Photodegradation of (-)-epigallocatechin-3-gallate in topical cream formulations and its photostabilization

Journal of Pharmaceutical and Biomedical Analysis

Volumn 56, Issue 4, 2011, Pages 692-697

  Bianchi, Anna ^a   Marchetti, Nicola ^a   Scalia, Santo ^a  

^a UNIVERSITY OF FERRARA   (Italy)

Author keywords

( ) Epigallocatechin 3 gallate; Photodegradation; Photostabilizers; Reversed phase chromatography; Topical formulations

Indexed keywords

ALPHA TOCOPHEROL; ANTIOXIDANT; BUTYLCRESOL; EPIGALLOCATECHIN GALLATE; SULISOBENZONE;

ARTICLE; CREAM; DRUG FORMULATION; DRUG STRUCTURE; ELECTROSPRAY MASS SPECTROMETRY; EMULSION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PHOTODEGRADATION; PHOTOLYSIS; PRIORITY JOURNAL; SKIN PROTECTION; ULTRAVIOLET RADIATION;

ADMINISTRATION, TOPICAL; ALKANES; ANTIOXIDANTS; BENZOPHENONES; CATECHIN; CHALCONES; CINNAMATES; DRUG COMPOUNDING; DRUG STABILITY; EMOLLIENTS; EMULSIONS; EXCIPIENTS; HUMANS; PHOTOLYSIS; REPRODUCIBILITY OF RESULTS; SKIN; SUNSCREENING AGENTS; TEA; ULTRAVIOLET RAYS;

EID: 84860395536     PISSN: 07317085     EISSN: 1873264X     Source Type: Journal    
DOI: 10.1016/j.jpba.2011.07.007     Document Type: Article

References (36)

1. Chen Q., Guo Z., Zhao J. Identification of green tea's (Camellia sinensis (L.)) quality level according to measurement of main catechins and caffeine contents by HPLC and support vector classification pattern recognition. J. Pharm. Biomed. Anal. 2008, 48:1321-1325.
2. Cao Y., Cao R. Angiogenesis inhibition by drinking tea. Nature 1999, 398:381.
3. Arts I.C.W., Hollman P.C.H. Polyphenols and diseases risk in epidemiological studies. Am. J. Clin. Nutr. 2005, 81:317S-325S.
4. Kuriyama S., Shimazu T., Ohmori K., Kikuchi N., Nakaya N., Nishino Y., Tsubono Y., Tsuji I. Green tea consumption and mortality due to cardiovascular disease, cancer, and all causes in Japan: the Ohsaki study. JAMA 2006, 296:1255-1265.
5. Katiyar S.K., Ahmad N., Mukhtar H. Green tea and the skin. Arch. Dermatol. 2000, 136:989-994.
6. Vayalil P.K., Elmets C.A., Katiyar S.K. Treatment of green tea polyphenols in hydrophilic cream prevents UVB-induced oxidation of lipids and proteins, depletion of antioxidant enzymes and phosphorylation of MAPK proteins in SKH-1 hairless mouse skin. Carcinogenesis 2003, 24:927-936.
7. Yusuf N., Irby C., Katiyar S.K., Elmets C.A. Photoprotective effects of green tea polyphenols. Photodermatol. Photoimmunol. Photomed. 2007, 23:48-56.
8. Beretta G., Furlanetto S., Regazzoni L., Zarrella M., Maffei Facino R. Quencing of αβ-unsaturated aldehydes by green tea polyphenols: HPLC-ESI-MS/MS studies. J. Pharm. Biomed. Anal. 2008, 48:606-611.
9. Lambert J.D., Elias R.J. The antioxidant and pro-oxidant activities of green tea polyphenols: a role in cancer prevention. Arch. Biochem. Biophys. 2010, 501:65-72.
10. Dvorakova K., Dorr R.T., Valcic S., Timmermann B., Alberts D.S. Pharmacokinetics of the green tea derivative, EGCG, by the topical route of administration in mouse and human skin. Cancer Chemother. Pharmacol. 1999, 43:331-335.
11. Proniuk S., Liederer B.M., Blanchard J. Preformulation study of epigallocatechin gallate, a promising antioxidant for topical skin cancer. J. Pharm. Sci. 2002, 91:111-116.
12. Elmets C., Katiyar S., Yusuf N. Photoprotection by green tea polyphenols. Sunscreens 2005, 639-651. Taylor Francis Group, Boca Raton, FL. third ed. N. Shaath (Ed.).
13. Katiyar S., Afaq F., Perez A., Mukhtar H. Green tea polyphenol (-)-epigallocatechin-3-gallate treatment of human skin inhibits ultraviolet radiation-induced oxidative stress. Carcinogenesis 2001, 22:287-294.
14. Tobi S., Gilbert M., Paul N., McMillan T. The green tea polyphenol, epigallocatechin-3-gallate, protects against the oxidative cellular and genotoxic damage of UVA radiation. Int. J. Cancer 2002, 102:439-444.
15. Lu Y.P., Lou Y.R., Xie J.G., Peng Q.Y., Liao J., Yang C.S., Huang M.-T., Conney A.H. Topical applications of caffeine or (-)-epigallocatechin gallate (EGCG) inhibit carcinogenesis and selectively increase apoptosis in UVB-induced skin tumors in mice. Proc. Natl. Acad. Sci. U. S. A. 2002, 99:12455-12460.
16. Mittal A., Piyathilake C., Hara Y., Katiyar S. Exceptionally high protection of photocarcinogenesis by topical application of (-)-epigallocatechin-3-gallate in hydrophilic cream in SKH-1 hairless mouse model: relationship to inhibition of UVB-induced global DNA hypomethylation. Neoplasia 2003, 5:555-565.
17. Katiyar S., Matsui M.S., Elmets C., Mukhtar H. Polyphenolic antioxidant (-)-epigallocatechin-3-gallate from green tea reduces UVB-induced inflammatory responses and infiltration of leukocytes in human skin. Photochem. Photobiol. 1999, 69:148-153.
18. Kim J., Hwang J.S., Cho Y.K., Han Y., Jeon Y., Yang K.H. Protective effects of (-)-epigallocatechin-3-gallate on UVA- and UVB-induced skin damage. Skin Pharmacol. Physiol. 2001, 14:11-19.
19. Mochizuki M., Yamazaki S., Kano K., Ikeda T. Kinetic analysis and mechanistic aspects of autoxidation of catechins. Biochim. Biophys. Acta 2002, 1569:35-44.
20. Mizooku Y., Yoshikawa M., Tsuneyoshi T., Arakawa R. Analysis of oxidized epigallocatechin gallate by liquid chromatography/mass spectrometry. Rapid Commun. Mass Spectrom. 2003, 17:1915-1918.
21. Wang R., Zhou W.B., Jiang X.H. Reaction kinetics of degradation and epimerization of epigallocatechin gallate (EGCG) in aqueous system over a wide range of temperature. J. Agric. Food Chem. 2008, 56:2694-2701.
22. Dube A., Ng K., Nicolazzo J.A., Larson I. Effective use of reducing agents and nanoparticle encapsulation in stabilizing catechins in alkaline solution. Food Chem. 2010, 12:662-667.
23. Rode T., Frauen M., Muller B.W., Schonrock U., Mundt C., Hintze U., Wenck H. The influence of antioxidant and chelating agents on the stability of catechins, with particular reference to (-)-epigallocatechin-gallate (EGCG) and (-)-epicatechin (EC) in topical emulsion based formulations. SOFW J. 2002, 128:24-26.
24. ICH Guidelines Q1B Photostability testing of new drug substances and products. Federal Register 1997, 62:27115-27122.
25. COLIPA - The European Cosmetic, Toiletry and Perfumery Association. International Sun Protection Factor (SPF) Test Method, 2006, http://www.colipa.com/.
26. Scalia S., Mezzena M. Incorporation of quercetin in lipid microparticles: effect on photo- and chemical-stability. J. Pharm. Biomed. Anal. 2009, 49:90-94.
27. Block L.H. Medicated topicals. Remington: The Science and Practice of Pharmacy 2000, 836. Lippincott Williams & Wilkins, Baltimore. A. Gennaro, A. Der Marderosian, G. Hanson, T. Medwick, N. Popovich, R. Schnaare, J. Schwartz, H. White (Eds.).
28. Zhu Q.Y., Zhang A., Tsang D., Huang Y., Chen Z.Y. Stability of green tea catechins. J. Agric. Food Chem. 1997, 45:4624-4628.
29. de Souza L.M., Cipriani T.R., Iacomini M., Gorin P.A.J., Sassaki G.L. HPLC/ESI-MS and NMR analysis of flavonoids and tannins in bioactive extract from leaves of Maytenus ilicifolia. J. Pharm. Biomed. Anal. 2008, 47:59-67.
30. Tønnesen H.H. Formulation and stability testing of photolabile drugs. Int. J. Pharm. 2001, 225:1-14.
31. Brisaert M., Plaizier-Vercammen J. Investigation on the photostability of a tretinoin lotion and stabilization with additives. Int. J. Pharm. 2000, 199:49-57.
32. Bonda C.A. The photostability of organic sunscreen actives. Sunscreens 2005, 323-345. Taylor Francis Group, Boca Raton, FL. third ed. N. Shaath (Ed.).
33. Gonzales S., Fernandez-Lorente M., Gilaberte-Calzada Y. The latest on skin photoprotection. Clin. Dermatol. 2008, 26:614-626.
34. Shang 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, 53:9478-9484.
35. Morsy M.A., Khaled M.M. Novel EPR characterization of the antioxidant activity of tea leaves. Spectrochim. Acta A 2002, 58:1271-1277.
36. Allwood M.C., Martin H.J. The photodegradation of vitamins A and E in parental nutrition mixtures during infusion. Clin. Nutr. 2000, 19:339-342.