Food Science and Biotechnology

Korean Society of Food Science and Technology (한국식품과학회)
권호 표지

Effects of Tea Constituents on Intracellular Level of the Major Tea Catechin, (-)-Epigallocatechin-3-gallate

  • Hong, Jun-Gil (Division of Food Science, College of Life Science, Seoul Women's University) ;
  • Yang, Chung-S. (Susan Lehman Cullman Laboratory for Cancer Research, Department of Chemical Biology, Ernest Mario School of Pharmacy, Rutgers, The State University of New Jersey)
  • Published : 2007.02.28
Download PDF
⟨ Previous Next ⟩

Abstract

(-)-Epigallocatechin-3-gallate (EGCG), a mai or tea catechin has been shown to have many interesting biological activities. In the present study, we studied the effects of green tea catechins, EGCG metabolites, and black tea theaflavins on accumulation of EGCG in HT-29 human colon cells. Intracellular levels of [$^3H$]-EGCG were not changed significantly in the presence of other tea catechins including (-)-epicatechin, (-)-epigallocatechin, and (-)-epicatechin-3-gallate. EGCG methyl metabolites and EGCG 4"-glucuronide did not affect cellular levels of [$^3H$]-EGCG. Black tea theaflavins and theasinensin A (TsA), an EGCG oxidative dimer, however, significantly decreased cellular accumulation of EGCG in HT-29 cells by 31-56%. This decrease was more pronounced when cells were incubated in the presence of theaflavin-3',3"-digallate (TFdiG) or TsA. When EGCG was added separately from TFdiG or TsA, the accumulation of EGCG in HT-29 cells was also significantly decreased regardless of when TFdiG or TsA was added during the uptake study (p<0.01). The results suggest that theaflavins and TsA may interrupt EGCG absorption through the gastrointestinal epithelium.

Keywords

References

  1. Yang CS, Landau JM. Effects of tea consumption on nutrition and health. J. Nutr. 130: 2409-2412 (2000)
  2. Balentine DA, Wiseman SA, Bouwens LC. The chemistry of tea flavonoids. Crit. Rev. Food Sci. 37: 693-704 (1997) https://doi.org/10.1080/10408399709527797
  3. Yang CS, Maliakal P, Meng X. Inhibition of carcinogenesis by tea. Annu. Rev. Pharmacol. 42: 25-54 (2002) https://doi.org/10.1146/annurev.pharmtox.42.082101.154309
  4. Khan N, Afaq F, Saleem M, Ahmad N, Mukhtar H. Targeting multiple signaling pathways by green tea polyphenol (-)-epigallocatechin-3-gallate. Cancer Res. 66: 2500-2505 (2006) https://doi.org/10.1158/0008-5472.CAN-05-3636
  5. Chung JY, Park JO, Phyu H, Dong Z, Yang CS. Mechanisms of inhibition of the Ras-MAP kinase signaling pathway in 30.7b Ras 12 cells by tea polyphenols (-)-epigallocatechin- 3-gallate and theaflavin 3,3'-digallate. FASEB J. 15: 2022-2024 (2001) https://doi.org/10.1096/fj.01-0031fje
  6. Sah JF, Balasubramanian S, Eckert RL, Rorke EA. Epigallocatechin-3-gallate inhibits epidermal growth factor receptor signaling pathway. Evidence for direct inhibition of ERK1/2 and AKT kinases. J. Biol. Chem. 279: 12755-12762 (2004) https://doi.org/10.1074/jbc.M312333200
  7. Shimizu M, Deguchi A, Hara Y, Moriwaki H, Weinstein IB. EGCG inhibits activation of the insulin-like growth factor-1 receptor in human colon cancer cells. Biochem. Bioph. Res. Co. 334: 947-953 (2005) https://doi.org/10.1016/j.bbrc.2005.06.182
  8. Berger SJ, Gupta S, Belfi CA, Gosky DM, Mukhtar H. Green tea constituent (-)-epigallocatechin- 3-gallate inhibits topoisomerase 1 activity in human colon carcinoma cells. Biochem. Bioph. Res. Co. 288: 101-105 (2001) https://doi.org/10.1006/bbrc.2001.5736
  9. Nam S, Smith DM, Dou QP. Ester bond-containing tea polyphenols potently inhibit proteasome activity in vitro and in vivo. J. Biol. Chem. 276: 13322-13330 (2001) https://doi.org/10.1074/jbc.M004209200
  10. Naasani I, Oh-Hashi F, Oh-Hara T, Feng WY, Johnston J, Chan K, Tsuruo T. Blocking telomerase by dietary polyphenols is a major mechanism for limiting the growth of human cancer cells in vitro and in vivo. Cancer Res. 63: 824-830 (2003)
  11. Hong J, Yang CS. Effect of purified green tea catechins on cytosolic phospholipase $A_2$ and arachidonic acid release in human gastrointestinal cancer cell lines. Food Sci. Biotechnol. 15: 799-804 (2006)
  12. Chen L, Lee MJ, Li H. Yang CS. Absorption, distribution, elimination of tea polyphenols in rats. Drug Metab. Dispos. 25: 1045-1050 (1997)
  13. Lee MJ, Maliakal P, Chen L, Meng X, Bondoc FY, Prabhu S, Lambert G, Mohr S, Yang CS. Pharmacokinetics of tea catechins after ingestion of green tea and (-)-epigallocatechin- 3-gallate by humans: formation of different metabolites and individual variability. Cancer Epidem. Biomar. 11: 1025-1032 (2002)
  14. Hong J, Lambert JD, Lee SH, Sinko PJ, Yang CS, Involvement of multi drug resistance-associated proteins in regulating cellular levels of (-)-epigallocatechin-3-gallate and its methyl metabolites. Biochem. Bioph. Res. Co. 310: 222-227 (2003) https://doi.org/10.1016/j.bbrc.2003.09.007
  15. Lu H, Meng X, Yang CS. Enzymology of methylation of tea catechins and inhibition of catechol-O-methyltransferase by (-)-epigallocatechin gallate. Drug Metab. Dispos. 31: 572-579 (2003) https://doi.org/10.1124/dmd.31.5.572
  16. Lu H, Meng X, Li C, Sang S, Patten C, Sheng S, Hong J, Bai N, Winnik B, Ho CT, Yang CS. Glucuronides of tea catechins: enzymology of biosynthesis and biological activities. Drug Metab. Dispos. 31: 452-461 (2003) https://doi.org/10.1124/dmd.31.4.452
  17. Lambert JD, Hong J, Kim DH, Mishin VM, Yang CS. Piperine enhances the bioavailability of the tea polyphenol (-)-epigallocatechin-3-gallate in mice. J. Nutr. 134: 1948-1952 (2004)
  18. Kohri T, Nanjo F, Suzuki M, Seto R, Matsumoto N, Yamakawa M, Hojo H, Hara Y, Desai D, Amin S, Conaway CC, Chung FL. Synthesis of (-)-[4-$^3H$] epigallocatechin gallate and its metabolic fate in rats after intravenous administration. J. Agr. Food Chem. 49: 1042-1048 (2001) https://doi.org/10.1021/jf0011236
  19. Meng X, Sang S, Zhu N, Lu H, Sheng S, Lee MJ, Ho CT, Yang CS. Identification and characterization of methylated and ring-fission metabolites of tea catechins formed in humans, mice, and rats. Chem. Res. Toxicol. 15: 1042-1050 (2002) https://doi.org/10.1021/tx010184a
  20. Hong J, Lu H, Meng X, Ryu JH, Hara Y, Yang CS. Stability, cellular uptake, biotransformation, and efflux of tea polyphenol (-)epigallocatechin-3-gallate in HT-29 human colon adenocarcinoma cells. Cancer Res. 62: 7241-7246 (2002)
  21. Yoshino K, Suzuki M, Sasaki K, Miyase T, Sano M. Formation of antioxidants from (-)-epigallocatechin gallate in mild alkaline fluids, such as authentic intestinal juice and mouse plasma. J. Nutr. Biochem. 10: 223-229 (1999) https://doi.org/10.1016/S0955-2863(98)00103-X