Epigenetic mechanisms underlying diet-sourced compounds in the prevention and treatment of gastrointestinal cancer

Anti-Cancer Agents in Medicinal Chemistry

Volumn 12, Issue 10, 2012, Pages 1203-1210

  Knackstedt, Rebecca W ^a   Moseley, Vondina R ^a   Wargovich, Michael J ^b  

^a MEDICAL UNIVERSITY OF SOUTH CAROLINA   (United States)

^b MEDICAL UNIVERSITY OF SOUTH CAROLINA   (United States)

Author keywords

Cancer; Cancer prevention; Colon; Colon cancer; Colon cancer prevention; Diet; Dietary intervention; Disease modification; DNA methyltransferases; Epigenetic dysregulation; Epigenetics; Gene silencing; Histone deacetylase; Inflammation; Natural products

Indexed keywords

5 AZA 2' DEOXYCYTIDINE; ACYLTRANSFERASE; ALLYLMERCAPTAN; AZACITIDINE; CAFFEIC ACID; CHLOROGENIC ACID; DIALLYL DISULFIDE; DNA METHYLTRANSFERASE 1; DNA METHYLTRANSFERASE 3A; DNA METHYLTRANSFERASE 3B; DNA METHYLTRANSFERASE INHIBITOR; EPIGALLOCATE CHINGALLATE; GENISTEIN; HISTONE DEACETYLASE; HISTONE DEACETYLASE 10; HISTONE DEACETYLASE 6; HISTONE DEACETYLASE INHIBITOR; NATURAL PRODUCT; POMIFERIN; SIRTUIN; SULFORAPHANE; UNCLASSIFIED DRUG; VORINOSTAT;

ARTICLE; BONE MARROW SUPPRESSION; COLON CANCER; CUTANEOUS T CELL LYMPHOMA; DIGESTIVE SYSTEM CANCER; DNA METHYLATION; DRUG BIOAVAILABILITY; DRUG MECHANISM; EPIGENETICS; FEVER; GASTROINTESTINAL SYMPTOM; GENE EXPRESSION; HEMATOLOGIC DISEASE; HISTONE MODIFICATION; HUMAN; INFLAMMATION; LUNG DISEASE; LUNG NON SMALL CELL CANCER; MUSCULOSKELETAL DISEASE; MYELODYSPLASTIC SYNDROME; MYELOID LEUKEMIA; NONHUMAN; PHASE 1 CLINICAL TRIAL (TOPIC); PHASE 2 CLINICAL TRIAL (TOPIC); PROTEIN EXPRESSION;

ANIMALS; BIOLOGICAL AGENTS; CLINICAL TRIALS AS TOPIC; DIET; EPIGENESIS, GENETIC; GASTROINTESTINAL NEOPLASMS; GENE-ENVIRONMENT INTERACTION; GENETIC PREDISPOSITION TO DISEASE; HUMANS;

EID: 84870208150     PISSN: 18715206     EISSN: 18755992     Source Type: Journal    
DOI: 10.2174/187152012803833053     Document Type: Article

References (106)

1. Society, A.C. Cancer Facts & Figures 2012. 2012, American Cancer Society: Atlanta.
2. Society, A.C. Colorectal Cancer Facts & Figures 2011-2013. 2011, American Cancer Society.
3. Lynch, H.T.; A. de la Chapelle. Hereditary Colorectal Cancer. New Engl. J. Med., 2003, 348(10), 919-932.
4. Boyle, P.; Langman J.S. ABC of colorectal cancer: Epidemiology. BMJ, 2000, 321(7264), 805-808.
5. Kono, S. Secular trend of colon cancer incidence and mortality in relation to fat and meat intake in Japan. Eur. J. Cancer Prev., 2004, 13(2), 127-132.
6. Newmark, H.L.; Yang, K.; Kurihara, N.; Fan, K.; Augenlicht, L.H.; Lipkin, M. Western-style diet-induced colonic tumors and their modulation by calcium and vitamin D in C57Bl/6 mice: a preclinical model for human sporadic colon cancer. Carcinogenesis, 2009, 30(1), 88-92.
7. Bird, A. DNA methylation patterns and epigenetic memory. Genes Dev., 2002, 16(1), 6-21.
8. Goll, M.G.; Bestor, T.H. Eukaryotic cytosine methyltransferases. Annu. Rev. Biochem., 2005, 74, 481-514.
9. Reik, W.; Dean, W.; Walter, J. Epigenetic reprogramming in mammalian development. Science, 2001, 293(5532), 1089-93.
10. Howard, G.; Eiges, R.; Gaudet, F.; Jaenisch, R.; Eden, A. Activation and transposition of endogenous retroviral elements in hypomethylation induced tumors in mice. Oncogene, 2008, 27(3), 404-408.
11. Gilbert, E.R.; Liu, D. Flavonoids influence epigenetic-modifying enzyme activity: structure - function relationships and the therapeutic potential for cancer. Curr. Med. Chem., 2010, 17(17), 1756-1768.
12. Jiang, Y.H.; Bressler, J.; Beaudet, A.L. Epigenetics and human disease. Annu. Rev. Genomics Hum. Genet., 2004, 5, 479-510.
13. Rhee, I.; Bachman, K.E.; Park, B.H.; Jair, K.W.; Yen, R.W.; Schuebel, K.E.; Cui, H.; Feinberg, A.P.; Lengauer, C.; Kinzler, K.W.; Baylin, S.B.; Vogelstein, B. DNMT1 and DNMT3b cooperate to silence genes in human cancer cells. Nature, 2002, 416(6880), 552-556.
14. Goll, M.G.; Kirpekar, F.; Maggert, K.A.; Yoder, J.A.; Hsieh, C.L.; Zhang, X.; Golic, K.G.; Jacobsen, S.E.; Bestor, T.H.; Methylation of tRNAAsp by the DNA methyltransferase homolog Dnmt2. Science, 2006, 311(5759), 395-398.
15. Ooi, S.K.; Qiu, C.; Bernstein, E.; Li, K.; Jia, D.; Yang, Z.; Erdjument-Bromage, H.; Tempst, P.; Lin, S.P.; Allis, C.D.; Cheng, X.; Bestor, T.H.DNMT3L connects unmethylated lysine 4 of histone H3 to de novo methylation of DNA. Nature, 2007, 448(7154), 714-717.
16. Holz-Schietinger, C.; Reich, N.O. The inherent processivity of the human de novo methyltransferase 3A (DNMT3A) is enhanced by DNMT3L. J. Biol. Chem., 2010, 285(38), 29091-100.
17. Jia, D.; Jurkowska, R.Z.; Zhang, X.; Jeltsch, A.; Cheng, X.Structure of Dnmt3a bound to Dnmt3L suggests a model for de novo DNA methylation. Nature, 2007, 449(7159), 248-251.
18. Denis, H.; Ndlovu, M.N.; Fuks, F. Regulation of mammalian DNA methyltransferases: a route to new mechanisms. E.M.B.O. Rep., 2011, 12(7), 647-656.
19. Antequera, F.; Bird, A. Number of CpG islands and genes in human and mouse. Proc. Natl. Acad. Sci. U. S. A., 1993, 90(24), 11995-11999.
20. Jenuwein, T.; Allis, C.D. Translating the histone code. Science, 2001, 293(5532), 1074-1080.
21. Keppler, B.R.; Archer, T.K. Chromatin-modifying enzymes as therapeutic targets - Part 1. Expert Opin. Ther.Targets, 2008, 12(10), 1301-1312.
22. Sengupta, N.; Seto, E. Regulation of histone deacetylase activities. J. Cell. Biochem., 2004, 93(1), 57-67.
23. Shakespear, M.R.; Halili, M.A.; Irvine, K.M.; Fairlie, D.P.; Sweet, M.J. Histone deacetylases as regulators of inflammation and immunity. Trends Immunol., 2011, 32(7), 335-43.
24. Yang, W.M., Tsai, S.C.; Wen, Y.D.; Fejer, G.; Seto, E. Functional domains of histone deacetylase-3. J. Biol. Chem., 2002, 277(11), 9447-54.
25. Yang, X.J.; Seto, E. The Rpd3/Hda1 family of lysine deacetylases: from bacteria and yeast to mice and men. Nat. Rev. Mol. Cell. Biol., 2008, 9(3), 206-18.
26. Grozinger, C.M.; Hassig, C.A.; Schreiber, S.L. Three proteins define a class of human histone deacetylases related to yeast Hda1p. Proc. Natl. Acad. Sci. U. S. A., 1999, 96(9), 4868-4873.
27. Haberland, M.; Montgomery, R.L.; Olson, E.N. The many roles of histone deacetylases in development and physiology: implications for disease and therapy. Nat. Rev. Genet., 2009, 10(1), 32-42.
28. Chang, S.; McKinsey, T.A.; Zhang, C.L.; Richardson, J.A.; Hill, J.A.; Olson, E.N. Histone deacetylases 5 and 9 govern responsiveness of the heart to a subset of stress signals and play redundant roles in heart development. Mol. Cell. Biol., 2004. 24(19): p. 8467-76.
29. Guardiola, A.R.; Yao, T.P. Molecular cloning and characterization of a novel histone deacetylase HDAC10. J. Biol. Chem., 2002, 277(5), 3350-3356.
30. Frye, R.A. Phylogenetic classification of prokaryotic and eukaryotic Sir2-like proteins. Biochem. Biophys. Res. Commun., 2000. 273(2), 793-798.
31. Robertson, K.D.DNA methylation and human disease. Nat. Rev. Genet., 2005, 6(8), 597-610.
32. Jones, P.A., Baylin, S.B. The fundamental role of epigenetic events in cancer. Nat. Rev. Genet., 2002, 3(6), 415-28.
33. Kanai, Y. Genome-wide DNA methylation profiles in precancerous conditions and cancers. Cancer Sci., 2010, 101(1), 36-45.
34. Issa, J.P.; Ahuja, N.; Toyota, M.; Bronner, M.P.; Brentnall, T.A. Accelerated Age-related CpG Island Methylation in Ulcerative Colitis. Cancer Res., 2001, 61(9), 3573-3577.
35. Foran, E.; Garrity-Park, M.M.; Mureau, C.; Newell, J.; Smyrk, T.C.; Limburg, P.J.; Egan, L.J. Upregulation of DNA methyltransferase-mediated gene silencing, anchorage-independent growth, and migration of colon cancer cells by interleukin-6. Mol. Cancer Res., 2010, 8(4), 471-481.
36. Hodge, D.R.; Cho, E.; Copeland, T.D.; Guszczynski T.; Yang, E.; Seth, A.K.; Farrar W.L. IL-6 enhances the nuclear translocation of DNA cytosine-5-methyltransferase 1 (DNMT1) via phosphorylation of the nuclear localization sequence by the AKT kinase. Cancer Genomics Proteomics, 2007, 4(6), 387-398.
37. Weber, M.; Davies, J.J.; Wittig, D.; Oakeley, E.J.; Haase, M.; Lam, W.L.; Schübeler D. Chromosome-wide and promoter-specific analyses identify sites of differential DNA methylation in normal and transformed human cells. Nat. Genet., 2005, 37(8), 853-862.
38. Keshet, I.; Schlesinger, Y.; Farkash, S.; Rand, E.; Hecht, M.; Segal, E.; Pikarski, E.; Young, R.A.; Niveleau A.; Cedar, H.; Simon, I. Evidence for an instructive mechanism of de novo methylation in cancer cells. Nat. Genet., 2006, 38(2), 149-153.
39. Pilarsky, C.; Wenzig, M.; Specht, T.; Saeger, H.D.; Grützmann, R.Identification and validation of commonly overexpressed genes in solid tumors by comparison of microarray data. Neoplasia, 2004, 6(6), 744-750.
40. Patra, S.K.; Patra, A.; Dahiya, R. Histone deacetylase and DNA methyltransferase in human prostate cancer. Biochem. Biophys. Res. Commun., 2001, 287(3), 705-13.
41. Wilson, A.J.; Byun, D.S.; Popova, N.; Murray, L.B.; L'Italien, K.; Sowa, Y.; Arango, D.; Velcich, A.; Augenlicht, L.H.; Mariadason, J. M. Histone deacetylase 3 (HDAC3) and other class I HDACs regulate colon cell maturation and p21 expression and are deregulated in human colon cancer. J. Biol. Chem., 2006, 281(19), 13548-58.
42. Mariadason, J.M. HDACs and HDAC inhibitors in colon cancer. Epigenetics, 2008, 3(1), 28-37.
43. Ishihama, K.; Yamakawa, M.; Semba, S.; Takeda, H.; Kawata, S.; Kimura, S.; Kimura, W. Expression of HDAC1 and CBP/p300 in human colorectal carcinomas. J. Clin. Pathol., 2007, 60(11), 1205-1210.
44. Zhu, P, Martin, E.; Mengwasser, J.; Schlag, P.; Janssen, K.P.; Göttlicher, M. Induction of HDAC2 expression upon loss of APC in colorectal tumorigenesis. Cancer Cell, 2004, 5(5), 455-63.
45. Glauben, R.; Batra, A.; Stroh, T.; Erben, U.; Fedke, I.; Lehr, H.A.; Leoni, F.; Mascagni, P.; Dinarello, C.A.; Zeitz, M.; Siegmund, B. Histone deacetylases: novel targets for prevention of colitisassociated cancer in mice. Gut, 2008, 57(5): p. 613-22.
46. Decitabine: 2'-deoxy-5-azacytidine, Aza dC, DAC, dezocitidine, NSC 127716. Drugs R. D., 2003, 4(6), 352-8.
47. Blum, W.; Klisovic, R.B.; Hackanson, B.; Liu, Z.; Liu, S.; Devine, H.; Vukosavljevic, T.; Huynh, L.; Lozanski, G.; Kefauver, C.; Plass, C.; Devine, S.M.; Heerema, N.A.; Murgo, A.; Chan, K.K.; Grever, M.R.; Byrd, J.C.; Marcucci G. Phase I study of decitabine alone or in combination with valproic acid in acute myeloid leukemia. J. Clin. Oncol., 2007, 25(25), 3884-91.
48. Kaminskas, E.; Farrell, A.T.; Wang, Y.C.; Sridhara, R.; Pazdur, R. FDA drug approval summary: azacitidine (5-azacytidine, Vidaza) for injectable suspension. Oncologist, 2005, 10(3), 176-82.
49. Daskalakis, M.; Blagitko-Dorfs, N.; Hackanson, B. Decitabine. Recent Results Cancer Res., 2010, 184, 131-57.
50. Duvic, M.; Vu, J. Vorinostat: a new oral histone deacetylase inhibitor approved for cutaneous T-cell lymphoma. Expert Opin. Investig. Drugs, 2007, 16(7), 1111-20.
51. Garcia-Manero, G.; Yang, H.; Bueso-Ramos, C.; Ferrajoli, A.; Cortes, J.; Wierda, W.G.; Faderl, S.; Koller, C.; Morris, G.; Rosner, G.; Loboda, A.; Fantin, V.R.; Randolph, S.S.; Hardwick, J.S.; Reilly, J.F.; Chen, C.; Ricker, J.L.; Secrist, J.P.; Richon, V.M.; Frankel, S.R.; Kantarjian, H.M. Phase 1 study of the histone deacetylase inhibitor vorinostat (suberoylanilide hydroxamic acid [SAHA]) in patients with advanced leukemias and myelodysplastic syndromes. Blood, 2008, 111(3), 1060-1066.
52. Watanabe, T.; Kato, H.; Kobayashi, Y.; Yamasaki, S.; Morita-Hoshi, Y.; Yokoyama, H.; Morishima, Y.; Ricker, J.L.; Otsuki, T.; Miyagi-Maesima, A.; Matsuno, Y.; Tobinai, K. Potential efficacy of the oral histone deacetylase inhibitor vorinostat in a phase I trial in follicular and mantle cell lymphoma. Cancer Sci., 2010, 101(1), 196-200.
53. Galanis, E.; Jaeckle, K.A.; Maurer, M.J.; Reid, J.M.; Ames, M.M.; Hardwick, J.S.; Reilly, J.F.; Loboda, A.; Nebozhyn, M.; Fantin, V.R.; Richon, V.M.; Scheithauer, B.; Giannini, C.; Flynn, P.J.; Moore, D.F.Jr.; Zwiebel, J.; Buckner, J.C. Phase II trial of vorinostat in recurrent glioblastoma multiforme: a north central cancer treatment group study. J. Clin. Oncol., 2009, 27(12), 2052-2058.
54. Ree, A.H.; Dueland, S.; Folkvord, S.; Hole, K.H.; Seierstad, T.; Johansen, M.; Abrahamsen, T.W.; Flatmark, K. Vorinostat, a histone deacetylase inhibitor, combined with pelvic palliative radiotherapy for gastrointestinal carcinoma: the Pelvic Radiation and Vorinostat (PRAVO) phase 1 study. Lancet Oncol., 2010, 11(5), 459-464.
55. Fang, M.Z.; Wang, Y.; Ai, N.; Hou, Z.; Sun, Y.; Lu, H.; Welsh, W.; Yang, C.S.Tea polyphenol (-)-epigallocatechin-3-gallate inhibits DNA methyltransferase and reactivates methylationsilenced genes in cancer cell lines. Cancer Res., 2003, 63(22), 7563-7570.
56. Volate, S.R.; Muga, S.J.; Issa, A.Y.; Nitcheva, D.; Smith, T.; Wargovich, M.J. Epigenetic modulation of the retinoid X receptor alpha by green tea in the azoxymethane-Apc Min/+ mouse model of intestinal cancer. Molecular Carcinogenesis, 2009, 48(10), 920-933.
57. Fang, M.; Chen, D.; Yang, C.S. Dietary polyphenols may affect DNA methylation. J. Nutr., 2007, 137(1 Suppl), 223S-228S.
58. Fini, L.; Selgrad, M.; Fogliano, V.; Graziani, G.; Romano, M.; Hotchkiss, E.; Daoud, Y.A.; De Vol, E.B.; Boland, C.R.; Ricciardiello, L. Annurca apple polyphenols have potent demethylating activity and can reactivate silenced tumor suppressor genes in colorectal cancer cells. J.Nutr., 2007. 137(12), 2622-8.
59. Meeran, S.M.; Ahmed, A.; Tollefsbol, T.O. Epigenetic targets of bioactive dietary components for cancer prevention and therapy. Clin. Epigenetics, 2010, 1(3-4), 101-116.
60. Fang, M.Z.; Chen, D.; Sun, Y.; Jin, Z.; Christman, J.K.; Yang, C.S. Reversal of hypermethylation and reactivation of p16INK4a, RARbeta, and MGMT genes by genistein and other isoflavones from soy. Clin. Cancer Res., 2005, 11(19 Pt 1), 7033-7041.
61. Li, Y.; Liu, L.; Andrews, L.G.; Tollefsbol, T.O. Genistein depletes telomerase activity through cross-talk between genetic and epigenetic mechanisms. Int. J. Cancer, 2009, 125(2), 286-96.
62. Traka, M.; Gasper, A.V.; Smith, J.A.; Hawkey, C.J.; Bao, Y.; Mithen, R.F. Transcriptome analysis of human colon Caco-2 cells exposed to sulforaphane. J. Nutr., 2005, 135(8), 1865-1872.
63. Nian, H.; Delage, B.; Pinto, J.T.; Dashwood, R.H. Allyl mercaptan, a garlic-derived organosulfur compound, inhibits histone deacetylase and enhances Sp3 binding on the P21WAF1 promoter. Carcinogenesis, 2008. 29(9), 1816-1824.
64. Druesne, N.; Pagniez, A.; Mayeur, C.; Thomas, M.; Cherbuy, C.; Duée, P.H.; Martel, P.; Chaumontet, C. Diallyl disulfide (DADS) increases histone acetylation and p21(waf1/cip1) expression in human colon tumor cell lines. Carcinogenesis, 2004. 25(7), 1227-36.
65. Waldecker, M.; Kautenburger, T.; Daumann, H.; Busch, C.; Schrenk, D. Inhibition of histone-deacetylase activity by shortchain fatty acids and some polyphenol metabolites formed in the colon. J. Nutr. Biochem., 2008, 19(9): p. 587-93.
66. Lawson, L.D.; Wang, Z.J.; Hughes, B.G. Identification and HPLC quantitation of the sulfides and dialk(en)yl thiosulfinates in commercial garlic products. Planta. Med., 1991. 57(4), 363-70.
67. Druesne-Pecollo, N.; Chaumontet, C.; Pagniez, A.; Vaugelade, P.; Bruneau, A.; Thomas, M.; Cherbuy, C.; Duée, P.H.; Martel, P. In vivo treatment by diallyl disulfide increases histone acetylation in rat colonocytes. Biochem. Biophys. Res. Commun., 2007, 354(1), 140-7.
68. Son, I.H.; Chung, I.M.; Lee, S.I.; Yang, H.D.; Moon, H.I. Pomiferin, histone deacetylase inhibitor isolated from the fruits of Maclura pomifera. Bioorg. Med. Chem. Lett., 2007, 17(17), 4753-4755.
69. Miller, S.J. Cellular and physiological effects of short-chain fatty acids. Mini. Rev. Med. Chem., 2004, 4(8), 839-845.
70. Myzak, M.C.; Karplus, P.A; Chung, F.L.; Dashwood, R.H. A Novel Mechanism of Chemoprotection by Sulforaphane. Cancer Res., 2004, 64(16), 5767-5774.
71. Myzak, M.C.; Dashwood, R.H.Chemoprotection by sulforaphane: keep one eye beyond Keap1. Cancer Lett., 2006, 233(2), 208-218.
72. Myzak, M.C.; Tong, P.; Dashwood, W.M.; Dashwood, R.H.; Ho, E. Sulforaphane retards the growth of human PC-3 xenografts and inhibits HDAC activity in human subjects. Exp. Biol. Med., 2007, 232(2), 227-34.
73. Hu, R.; Khor, T.O.; Shen, G.; Jeong, W.S.; Hebbar, V.; Chen, C.; Xu, C.; Reddy, B.; Chada, K.; Kong, A.N. Cancer chemoprevention of intestinal polyposis in ApcMin/+ mice by sulforaphane, a natural product derived from cruciferous vegetable. Carcinogenesis, 2006, 27(10), 2038-2046.
74. Kanadzu, M.; Lu, Y.; Morimoto, K. Dual function of (--)-epigallocatechin gallate (EGCG) in healthy human lymphocytes. Cancer Lett., 2006, 241(2), 250-255.
75. Siddiqui, I.A.; Asim, M.; Hafeez, B.B.; Adhami, V.M.; Tarapore, R.S.; Mukhtar, H. Green tea polyphenol EGCG blunts androgen receptor function in prostate cancer. FASEB J., 2011, 25(4), 1198-1207.
76. Murase, T.; Haramizu, S.; Shimotoyodome, A.; Nagasawa, A.; Tokimitsu, I. Green tea extract improves endurance capacity and increases muscle lipid oxidation in mice. Am. J. Physiol. Regul. Integr. Comp. Physiol., 2005, 288(3), R708-15.
77. Waltner-Law, M.E.; Wang, X.L.; Law, B.K.; Hall, R.K.; Nawano, M.; Granner, D.K. Epigallocatechin gallate, a constituent of green tea, represses hepatic glucose production. J. Biol. Chem., 2002, 277(38), 34933-34940.
78. Yu, R.; Jiao, J.J.; Duh, J.L.; Gudehithlu, K.; Tan, T.H.; Kong, A.N. Activation of mitogen-activated protein kinases by green tea polyphenols: potential signaling pathways in the regulation of antioxidant-responsive element-mediated phase II enzyme gene expression. Carcinogenesis, 1997, 18(2), 451-456.
79. McKay, D.L.; Blumberg, J.B. The role of tea in human health: an update. J. Am. Coll. Nutr., 2002, 21(1), 1-13.
80. Bouayed, J.; Rammal, H.; Dicko, A.; Younos, C.; Soulimani, R.Chlorogenic acid, a polyphenol from Prunus domestica (Mirabelle), with coupled anxiolytic and antioxidant effects. J. Neurol. Sci., 2007, 262(1-2), 77-84.
81. Ramos, S. Effects of dietary flavonoids on apoptotic pathways related to cancer chemoprevention. J. Nutr. Biochem., 2007, 18(7), 427-442.
82. Banerjee, S.; Li, Y.; Wang, Z.; Sarkar, F.H. Multi-targeted therapy of cancer by genistein. Cancer Lett., 2008, 269(2), 226-242.
83. Sarkar, F.H.; Li, Y. The role of isoflavones in cancer chemoprevention. Front Biosci., 2004, 9, 2714-2724.
84. Iciek, M.B.; Kowalczyk-Pachel, D.; Kwiecień, I.; Dudek, M.B. Effects of different garlic-derived allyl sulfides on peroxidative processes and anaerobic sulfur metabolism in mouse liver. Phytother. Res., 2012, 26(3), 425-431.
85. Sato, Y.; Itagaki, S.; Kurokawa, T.; Ogura, J.; Kobayashi, M.; Hirano, T.; Sugawara, M.; Iseki, K. In vitro and in vivo antioxidant properties of chlorogenic acid and caffeic acid. Int. J. Pharm., 2011, 403(1-2), 136-138.
86. Ikeda, K.; Tsujimoto, K.; Uozaki, M.; Nishide, M.; Suzuki, Y.; Koyama, A.H.; Yamasaki, H. Inhibition of multiplication of herpes simplex virus by caffeic acid. Int. J. Mol. Med., 2011, 28(4), 595-598.
87. Wang, L.C.; Lin, Y.L.; Liang, Y.C.; Yang, Y.H.; Lee, J.H.; Yu, H.H.; Wu, W.M.; Chiang, B.L. The effect of caffeic acid phenethyl ester on the functions of human monocyte-derived dendritic cells. B.M.C. Immunol., 2009, 10, 39.
88. Kwon, K.B.; Yoo, S.J.; Ryu, D.G.; Yang, J.Y.; Rho, H.W.; Kim, J.S.; Park, J.W.; Kim, H.R.; Park, B.H. Induction of apoptosis by diallyl disulfide through activation of caspase-3 in human leukemia HL-60 cells. Biochem. Pharmacol., 2002, 63(1), 41-47.
89. Nakagawa, H.; Tsuta, K.; Kiuchi, K.; Senzaki, H.; Tanaka, K.; Hioki, K.; Tsubura, A. Growth inhibitory effects of diallyl disulfide on human breast cancer cell lines. Carcinogenesis, 2001, 22(6), 891-897.
90. Hong, Y.S.; Ham, Y.A.; Choi, J.H.; Kim, J. Effects of allyl sulfur compounds and garlic extract on the expression of Bcl-2, Bax, and p53 in non small cell lung cancer cell lines. Exp. Mol. Med., 2000, 32(3), 127-134.
91. Yang, R.; Hanwell, H.; Zhang, J.; Tsao, R.; Meckling, K.A. Antiproliferative activity of pomiferin in normal (MCF-10A) and transformed (MCF-7) breast epithelial cells. J. Agric. Food. Chem., 2011, 59(24), 13328-13336.
92. Svasti, J.; Srisomsap, C.; Subhasitanont, P.; Keeratichamroen, S.; Chokchaichamnankit, D.; Ngiwsara, L.; Chimnoi, N.; Pisutjaroenpong, S.; Techasakul, S.; Chen, S.T. Proteomic profiling of cholangiocarcinoma cell line treated with pomiferin from Derris malaccensis. Proteomics, 2005, 5(17), 4504-4509.
93. Lambert, J.D.; Hong, J.; Kim, D.H.; Mishin, V.M.; Yang, C.S. Piperine enhances the bioavailability of the tea polyphenol (-)-epigallocatechin-3-gallate in mice. J. Nutr., 2004, 134(8), 1948-1952.
94. Gawande, S.; Kale, A.; Kotwal, S. Effect of nutrient mixture and black grapes on the pharmacokinetics of orally administered (-)epigallocatechin-3-gallate from green tea extract: a human study. Phytother. Res., 2008, 22(6), 802-808.
95. Henning, S.M.; Choo, J.J.; Heber, D. Nongallated compared with gallated flavan-3-ols in green and black tea are more bioavailable. J. Nutr., 2008, 138(8), 1529S-1534S.
96. Moon, Y.J.; Morris, M.E. Pharmacokinetics and bioavailability of the bioflavonoid biochanin A: effects of quercetin and EGCG on biochanin A disposition in rats. Mol. Pharm., 2007, 4(6), 865-872.
97. Smith, A.; Giunta, B.; Bickford, P.C.; Fountain, M.; Tan, J.; Shytle, R.D. Nanolipidic particles improve the bioavailability and alphasecretase inducing ability of epigallocatechin-3-gallate (EGCG) for the treatment of Alzheimer's disease. Int. J. Pharm., 2010, 389(1-2), 207-212.
98. Lee, W.J.; Zhu, B.T. Inhibition of DNA methylation by caffeic acid and chlorogenic acid, two common catechol-containing coffee polyphenols. Carcinogenesis, 2006, 27(2), 269-277.
99. Martignoni, M.; Groothuis, G.M.; de Kanter, R. Species differences between mouse, rat, dog, monkey and human CYP-mediated drug metabolism, inhibition and induction. Expert Opin. Drug Metab. Toxicol., 2006, 2(6), 875-894.
100. Sang, S.; Lee, M.J.; Yang, I.; Buckley, B.; Yang, C.S. Human urinary metabolite profile of tea polyphenols analyzed by liquid chromatography/electrospray ionization tandem mass spectrometry with data-dependent acquisition. Rapid Commun. Mass Spectrom., 2008, 22(10), 1567-1578.
101. Henning, S.M.; Niu, Y.; Lee, N.H.; Thames, G.D.; Minutti, R.R.; Wang, H.; Go, V.L.; Heber, D. Bioavailability and antioxidant activity of tea flavanols after consumption of green tea, black tea, or a green tea extract supplement. Am. J. Clin. Nutr., 2004, 80(6), 1558-1564.
102. Fimognari, C.; Lenzi, M.; Hrelia, P. Interaction of the isothiocyanate sulforaphane with drug disposition and metabolism: pharmacological and toxicological implications. Curr. Drug Metab., 2008, 9(7), 668-678.
103. Manson, M.M.; Ball, H.W.; Barrett, M.C.; Clark, H.L.; Judah, D.J.; Williamson, G.; Neal, G.E. Mechanism of action of dietary chemoprotective agents in rat liver: induction of phase I and II drug metabolizing enzymes and aflatoxin B1 metabolism. Carcinogenesis, 1997, 18(9), 1729-1738.
104. Wang, B.H.; Zuzel, K.A.; Rahman, K.; Billington, D. Treatment with aged garlic extract protects against bromobenzene toxicity to precision cut rat liver slices. Toxicology, 1999, 132(2-3), 215-225.
105. Makheja, A.N.; Bailey, J.M. Antiplatelet constituents of garlic and onion. Agents Actions, 1990, 29(3-4), 360-363.
106. Bora-Tatar, G.; Dayangaç-Erden, D.; Demir, A.S.; Dalkara, S.; Yelekçi, K.; Erdem-Yurter, H. Molecular modifications on carboxylic acid derivatives as potent histone deacetylase inhibitors: Activity and docking studies. Bioorg. Med. Chem., 2009, 17(14), 5219-5228.