Naturally occurring Ah-receptor agonists in foods: Implications regarding dietary dioxin exposure and health risk

Human and Ecological Risk Assessment

Volumn 9, Issue 7, 2003, Pages 1747-1763

  Connor, Kevin ^a   Finley, Brent ^a,b  

^a EXPONENT INC   (United States)

^b NONE   (United States)

Author keywords

Dietary intakes; Dioxins; Indoles; Relative potencies; Risk assessment

Indexed keywords

ANIMALIA;

EID: 2342644156     PISSN: 10807039     EISSN: None     Source Type: Journal    
DOI: 10.1080/714044795     Document Type: Article

References (55)

1. Abraham K, Krowke R, and Neubert D. 1988. Pharmacokinetics and biological activity of 2,3,7,8-tetrachlorodibenzo-p-dioxin. 1. Dose-dependent tissue distribution and induction of hepatic ethoxyresorufin O-deethylase in rats following a single injection. Arch Toxicol 62(5):359-68
2. Adami H, Cole P, Mandel J, et al. 2000. Dioxin and Cancer. (Submitted for publication.) Also: Submitted as part of comments on the USEPA Science Advisory Board (SAB) Draft Report to EPA on the Exposure and Human Health Reassessment of 2,3,7,8-Tetrachlorodibenzo-p-dioxin (TCDD) and Related Compounds. US Environmental Protection Agency, Office of Research and Development, Washington, DC, USA. August 7
3. Ashida H, Fukuda I, Yamashita T, et al. 2000. Flavones and flavonols at dietary levels inhibit a transformation of aryl hydrocarbon receptor induced by dioxin. FEBS Lett 476:213-7
4. Bergman J, Wahlström N, Yudina YN, et al. 2002. Synthesis of indolocarbazole quinines; potent aryl hydrocarbon receptor ligands. Tetrahedron 58(7):1443-52
5. Bjeldanes LF, Kim JY, Grose KR, et al. 1991. Aromatic hydrocarbon responsiveness-receptor agonists generated from indole-3-carbinol in vitro and in vivo: Comparisons with 2,3,7,8-tetrachlorodibenzo-p-dioxin. Proc Natl Acad Sci USA 88:9543-7
6. Bradfield CA and Bjeldanes LF. 1984. Effect of dietary indole-3-carbinol on intestinal and hepatic monooxygenase, glutathione S-transferase and epoxide hydrolase activities in the rat. Food Chem Toxicol 22:977-82
7. Bradfield CA and Bjeldanes LF. 1987. Structure-activity relationships of dietary indoles: A proposed mechanism of action as modifiers of xenobiotic metabolism. J Toxicol Environ Health 21:311-23
8. Chen YH, Riby J, Srivastava P, et al. 1995. Regulation of CYP1A1 by indolo[3,2-b]carbazole in murine hepatoma cells. J Biol Chem 270:22548-55
9. d'Argy R, Bergman J, and Dencker L. 1989. Effects of immunosuppressive chemicals on lymphoid development in foetal thymus organ cultures. Pharmacol Toxicol 64:33-8
10. Dashwood RH, Fong AT, Williams DE, et al. 1991. Promotion of aflatoxin B1 carcinogenesis by the natural tumor modulator indole-3-carbinol: Influence of dose, duration, and intermittent exposure on indole-3-carbinol promotional potency. Cancer Res 51:2362-5
11. Denison MS and Heath-Pagliuso S. 1998. The Ah receptor: A regulator of the biochemical and toxicological actions of structurally diverse chemicals. Bull Environ Contam Toxicol 61:557-68
12. DeVito MJ and Birnbaum LS. 1996. The use of body burden vs. daily dose in comparisons of endo-and exo-dioxins and in assessing human health risks. Organohal Compounds 29:424-9
13. Finley BL, Fehling K, Greene J, et al. 2000. The presence of Ah-receptor agonists in the diet: Implications for risk assessment and risk management. Organohal Compounds 47:365-8
14. Flesch-Janys D, Becher H, Gurn P, et al. 1996. Elimination of polychlorinated dibenzo-p-dioxins and dibenzofurans in occupationally exposed persons. J Toxicol Environ Health 47:363-78
15. Gillner M, Bergman J, Cambillau C, et al. 1993. Interactions of indolo[3,2-6]carbazoles and related polycyclic aromatic hydrocarbons with specific binding sites for 2,3,7,8-tetrachlorodibenzo-p-dioxin in rat liver. Mol Pharmacol 44:336-45
16. Gradelet S, Leclerc J, Siess M-H, et al. 1996a. Beta-Apo-8′- carotenal, but not β-carotene is a strong inducer of liver cytochromes P4501A1 and 1A2 in rat. Xenobiotica 26:909-19
17. Graham S and Mettlin C. 1979. Diet and colon cancer. AmJ Epidemiol 109:1
18. Graham S, Dayal S, Swanson M, et al. 1978. Diet in the epidemiology of cancer of the colon and rectum. J Natl Cancer Inst 61:709
19. Jellinck PH, Forkert PG, Riddick DS, et al. 1993. Ah receptor binding properties of indole carbinols and induction of hepatic estradiol hydroxylation. Biochem Pharmacol 45:1129-36
20. Johansson G, Gillner M, Hogberg B, et al. 1982. The TCDD receptor in rat intestinal mucosa and its possible dietary ligands. Nutr Cancer 3:134-44
21. Kim DJ, Han BS, Ahn B, et al. 1997. Enhancement by indole-3-carbinol of liver and thyroid gland neoplastic development in a rat medium-term multiorgan carcinogenesis model. Carcinogenesis 18:377-81
22. Kleman M and Gustafsson JA. 1996. Interactions of procarcinogenic heterocyclic amines and indolocarbazoles with the dioxin receptor. Biol Chem 377:741-62
23. Kleman MI, Poellinger L, and Gustafsson JA. 1994. Regulation of human dioxin receptor function by indolocarbazoles, receptor ligands of dietary origin. J Biol Chem 269:5137-44
24. Kuhnau J. 1976. The flavonoids. A class of semi-essential food components: Their role in human nutrition. World Rev Nutr Diet 24:117-91
25. Kushad MM, Brown AF, Kurilich AC, et al. 1999. Variation of glucosinolates in vegetable crops of Brassica oleracea. J Agric Food Chem 47:1541-8
26. Kwon C, Grose KR, Riby J, et al. 1994. In vivo production and enzyme-inducing activity of indolo [3,2-b] carbazole. J Agric Food Chem 42:2536-40
27. Lampe JW, King IB, Li S, et al 2000. Brassica vegetables increase and apiaceous vegetables decrease cytochrome P450 1A2 activity in humans: Changes in caffeine metabolite ratios in response to controlled vegetable diets. Carcinogenesis 21:1157-62
28. Layton DW, Bogen KT, Knize MG, et al. 1995. Cancer risk of heterocyclic amines in cooked foods: An analysis and implications for research. Carcinogenesis 16:39-52
29. Liu H, Wormke M, Safe SH, et al. 1994. Indolo[3,2-b]carbazole: A dietary-derived factor that exhibits both antiestrogenic and estrogenic activity. J Natl Cancer Inst 86:1758-65
30. Lutz WK and Schlatter J. 1992. Chemical carcinogens and overnutrition in diet-related cancer. Carcinogenesis 13:2211-6
31. McDanell R, McLean AE, Hanley AB, et al. 1988. Chemical and biological properties of indole glucosinolates (glucobrassicins) : A review. Food Chem Toxicol 26:59-70
32. Michnovicz JJ and Bradlow HL. 1990. Induction of estradiol metabolism by dietary indole-3-carbinol in humans. J Natl Cancer Inst 82:947-9
33. Michnovicz JJ and Bradlow HL. 1991. Altered estrogen metabolism and excretion in humans following consumption of indole-3-carbinol. Nutr Cancer 16:59-66
34. Michnovicz JJ, Adlercreutz H, and Bradlow HL. 1997. Changes in levels of urinary estrogen metabolites after oral indole-3-carbinol treatment in humans. J Natl Cancer Inst 89:718-23
35. Munro I, Delzell E, Giesy J, et al. 1994. Interpretive review of the potential adverse effects of chlorinated organic chemicals on human health and the environment. Appendix J: Polychlorinated dibenzo-p-dioxins and polychlorinated dibenzofurans. Regul Toxicol Pharmacol 20:S690-S1029
36. Odum J, Tinwell H, Jones K, et al. 2001. Effect of rodent diets on the sexual development of the rat. Toxicol Sci 61:115-27
37. Park JY, Shigenaga MK, and Ames BN. 1996. Induction of cytochrome P4501A1 by 2,3,7,8-tetrachlorodibenzo-p-dioxin or indolo(3,2-b)carbazole is associated with oxidative DNA damage. Proc Natl Acad Sci USA 93:2322-7
38. Petrulis JR and Bunce NJ. 1999. Competitive inhibition by inducer as a confounding factor in the use of ethoxyresorufin-O-deethylase (EROD) assay to estimate exposure to dioxin-like compounds. Toxicol Lett 105:251-60
39. Pohjanvirta R, Korkalainen M, McGuire J, et al. 2002. Comparison of acute toxicities of indolo[3,2-b] carbazole (ICZ) and 2,3,7,8-tetrachlorodibenzo-p- dioxin (TCDD) in TCDD-sensitive rats. Food Chem Toxicol 40(7):1023-32
40. Riby JE, Feng C, Chang Y-C, et al. 2000. The major trimeric product of indole-3-carbinol is a strong agonist of the estrogen receptor signaling pathway. Biochemistry 39:910-18
41. Safe SH. 1998. Limitations of the toxic equivalency factor approach for risk assessment of TCDD and related compounds. Teratogen Carcino Mutatagen 17:285-304
42. Savouret JF, Antenos M, Quesne M, et al. 2001. 7-ketocholesterol is an endogenous modulator for the arylhydrocarbon receptor. J Biol Chem 276:3054-9
43. Schrenk D, Riebniger D, Till M, et al. 1997. Tryptanthrins: A novel class of agonists of the aryl hydrocarbon receptor. Biochem Pharmacol 54:165-71
44. Schrenk D, Riebniger D, Till M, et al. 1999. Tryptanthrins and other tryptophan-derived agonists of the dioxin receptor. Adv Exp Med Biol 467:403-8
45. Sinha R, Rothman N, Brown ED, et al. 1994. Pan-fried meat containing high levels of heterocyclic aromatic amines but low levels of polycyclic aromatic hydrocarbons induces cytochrome P4501A2 activity in humans. Cancer Res 54:6154-9
46. Stephensen PU, Bonnesen C, Schaldach C, et al. 2000. N-methoxyindole-3- carbinol is a more efficient inducer of cytochrome P-450 1A1 in cultured cells than indol-3-carbinol. Nutr Cancer 36:112-21
47. USEPA (U.S. Environmental Protection Agency). 1994. Estimating Exposure to Dioxin-Like Compounds. (External Review Draft). EPA/600/6-88/005Ca. Office of Health and Environmental Assessment. Washington, DC, USA. June
48. USEPA (U.S. Environmental Protection Agency). 1997. Exposure Factors Handbook. National Center for Environmental Assessment, Washington, DC, USA
49. USEPA (U.S. Environmental Protection Agency). 2000. Exposure and Human Health Reassessment of 2,3,7,8-Tetrachlorodibenzo-p-dioxin (TCDD) and Related Compounds. National Center for Environmental Assessment, Office of Research and Development. Washington, DC, USA
50. Van den Berg M, Birnbaum L, Bosveld ATC, et al. 1998. Toxicity equivalency factors (TEFs) for PCBs, PCDDs, PCDFs for humans and wildlife. Environ Health Perspect 106:775-92
51. Vanden Heuvel JP, Clark GC, Kohn MC, et al. 1994. Dioxin-responsive genes: Examination of dose-response relationships using quantitative reverse transcriptase-polymerase chain reaction. Cancer Res 54:62-8
52. Vang O, Jensen MB, and Autrup H. 1990. Induction of cytochrome P450IA1 in rat colon and liver by indole-3-carbinol and 5,6-benzoflavone. Carcinogenesis 11:1259-6360
53. Van Poppel G, Verhoeven DT, Verhagen H, et al. 1999. Brassica vegetables and cancer prevention. Epidemiology and mechanisms. Adv Exp Med Biol 472:159-68
54. Wilker C, Johnson L, and Safe S. 1996. Effects of developmental exposure to indole-3-carbinol or 2,3,7,8-tetrachlorodibenzo-p-dioxin on reproductive potential of male rat offspring. Toxicol Appl Pharmacol 141:68-75
55. Wille G, Mayser P, Thoma W, et al. 2001. Malassezin - A novel agonist of the arylhydrocarbon receptor from the yeast Malassezia furfur. Bioorg Med Chem 9:955