Validation of a high performance liquid chromatography method for the stabilization of epigallocatechin gallate

International Journal of Pharmaceutics

Volumn 475, Issue 1-2, 2014, Pages 181-190

  Fangueiro, Joana F ^a,b   Parra, Alexander ^c   Silva, Amélia M ^d,e   Egea, Maria A ^c   Souto, Eliana B ^a,b,d   Garcia, Maria L ^c   Calpena, Ana C ^c  

^a Pessoa University   (Portugal)

^b UNIVERSIDADE FERNANDO PESSOA   (Portugal)

^c UNIVERSITY OF BARCELONA   (Spain)

^d UNIVERSITY OF TRÁS OS MONTES AND ALTO DOURO   (Portugal)

^e UNIVERSITY OF TRÁS OS MONTES AND ALTO DOURO   (Portugal)

Author keywords

Catechins; Epigallocatechin gallate (EGCG); Reverse phase high performance liquid chromatography (RP HPLC); Validation

Indexed keywords

ALCOHOL; ASCORBIC ACID; DIETHYLENE GLYCOL MONOETHYL ETHER; EPIGALLOCATECHIN GALLATE; 4 (2 HYDROXYETHYL) 1 PIPERAZINEETHANESULFONIC ACID; ANTINEOPLASTIC AGENT; ANTIOXIDANT; BUFFER; CATECHIN; ETHYLENE GLYCOL DERIVATIVE; EXCIPIENT; NONSTEROID ANTIINFLAMMATORY AGENT; REDUCING AGENT; SOLVENT;

ACCURACY; ARTICLE; DRUG DEGRADATION; EPIMERIZATION; LIMIT OF DETECTION; LIMIT OF QUANTITATION; PH; PHYSICAL CHEMISTRY; PRIORITY JOURNAL; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; STORAGE TEMPERATURE; THERMOSTABILITY; ADVERSE EFFECTS; ANALOGS AND DERIVATIVES; CHEMISTRY; DRUG STABILITY; DRUG STORAGE; HEAT; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MEDICINAL CHEMISTRY; OXIDATION REDUCTION REACTION; PROCEDURES; REVERSED PHASE LIQUID CHROMATOGRAPHY; SPECTROPHOTOMETRY; VALIDATION STUDY;

ANTI-INFLAMMATORY AGENTS, NON-STEROIDAL; ANTICARCINOGENIC AGENTS; ANTIOXIDANTS; ASCORBIC ACID; BUFFERS; CATECHIN; CHEMISTRY, PHARMACEUTICAL; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CHROMATOGRAPHY, REVERSE-PHASE; DRUG STABILITY; DRUG STORAGE; ETHYLENE GLYCOLS; EXCIPIENTS; HEPES; HOT TEMPERATURE; HYDROGEN-ION CONCENTRATION; OXIDATION-REDUCTION; REDUCING AGENTS; SOLVENTS; SPECTROPHOTOMETRY;

EID: 84906926999     PISSN: 03785173     EISSN: 18733476     Source Type: Journal    
DOI: 10.1016/j.ijpharm.2014.08.053     Document Type: Article

References (41)

1. M.E. Cavet, K.L. Harrington, T.R. Vollmer, K.W. Ward, and J.Z. Zhang Anti-inflammatory and anti-oxidative effects of the green tea polyphenol epigallocatechin gallate in human corneal epithelial cells Mol. Vis. 17 2011 533 542
2. Z. Chen, Q.Y. Zhu, D. Tsang, and Y. Huang Degradation of green tea catechins in tea drinks J. Agric. Food Chem. 49 2001 477 482
3. G.J. Du, C.Z. Wang, L.W. Qi, Z.Y. Zhang, T. Calway, T.C. He, W. Du, and C.S. Yuan The synergistic apoptotic interaction of panaxadiol and epigallocatechin gallate in human colorectal cancer cells Phytother. Res. 27 2013 272 277
4. X. Du, X. Huang, C. Huang, Y. Wang, and Y. Zhang Epigallocatechin-3- gallate (EGCG) enhances the therapeutic activity of a dental adhesive J. Dent. 40 2012 485 492
5. A. Dube, K. Ng, J.A. Nicolazzo, and I. Larson Effective use of reducing agents and nanoparticle encapsulation in stabilizing catechins in alkaline solution Food Chem. 122 2010 662 667
6. A. Dube, J.A. Nicolazzo, and I. Larson Chitosan nanoparticles enhance the intestinal absorption of the green tea catechins (+)-catechin and (-)-epigallocatechin gallate Eur. J. Pharm. Sci. 41 2010 219 225
7. A. Dube, J.A. Nicolazzo, and I. Larson Assessment of plasma concentrations of (-)-epigallocatechin gallate in mice following administration of a dose reflecting consumption of a standard green tea beverage Food Chem. 128 2011 7 13
8. F. Fernandez-Campos, B. Clares Naveros, O. Lopez Serrano, C. Alonso Merino, and A.C. Calpena Campmany Evaluation of novel nystatin nanoemulsion for skin candidosis infections Mycoses 56 2013 70 81
9. F. Fernandez Campos, A.C. Calpena Campmany, G. Rodriguez Delgado, O. Lopez Serrano, and B. Clares Naveros Development and characterization of a novel nystatin-loaded nanoemulsion for the buccal treatment of candidosis: ultrastructural effects and release studies J. Pharm. Sci. 101 2012 3739 3752
10. N.C. Gordon, and D.W. Wareham Antimicrobial activity of the green tea polyphenol (-)-epigallocatechin-3-gallate (EGCG) against clinical isolates of Stenotrophomonas maltophilia Int. J. Antimicrob. Agents 36 2010 129 131
11. M.C. Güida, M.I. Esteva, A. Camino, M.M. Flawiá, H.N. Torres, and C. Paveto Trypanosoma cruzi: in vitro and in vivo antiproliferative effects of epigallocatechin gallate (EGCg) Exp. Parasitol. 117 2007 188 194
12. Guideline I.H.T., 1994. Validation of analytical procedures: text and methodology Q2(R1). Current Step 4 version Parent Guideline dated 27 October 1994 [complementary Guideline on Methodology dated 6 November 1996 incorporated in 2005].
13. H. Hajimehdipoor, B.M. Kondori, G.R. Amin, N. Adib, H. Rastegar, and M. Shekarchi Development of a validated HPLC method for the simultaneous determination of flavonoids in Cuscuta chinensis Lam. by ultra-violet detection Daru 20 2012 57
14. T. Hatano, M. Tsugawa, M. Kusuda, S. Taniguchi, T. Yoshida, S. Shiota, and T. Tsuchiya Enhancement of antibacterial effects of epigallocatechin gallate, using ascorbic acid Phytochemistry 69 2008 3111 3116
15. K.E. Heim, A.R. Tagliaferro, and D.J. Bobilya Flavonoid antioxidants: chemistry, metabolism and structure-activity relationships J. Nutr. Biochem. 13 2002 572 584
16. S.M. Henning, Y. Niu, Y. Liu, N.H. Lee, Y. Hara, G.D. Thames, R.R. Minutti, C.L. Carpenter, H. Wang, and D. Heber Bioavailability and antioxidant effect of epigallocatechin gallate administered in purified form versus as green tea extract in healthy individuals J. Nutr. Biochem. 16 2005 610 616
17. C. Hu, and D.D. Kitts Evaluation of antioxidant activity of epigallocatechin gallate in biphasic model systems in vitro Mol. Cell. Biochem. 218 2001 147 155
18. I. Ikeda, M. Kobayashi, T. Hamada, K. Tsuda, H. Goto, K. Imaizumi, A. Nozawa, A. Sugimoto, and T. Kakuda Heat-epimerized tea catechins rich in gallocatechin gallate and catechin gallate are more effective to inhibit cholesterol absorption than tea catechins rich in epigallocatechin gallate and epicatechin gallate J. Agric. Food Chem. 51 2003 7303 7307
19. J.S. Kim, E.S. Oh, and J.-M. Kim Nitric oxyde synthase, green tea catechins and Parkinsons disease V.R. Preedy, Tea in Health and Disease Prevention 2012 American Publishers San Diego, USA 1425 1434
20. Y. Komatsu, S. Suematsu, Y. Hisanobu, H. Saigo, R. Matsuda, and K. Hara Studies on preservation of constituents in canned drinks. Part II. Effects of pH and temperature on reaction kinetics of catechins in green tea infusion Biosci. Biotechnol. Biochem. 57 1993 907 910
21. M. Kumamoto, T. Sonda, K. Nagayama, and M. Tabata Effects of pH and metal ions on antioxidative activities of catechins Biosci. Biotechnol. Biochem. 65 2001 126 132
22. S.M. Lee, C.W. Kim, J.K. Kim, H.J. Shin, and J.H. Baik GCG-rich tea catechins are effective in lowering cholesterol and triglyceride concentrations in hyperlipidemic rats Lipids 43 2008 419 429
23. Y. Lun Su, L.K. Leung, Y. Huang, and Z.-Y. Chen Stability of tea theaflavins and catechins Food Chem. 83 2003 189 195
24. Y. Matsuo, Y. Yamada, T. Tanaka, and I. Kouno Enzymatic oxidation of gallocatechin and epigallocatechin: effects of C-ring configuration on the reaction products Phytochemistry 69 2008 3054 3061
25. Y. Mizooku, M. Yoshikawa, T. Tsuneyoshi, and R. Arakawa Analysis of oxidized epigallocatechin gallate by liquid chromatography/mass spectrometry Rapid Commun. Mass Spectrom. 17 2003 1915 1918
26. M. Mochizuki, S. Yamazaki, K. Kano, and T. Ikeda Kinetic analysis and mechanistic aspects of autoxidation of catechins Biochim. Biophys. Acta 1569 2002 35 44
27. M. Muzolf-Panek, A. Gliszczynska-Swigło, H. Szymusiak, and B. Tyrakowska The influence of stereochemistry on the antioxidant properties of catechin epimers Eur. Food Res. Technol. 235 2012 1001 1009
28. D.G. Nagle, D. Ferreira, and Y.D. Zhou Epigallocatechin-3-gallate (EGCG): chemical and biomedical perspectives Phytochemistry 67 2006 1849 1855
29. K. Rathore, S. Choudhary, A. Odoi, and H.C. Wang Green tea catechin intervention of reactive oxygen species-mediated ERK pathway activation and chronically induced breast cell carcinogenesis Carcinogenesis 33 2012 174 183
30. S. Sang, S. Tian, R.E. Stark, C.S. Yang, and C.-T. Ho New dibenzotropolone derivatives characterized from black tea using LC/MS/MS Bioorg. Med. Chem. 12 2004 3009 3017
31. M. Suganuma, S. Okabe, Y. Kai, N. Sueoka, E. Sueoka, and H. Fujiki Synergistic effects of (-)-epigallocatechin gallate with (-)-epicatechin, sulindac, or tamoxifen on cancer-preventive activity in the human lung cancer cell line PC-9 Cancer Res. 59 1999 44 47
32. T. Tanaka, Y. Matsuo, and I. Kouno Chemistry of secondary polyphenols produced during processing of tea and selected foods Int. J. Mol. Sci. 11 2010 14 40
33. E. Tedeschi, H. Suzuki, and M. Menegazzi Antiinflammatory action of EGCG the main component of green tea, through STAT-1 inhibition Ann. N. Y. Acad. Sci. 973 2002 435 437
34. R. Wang, W. Zhou, and X. Jiang Reaction kinetics of degradation and epimerization of epigallocatechin gallate (EGCG) in aqueous system over a wide temperature range J. Agric. Food Chem. 56 2008 2694 2701
35. R. Wang, W. Zhou, and R.A. Wen Kinetic study of the thermal stability of tea catechins in aqueous systems using a microwave reactor J. Agric. Food Chem. 54 2006 5924 5932
36. J.Z. Xu, S.Y. Yeung, Q. Chang, Y. Huang, and Z.Y. Chen Comparison of antioxidant activity and bioavailability of tea epicatechins with their epimers Br. J. Nutr. 91 2004 873 881
37. Y. Zhong, Y.-S. Chiou, M.-H. Pan, C.-T. Ho, and F. Shahidi Protective effects of epigallocatechin gallate (EGCG) derivatives on azoxymethane-induced colonic carcinogenesis in mice J. Funct. Foods 4 2012 323 330
38. Y. Zhong, Y.S. Chiou, M.H. Pan, and F. Shahidi Anti-inflammatory activity of lipophilic epigallocatechin gallate (EGCG) derivatives in LPS-stimulated murine macrophages Food Chem. 134 2012 742 748
39. Y. Zhong, C.-M. Ma, and F. Shahidi Antioxidant and antiviral activities of lipophilic epigallocatechin gallate (EGCG) derivatives J. Funct. Foods 4 2012 87 93
40. Y. Zhong, and F. Shahidi Lipophilised epigallocatechin gallate (EGCG) derivatives and their antioxidant potential in food and biological systems Food Chem. 131 2012 22 30
41. J. Zimeri, and C.H. Shahidi Degradation kinetics of (-)-epigallocatechin gallate as a function of pH and dissolved oxygen in a liquid model system J. Food Sci. 64 1999 753 758