-epicatechin by the human and rat enzymes Drug Metab. Dispos. 2002, 30 (8) 897-903
24. Zhang, L.; Gu, F. X.; Chan, J. M.; Wang, A. Z.; Langer, R. S.; Farokhzad, O. C. Nanoparticles in medicine: therapeutic applications and developments Clin. Pharmacol. Ther. 2008, 83 (5) 761-769
25. Puri, A.; Loomis, K.; Smith, B.; Lee, J. H.; Yavlovich, A.; Heldman, E.; Blumenthal, R. Lipid-based nanoparticles as pharmaceutical drug carriers: from concepts to clinic Crit. Rev. Ther. Drug Carrier Syst. 2009, 26 (6) 523-580
26. Dube, A.; Nicolazzo, J. A.; Larson, I. Chitosan nanoparticles enhance the intestinal absorption of the green tea catechins (+)-catechin and (-)-epigallocatechin gallate Eur. J. Pharm. Sci. 2010, 41 (2) 219-225
27. Dube, A.; Nicolazzo, J. A.; Larson, I. Chitosan nanoparticles enhance the plasma exposure of (-)-epigallocatechin gallate in mice through an enhancement in intestinal stability Eur. J. Pharm. Sci. 2011, 44 (3) 422-426
28. Heurtault, B.; Saulnier, P.; Pech, B.; Proust, J. E.; Benoit, J. P. A novel phase inversion-based process for the preparation of lipid nanocarriers Pharm. Res. 2002, 19 (6) 875-880
29. de Pace, R. C.; Liu, X.; Sun, M.; Nie, S.; Zhang, J.; Cai, Q.; Gao, W.; Pan, X.; Fan, Z.; Wang, S. Anticancer activities of (-)-epigallocatechin-3- gallate encapsulated nanoliposomes in MCF7 breast cancer cells J. Liposome Res. 2013, 23 (3) 187-196
30. Wang, S.; Wu, D.; Lamon-Fava, S.; Matthan, N. R.; Honda, K. L.; Lichtenstein, A. H. In vitro fatty acid enrichment of macrophages alters inflammatory response and net cholesterol accumulation Br. J. Nutr. 2009, 102 (4) 497-501
31. Lam, W. H.; Kazi, A.; Kuhn, D. J.; Chow, L. M.; Chan, A. S.; 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 (21) 5587-5593
32. Zhong, Y.; Chiou, Y. S.; Pan, M. H.; Shahidi, F. Anti-inflammatory activity of lipophilic epigallocatechin gallate (EGCG) derivatives in LPS-stimulated murine macrophages Food Chem. 2012, 134 (2) 742-748
33. Barras, A.; Mezzetti, A.; Richard, A.; Lazzaroni, S.; Roux, S.; Melnyk, P.; Betbeder, D.; Monfilliette-Dupont, N. Formulation and characterization of polyphenol-loaded lipid nanocapsules Int. J. Pharm. 2009, 379 (2) 270-277
34. Nishiyama, N. Nanomedicine: nanocarriers shape up for long life Nat. Nanotechnol. 2007, 2 (4) 203-204
35. Dube, A.; Nicolazzo, J. A.; Larson, I. Chitosan nanoparticles enhance the intestinal absorption of the green tea catechins (+)-catechin and (-)-epigallocatechin gallate Eur. J. Pharm. Sci. 2010, 41 (2) 219-225
36. Dhawan, S.; Kapil, R.; Singh, B. Formulation development and systematic optimization of solid lipid nanoparticles of quercetin for improved brain delivery J. Pharm. Pharmacol. 2011, 63 (3) 342-351
37. Iqbal, M. A.; Md, S.; Sahni, J. K.; Baboota, S.; Dang, S.; Ali, J. Nanostructured lipid carriers system: recent advances in drug delivery J. Drug Target 2012, 20 (10) 813-830
38. Chen, Z.; Zhu, Q. Y.; Tsang, D.; Huang, Y. Degradation of green tea catechins in tea drinks J. Agric. Food Chem. 2001, 49 (1) 477-482
39. Teeranachaideekul, V.; Muller, R. H.; Junyaprasert, V. B. Encapsulation of ascorbyl palmitate in nanostructured lipid carriers (NLC)-effects of formulation parameters on physicochemical stability Int. J. Pharm. 2007, 340 (1-2) 198-206
40. Wang, R.; Zhou, W.; Jiang, X. Reaction kinetics of degradation and epimerization of epigallocatechin gallate (EGCG) in aqueous system over a wide temperature range J. Agric. Food Chem. 2008, 56 (8) 2694-2701
41. Dube, A.; Nicolazzo, J. A.; Larson, I. Chitosan nanoparticles enhance the plasma exposure of (-)-epigallocatechin gallate in mice through an enhancement in intestinal stability Eur. J. Pharm. Sci. 2011, 44 (3) 422-426
42. Sang, S.; Lee, M. J.; Hou, Z.; Ho, C. T.; Yang, C. S. Stability of tea polyphenol (-)-epigallocatechin-3-gallate and formation of dimers and epimers under common experimental conditions J. Agric. Food Chem. 2005, 53 (24) 9478-9484
43. Long, L. H.; Clement, M. V.; Halliwell, B. Artifacts in cell culture: rapid generation of hydrogen peroxide on addition of (-)-epigallocatechin, (-)-epigallocatechin gallate, (+)-catechin, and quercetin to commonly used cell culture media Biochem. Biophys. Res. Commun. 2000, 273 (1) 50-53
44. 2 production in transformed and non-transformed human bronchial cell lines: possible mechanisms of cell growth inhibition and apoptosis induction Carcinogenesis 2000, 21 (11) 2035-2039
45. Borst, P.; Evers, R.; Kool, M.; Wijnholds, J. A family of drug transporters: the multidrug resistance-associated proteins J. Natl. Cancer Inst. 2000, 92 (16) 1295-1302
46. Bursill, C. A.; Roach, P. D. Modulation of cholesterol metabolism by the green tea polyphenol (-)-epigallocatechin gallate in cultured human liver (HepG2) cells J. Agric. Food Chem. 2006, 54 (5) 1621-1626
47. Miura, Y.; Chiba, T.; Tomita, I.; Koizumi, H.; Miura, S.; Umegaki, K.; Hara, Y.; Ikeda, M.; Tomita, T. Tea catechins prevent the development of atherosclerosis in apoprotein E-deficient mice J. Nutr. 2001, 131 (1) 27-32
48. Deo, R.; Khera, A.; McGuire, D. K.; Murphy, S. A.; Meo Neto Jde, P.; Morrow, D. A.; de Lemos, J. A. Association among plasma levels of monocyte chemoattractant protein-1, traditional cardiovascular risk factors, and subclinical atherosclerosis J. Am. Coll. Cardiol. 2004, 44 (9) 1812-1818
49. Bose, M.; Lambert, J. D.; Ju, J.; Reuhl, K. R.; Shapses, S. A.; Yang, C. S. The major green tea polyphenol, (-)-epigallocatechin-3-gallate, inhibits obesity, metabolic syndrome, and fatty liver disease in high-fat-fed mice J. Nutr. 2008, 138 (9) 1677-1683
50. Senthil Kumaran, V.; Arulmathi, K.; Sundarapandiyan, R.; Kalaiselvi, P. Attenuation of the inflammatory changes and lipid anomalies by epigallocatechin-3-gallate in hypercholesterolemic diet fed aged rats Exp. Gerontol. 2009, 44 (12) 745-751