Molecular mechanisms of chemopreventive effects of selected dietary and medicinal phenolic substances

Young-Joon Surh1
1Laboratory of Biochemistry and Molecular Toxicology, College of Pharmacy, Seoul National University, Shinlim-dong, Kwanak-gu, Seoul 151-742, South Korea

Tài liệu tham khảo

Morse, 1993, Cancer chemoprevention: principles and prospects, Carcinogenesis, 14, 1737, 10.1093/carcin/14.9.1737 Kelloff, 1996, Strategies for identification and clinical evaluation of promising chemopreventive agents, Oncology, 10, 1471 Mettlin, 1997, Chemoprevention: will it work?, Int. J. Cancer, Suppl., 10, 18, 10.1002/(SICI)1097-0215(1997)10+<18::AID-IJC6>3.0.CO;2-C Sporn, 1984, Role of retinoids in differentiation and carcinogenesis, J. Natl. Cancer Inst., 73, 1381 Wattenberg, 1985, Chemoprevention of cancer, Cancer Res., 45, 1 De Flora, 1998, Mechanisms of inhibitors of mutagenesis and carcinogenesis, Mutat. Res., 402, 151, 10.1016/S0027-5107(97)00292-3 Ferguson, 1994, Antimutagens as cancer chemopreventive agents in the diet, Mutat. Res., 307, 395, 10.1016/0027-5107(94)90313-1 Johnson, 1994, Anticarcinogenic factors in plant foods: a new class of nutrients?, Nutr. Res., 7, 175, 10.1079/NRR19940011 Muto, 1990, Present status of research on cancer chemoprevention in Japan, Jpn. J. Oncol., 20, 219 1994, The effect of vitamin E and beta-carotene on the incidence of lung cancer and other cancers in male smokers, N. Engl. J. Med., 330, 1029, 10.1056/NEJM199404143301501 Edes, 1993, Beta-carotene and mammary carcinogenesis, J. Am. Coll. Nutr., 8, 426 Chen, 1993, Differential effects of dietary β-carotene on papilloma and carcinoma formation induced by an initiation–promotion protocol in SENCAR mouse skin, Carcinogenesis, 14, 713, 10.1093/carcin/14.4.713 Yang, 1994, Cytochrome P450 enzymes as targets for chemoprevention against chemical carcinogenesis: opportunities and limitations, Cancer Res., 54, 1982s Paolini, 1995, On cancer chemoprevention: complications and limitations of some proposed strategies, Carcinogenesis, 16, 971, 10.1093/carcin/16.4.971 Paolini, 1992, Healthy broccoli?, Nature, 357, 448, 10.1038/357448a0 G.J. Kelloff, C.W. Boone, V.E. Steele, J.R. Fay, C.C. Sigman, Inhibition of chemical carcinogenesis, in: J.C. Arcos (Ed.), Chemical Induction of Cancer, Birkäuser, Basel, 1995, pp. 401–410. Lotan, 1995, Retinoids and apoptosis: implications for cancer chemoprevention and therapy, J. Natl. Cancer Inst., 87, 1655, 10.1093/jnci/87.22.1655 Holzman, 1996, Apoptosis provides new targets for chemotherapy, J. Natl. Cancer Inst., 88, 1098, 10.1093/jnci/88.16.1098 Fesüs, 1995, Probing the molecular program of apoptosis by cancer chemopreventive agents, J. Cell. Biochem., Suppl., 22, 151, 10.1002/jcb.240590820 Müller, 1997, Effect of concentration on the cytotoxic mechanism of doxorubicin—apoptosis and oxidative DNA damage, Biochem. Biophys. Res. Commun., 230, 254, 10.1006/bbrc.1996.5898 Yu, 1997, RRR-α-Tocopheryl succinate inhibits EL4 thymic lymphoma cell growth by inducing apoptosis and DNA synthesis arrest, Nutr. Cancer, 27, 92, 10.1080/01635589709514508 Delia, 1995, Regulation of apoptosis induced by the retinoid N-(4-hydroxyphenyl)retinamide and effect of deregulated bcl-2, Blood, 85, 359, 10.1182/blood.V85.2.359.359 Amato, 1998, Transient stimulation of the c-Jun-NH2-terminal kinase/activator protein 1 pathway and inhibition of extracellular signal-regulated kinase are early effects in paclitaxel-mediated apoptosis in human B lymphoblasts, Cancer Res., 58, 241 Yu, 1998, Chemopreventive isothiocyanates induce apoptosis and caspase-3-like protease activity, Cancer Res., 58, 402 Sundaram, 1996, Diallyl disulfide induces apoptosis of human colon tumor cells, Carcinogenesis, 17, 669, 10.1093/carcin/17.4.669 Rigas, 1993, Altered eicosanoid levels in human colon cancer, J. Lab. Clin. Med., 122, 518 Levy, 1997, Prostaglandin H synthases, nonsteroidal anti-inflammatory drugs, and colon cancer, FASEB J., 11, 234, 10.1096/fasebj.11.4.9068612 Dubois, 1995, Nonsteroidal anti-inflammatory drug use and sporadic colorectal adenomas, Gastroenterology, 108, 1310, 10.1016/0016-5085(95)90235-X Giardiello, 1993, Treatment of colorectal adenomas with sulindac in familial adenomatous polyposis, N. Engl. J. Med., 328, 1313, 10.1056/NEJM199305063281805 Bellosillo, 1998, Aspirin and salicylate induce apoptosis and activation of caspases in B cell chronic lymphotropic leukemia cells, Blood, 92, 1406, 10.1182/blood.V92.4.1406 Piazza, 1995, Antineoplastic drugs sulindac sulfide and sulfone inhibit cell growth by inducing apoptosis, Cancer Res., 55, 3110 Samaha, 1997, Modulation of apoptosis by sulindac, curcumin, phenethyl-3-methylcaffeate, and 6-phenylhexyl isothiocyanate: apoptosis index as a biomarker in colon cancer chemoprevention and promotion, Cancer Res., 57, 1301 Lee, 1998, Suppression of mouse skin tumor promotion and induction of apoptosis in HL-60 cells by Alpinia oxyphylla Miquel (Zingiberaceae), Carcinogenesis, 19, 1377, 10.1093/carcin/19.8.1377 Kuo, 1996, Curcumin, an antioxidant and anti-tumor promoter, induces apoptosis in human leukemia cells, Biochim. Biophys. Acta, 1317, 95, 10.1016/S0925-4439(96)00032-4 Jiang, 1996, Curcumin induces apoptosis in immortalized NIH3T3 and malignant cancer cell lines, Nutr. Cancer, 26, 111, 10.1080/01635589609514468 Lee, 1998, Induction of apoptosis in HL-60 cells by pungent vanilloids, [6]-gingerol and [6]-paradol, Cancer Lett., 134, 163, 10.1016/S0304-3835(98)00253-5 Surh, 1995, Capsaicin, a double-edged sword: toxicity, metabolism, and chemopreventive potential, Life Sci., 56, 1845, 10.1016/0024-3205(95)00159-4 Surh, 1996, Capsaicin in hot chili pepper: carcinogen, co-carcinogen or anticarcinogen?, Food Chem. Toxicol., 34, 313, 10.1016/0278-6915(95)00108-5 Miller, 1983, Interactions of capsaicinoids with drug-metabolizing systems, Biochem. Pharmacol., 32, 547, 10.1016/0006-2952(83)90537-3 Surh, 1995, Metabolism of capsaicinoids: evidence for aliphatic hydroxylation and its pharmacological implications, Life Sci., 56, PL305, 10.1016/0024-3205(95)00091-7 Hamid, 1995, Interaction of capsaicin with mixed function oxidases: ex vivo and in vivo studies, J. Drug Res. Egypt, 16, 29 Modly, 1986, Capsaicin as an in vitro inhibitor of benzo[a]pyrene metabolism and its DNA binding in human and murine keratinocytes, Drug Metab. Dispos., 14, 413 Jang, 1989, Inhibitory effect of capsaicin on mouse lung tumor development, In Vivo, 33, 49 Teel, 1991, Effects of capsaicin on rat liver S9-mediated metabolism and DNA binding of aflatoxin B1, Nutr. Cancer, 15, 27, 10.1080/01635589109514108 Miller, 1993, Effects of capsaicin on liver microsomal metabolism of the tobacco-specific nitrosamine NNK, Cancer Lett., 75, 45, 10.1016/0304-3835(93)90206-O Teel, 1993, Effect of phytochemicals on the mutagenicity of the tobacco-specific nitrosamine 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) in Salmonella typhimurium strain TA1535, Phytother. Res., 7, 248, 10.1002/ptr.2650070308 Zhang, 1993, Inhibition of liver microsomal cytochrome P450 activity and metabolism of the tobacco-specific nitrosamine NNK by capsaicin and ellagic acid, Anticancer Res., 13, 2341 Gannett, 1990, The mechanism of inhibition of cytochrome P450 IIE1 by dihydrocapsaicin, Bioorg. Chem., 18, 185, 10.1016/0045-2068(90)90041-3 Surh, 1995, Chemoprotective effects of capsaicin and diallyl sulfide against mutagenesis or tumorigenesis by vinyl carbamate and N-nitrosodimethylamine, Carcinogenesis, 16, 2467, 10.1093/carcin/16.10.2467 De, 1992, Studies on capsaicin inhibition of chemically-induced lipid peroxidation in the lung and liver tissues of rat, Phytother. Res., 6, 34, 10.1002/ptr.2650060109 De, 1989, Capsaicin pretreatment protects free radical induced rat lung damage on exposure to gaseous chemical lung irritants, Phytother. Res., 3, 159, 10.1002/ptr.2650030411 De, 1995, Inhibition by capsaicin against cyclophosphamide-induced clastogenicity and DNA damage in mice, Mutat. Res., 335, 253, 10.1016/0165-1161(95)00028-3 Gabor, 1992, Development and inhibition of mouse ear edema induced with capsaicin, Agents and Actions, 36, 83, 10.1007/BF01991233 Inoue, 1995, Involvement of substance P as a mediator in capsaicin-induced mouse ear edema, Inflammation Res., 44, 470, 10.1007/BF01837912 Pulla Reddy, 1994, Studies on anti-inflammatory activity of spice principles and dietary n-3 polyunsaturated fatty acids on carrageenan-induced inflammation in rats, Ann. Nutr. Metab., 38, 349, 10.1159/000177833 Wang, 1984, Antiplatelet effect of capsaicin, Thromb. Res., 36, 497, 10.1016/0049-3848(84)90189-0 Wang, 1985, Antihemostatic and antithrombotic effects of capsaicin in comparison with aspirin and indomethacin, Thromb. Res., 37, 669, 10.1016/0049-3848(85)90196-3 Sylvester, 1989, Effects of capsaicinoids on platelet aggregations, Proc. West. Pharmacol. Soc., 32, 95 H.O.J. Collier, W.J. McDonald-Gibson, S.A. Saeed, Stimulation of prostaglandin biosynthesis by capsaicin, ethanol, and tyramine, Lancet (1975) 702. Wang, 1984, Antiplatelet effect of capsaicin, Thromb. Res., 36, 497, 10.1016/0049-3848(84)90189-0 Clementi, 1994, Effects of CGRP in different models of mouse ear inflammation, Life Sci., 54, PL119, 10.1016/0024-3205(94)90011-6 Park, 1998, Lack of tumor promoting activity of capsaicin, a principal pungent ingredient of red pepper, in mouse skin carcinogenesis, Anticancer Res., 18, 4201 Morre, 1995, Capsaicin inhibits preferentially the NADH oxidase and growth of transformed cells in culture, Proc. Natl. Acad. Sci. U.S.A., 92, 1831, 10.1073/pnas.92.6.1831 Morre, 1996, Capsaicin inhibits plasma membrane NADH oxidase and growth of human and mouse melanoma lines, Eur. J. Cancer, 32A, 1995, 10.1016/0959-8049(96)00234-1 Wolvetang, 1996, Apoptosis induced by inhibitors of the plasma membrane NADH-oxidase involves Bcl-2 and calcineurin, Cell Growth Differ., 7, 1315 Kim, 1997, Capsaicin can alter the expression of tumor forming-related genes which might be followed by induction of apoptosis of a Korean stomach cancer cell line, SNU-1, Cancer Lett., 120, 235, 10.1016/S0304-3835(97)00321-2 Sen, 1996, Antioxidant and redox regulation of gene transcription, FASEB J., 10, 709, 10.1096/fasebj.10.7.8635688 Leonardo, 1989, NF-κB: a pleiotropic mediator of inducible and tissue-specific gene control, Cell, 58, 227, 10.1016/0092-8674(89)90833-7 Schreck, 1992, Nuclear factor κB: an oxidative stress-responsive transcription factor of eukaryotic cells, Free Radical Res. Commun, 17, 221, 10.3109/10715769209079515 Handel, 1997, Transcription factors AP-1 and NF-κB: where steroids meet the gold standard of anti-rheumatic drugs, Inflammation Res., 46, 282, 10.1007/s000110050188 Chabot-Fletcher, 1997, A role for transcription factor NF-κB in inflammation, Inflammation Res., 46, 1 Schreck, 1991, Reactive oxygen intermediates as apparently widely used messengers in the activation of the NF-κB transcription factor and HIV-1, EMBO J., 10, 2247, 10.1002/j.1460-2075.1991.tb07761.x Kaul, 1998, Transmembrane redox signaling activates NF-κB in macrophages, Free Radical Biol. Med., 24, 202, 10.1016/S0891-5849(97)00209-8 Singh, 1996, Capsaicin (8-methyl-N-vanillyl-6-nonenamide) is a potent inhibitor of nuclear transcription factor-κB activation by diverse agents, J. Immunol., 157, 4412, 10.4049/jimmunol.157.10.4412 Xia, 1995, Opposing effects of ERK and JNK-p38 MAP kinases on apoptosis, Science, 270, 1326, 10.1126/science.270.5240.1326 Macho, 1998, Induction of apoptosis by vanilloid compounds does not require de novo gene transcription and activator protein 1 activity, Cell Growth Differ., 9, 277 Mustafa, 1993, Drug development report (9): pharmacology of ginger, Zingiber officinale, J. Drug Dev., 6, 25 Mascolo, 1989, Ethnopharmacologic investigation of ginger (Zingiber officinale), J. Ethnopharmacol., 27, 129, 10.1016/0378-8741(89)90085-8 Aeschbach, 1994, Antioxidant actions of thymol, carbacrol, 6-gingerol, zingerone and hydroxytyrosol, Food Chem. Toxicol., 32, 31, 10.1016/0278-6915(84)90033-4 Kikuzaki, 1993, Antioxidant effects of some ginger constituents, J. Food Sci., 58, 1407, 10.1111/j.1365-2621.1993.tb06194.x H. Kikuzaki, Y. Kawasaki, N. Nakatani, Structure of antioxidative compounds in ginger, in: C.-T. Ho, T. Osawa, M.-T. Huang, R.T. Rosen (Eds.), Food Phytochemicals for Cancer Prevention II, American Chemical Society, Washington, DC, 1994, pp. 237–243. Chang, 1994, Inhibitory effects of phenolics on xanthine oxidase, Anticancer Res., 14, 501 Guh, 1995, Antiplatelet effect of gingerol isolated from Zingiber officinale, J. Pharm. Pharmacol., 47, 329, 10.1111/j.2042-7158.1995.tb05804.x S. Kawakishi, Y. Morimitsu, T. Osawa, Chemistry of ginger components and inhibitory factors of the arachidonic acid cascade, in: C.-T. Ho, T. Osawa, M.-T. Huang, R. Rosen (Eds.), Food Phytochemicals for Cancer Prevention II, American Chemical Society, Washington, DC, 1994, pp. 244–250. Flynn, 1986, Inhibition of 5-hydroxy-eicosatetraenoic acid (5-HETE) formation in intact human neutrophils by naturally occurring diarylheptanoids: inhibitory activities of curcuminoids and yakuchinones, Prostaglandins, Leukotrienes and Medicine, 22, 357, 10.1016/0262-1746(86)90146-0 Kiuchi, 1982, Inhibitors of prostaglandin biosynthesis from Alpinia officinarum, Chem. Pharm. Bull., 30, 2279, 10.1248/cpb.30.2279 Kiuchi, 1992, Inhibition of prostaglandin and leukotriene biosynthesis by gingerols and diarylheptanoids, Chem. Pharm. Bull., 40, 387, 10.1248/cpb.40.387 Park, 1998, Inhibitory effects of [6]-gingerol, a major pungent principle of ginger, on phorbol ester-induced inflammation, epidermal ornithine decarboxylase activity and skin tumor promotion in ICR mice, Cancer Lett., 129, 139, 10.1016/S0304-3835(98)00081-0 Katiyar, 1996, Inhibition of tumor promotion in SENKAR mouse skin by ethanol extract of Zingiber officinale rhizome, Cancer Res., 56, 1023 Yoshimi, 1992, Modifying effects of fungal and herb metabolites on azoxymethane-induced intestinal carcinogenesis in rats, Jpn. J. Cancer Res., 83, 1273, 10.1111/j.1349-7006.1992.tb02758.x Suzuki, 1997, Keishi-ka-kai-to, a traditional Chinese herbal medicine, inhibits pulmonary metastasis of B16 melanoma, Anticancer Res., 17, 873 Surh, 1999, Anti-tumor promoting activities of selected pungent phenolic substances present in ginger, J. Environ. Toxicol. Pathol. Oncol., 18, 131 Ammon, 1991, Pharmacology of Curcuma longa, Planta Med., 57, 1, 10.1055/s-2006-960004 Srimal, 1973, Pharmacology of diferuloyl methane (curcumin), a non-steroidal anti-inflammatory agent, J. Pharm. Pharmacol., 25, 447, 10.1111/j.2042-7158.1973.tb09131.x Sharma, 1976, Antioxidative activity of curcumin and related compounds, Biochem. Pharmacol., 25, 1811, 10.1016/0006-2952(76)90421-4 Rao, 1982, Anti-inflammatory activity of curcumin analogs, Indian J. Med. Sci., 75, 574 Mukhopadhyay, 1982, Anti-inflammatory and irritant activities of curcumin analogues in rats, Agents and Actions, 12, 508, 10.1007/BF01965935 Toda, 1985, Natural antioxidants: III. Antioxidative components isolated from rhizome of Curcuma longa L., Chem. Pharm. Bull., 33, 1725, 10.1248/cpb.33.1725 Srivastava, 1985, Modification of certain inflammation-induced biochemical changes by curcumin, Indian J. Med. Res., 81, 215 Subramanian, 1994, Diminution of singlet oxygen-induced DNA damage by curcumin and related antioxidants, Mutat. Res., 311, 249, 10.1016/0027-5107(94)90183-X Lin, 1994, Inhibitory effect of curcumin on xanthine dehydrogenase/oxidase induced by phorbol-12-myristate-13-acetate in NIH3T3 cells, Carcinogenesis, 15, 1717, 10.1093/carcin/15.8.1717 Sugiyama, 1996, Involvement of the β-diketone moiety in the antioxidative mechanism of tetrahydrocurcumin, Biochem. Pharmacol., 52, 519, 10.1016/0006-2952(96)00302-4 Nagabhusan, 1987, In vitro antimutagenicity of curcumin against environmental mutagens, Food Chem. Toxicol., 25, 545, 10.1016/0278-6915(87)90207-9 Abraham, 1993, Protective effects of chlorogenic acid, curcumin and β-carotene against γ-radiation-induced in vivo chromosome damage, Mutat. Res., 303, 109, 10.1016/0165-7992(93)90022-N Lahiri, 1993, Effect of four plant phenols, β-carotene and α-tocopherol on benzo[a]pyrene-induced DNA damage in the mouse forestomach mucosa (target organ) and bone marrow polychromatic erythrocytes (non-target organ), Mutat. Res., 303, 97, 10.1016/0165-7992(93)90101-Z Mukundan, 1993, Effect of turmeric and curcumin on BP–DNA adducts, Carcinogenesis, 14, 493, 10.1093/carcin/14.3.493 Lahiri, 1993, Effect of four plant phenols, β-carotene and α-tocopherol on (3H)benzopyrene–DNA interaction in vitro in the presence of rat and mouse liver postmitochondrial fraction, Cancer Lett., 73, 35, 10.1016/0304-3835(93)90185-C Deshpande, 1995, Effects of curcumin on the formation of benzo[a]pyrene derived DNA adducts in vitro, Cancer Lett., 96, 71, 10.1016/0304-3835(95)03903-A Kiso, 1983, Antihepatotoxic principles of curcumin longa rhizomes, Planta Med., 49, 185, 10.1055/s-2007-969845 Soni, 1992, Reversal of aflatoxin induced liver damage by turmeric and curcumin, Cancer Lett., 66, 115, 10.1016/0304-3835(92)90223-I Soudamini, 1989, Inhibition of chemical carcinogenesis by curcumin, J. Ethnopharmacol., 27, 227, 10.1016/0378-8741(89)90094-9 Nagabhushan, 1992, Curcumin as an inhibitor of cancer, J. Am. Coll. Nutr., 11, 192, 10.1080/07315724.1992.12098244 Conney, 1997, Some perspectives on dietary inhibition of carcinogenesis; studies with curcumin and tea, Proc. Soc. Exp. Biol. Med., 216, 234, 10.3181/00379727-216-44173 Huang, 1988, Inhibitory effect of curcumin, chlorogenic acid, caffeic acid, and ferulic acid on tumor promotion in mouse skin by 12-O-tetradecanoylphorbol-13-acetate, Cancer Res., 48, 5941 Lu, 1993, Inhibitory effects of topical application of low doses of curcumin on 12-O-tetradecanoylphorbol-13-acetate-induced increase in ornithine decarboxylase mRNA in mouse epidermis, Carcinogenesis, 14, 293, 10.1093/carcin/14.2.293 Huang, 1997, Inhibitory effects of topical application of low doses of curcumin on 12-O-tetradecanoylphorbol-13-acetate-induced tumor promotion and oxidized DNA bases in mouse epidermis, Carcinogenesis, 18, 83, 10.1093/carcin/18.1.83 Huang, 1991, Inhibitory effects of curcumin on in vitro lipoxygenase and cyclooxygenase activities in mouse epidermis, Cancer Res., 51, 813 Rao, 1995, Chemoprevention of colon carcinogenesis by dietary curcumin, a naturally occurring plant phenolic compound, Cancer Res., 55, 259 Shih, 1993, Inhibition of 8-hydroxyguanosine formation by curcumin in mouse fibroblast cells, Carcinogenesis, 14, 709, 10.1093/carcin/14.4.709 Joe, 1994, Role of capsaicin, curcumin and dietary n-3 fatty acids in lowering the generation of reactive oxygen species in rat peritoneal macrophages, Biochim. Biophys. Acta, 1224, 255, 10.1016/0167-4889(94)90198-8 Ruby, 1995, Anti-tumor and antioxidant activity of natural curcuminoids, Cancer Lett., 94, 79, 10.1016/0304-3835(95)03827-J Brouet, 1995, Curcumin, an anti-tumor promoter and anti-inflammatory agent, inhibits induction of nitric oxide synthase in activated macrophages, Biochem. Biophys. Res. Commun., 206, 533, 10.1006/bbrc.1995.1076 Chan, 1995, Effects of three dietary phytochemicals from tea, rosemary and turmeric on inflammation-induced nitrite production, Cancer Lett., 96, 23, 10.1016/0304-3835(95)03913-H Chan, 1998, In vivo inhibition of nitric oxide synthase gene expression by curcumin, a cancer preventive natural product with anti-inflammatory properties, Biochem. Pharmacol., 55, 1955, 10.1016/S0006-2952(98)00114-2 Liu, 1993, Inhibitory effects of curcumin on protein kinase C activity induced by 12-O-tetradecanoylphorbol-13-acetate in NIH3T3 cells, Carcinogenesis, 14, 857, 10.1093/carcin/14.5.857 Kakar, 1994, Curcumin inhibits TPA induced expression of c-fos, c-jun and c-myc proto-oncogenes messenger RNAs in mouse skin, Cancer Lett., 87, 85, 10.1016/0304-3835(94)90413-8 Korutla, 1994, Inhibitory effect of curcumin on epidermal growth factor receptor kinase activity in A431 cells, Biochim. Biophys. Acta, 1224, 597, 10.1016/0167-4889(94)90299-2 Korutla, 1995, Inhibition of ligand-induced activation of epidermal growth factor receptor tyrosine phosphorylation by curcumin, Carcinogenesis, 16, 1741, 10.1093/carcin/16.8.1741 Reddy, 1994, Curcumin is a non-competitive and selective inhibitor of phosphorylase kinase, FEBS Lett., 341, 19, 10.1016/0014-5793(94)80232-7 Bierhaus, 1997, The dietary pigment curcumin reduces endothelial tissue factor gene expression by inhibiting binding of AP-1 to the DNA and activation of NF-κB, Thrombosis and Haemostasis, 77, 772, 10.1055/s-0038-1656049 Huang, 1991, Suppression of c-Jun/AP-1 activation by an inhibitor of tumor promotion in mouse fibroblast cells, Proc. Natl. Acad. Sci. U.S.A., 88, 5292, 10.1073/pnas.88.12.5292 Chan, 1995, Inhibition of tumor necrosis factor by curcumin, a phytochemical, Biochem. Pharmacol., 49, 1551, 10.1016/0006-2952(95)00171-U Singh, 1995, Activation of transcription factor NF-κB is suppressed by curcumin, J. Biol. Chem., 270, 24995, 10.1074/jbc.270.42.24995 Hanif, 1997, Curcumin, a natural plant phenolic food additive, inhibits cell proliferation and induces cell cycle changes in colon adenocarcinoma cell lines by a prostaglandin-independent pathway, J. Lab. Clin. Med., 130, 576, 10.1016/S0022-2143(97)90107-4 Mehta, 1997, Antiproliferative effect of curcumin (diferuloylmethane) against human breast tumor cell lines, Anti-Cancer Drugs, 8, 470, 10.1097/00001813-199706000-00010 Chen, 1997, Inhibition of farnesyl protein transferase by monoterpene, curcumin derivatives and gallotannin, Anticancer Res., 17, 2555 Ciolino, 1998, Effects of curcumin on the arylhydrocarbon receptor and cytochrome P450 1A1 in MCF-7 human breast carcinoma cells, Biochem. Pharmacol., 56, 197, 10.1016/S0006-2952(98)00143-9 Lin, 1998, Curcumin inhibits SK-Hep-1 hepatocellular carcinoma cell division in vitro and suppresses matrix metalloproteinase-9 secretion, Oncology, 55, 349, 10.1159/000011876 Kang, 1998, Induction of apoptosis in HL-60 cells and inhibition of mouse skin tumor promotion by diarylheptanoids from Alpinia oxyphylla Miquel (Zingiberaceae), Proc. Am. Assoc. Cancer Res., 39, 641 Chun, 1999, Inhibition of mouse skin tumor promotion and suppression of phorbol ester-induced NF-κB and AP-1 activation by diarylheptanoids derived from Alpinia oxyphylla Miquel, Proc. Am. Assoc. Cancer Res., 40, 363 Claeson, 1996, Non-phenolic linear diarylheptanoids from Curcuma xanthorrhiza: a novel type of topical anti-inflammatory agents: structure–activity relationship, Planta Med., 62, 236, 10.1055/s-2006-957867 Doug, 1998, A new antiplatelet diarylheptanoid from Alpinia blepharocalyx, J. Nat. Prod., 61, 142, 10.1021/np970293i Prasain, 1998, Inhibitory effect of diarylheptanoids on nitric oxide production in activated murine macrophages, Biol. Pharm. Bull., 21, 371, 10.1248/bpb.21.371 Syu, 1998, Cytotoxicity of curcuminoids and some novel compounds from Curcuma zedoaria, J. Nat. Prod., 61, 1531, 10.1021/np980269k Roth, 1998, Novel bioactivities of Curcuma longa constituents, J. Nat. Prod., 61, 542, 10.1021/np970459f Pace-Asciak, 1995, The red wine phenolics trans-resveratrol and quercetin block human platelet aggregation and eicosanoid synthesis: implications for protection against coronary heart disease, Clin. Chim. Acta, 235, 207, 10.1016/0009-8981(95)06045-1 Fauconneau, 1997, Comparative study of radical scavenger and antioxidant properties of phenolic compounds from Vitis vinifera cell cultures using in vitro tests, Life Sci., 61, 2103, 10.1016/S0024-3205(97)00883-7 Kimura, 1995, Effects of stilbenes isolated from medicinal plants on arachidonate metabolism and degranulation in human polymorphonuclear leukocytes, J. Ethnopharmacol., 45, 131, 10.1016/0378-8741(94)01206-F Jang, 1997, Cancer chemopreventive activity of resveratrol, a natural product derived from grapes, Science, 275, 218, 10.1126/science.275.5297.218 Teel, 1998, Modulation by phytochemicals of cytochrome P450-linked enzyme activity, Cancer Lett., 133, 135, 10.1016/S0304-3835(98)00218-3 Uenobe, 1997, Antimutagenic effect of resveratrol against Trp-P-1, Mutat. Res., 373, 197, 10.1016/S0027-5107(96)00191-1 Chanvitayapongs, 1997, Amelioration of oxidative stress by antioxidants and resveratrol in PC12 cells, NeuroReport, 8, 1499, 10.1097/00001756-199704140-00035 Sun, 1997, Ethanol-induced cell death by lipid peroxidation in PC12 cells, Neurochem. Res., 22, 1187, 10.1023/A:1021968526696 Draczynska-Lusiak, 1998, Oxidized lipoproteins may play a role in neuronal cell death in Alzheimer's disease, Mol. Chem. Neuropathol., 33, 139, 10.1007/BF02870187 Draczynska-Lusiak, 1998, Oxidized lipoproteins activate NF-κB binding activity and apoptosis in PC12 cells, NeuroReport, 9, 527, 10.1097/00001756-199802160-00028 Mgbonyebi, 1998, Antiproliferative effect of synthetic resveratrol on human breast epithelial cells, Int. J. Oncol., 12, 865 Fontecave, 1998, Resveratrol, a remarkable inhibitor of ribonucleotide reductase, FEBS Lett., 421, 277, 10.1016/S0014-5793(97)01572-X Subbaramaiah, 1998, Resveratrol inhibits cyclooxygenase-2 transcription and activity in phorbol ester-treated human mammary epithelial cells, J. Biol. Chem., 273, 21875, 10.1074/jbc.273.34.21875 Jang, 1998, Effects of resveratrol on 12-O-tetradecanoylphorbol-13-acetate-induced oxidative events and gene expression in mouse skin, Cancer Lett., 134, 81, 10.1016/S0304-3835(98)00250-X Surh, 1999, Resveratrol, an antioxidant present in red wine, induces apoptosis in human promyelocytic leukemia (HL-60) cells, Cancer Lett., 136, 1, 10.1016/S0304-3835(99)00039-7 Ragione, 1998, Resveratrol arrests the cell division cycle at S/G2 phase transition, Biochem. Biophys. Res. Commun., 250, 53, 10.1006/bbrc.1998.9263 Clement, 1998, Chemopreventive agent resveratrol, a natural product derived from grapes, triggers CD95 signaling-dependent apoptosis in human tumor cells, Blood, 92, 996, 10.1182/blood.V92.3.996 Gehm, 1997, Resveratrol, a polyphenolic compound found in grapes and wine, is an agonist for the estrogen receptor, Proc. Natl. Acad. Sci. U.S.A., 94, 14138, 10.1073/pnas.94.25.14138 Stahl, 1998, Phytoestrogens act as estrogen agonists in an estrogen-responsive pituitary cell line, Toxicol. Appl. Pharmacol., 152, 41, 10.1006/taap.1998.8500 Fujiki, 1996, Japanese green tea as a cancer preventive in humans, Nutr. Rev., 54, S67, 10.1111/j.1753-4887.1996.tb03821.x Fujiki, 1998, Cancer inhibition by green tea, Mutat. Res., 402, 307, 10.1016/S0027-5107(97)00310-2 Jankun, 1997, Why drinking green tea could prevent cancer, Nature, 387, 561, 10.1038/42381 Yang, 1997, Inhibition of carcinogenesis by tea, Nature, 389, 134, 10.1038/38154 Nakachi, 1998, Influence of drinking green tea on breast cancer malignancy among Japanese patients, Jpn. J. Cancer Res., 89, 254, 10.1111/j.1349-7006.1998.tb00556.x Fujiki, 1992, Anticarcinogenic effects of (−)-epigallocatechin gallate, Prev. Med., 21, 503, 10.1016/0091-7435(92)90057-O Komori, 1993, Anticarcinogenic activity of green tea polyphenols, Jpn. J. Clin. Oncol., 23, 186 Fujiki, 1994, A new tumor promotion pathway and its inhibitors, Cancer Detect. Prev., 18, 1 Ho, 1992, Antioxidative effect of polyphenol extract prepared from various Chinese teas, Prev. Med., 21, 520, 10.1016/0091-7435(92)90059-Q Wei, 1993, Relationship of oxidative events and DNA oxidation in SENCAR mice to in vivo promoting activity of phorbol ester-type tumor promoters, Carcinogenesis, 14, 1195, 10.1093/carcin/14.6.1195 Bhimani, 1993, Inhibition of oxidative stress in HeLa cells by chemopreventive agents, Cancer Res., 53, 4528 Yoshino, 1994, Antioxidative effects of black tea theaflavins and thearubigin on lipid peroxidation of rat liver homogenates induced by tert-butyl hydroperoxide, Biol. Pharm. Bull., 17, 146, 10.1248/bpb.17.146 Miura, 1995, Effects of various natural antioxidants on the Cu2+-mediated oxidative modification of low density lipoprotein, Biol. Pharm. Bull., 18, 1, 10.1248/bpb.18.1 Sano, 1995, Effect of tea (Camellia sinensis L.) on lipid peroxidation in rat liver and kidney: a comparison of green and black tea feeding, Biol. Pharm. Bull., 18, 1006, 10.1248/bpb.18.1006 Hasegawa, 1995, Preventive effects of green tea against liver oxidative DNA damage and hepatotoxicity in rats treated with 2-nitropropane, Food Chem. Toxicol., 33, 961, 10.1016/0278-6915(95)00064-9 Sai-Kato, 1995, Pentachlorophenol-induced oxidative DNA damage in mouse liver and protective effect of antioxidants, Food Chem. Toxicol., 33, 877, 10.1016/0278-6915(95)00056-8 Fiala, 1996, (−)-Epigallocatechin gallate, a polyphenolic tea antioxidant, inhibits peroxynitrite-mediated formation of 8-oxodeoxyguanosine and 3-nitrotyrosine, Experientia, 52, 922, 10.1007/BF01938881 Yoshioka, 1996, Protecting effect of a green tea percolate and its main constituents against gamma ray-induced scission of DNA, Biosci. Biotechnol. Biochem., 60, 117, 10.1271/bbb.60.117 Yoshioka, 1997, Beta-ray-induced scission of DNA in tritiated water and protection by a green tea percolate and (−)-epigallocatechin gallate, Biosci. Biotechnol. Biochem., 61, 1560, 10.1271/bbb.61.1560 Ishikawa, 1997, Effect of tea flavonoid supplementation on the susceptibility of low-density lipoprotein to oxidative modification, Am. J. Clin. Nutr., 66, 261, 10.1093/ajcn/66.2.261 Hasaniya, 1997, Inhibitory activity of green and black tea in a free radical-generating system using 2-amino-3-methylimidazo[4,5-f]-quinoline as substrate, Jpn. J. Cancer Res., 88, 553, 10.1111/j.1349-7006.1997.tb00418.x Aucamp, 1997, Inhibition of xanthine oxidase by catechins from tea (Camellia sinensis), Anticancer Res., 17, 4381 Lin, 1997, (−)-Epigallocatechin-3-gallate blocks the induction of nitric oxide synthase by down-regulating lipopolysaccharide-induced activity of transcription factor nuclear factor-κB, Mol. Pharmacol., 52, 465, 10.1124/mol.52.3.465 Soliman, 1998, In vitro attenuation of nitric oxide production in C6 astrocyte cell culture by various dietary compounds, Proc. Soc. Exp. Biol. Med., 218, 390, 10.3181/00379727-218-44309 Chan, 1997, Inhibition of inducible nitric oxide synthase gene expression and enzyme activity by epigallocatechin gallate, a natural product from green tea, Biochem. Pharmacol., 54, 1281, 10.1016/S0006-2952(97)00504-2 Chan, 1995, Effects of three dietary phytochemicals from tea, rosemary and turmeric on inflammation-induced nitrite production, Cancer Lett., 96, 23, 10.1016/0304-3835(95)03913-H Kuroda, 1999, Antimutagenic and anticarcinogenic activity of tea polyphenols, Mutat. Res., 436, 69, 10.1016/S1383-5742(98)00019-2 Fujita, 1989, Inhibitory effect of (−)-epigallocatechin gallate on carcinogenesis with N-ethyl-N′-nitro-N-nitrosoguanidine in mouse duodenum, Jpn. J. Cancer Res., 80, 503, 10.1111/j.1349-7006.1989.tb01666.x Yamane, 1996, Inhibitory effects and toxicity of green tea polyphenols for gastrointestinal carcinogenesis, Cancer, 77, 1662, 10.1002/(SICI)1097-0142(19960415)77:8<1662::AID-CNCR36>3.0.CO;2-W Yamane, 1995, Inhibition of N-methyl-N′-nitro-N-nitrosoguanidine-induced carcinogenesis by (−)-epigallocatechin gallate in the rat glandular stomach, Cancer Res., 55, 2081 Matsumoto, 1996, Inhibitory effects of tea catechins, black tea extract and oolong tea extract on hepatocarcinogenesis in rat, Jpn. J. Cancer Res., 87, 1034, 10.1111/j.1349-7006.1996.tb03106.x Huang, 1992, Inhibitory effect of topical application of a green tea polyphenol fraction on tumor initiation and promotion in mouse skin, Carcinogenesis, 13, 947, 10.1093/carcin/13.6.947 Katiyar, 1992, (−)-Epigallocatechin-3-gallate in Camellia sinensis leaves from Himalayan region of Sikkim: inhibitory effects against biochemical events and tumor initiation in SENCAR mouse skin, Nutr. Cancer, 18, 73, 10.1080/01635589209514207 Wang, 1992, Inhibitory effect of green tea on the growth of established skin papillomas in mice, Cancer Res., 52, 6657 Katiyar, 1997, Protection against induction of mouse skin papillomas with low and high risk of conversion to malignancy by green tea polyphenols, Carcinogenesis, 18, 497, 10.1093/carcin/18.3.497 Gensler, 1996, Prevention of photocarcinogenesis by topical administration of pure epigallocatechin gallate isolated from green tea, Nutr. Cancer, 26, 325, 10.1080/01635589609514488 Xu, 1992, Inhibition of tobacco-specific nitrosamine-induced lung tumorigenesis in A/J mice by green tea and its major polyphenol as antioxidants, Cancer Res., 52, 3875 Chung, 1993, Inhibition of tobacco-specific nitrosamine-induced lung tumorigenesis by compounds derived from cruciferous vegetables and green tea, Ann. N. Y. Acad. Sci., 686, 186, 10.1111/j.1749-6632.1993.tb39174.x Horikawa, 1994, Moderate inhibition of mutagenicity and carcinogenicity of benzo[a]pyrene, 1,6-dinitropyrene and 3,9-dinitrofluoranthene by Chinese medicinal herbs, Mutagenesis, 9, 523, 10.1093/mutage/9.6.523 Nishida, 1994, Inhibitory effects of (−)-epigallocatechin gallate on spontaneous hepatoma in C3H/HeNCrj mice and human hepatoma-derived PLC/PRF/5 cells, Jpn. J. Cancer Res., 85, 221, 10.1111/j.1349-7006.1994.tb02085.x Komatsu, 1997, Inhibitory action of (−)-epigallocatechin gallate on radiation-induced mouse oncogenic transformation, Cancer Lett., 112, 135, 10.1016/S0304-3835(96)04555-7 Kitano, 1997, Sealing effects of (−)-epigallocatechin gallate on protein kinase C and protein phosphatase 2A, Biophys. Chem., 65, 157, 10.1016/S0301-4622(96)02254-5 Suganuma, 1996, A new process of cancer prevention mediated through inhibition of tumor necrosis factor-α expression, Cancer Res., 56, 3711 Sigler, 1993, Enhancement of gap junctional intercellular communication in tumor promoter-treated cells by components of green tea, Cancer Lett., 69, 15, 10.1016/0304-3835(93)90026-6 Hu, 1995, Inhibition of oncogene expression by green tea and (−)-epigallocatechin gallate in mice, Nutr. Cancer, 24, 203, 10.1080/01635589509514408 Katiyar, 1995, Inhibition of 12-O-tetradecanoylphorbol-13-acetate and other skin-tumor promoter-caused induction of epidermal interleukin-1α mRNA and protein expression in SENCAR mice by green tea polyphenols, J. Invest. Dermatol., 105, 394, 10.1111/1523-1747.ep12321030 Sakagami, 1995, Stimulation by epigallocatechin gallate of interleukin-1 production by human peripheral blood mononuclear cells, Anticancer Res., 15, 971 Lee, 1997, Inhibitory effects of phytopolyphenols on TPA-induced transformation, PKC activation, and c-jun expression in mouse fibroblast cells, Nutr. Cancer, 28, 177, 10.1080/01635589709514572 Dong, 1997, Inhibition of tumor promoter-induced activator protein 1 activation and cell transformation by tea polyphenols, (−)-epigallocatechin gallate, and theaflavins, Cancer Res., 57, 414 Weisburger, 1998, Effect of tea extracts, polyphenols, and epigallocatechin gallate on azoxymethane-induced colon cancer, Proc. Soc. Exp. Biol. Med., 217, 104, 10.3181/00379727-217-44211 Liao, 1995, Growth inhibition and regression of human prostate and breast tumors in athymic mice by tea epigallocatechin gallate, Cancer Lett., 96, 239, 10.1016/0304-3835(95)03948-V Araki, 1995, Chemoprevention of mammary preneoplasia, in vitro effects of a green tea polyphenol, Ann. N. Y. Acad. Sci., 768, 215, 10.1111/j.1749-6632.1995.tb12125.x Katdare, 1997, Prevention of mammary preneoplastic transformation by naturally-occurring tumor inhibitors, Cancer Lett., 111, 141, 10.1016/S0304-3835(96)04523-5 Hirose, 1997, Effects of green tea catechins on the progression or late promotion stage of mammary gland carcinogenesis in female Sprague–Dawley rats pretreated with 7,12-dimethylbenz(a)anthracene, Cancer Lett., 112, 141, 10.1016/S0304-3835(96)04560-0 Lea, 1993, Inhibitory effects of tea extracts and (−)-epigallocatechin gallate on DNA synthesis and proliferation of hepatoma and erythroleukemia cells, Cancer Lett., 68, 231, 10.1016/0304-3835(93)90151-X Valcic, 1996, Inhibitory effect of six green tea catechins and caffeine on the growth of four selected human tumor cell lines, Anti-Cancer Drugs, 7, 461, 10.1097/00001813-199606000-00011 Hibasami, 1996, Induction of programmed cell death (apoptosis) in human lymphoid leukemia cells by catechin compounds, Anticancer Res., 16, 1943 Achiwa, 1997, Inhibitory effects of persimmon (Diospyros kaki) extract and related polyphenol compounds on growth of human lymphoid leukemia cells, Biosci. Biotechnol. Biochem., 61, 1099, 10.1271/bbb.61.1099 Okabe, 1997, Mechanisms of growth inhibition of human lung cancer cell line, PC-9, by tea polyphenols, Jpn. J. Cancer Res., 88, 639, 10.1111/j.1349-7006.1997.tb00431.x Suganuma, 1999, 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, 44 Ahmad, 1997, Green tea constituent epigallocatechin-3-gallate and induction of apoptosis and cell cycle arrest in human carcinoma cells, J. Natl. Cancer Inst., 89, 1881, 10.1093/jnci/89.24.1881 Liang, 1997, Suppression of extracellular signals and cell proliferation through EGF receptor binding by (−)-epigallocatechin gallate in human A431 epidermoid carcinoma cells, J. Cell. Biochem., 67, 55, 10.1002/(SICI)1097-4644(19971001)67:1<55::AID-JCB6>3.0.CO;2-V Kennedy, 1998, Involvement of protein tyrosine phosphorylation in the effect of green tea polyphenols on Ehrlich ascites tumor cells in vitro, Chem.-Biol. Interact., 110, 159, 10.1016/S0009-2797(98)00005-2 Khafif, 1998, Quantitation of chemopreventive synergism between (−)-epigallocatechin-3-gallate and curcumin in normal, premalignant and malignant human oral epithelial cells, Carcinogenesis, 19, 419, 10.1093/carcin/19.3.419 Khafif, 1998, Green tea regulates cell cycle progression in oral leukoplakia, Head and Neck, 20, 528, 10.1002/(SICI)1097-0347(199809)20:6<528::AID-HED7>3.0.CO;2-3 Katdare, 1998, Inhibition of aberrant proliferation and induction of apoptosis in pre-neoplastic human mammary epithelial cells by natural phytochemicals, Oncol. Rep., 5, 311 Hibasami, 1998, Induction of apoptosis in human stomach cancer cells by green tea catechins, Oncol. Rep., 5, 527 Yang, 1998, Inhibition of growth and induction of apoptosis in human cancer cell lines by tea polyphenols, Carcinogenesis, 19, 611, 10.1093/carcin/19.4.611 Paschka, 1998, Induction of apoptosis in prostate cancer cell lines by the green tea component, (−)-epigallocatechin-3-gallate, Cancer Lett., 130, 1, 10.1016/S0304-3835(98)00084-6 Liao, 1995, Selective inhibition of steroid 5 α-reductase isozymes by tea epicatechin-3-gallate and epigallocatechin-3-gallate, Biochem. Biophys. Res. Commun., 214, 833, 10.1006/bbrc.1995.2362 Chen, 1998, Green tea epigallocatechin gallate shows a pronounced growth inhibitory effect on cancerous cells but not on their normal counterparts, Cancer Lett., 129, 173, 10.1016/S0304-3835(98)00108-6 Sazuka, 1997, Inhibition of collagenases from mouse lung carcinoma cells by green tea catechins and black tea theaflavins, Biosci. Biotechnol. Biochem., 61, 1504, 10.1271/bbb.61.1504 Taniguchi, 1992, Effect of (−)-epigallocatechin gallate, the main constituent of green tea, on lung metastasis with mouse B16 melanoma cell lines, Cancer Lett., 65, 51, 10.1016/0304-3835(92)90212-E Isemura, 1993, Effects of catechins on the mouse lung carcinoma cell adhesion to the endothelial cells, Cell Biol. Int., 17, 559, 10.1006/cbir.1993.1099 Naasani, 1998, Telomerase inhibition, telomere shortening, and senescence of cancer cells by tea catechins, Biochem. Biophys. Res. Commun., 249, 391, 10.1006/bbrc.1998.9075