In silico methods for physiologically based biokinetic models describing bioactivation and detoxification of coumarin and estragole: Implications for risk assessment

Molecular Nutrition and Food Research

Volumn 54, Issue 2, 2010, Pages 195-207

  Rietjens, Ivonne M C M ^a   Punt, Ans ^a   Schilter, Benoît ^b   Scholz, Gabriele ^b   Delatour, Thierry ^b   van Bladeren, Peter J ^a,b  

^a WAGENINGEN UNIVERSITY   (Netherlands)

^b NESTLÉ RESEARCH CENTER   (Switzerland)

Author keywords

Coumarin; Estragole; Metabolism; Physiologically based biokinetic models; Risk assessment

Indexed keywords

ANISOLE DERIVATIVE; CARCINOGEN; COUMARIN; COUMARIN DERIVATIVE; ESTRAGOLE; MUTAGENIC AGENT;

ANIMAL; BIOLOGICAL MODEL; BIOLOGY; BIOTRANSFORMATION; CHEMISTRY; EXPERT SYSTEM; HUMAN; MEDICINAL PLANT; METABOLISM; METHODOLOGY; PLANT; REVIEW; RISK ASSESSMENT; SPECIES DIFFERENCE;

ANIMALS; ANISOLES; BIOTRANSFORMATION; CARCINOGENS; COMPUTATIONAL BIOLOGY; COUMARINS; EXPERT SYSTEMS; HUMANS; MODELS, BIOLOGICAL; MUTAGENS; PLANTS, EDIBLE; PLANTS, MEDICINAL; RISK ASSESSMENT; SPECIES SPECIFICITY;

ANIMALIA; RATTUS;

EID: 76749144742     PISSN: 16134125     EISSN: 16134133     Source Type: Journal    
DOI: 10.1002/mnfr.200900211     Document Type: Review

References (65)

1. Smith, R. L., Adams, T. B., Doull, J., Feron, V. J. et al., Safety assessment of allylalkoxybenzene derivatives used as flavouring substances - methyl eugenol and estragole. Food Chem. Toxicol. 2002, 40, 851-870.
2. Siano, F., Ghizzoni, C., Gionfriddo, F., Colombo, E. et al., Determination of estragole, safrole and eugenol methyl ether in food products. Food Chem. 2003, 81, 469-475.
3. SCF (Scientific Committee on Food), Opinion of the scientific committee on food on estragole (1-allyl-4-methoxy-benzene), 2001.
4. Drinkwater, N. R., Miller, E. C., Miller, J. A., Pitot, H. C., Hepatocarcinogenicity of estragole(1-allyl-4-methoxy-benzene) and 10-hydroxyestragole in the mouse and mutagenicity of 10-acetoxyestragole in bacteria. J. Natl. Cancer Inst. 1976, 57, 1323-1331.
5. Miller, E. C., Swanson, A. B., Phillips, D. H., Fletcher, T. L. et al., Structure-activity studies of the carcinogenicities in the mouse and rat of some naturally occurring and synthetic alkenylbenzene derivatives related to safrole and estragole. Cancer Res. 1983, 43, 1124-1134.
6. Wiseman, R. W., Miller, E. C., Miller, J. A., Liem, A., Structure-activity studies of the hepatocarcinogenicities of alkenylbenzene derivatives related to estragole and safrole on administration to preweanling male C57BL/6J x C3H/HeJ F1mice. Cancer Res. 1987, 47, 2275-2283.
7. Anthony, A., Caldwell, J., Hutt, A. J., Smith, R. L., Metabolism of estragole in rat and mouse and influence of dose size on excretion of the proximate carcinogen 10-hydroxyestragole. Food Chem. Toxicol. 1987, 25, 799-806.
8. Sangster, S. A., Caldwell, J., Hutt, A. J., Anthony, A., Smith, R. L., The metabolic disposition of [methoxy-14C] -labelled trans-anethole, estragole and p-propylanisole in human volunteers. Xenobiotica 1987, 17, 1223-1232.
9. Hall, R. L., Oser, B. L., Recent progress in the consideration of flavoring ingredients under the food additives amendment III. GRAS substances. Food Technol. 1965, 253, 151-197.
10. JECFA, Sixty-ninth Meeting, Rome, Italy, 17-26 June 2008.
11. Lake, B. G., Coumarin metabolism, toxicity and carcinogenicity: relevance for human risk assessment. Food Chem. Toxicol. 1999, 37, 423-453.
12. SCF (Scientific Committee on Food), Opinion on coumarin (a constituent of natural flavouring source materials limited by annex II of flavourings directive 88/388/EC) expressed on 16 December 1994. Reports of the Scientific Committee on Food. Thirty-sixth series, 1997, pp. 13-20.
13. EFSA, Opinion of the Scientific Panel on Food additives, flavourings, processing aids and materials in contact with food (AFC) on a request from the commission related to coumarin. Question number EFSA-Q-2003-118. EFSA J. 2004, 104, 1-36.
14. NTP (National Toxicology Program), Toxicology and carcinogenesis studies of coumarin (CAS No. 91-64-5) in F344/N rats and B6C3F1 mice (gavage studies). Technical Report No. NTP TR 422. NIH Publication No 93-3153, US Department of Health and Human Services, NIH, Research Triangle Park, NC 1993.
15. Carlton, B. D., Aubrun, J.-C., Simon, G. S., Effects of coumarin following perinatal and chronic exposure in Sprague-Dawley rats and CD-1 mice. Fundam. Appl. Toxicol. 1996, 30, 145-151.
16. Born, S. L., Rodriguez, P. A., Eddy, C. L., Lehman-McKeeman, L. D., Synthesis and reactivity of coumarin 3,4-epoxide. Drug Metab. Dispos. 1997, 25, 1318-1324.
17. Lake, B. G., Gray, T. J. B., Evans, J. G., Lewis, D. F. V. et al., Studies on the mechanism of coumarin-induced toxicity in rat hepatocytes: comparison with dihydrocoumarin and other coumarin metabolites. Toxicol. Appl. Pharmacol. 1989,97,311-323.
18. Vassallo, J. D., Hicks, S. M., Daston, G. P., Lehman-McKeeman, L. D., Metabolic detoxification determines species differences in coumarin-induced hepatotoxicity. Toxicol. Sci. 2004, 80, 249-257.
19. Felter, S. P., Vassallo, J. D., Carlton, B. D., Daston, G. P., A safety assessment of coumarin taking into account species-specificity of toxicokinetics. Food Chem. Toxicol. 2006,44,462-475.
20. Born, S. L., Caudill, D., Smith, B. J., Lehman-McKeeman, L. D., In vitro kinetics of coumarin 3,4-epoxidation: application to species differences in toxicity and carcinogenicity. Toxicol. Sci. 2000, 58, 23-31.
21. Fentem, J. H., Fry, J. R., Whiting, D. A., o-Hydro-xyphenylacetaldehyde: a major novel metabolite of coumarin formed by rat, gerbil and human liver microsomes. Biochem. Bioophys. Res. Commun. 1991, 179, 197-203.
22. Lake, B. G., Osborne, D. J., Walters, D. G., Price, R. J., Identification of o-hydroxyphenylacetaldehyde as a major metabolite of coumarin in rat hepatic microsomes. Food Chem. Toxicol. 1992, 30, 99-104.
23. Born, S. L., Api, A. M., Ford, R. A., Lefever, F. R., Hawkins, D. R., Comparative metabolism and kinetics of coumarin in mice and rats. Food Chem. Toxicol. 2003, 41, 247-258.
24. Van Iersel, M., Walters, D. G., Price, R. J., Lovell, D. P., Lake, B. G., Sex and strain differences in mouse hepatic coumarin 7-hydroxylase activity. Food Chem. Toxicol. 1994, 32, 387-390.
25. Van Iersel, M. L., Henderson, C. J., Walters, D. G., Price, R. J. et al., Metabolism of [3-14C] coumarin by human liver microsomes. Xenobiotica 1994, 24, 795-803.
26. Draper, A. J., Madan, A., Parkinson, A., Inhibition of coumarin 7-hydroxylase activity in human liver microsomes. Arch. Biochem. Biophys. 1997, 341, 47-61.
27. Bogan, D. P., Deasy, B., O'Kennedy, R., Smyth, M. R., Interspecies differences in coumarin metabolism in liver microsomes examined by capillary electrophoresis. Xenobiotica 1996, 26, 437-445.
28. Fernandez-Salguero, P., Hoffman, S. M. G., Cholerton, S., Mohrenweiser, H. et al., A genetic polymorphism in coumarin 7-hydroxylation: sequence of the human CYP2A genes and identification of variant CYP2A6 alleles. Am. J. Human Genet. 1995, 57, 651-660.
29. Hadidi, H., Zahlsen, K., Idel, J. R., Cholerton, S., A single amino acid substitution (Leu160His) in cytochrome P450 CYP2A6causes switching from7-hydroxylation to 3-hydroxylation of coumarin. Food Chem. Toxicol. 1997, 35, 903-907.
30. Hadidi, H., Irshaid, Y., Vågbø, C. B., Brunsvik, A. et al., Variability of coumarin 7- and 3-hydroxylation in a Jordanian population is suggestive of a functional polymorphism in cytochrome P450 of CYP2A6. Eur. J. Clin. Pharmacol. 1998,54,437-441.
31. Andersen, M. E., Krishnan, K., Physiologically based pharmacokinetics cancer risk assessment. Environ. Health. Persp. 1994, 102, 103-108.
32. Clewell, H. J., Gentry, P. R., Gearhart, J. M., Allen, B. C., Andersen, M. E., Comparison of cancer risk estimates for vinyl chloride using animal and human data with a PBPK model. Sci. Total Environ. 2001, 274, 37-66.
33. Clewell, H. J., III, Andersen, M. E., Barton, H. A., A consistent approach for the application of pharmacokinetic modeling in cancer and non-cancer risk assessment. Environ. Health Perspect. 2002, 110, 85-93.
34. Krewski, D., Withey, J. R., Ku, L. F., Andersen, M. E., Applications of physiologic pharmacokinetic modeling in carcinogenic risk assessment. Environ. Health. Perspect. 1994,102,37-50.
35. Krishnan, K., Andersen, M. E., Physiologically based pharmacokinetic modeling and toxicology. In: Hayes, A. W. (Ed.), Principles and Methods of Toxicology, Raven Press, New York 2001 pp. 193-241.
36. Chiu, W. A., Barton, H. A., DeWoskin, R. S., Schlosser, P. et al., Evaluation of physiologically based pharmacokinetic models for use in risk assessment. J. Appl. Toxicol. 2007, 27,218-237.
37. Clewell, R. A., Clewell, H. J., III, Development and specification of physiologically based pharmacokinetic models for use in risk assessment. Regul. Toxicol. Pharmacol. 2008, 50, 129-143.
38. Bogaards, J. J. P., Hissink, E. M., Briggs, M., Weaver, R. et al., Prediction of interindividual variation in drug plasma levels in vivo from individual enzyme kinetic data and physiologically based pharmacokinetic modeling. Eur. J. Pharm. Sci. 2000, 12, 117-124.
39. Brown, R. P., Delp, M. D., Lindstedt, S. L., Rhomberg, L. R., Beliles, R. P., Physiological parameter values for physiologically based pharmacokinetic models. Toxicol. Indust. Health 1997, 13, 407-484.
40. Gargas, M. L., Burgess, R. J., Voisard, D. E., Cason, G. H., Andersen, M. E., Partition coefficients of low-molecular-weight volatile chemicals in various liquids and tissues. Toxicol. Appl. Pharmacol. 1989, 98, 87-99.
41. Jepson, G. W., Hoover, D. K., Black, R. K., McCafferty, J. D. et al., Partition coefficient determination for non-volatile and intermediate volatility chemicals in biological tissues. Toxicologist 1992, 12, 262.
42. Payne, M. P., Kenny, L. C., Comparison of models for the estimation of biological partition coefficients. J. Toxicol. Environ. Health A 2002, 65, 897-931.
43. Lipscomb, J. C., Poet, T. S., In vitro measurements of metabolism for application in pharmacokinetic modeling. Pharmacol. Ther. 2008, 118, 82-103.
44. Punt, A., Delatour, T., Scholz, G., Schilter, B. et al., Tandem mass spectrometry analysis of N2-(trans-isoestragole-30-yl)-2 0as a strategy to study species differences in sulfo-transferase conversion of the proximate carcinogen 10-hydroxyestragole. Chem. Res. Toxicol. 2007, 20, 991-998.
45. Punt, A., Freidig, A., Delatour, T., Scholz, G. et al., A physiologically based biokinetic (PBBK) model for estragole bioactivation and detoxification in rat. Toxicol. Appl. Pharmacol. 2008, 231, 248-259.
46. Rietjens, I. M. C. M., Zaleska, M., Boersma, M. G., Punt, A., Differences in simulated liver concentrations of toxic coumarin metabolites in rats and different human populations evaluated through physiologically based biokinetic (PBBK) modeling. Toxicol. In Vitro 2008, 22, 1890-1901.
47. Punt, A., Paini, A., Boersma, M. G., Freidig, A. et al., Use of physiologically based biokinetic (PBBK) modeling to study estragole bioactivation and detoxification in human as compared to male rats. Toxicol Sci. 2009, 110, 255-269.
48. Ramsey, J. C., Andersen, M. E., A physiologically based description of the inhalation pharmacokinetics of styrene in rats and humans. Toxicol. Appl. Pharmacol. 1984, 73, 159-175.
49. DeJongh, J., Verhaar, H. J., Hermens, J. L., A quantitative property-property relationship (QPPR) approach to estimate in vitro tissue-blood partition coefficients of organic chemicals in rats and humans. Arch. Toxicol. 1997, 72, 17-25.
50. Barter, Z. E., Bayliss, M. K., Beaune, P. H., Boobis, A. R. et al., Scaling factors for the extrapolation of in vivo metabolic drug clearance from in vitro data: reaching a consensus on values of human microsomal protein and hepatocellularity per gram of liver. Curr. Drug Metab. 2007, 8, 33-45.
51. Medinsky, M. A., Leavens, T. L., Csanády, G. A., Gargas, M. L., Bond, J. A., In vivo metabolism of butadiene by mice and rats: a comparison of physiological model predictions and experimental data. Carcinogenesis 1994, 7, 1329-1340.
52. Beierschmitt, W. P., Weiner, M., Age-related changes in renal metabolism of acetaminophen in male Fischer 344 rats. Age 1986, 9, 7-13.
53. Solheim, E., Scheline, R. R., Metabolism of alkenebenzene derivatives in the rat. I. p-Methoxyallylbenzene (Estragole) and p-methoxypropenylbenzene (Anethole). Xenobiotica 1973,3,493-510.
54. WHO, International Programme on Chemical Safety (IPCS): Assessing human health risks of chemicals: principles for the assessment of risk to human health from exposure to chemicals, Environmental Health Criteria 210, World Health Organisation, Geneva 1999.
55. Loprinzi, C. L., Kugler, J. W., Sloan, J. A., Rooke, T. W. et al., Lack of effect of coumarin in women with lymphedema after treatment for breast cancer. New Engl. J. Med. 1999, 340,346-350.
56. Schmeck-Lindenau, H. J., Naser-Hijazi, B., Becker, E. W., Henneicke-von Zepelin, H. H., Schnitker, J., Safety aspects of a coumarin-troxerutin combination regarding liver function in a double-blind placebo-controlled study. Int. J. Clin. Pharmacol. Therapeut. 2003, 41, 193-199.
57. Vanscheidt, W., Rabe, E., Naser-Hijazi, B., Ramelet, A. A. et al., The efficacy and safety of a coumarin-/troxerutin-combination (SB-LOT) in patients with chronic venous insufficiency: a double blind placebo-controlled randomised study. Vasa 2002, 31, 185-190.
58. Burian, M., Freudenstein, J., Tegtmeier, M, Naser-Hijazi, B. et al., Single copy of variant CYP2A6 alleles does not confer susceptibility to liver dysfunction in patients treated with coumarin. Int. J. Clin. Pharmacol. Therapeut. 2003, 41, 141-147.
59. COC (Committee on Carcinogenicity of Chemicals in Food, consumer products and the environment), Guidance on a strategy for the risk assessment of chemical carcinogens, 2004.
60. EFSA, Opinion of the scientific committee on a request from EFSA related to a harmonised approach for risk assessment of substances which are both genotoxic and carcinogenic. EFSA J. 2005, 282, 1-31.
61. Barlow, S., Renwick, A. G., Kleiner, J., Bridges, J. W. et al., Risk assessment of substances that are both genotoxic and carcinogenic report of an International Conference organized by EFSA and WHO with support of ILSI Europe. Food Chem. Toxicol. 2006, 44, 1636-1650.
62. Dybing, E., O'Brien, J., Renwick, A. G., Sanner, T., Risk assessment of dietary exposures to compounds that are genotoxic and carcinogenic, an overview. Toxicol. Lett. 2008,180,110-117.
63. EPA, Guidelines for carcinogen risk assessment and supplemental guidance for assessing susceptibility from early-life exposure to carcinogens, Environmental Protection Agency, Washington, DC, USA 2005.
64. Schilter, B., Andersson, C., Anton, R., Constable, A. et al., Guidance for the safety assessment of botanicals and botanical preparation for use in food and food supplements. Food Chem. Toxicol. 2003, 41, 1625-1649.
65. Jeurissen, S. M. F., Punt, A., Delatour, Th., Rietjens, I. M. C. M., Basil extract inhibits the sulfotransferase mediated formation of DNA aducts of the procarcinogen 10-hydroxyestragole by rat and human liver S9 homogenates and in HepG2 human hepatoma cells. Food Chem. Toxicol. 2008, 46, 2296-2302.