Inhibitory effect(s) of polymeric black tea polyphenol fractions on the formation of [3H]-B(a)P-derived DNA adducts

Journal of Agricultural and Food Chemistry

Volumn 52, Issue 13, 2004, Pages 4261-4269

  Krishnan, Rajesh ^a   Maru, Girish B ^a  

^a TATA MEMORIAL HOSPITAL   (India)

Author keywords

Benzo a pyrene; Cytochrome P450 isozymes; DNA adducts; Epigallocatechin gallate; In vitro; Inhibition; Polymeric black tea polyphenol fractions; Rat liver microsomes

Indexed keywords

BLACK TEA EXTRACT; CYTOCHROME P450; DNA; EPIGALLOCATECHIN GALLATE; POLYPHENOL; PROTEIN;

ANIMAL CELL; ARTICLE; CONTROLLED STUDY; DNA ADDUCT; DOSE RESPONSE; ENZYME ACTIVITY; FLUOROMETRY; INFRARED SPECTROSCOPY; MALE; NONHUMAN; PH; PROTON NUCLEAR MAGNETIC RESONANCE; RAT; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; TEA; THIN LAYER CHROMATOGRAPHY; ULTRAVIOLET SPECTROSCOPY;

ANIMALS; BENZO(A)PYRENE; CAMELLIA SINENSIS; CATECHIN; CYTOCHROME P-450 ENZYME SYSTEM; DNA ADDUCTS; FLAVONOIDS; MALE; MICROSOMES, LIVER; OXAZINES; PHENOLS; PLANT LEAVES; RATS; RATS, SPRAGUE-DAWLEY; TRITIUM;

ANIMALIA; CAMELLIA SINENSIS;

EID: 3042522767     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf049979o     Document Type: Article

References (36)

1. Trevisanato, S.; Kim, Y.-I. Tea and Health. Nutr. Rev. 2000, 58, 1-10.
2. Yang, C.; Wang, Z. Tea and Cancer. J. Natl. Cancer Inst. 1993, 85, 1038-1045.
3. Xu, Y.; Ho, C.-T.; Amin, S.; Han, C.; Chung, F. L. Inhibition of tobacco-specific nitrosamine-induced lung tumorigenesis in A/J mice by green tea and its major polyphenol as antioxidants. Cancer Res. 1992, 52, 3875-3879.
4. Mukhtar, H.; Wang, Z.; Katiyar, S.; Agarwal, R. Tea components: Antimutagenic and anticarcinogenic effects. Prev. Med. 1992, 21, 351-360.
5. Katiyar, S.; Agarwal, R.; Zaim, M.; Mukhtar, H. Protection against N-nitrosodiethylamine and benzo[a]pyrene-induced fore-stomach and lung tumorigenesis in A/J mice by green tea. Carcinogenesis 1993, 14, 849-855.
6. Wang, Z.; Khan, W.; Bickers, D.; Mukhtar, H. Protection against polycyclic aromatic hydrocarbon-induced skin tumor initiation in mice by green tea polyphenols. Carcinogenesis 1989, 10, 411-415.
7. Huang, M.-T.; Ho, C.-T.; Wang, Z.; Ferraro, T.; Finnegan-Olive, T.; Lou, Y.-R.; Mitchell, J.; Laskin, J.; Newmark, H.; Yang, C.; Conney, A. Inhibitory effect of topical application of green tea polyphenol fraction on tumor initiation and promotion in mouse skin. Carcinogenesis 1992, 13, 947-954.
8. Katiyar, S.; Agarwal, R.; Woods, G.; Mukhtar, H. Inhibition of 12-O-tetradecanoylphorbol-13-acetate-caused tumor promotion in 7,12-dimethylbenz[a]anthracene-initiated SENCAR mouse skin by a polyphenolic fraction isolated from green tea. Cancer Res. 1992, 52, 6890-6897.
9. Wang, Z.; Huang, M.-T.; Lou, Y.-R.; Xei, J.; Reuhl, K.; Newmark, H.; Ho, C.-T.; Yang, C.; Conney, A. H. Inhibitory effects of black tea, green tea, decaffeinated black tea and decaffeinated green tea on ultraviolet B light-induced skin carcinogenesis in 7,12-dimethylbenz[a]anthracene-initiated SKH-1 mice. Cancer Res. 1994, 54, 3428-3435.
10. Katiyar, S.; Agarwal, R.; Mukhtar, H. Protection against malignant conversion of chemically induced benign skin papillomas to squamous cell carcinomas in SENCAR mice by a polyphenolic fraction isolated from green tea. Cancer Res. 1993, 53, 5409-5412.
11. Harbowy, M.; Balentine, D. Tea chemistry. Crit. Rev. Plant Sci. 1997, 16, 415-480.
12. Cattell, D.; Nursten, H. Fractionation and chemistry of ethyl acetate-soluble thearubigins from black tea. Phytochemistry 1976, 15, 1967-1970.
13. Robertson, A.; Bendal, D. Production and HPLC analysis of black tea theaflavins and thearubigins. Phytochemistry 1983, 22, 883-887.
14. Degenhardt, A.; Engelhardt, U.; Winterhalter, P.; Ito, Y. Centrifugal precipitation chromatography - a novel chromatographic system for fractionation of polymeric pigments from black tea and red wine. J. Agric. Food Chem. 2001, 49, 1730-1736.
15. Brown, A.; Eyton, W.; Holmes, A.; Ollis, W. Identification of the thearubigins as polymeric proanthocyanidins. Nature 1969, 221, 742-744.
16. Hashimoto, F.; Nonaka, G.; Nishioka, I. Novel chalcan-flavan dimers, Assamicains A, B and C, and a new flavan-3-ol and proanthocyanidins from fresh leaves of Camellia sinensis. Chem. Pharm. Bull 1989, 37, 77-85.
17. Ames, B.; McCann, J.; Yamasaki, E. Methods for detecting carcinogens and mutagens with the Salmonella/mammalian microsome mutagenicity test. Mutat. Res. 1975, 31, 347-364.
18. Lowry, O.; Rosebrough, N.; Farr, A.; Randall, R. Protein measurements with the Folin phenol reagent. J. Biol. Chem. 1951, 193, 265-275.
19. Deshpande, S.; Maru, G. Effects of curcumin on the formation of benzo[a]pyrene derived DNA adducts in vitro. Cancer Lett. 1995, 96, 71-80.
20. Omura, J.; Sato, R. The carbon monoxide binding pigment of liver microsomes. Evidence for its hemoprotein nature. J. Biol. Chem. 1980, 239, 2370-2378.
21. Pohl, R.; Fouts, J. A rapid method for assaying the metabolism of 7-ethoxyresorufin by microsomal subcellular fractions. Anal. Biochem. 1980, 107, 150-155.
22. Burke, M.; Thompson, S.; Elcombe, C.; Halpert, J.; Haaparanta, T.; Mayer, R. Ethoxy-, pentoxy- and benzoxyphenoxazones and homologues: a series of substrates to distinguish between different induced cytochromes P450. Biochem. Pharmacol. 1985, 34, 3337-3345.
23. Harborne, J. Phytochemical Methods-A Guide to Modern Techniques of Plant Analysis; Chapman and Hall: London, U.K., 1973; pp 33-88.
24. Miller, E.; Miller, J. Searches for ultimate chemical carcinogens and their reactions with cellular macromolecules. Cancer 1981, 47, 2327-2345.
25. Thapliyal, R.; Maru, G. Inhibition of cytochrome P450 isozymes by curcumins in vitro and in vivo. Food Chem. Toxicol. 2001, 39, 541-547.
26. Lahiri, M.; Maru, G.; Amonkar, A.; Bhide, S. Modulation of B(a)P induced DNA damage by some chemopreventive agents. In Chemoprevention of Cancer; Omega Scientific Publishers: New Delhi, India, 1991; pp 152-161.
27. Thapliyal, R.; Maru, G. Mechanism(s) of turmeric-mediated protective effects against benzo[a]pyrene-derived DNA adducts. Cancer Lett. 2002, 175, 79-88.
28. Finger, A.; Kuhr, S.; Engelhardt, U. Chromatography of tea constituents. J. Chromatogr. 1992, 624, 293-315.
29. Wang, Z.; Das, M.; Bickers, D.; Mukhtar, H. Interaction of epicatechins derived from green tea with rat hepatic cytochrome P450. Drug Metab. Dispos. 1988, 16, 98-103.
30. Bailley, R.; Nursten, H.; McDowell, I. Isolation and analysis of a polymeric thearubigin fraction from tea. J. Sci. Food Agric. 1992, 59, 365-375.
31. Degenhardt, A.; Engelhardt, U.; Wendt, A.-S.; Winterhalter, P. Isolation of black tea pigments using high-speed countercurrent chromatography and studies on the properties of black tea polymers. J. Agric. Food Chem. 2000, 48, 5200-5205.
32. Graham, H. Tea; the plant and its manufacture; chemistry and consumption of the beverage. In The Methylxanthine Beverages and Foods: Chemistry, Consumption and Health Effects; Spiller, G., Ed.; Liss R. Alan Inc.: New York, 1984; pp 29-74.
33. Guo, Z.; Smith, T.; Wang, E.; Eklind, K.; Chung, F.-L.; Yang, C. S. Structure activity relationships of arylalkyl isothiocyanates for the inhibition of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone metabolism and modulation of xenobiotic-metabolizing enzymes in rats and mice. Carcinogenesis 1993, 14, 1167-1173.
34. Yang, C.; Smith, T.; Hong, J. Cytochrome P450 enzymes as targets for chemoprevention against chemical carcinogenesis and toxicity: opportunities and limitations. Cancer Res. 1994, 54 (Suppl.), 1982s-1986s.
35. Wattenberg, L. Inhibitory effects of benzylisothiocyanates administered shortly before diethylnitrosamine or benzo[a]pyrene on pulmonary and stomach neoplasia in A/J mice. Carcinogenesis 1987, 8, 1971-1973.
36. Morse, M.; Eklind, K.; Amin, S.; Hecht, S.; Chung, F.-L. Effect of alkyl chain length on the initiation of 4-(methylnitrosamino)-1-(3-pyridyl)-1- butanone-induced lung neoplasia in A/J mice. Carcinogenesis 1989, 10, 1757-1759.