Influence of Gallate and Pyrogallol Moieties on the Intestinal Absorption of (-)-Epicatechin and (-)-Epicatechin Gallate

Journal of Food Science

Volumn 77, Issue 10, 2012, Pages

  Tagashira, Tomohiko ^a   Choshi, Tominari ^a   Hibino, Satoshi ^a   Kamishikiryou, Jun ^a   Sugihara, Narumi ^a  

^a FUKUYAMA UNIVERSITY   (Japan)

Author keywords

Catechin; Gallate alkyl ester; Gallate moiety; Hydrophobicity; Intestinal absorption

Indexed keywords

CATECHIN; DRUG DERIVATIVE; EPICATECHIN GALLATE; EPIGALLOCATECHIN GALLATE; PYROGALLOL;

ARTICLE; BIOAVAILABILITY; CELL STRAIN CACO 2; CHEMISTRY; DRUG EFFECT; FUNCTIONAL FOOD; HUMAN; INTESTINE ABSORPTION; STRUCTURE ACTIVITY RELATION; TEA;

BIOLOGICAL AVAILABILITY; CACO-2 CELLS; CATECHIN; FUNCTIONAL FOOD; HUMANS; INTESTINAL ABSORPTION; PYROGALLOL; STRUCTURE-ACTIVITY RELATIONSHIP; TEA;

EID: 84867656765     PISSN: 00221147     EISSN: 17503841     Source Type: Journal    
DOI: 10.1111/j.1750-3841.2012.02902.x     Document Type: Article

References (38)

1. Alam A, Takaguchi Y, Ito H, Yoshida T, Tsuboi S. 2005.Multi-functionalization of gallic acid towards improved synthesis of a- and b-DDB. Tetrahedron 61:1909-18.
2. Annaba F, Kumar P, Dudeja AK, Saksena S, Gill RK, Alrefai WA. 2010. Green tea catechin EGCG inhibits ileal apical sodium bile acid transporter ASBT. Am J Physiol Gastrointest Liver Physiol 298:G467-73.
3. Artursson P, Karlsson J. 1991. Correlation between oral drug absorption in humans and apparent drug permeability coefficients in human intestinal epithelial (Caco-2) cells. Biochem Biophys Res Commun 175:880-5.
4. Chan KY, Zhang L, Zuo Z. 2007. Intestinal efflux transport kinetics of green tea catechins in Caco-2 monolayer model. J Pharm Pharmacol 59:395-400.
5. Chow HH, Hakim IA. 2011. Pharmacokinetic and chemoprevention studies on tea in humans. Pharmacol Res 64:105-12.
6. Donovan JL, Crespy V, Manach C, Morand C, Besson C, Scalbert A, Remesy C. 2001. Catechin is metabolized by both the small intestine and liver of rats. J Nutr 131:1753-7.
7. Duffy SJ, Vit JA, Holbrook M, Swerdloff PL, Keaney JF. 2001. Effect of acute and chronic tea consumption on platelet aggregation in patients with coronary artery disease. Arterioscler Thromb Vasc 21:1084-9.
8. Farabegoli F, Papi A, Bartolini G, Ostan R, Orlandi M. 2010. (-)-Epigallocatechin-3-gallate downregulates Pg-P and BCRP in a tamoxifen resistant MCF-7 cell line. Phytomedicine 17: 356-62.
9. Kadowaki M, Sugihara N, Tagashira T, Terao K, Furuno K. 2008. Presence or absence of a gallate moiety on catechins affects their cellular transport. J Pharm Pharmacol 60:1189-95.
10. Kajiya K, Kumazawa S, Nakayama T. 2001. Steric effects on interaction of tea catechins with lipid bilayers. Biosci Biotechnol Biochem 65:2638-43.
11. Katiyar SK, Mukhtar H. 1997. Tea antioxidants in cancer chemoprevention. J Cell Biochem Suppl 27:59-67.
12. Kitagawa S, Nabekura T, Kamiyama S. 2004. Inhibition of P-glycoprotein function by tea catechins in KB-C2 cells. J Pharm Pharmacol 56:1001-5.
13. Kitagawa S, Nabekura T, Kamiyama S, Takahashi T, Nakamura Y, Kashiwada Y, Ikeshiro Y. 2005. Effects of alkyl gallates on P-glycoprotein function. Biochem Pharmacol 70:1262-6.
14. Koo MWL, Cho CH. 2004. Pharmacological effects of green tea on the gastrointestinal system. Eur J Pharmacol 500:177-85.
15. Kuhnle G, Spencer JP, Schroeter H, Shenoy B, Debnaam ES, Srai SK, Rice-Evans C, Hahn U. 2000. Epicatechin and catechin are O-methylated and glucuronidated in the small intestine. Biochem Biophys Res Commun 277:507-12.
16. Larsen CA, Bisson WH, Dashwood RH. 2009. Tea catechins inhibit hepatocyte growth factor receptor (MET kinase) activity in human colon cancer cells: kinetic and molecular docking studies. J Med Chem 52:6543-5.
17. Lee MJ, Wang ZY, Li H, Chen L, Sun Y, Gobbo S, Balentine DA, Yang CS. 1995. Analysis of plasma and urinary tea poylphenols in human subjects. Cancer Epidemiol Biomarkers Prev 4: 393-9.
18. Liang G, Tang A, Lin X, Li L, Zhang S, Huang Z, Tang H, Li Q. 2010. Green tea catechins augment the antitumor activity of doxorubicin in an in vivo mouse model for chemoresistant liver cancer. Int J Oncol 37:111-23.
19. Lowry OH, Rosebrough N J, Farr AL, Randall RJ. 1951. Protein measurement with the Folin phenol reagent. J Biol Chem 193: 265-75.
20. Maki KC, Reeves MS, Farmer M, Yasunaga K, Matsuo N, Katsuragi Y, Komikado M, Tokimitsu I, Wilder D, Jones F, Blumberg JB, Cartwright Y. 2009. Green tea catechin consumption enhances exercise-induced abdominal fat loss in overweight and obese adults. J Nutr 139:264-70.
21. +- ATPase by flavonoids: a structure-activity study. J Enzyme Inhib 14:151-66.
22. Naftalin RJ, Afzal I, Cunningham P, Halai M, Ross C, Salleh N, Milligan SR. 2003 Interactions of androgens, green tea catechins and the antiandrogen flutamide with the external glucose-binding site of the human erythrocyte glucose transporter GLUT1. Br J Pharmacol 140:487-99.
23. Nakagawa K, Okuda S, Miyazawa T. 1997. Dose-dependent incorporation of tea catechins, (-)-epigallocatechin-3-gallate and (-)-epigallocatechin, into human plasma. Biosci Biotech Biochem 61:1981-5.
24. Nakagawa K, Ninomiya M, Okubo T, Aoi N, Juneja LR, Kim M, Yamanaka K, Miyazawa T. 1999. Tea catechin supplementation increases antioxidant capacity and prevents phospholipid hydroperoxidation in plasma of humans. J Agric Food Chem 47:3967-73.
25. Node M, Kodama S, Hamashima Y, Katoh T, Nishida K, Kajimoto T. 2006. Biomimetic synthesis of (±)-galanthamine and asymmetric synthesis of (-)-galanthamine using remote asymmetric induction. Chem Pharm Bull 54: 1662-79.
26. Rehberg CE. 1955. Allyl lactate. Org Synth 3:46-8.
27. Sang S, Lambert JD, Ho CT, Yang CS. 2011. The chemistry and biotransformation of tea constituents. Pharmacol Res 64:87-99.
28. Sugihara N, Tsutsui Y, Tagashira T, Choshi T, Hibino S, Kamishikiryou J, Furuno K. 2011. The ability of gallate and pyrogallol moieties of catechins to inhibit P-glycoprotein function. J Functional Food 3:298-304.
29. Tatsumura K, Kokuni I, Ise M, Sugiyama K, Yamamoto M. 2002. Health science of tea new possibility for physiological function. Japan: Scientific Societies Press. p 52-64. [ISBN-4-7622-2991-1].
30. Vaidyanathan JB, Walle T. 2001.Transport and metabolism of the tea flavonoid (-)-epicatechin by the human intestinal cell line Caco-2. Pharm Res 18:1420-5.
31. Vaidyanathan JB, Walle T. 2002 Glucuronidation and sulfation of the tea flavonoid (-)-epicatechin by the human and rat enzymes. Drug Metab Dispos 30:897-903.
32. Vaidyanathan JB, Walle T. 2003. Cellular uptake and efflux of the tea flavonoid (-)-epikatechin-3-gallate in the human intestinal cell line Caco-2. J Pharmacol Exp Ther 307: 745-52.
33. Wang EJ, Barecki-Roach M, Johnson WW. 2002. Elevation of P-glycoprotein function by a catechin in green tea. Biochem Biophys Res Commun 297:412-8.
34. Watanabe I, Kuriyama S, Kakizaki M, Sone T, Ohmori-Matsuda K, Nakaya N, Hozawa A, Tsuji I. 2009. Green tea and death from pneumonia in Japan: the Ohsaki cohort study. Am J Clin Nutr 90:672-9.
35. Young JF, Dragsted LO, Haraldsdottir J, Daneshvar B, Kall MA, Loft S, Nilsson L, Nielsen SE, Mayer B, Skibsted LH, Huynh-Ba T, Hermetter A, Sandstrom B. 2002. Green tea extract only affects markers of oxidative status postprandially: lasting antioxidant effect of flavonoid-free diet. Br J Nutr 87:343-55.
36. Zhang S, Yang X, Morris ME. 2004a. Flavonoids are inhibitors of breast cancer resistance protein(ABCG2)-mediated transport. Am Soc Pharmacol Exp Therapeut 65:1208-16.
37. Zhang L, Zheng Y, Chow MSS, Zuo Z. 2004b. Investigation of intestinal absorption and disposition of green tea catechins by Caco-2 monolayer model. Int J Pharmaceut 287:1-12.
38. Zhang L, Chow MS, Zuo Z. 2006. Effect of the co-occurring components from green tea on the intestinal absorption and disposition of green tea polyphenols in Caco-2 monolayer model. J Pharm Pharmacol 58:37-44.