메뉴 건너뛰기




Volumn 27, Issue 7, 2014, Pages 1092-1103

Impact of structural and metabolic variations on the toxicity and carcinogenicity of hydroxy- and alkoxy-substituted allyl- and propenylbenzenes

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL COMPOUND; ANETHOLE; BENZENE DERIVATIVE; CHAVICOL; ESTRAGOLE; EUGENOL; ISOCHAVICOL; ISOEUGENOL; METHYLEUGENOL; METHYLISOEUGENOL; PHENOL DERIVATIVE; SAFROLE; UNCLASSIFIED DRUG; CARCINOGEN;

EID: 84904641005     PISSN: 0893228X     EISSN: 15205010     Source Type: Journal    
DOI: 10.1021/tx500109s     Document Type: Review
Times cited : (52)

References (98)
  • 2
    • 0019521510 scopus 로고
    • The role of cyanide liberation in the acute toxicity of aliphatic nitriles
    • Willhite, C. C. and Smith, R. P. (1981) The role of cyanide liberation in the acute toxicity of aliphatic nitriles Toxicol. Appl. Pharmacol. 59, 589-602
    • (1981) Toxicol. Appl. Pharmacol. , vol.59 , pp. 589-602
    • Willhite, C.C.1    Smith, R.P.2
  • 3
    • 0035082174 scopus 로고    scopus 로고
    • Urinary thiocyanate as a biomarker for the generation of inorganic cyanide from benzyl cyanide in the rat
    • Potter, J., Smith, R. L., and Api, A. M. (2001) Urinary thiocyanate as a biomarker for the generation of inorganic cyanide from benzyl cyanide in the rat Food Chem. Toxicol. 39, 141-146
    • (2001) Food Chem. Toxicol. , vol.39 , pp. 141-146
    • Potter, J.1    Smith, R.L.2    Api, A.M.3
  • 4
    • 0021262884 scopus 로고
    • Studies on the mechanism of acute toxicity of nitriles in mice
    • Tanii, H. and Hashimoto, K. (1984) Studies on the mechanism of acute toxicity of nitriles in mice Arch. Toxicol. 56, 47-54
    • (1984) Arch. Toxicol. , vol.56 , pp. 47-54
    • Tanii, H.1    Hashimoto, K.2
  • 7
    • 0015523324 scopus 로고
    • The conjugation of phenylacetic acid in man, sub-human primates and some non-primate species
    • James, M. O., Smith, R. L., Williams, R. T., Reidenberg, F. R. S., and Reidenberg, M. (1972) The conjugation of phenylacetic acid in man, sub-human primates and some non-primate species Proc. R. Soc. B 182, 25-35
    • (1972) Proc. R. Soc. B , vol.182 , pp. 25-35
    • James, M.O.1    Smith, R.L.2    Williams, R.T.3    Reidenberg, F.R.S.4    Reidenberg, M.5
  • 8
    • 0017649127 scopus 로고
    • Metabolism of arylacetic acids. 2. The fate of hydratropic acid and its variation with species
    • Dixon, P. A. F., Caldwell, J., and Smith, R. L. (1977) Metabolism of arylacetic acids. 2. The fate of hydratropic acid and its variation with species Xenobiotica 7, 707-715
    • (1977) Xenobiotica , vol.7 , pp. 707-715
    • Dixon, P.A.F.1    Caldwell, J.2    Smith, R.L.3
  • 9
    • 0017029682 scopus 로고
    • Hepatocarcinogenicity of estragole (1-allyl-4-methoxybenzene) and 1′-hydroxyestragole in the mouse and mutagenicity of 1′- acetoxyestragole in bacteria
    • Drinkwater, N. R., Miller, E. C., Miller, J. A., and Pitot, H. C. (1976) Hepatocarcinogenicity of estragole (1-allyl-4-methoxybenzene) and 1′-hydroxyestragole in the mouse and mutagenicity of 1′- acetoxyestragole in bacteria J. Natl. Cancer Inst. 57, 1323-1331
    • (1976) J. Natl. Cancer Inst. , vol.57 , pp. 1323-1331
    • Drinkwater, N.R.1    Miller, E.C.2    Miller, J.A.3    Pitot, H.C.4
  • 10
    • 0020692513 scopus 로고
    • Structure-activity studies of the carcinogenicities in the mouse and rat of some naturally occurring and synthetic alkenylbenzene derivatives related to safrole and estragole
    • Miller, E. C., Swanson, A. B., Phillips, D. H., Fletcher, T. L., Liem, A., and Miller, J. (1983) 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. 43, 1124-1134
    • (1983) Cancer Res. , vol.43 , pp. 1124-1134
    • Miller, E.C.1    Swanson, A.B.2    Phillips, D.H.3    Fletcher, T.L.4    Liem, A.5    Miller, J.6
  • 11
    • 0023241740 scopus 로고
    • Structure-activity studies of the hepatocarcinogenicities of alkenylbenzene derivatives related to estragole and safrole on administration to preweanling male C57BL/6J x C3H/HeJ F1 mice
    • Wiseman, R. W., Miller, E. C., Miller, J. A., and Liem, A. (1987) Structure-activity studies of the hepatocarcinogenicities of alkenylbenzene derivatives related to estragole and safrole on administration to preweanling male C57BL/6J x C3H/HeJ F1 mice Cancer Res. 47, 2275-2283
    • (1987) Cancer Res. , vol.47 , pp. 2275-2283
    • Wiseman, R.W.1    Miller, E.C.2    Miller, J.A.3    Liem, A.4
  • 12
    • 0345235084 scopus 로고    scopus 로고
    • SCF, European Commission. Health and Consumer Protection Directorate-General. Directorate C, Scientific Opinions, Brussels, Belgium
    • SCF, European Commission (2001a) Opinion of the Scientific Committee on Food on Estragole (1-Allyl-4-methoxybenzene). Health and Consumer Protection Directorate-General. Directorate C, Scientific Opinions, Brussels, Belgium. Available at http://ec.europa.eu/food/fs/sc/scf/out104-en.pdf.
    • (2001) Opinion of the Scientific Committee on Food on Estragole (1-Allyl-4-methoxybenzene)
  • 13
    • 0013151764 scopus 로고    scopus 로고
    • SCF, European Commission. Health and Consumer Protection Directorate-General. Directorate C, Scientific Opinions, Brussels, Belgium
    • SCF, European Commission (2001b) Opinion of the Scientific Committee on Food on Methyleugenol (4-Allyl-1,2-dimethoxybenzene). Health and Consumer Protection Directorate-General. Directorate C, Scientific Opinions, Brussels, Belgium. Available at http://ec.europa.eu/food/fs/sc/scf/out102-en.pdf.
    • (2001) Opinion of the Scientific Committee on Food on Methyleugenol (4-Allyl-1,2-dimethoxybenzene)
  • 17
    • 0015591485 scopus 로고
    • 1′-Hydroxysafrole a proximate carcinogenic metabolite of safrole in the rat and mouse
    • Borchert, P., Miller, J. A., Miller, E. C., and Shires, T. K. (1973) 1′-Hydroxysafrole a proximate carcinogenic metabolite of safrole in the rat and mouse Cancer Res. 33, 590-600
    • (1973) Cancer Res. , vol.33 , pp. 590-600
    • Borchert, P.1    Miller, J.A.2    Miller, E.C.3    Shires, T.K.4
  • 18
    • 0017194810 scopus 로고
    • The metabolic activation of the carcinogen 1′-hydroxysafrole in vivo and in vitro and the electrophilic reactivities of possible ultimate carcinogens
    • Wislocki, P. G., Borchert, P., Miller, J. A., and Miller, E. C. (1976) The metabolic activation of the carcinogen 1′-hydroxysafrole in vivo and in vitro and the electrophilic reactivities of possible ultimate carcinogens Cancer Res. 36, 1686-1695
    • (1976) Cancer Res. , vol.36 , pp. 1686-1695
    • Wislocki, P.G.1    Borchert, P.2    Miller, J.A.3    Miller, E.C.4
  • 19
    • 0017405097 scopus 로고
    • Carcinogenic and mutagenic activities of safrole, 1′- hydroxysafrole, and some known or possible metabolites
    • Wislocki, P. G., Miller, E. C., Miller, J. A., McCoy, E. C., and Rosenkranz, H. S. (1977) Carcinogenic and mutagenic activities of safrole, 1′-hydroxysafrole, and some known or possible metabolites Cancer Res. 37, 1883-1891
    • (1977) Cancer Res. , vol.37 , pp. 1883-1891
    • Wislocki, P.G.1    Miller, E.C.2    Miller, J.A.3    McCoy, E.C.4    Rosenkranz, H.S.5
  • 20
    • 0021856770 scopus 로고
    • Further characterization of the DNA adducts formed by electrophilic esters of the hepatocarcinogens 1′-hydroxysafrole and 1′- hydroxyestragole in vitro and in mouse liver in vivo, including new adducts at C-8 and N-7 of guanine residues
    • Wiseman, R. W., Fennell, T. R., Miller, J. A., and Miller, E. C. (1985) Further characterization of the DNA adducts formed by electrophilic esters of the hepatocarcinogens 1′-hydroxysafrole and 1′-hydroxyestragole in vitro and in mouse liver in vivo, including new adducts at C-8 and N-7 of guanine residues Cancer Res. 45, 3096-3105
    • (1985) Cancer Res. , vol.45 , pp. 3096-3105
    • Wiseman, R.W.1    Fennell, T.R.2    Miller, J.A.3    Miller, E.C.4
  • 22
    • 0021054404 scopus 로고
    • Strong evidence from studies with Brachymorphic mice and pentachlorophenol that 1′-sulfooxysafrole is the major ultimate electrophilic and carcinogenic metabolite of 1′-hydroxysafrole in mouse liver
    • Boberg, E. W., Miller, E. C., Miller, J. A., Poland, A., and Liem, A. (1983) Strong evidence from studies with Brachymorphic mice and pentachlorophenol that 1′-sulfooxysafrole is the major ultimate electrophilic and carcinogenic metabolite of 1′-hydroxysafrole in mouse liver Cancer Res. 43, 5163-5173
    • (1983) Cancer Res. , vol.43 , pp. 5163-5173
    • Boberg, E.W.1    Miller, E.C.2    Miller, J.A.3    Poland, A.4    Liem, A.5
  • 23
    • 84863458837 scopus 로고    scopus 로고
    • Identification of human and murine sulfotransferases able to activate hydroxylated metabolites of methyleugenol to mutagens in Salmonella typhimurium and detection of associated DNA adducts using UPLC-MS/MS methods
    • Herrmann, K., Engst, W., Appel, K. E., Monien, B. H., and Glatt, H. (2012) Identification of human and murine sulfotransferases able to activate hydroxylated metabolites of methyleugenol to mutagens in Salmonella typhimurium and detection of associated DNA adducts using UPLC-MS/MS methods Mutagenesis 27, 453-462
    • (2012) Mutagenesis , vol.27 , pp. 453-462
    • Herrmann, K.1    Engst, W.2    Appel, K.E.3    Monien, B.H.4    Glatt, H.5
  • 24
    • 84894561504 scopus 로고    scopus 로고
    • Formation of hepatic DNA adducts by methyleugenol in mouse models: Drastic decrease by Sult1a1 knockout and strong increase by transgenic human SULT1A1/2
    • Herrmann, K., Engst, W., Meinl, W., Florian, S., Cartus, A. T., Schrenk, D., Appel, K. E., Nolden, T., Himmelbauer, H., and Glatt, H. (2013) Formation of hepatic DNA adducts by methyleugenol in mouse models: drastic decrease by Sult1a1 knockout and strong increase by transgenic human SULT1A1/2 Carcinogenesis 35, 935-941
    • (2013) Carcinogenesis , vol.35 , pp. 935-941
    • Herrmann, K.1    Engst, W.2    Meinl, W.3    Florian, S.4    Cartus, A.T.5    Schrenk, D.6    Appel, K.E.7    Nolden, T.8    Himmelbauer, H.9    Glatt, H.10
  • 25
    • 42749087687 scopus 로고    scopus 로고
    • Basil extract inhibits the sulfotransferase mediated formation of DNA adducts of the procarcinogen 1′-hydroxyestragole by rat and human liver S9 homogenates and in HepG2 human hepatoma cells
    • Jeurissen, S. M. F., Punt, A., Delatour, T., and Rietjens, I. M. C. M. (2008) Basil extract inhibits the sulfotransferase mediated formation of DNA adducts of the procarcinogen 1′-hydroxyestragole by rat and human liver S9 homogenates and in HepG2 human hepatoma cells Food. Chem. Toxicol. 46, 2296-2302
    • (2008) Food. Chem. Toxicol. , vol.46 , pp. 2296-2302
    • Jeurissen, S.M.F.1    Punt, A.2    Delatour, T.3    Rietjens, I.M.C.M.4
  • 27
    • 84886785652 scopus 로고    scopus 로고
    • In vivo validation and physiologically based modelling of the inhibition of SULT-mediated estragole DNA adduct formation in the liver of male Sprague-Dawley rats by the basil flavonoid nevadensin
    • Alhusainy, W., Paini, A., van den Berg, J. H. J., Punt, A., Scholz, G., Schilter, B., van Bladeren, P. J., Taylor, S., Adams, T. B., and Rietjens, I. M. C. M. (2013) In vivo validation and physiologically based modelling of the inhibition of SULT-mediated estragole DNA adduct formation in the liver of male Sprague-Dawley rats by the basil flavonoid nevadensin Mol. Nutr. Food Res. 57, 1969-1978
    • (2013) Mol. Nutr. Food Res. , vol.57 , pp. 1969-1978
    • Alhusainy, W.1    Paini, A.2    Van Den Berg, J.H.J.3    Punt, A.4    Scholz, G.5    Schilter, B.6    Van Bladeren, P.J.7    Taylor, S.8    Adams, T.B.9    Rietjens, I.M.C.M.10
  • 29
    • 0018952570 scopus 로고
    • Mutagenicity of constituents identified in pulp and paper mill effluents using the Salmonella/mammalian-microsome assay
    • Nestmann, E. R., Lee, E. G. H., Matula, T. I., Douglas, G. R., and Mueller, J. C. (1980) Mutagenicity of constituents identified in pulp and paper mill effluents using the Salmonella/mammalian-microsome assay Mutat. Res. 79, 203-212
    • (1980) Mutat. Res. , vol.79 , pp. 203-212
    • Nestmann, E.R.1    Lee, E.G.H.2    Matula, T.I.3    Douglas, G.R.4    Mueller, J.C.5
  • 32
    • 0028869545 scopus 로고
    • Genotoxicity of trans -anethole in vitro
    • Gorelick, N. J. (1995) Genotoxicity of trans -anethole in vitro Mutat. Res. 326, 199-209
    • (1995) Mutat. Res. , vol.326 , pp. 199-209
    • Gorelick, N.J.1
  • 33
    • 0345400119 scopus 로고
    • Induction of unscheduled DNA synthesis in cultured rat hepatocytes by natural food flavours
    • Howes, A. J., Chan, V. S. W., and Caldwell, J. (1990a) Induction of unscheduled DNA synthesis in cultured rat hepatocytes by natural food flavours Mutagenesis 5, 85
    • (1990) Mutagenesis , vol.5 , pp. 85
    • Howes, A.J.1    Chan, V.S.W.2    Caldwell, J.3
  • 34
    • 0025113923 scopus 로고
    • Structure-specificity of the genotoxicity of some naturally occurring alkenylbenzenes determined by the unscheduled DNA synthesis assay in rat hepatocytes
    • Howes, A. J., Chan, V. S. W, and Caldwell, J. (1990b) Structure-specificity of the genotoxicity of some naturally occurring alkenylbenzenes determined by the unscheduled DNA synthesis assay in rat hepatocytes Food Chem. Toxicol. 28, 537-542
    • (1990) Food Chem. Toxicol. , vol.28 , pp. 537-542
    • Howes, A.J.1    Chan, V.S.W.2    Caldwell, J.3
  • 35
    • 0026722898 scopus 로고
    • Influence of modulators of epoxide metabolism on the cytotoxicity of trans -anethole in freshly isolated rat hepatocytes
    • Marshall, A. D. and Caldwell, J. (1992) Influence of modulators of epoxide metabolism on the cytotoxicity of trans -anethole in freshly isolated rat hepatocytes Food Chem. Toxicol. 30, 467-473
    • (1992) Food Chem. Toxicol. , vol.30 , pp. 467-473
    • Marshall, A.D.1    Caldwell, J.2
  • 36
    • 0029874238 scopus 로고    scopus 로고
    • Lack of influence of modulators of epoxide metabolism on the genotoxicity of trans -anethole in freshly isolated rat hepatocytes assessed with the unscheduled DNA synthesis assay
    • Marshall, A. D. and Caldwell, J. (1996) Lack of influence of modulators of epoxide metabolism on the genotoxicity of trans -anethole in freshly isolated rat hepatocytes assessed with the unscheduled DNA synthesis assay Food Chem. Toxicol. 34, 337-345
    • (1996) Food Chem. Toxicol. , vol.34 , pp. 337-345
    • Marshall, A.D.1    Caldwell, J.2
  • 37
    • 0009502621 scopus 로고
    • 1′-Hydroxylation is the only metabolic pathway of simple alkenylbenzenes involved in their genotoxicity
    • Caldwell, J., Chan, V. S. W., Marshall, A. D., Hasheminejad, G., and Bounds, S. V. J. (1992) 1′-Hydroxylation is the only metabolic pathway of simple alkenylbenzenes involved in their genotoxicity Toxicologist 12, 56
    • (1992) Toxicologist , vol.12 , pp. 56
    • Caldwell, J.1    Chan, V.S.W.2    Marshall, A.D.3    Hasheminejad, G.4    Bounds, S.V.J.5
  • 38
    • 0021646473 scopus 로고
    • 32P-post-labelling analysis of DNA adducts formed in the livers of animals treated with safrole, estragole and other naturally-occurring alkenylbenzenes. I. Adult female CD-1 mice
    • Randerath, K., Haglund, R. E., Phillips, D. H., and Reddy, M. V. (1984) 32P-post-labelling analysis of DNA adducts formed in the livers of animals treated with safrole, estragole and other naturally-occurring alkenylbenzenes. I. Adult female CD-1 mice Carcinogenesis 5, 1613-1622
    • (1984) Carcinogenesis , vol.5 , pp. 1613-1622
    • Randerath, K.1    Haglund, R.E.2    Phillips, D.H.3    Reddy, M.V.4
  • 39
    • 0021646474 scopus 로고
    • 32P-post-labelling analysis of DNA adducts formed in the livers of animals treated with safrole, estragole and other naturally-occurring alkenylbenzenes. II. Newborn male B6C3F1 mice
    • Phillips, D. H., Reddy, M. V., and Randerath, K. (1984) 32P-post-labelling analysis of DNA adducts formed in the livers of animals treated with safrole, estragole and other naturally-occurring alkenylbenzenes. II. Newborn male B6C3F1 mice Carcinogenesis 5, 1623-1628
    • (1984) Carcinogenesis , vol.5 , pp. 1623-1628
    • Phillips, D.H.1    Reddy, M.V.2    Randerath, K.3
  • 41
    • 0020457677 scopus 로고
    • Mutagenicity of trans -anethole, estragole, eugenol and safrole in the Ames Salmonella typhimurium assay
    • To, L. P., Hunt, T. P., and Andersen, M. E. (1982) Mutagenicity of trans -anethole, estragole, eugenol and safrole in the Ames Salmonella typhimurium assay Bull. Environ. Contam. Toxicol. 28, 647-654
    • (1982) Bull. Environ. Contam. Toxicol. , vol.28 , pp. 647-654
    • To, L.P.1    Hunt, T.P.2    Andersen, M.E.3
  • 42
    • 0018379379 scopus 로고
    • The mutagenicities of safrole, estragole, eugenol, trans -anethole and some of their known or possible metabolites for Salmonella typhimurium mutants
    • Swanson, A. B., Chambliss, D. D., Blomquist, J. C., Miller, E. C., and Miller, J. A. (1979) The mutagenicities of safrole, estragole, eugenol, trans -anethole and some of their known or possible metabolites for Salmonella typhimurium mutants Mutat. Res. 60, 143-153
    • (1979) Mutat. Res. , vol.60 , pp. 143-153
    • Swanson, A.B.1    Chambliss, D.D.2    Blomquist, J.C.3    Miller, E.C.4    Miller, J.A.5
  • 43
    • 0020028632 scopus 로고
    • Genotoxicity of safrole-related chemicals in microbial test systems
    • Sekizawa, J. and Shibamoto, T. (1982) Genotoxicity of safrole-related chemicals in microbial test systems Mutat. Res. 101, 127-140
    • (1982) Mutat. Res. , vol.101 , pp. 127-140
    • Sekizawa, J.1    Shibamoto, T.2
  • 44
    • 0020676427 scopus 로고
    • Mutagenicity of constituents of pulp and paper mill effluent in growing cells of Saccharomyces cerevisiae
    • Nestmann, E. R. and Lee, E. G. H. (1983) Mutagenicity of constituents of pulp and paper mill effluent in growing cells of Saccharomyces cerevisiae Mutat. Res. 119, 273-280
    • (1983) Mutat. Res. , vol.119 , pp. 273-280
    • Nestmann, E.R.1    Lee, E.G.H.2
  • 45
    • 0028170840 scopus 로고
    • The genotoxic potential in vitro and in vivo of the allyl benzene etheric oils estragole, basil oil and trans -anethole
    • Muller, L., Kasper, P., Muler-Tegethoff, K., and Petr, T. (1994) The genotoxic potential in vitro and in vivo of the allyl benzene etheric oils estragole, basil oil and trans -anethole Mutat. Res. 325, 129-136
    • (1994) Mutat. Res. , vol.325 , pp. 129-136
    • Muller, L.1    Kasper, P.2    Muler-Tegethoff, K.3    Petr, T.4
  • 46
    • 84904684477 scopus 로고
    • Lorillard Inc., Study No. T5407.380, Microbiological Associates, Inc. Rockville, MD, unpublished report to the Flavor and Extract Manufacturers Association of the USA, Washington, DC
    • Lorillard Inc. (1987) Unscheduled DNA Synthesis in Rat Primary Hepatocytes Test Article Anethole Lot No. 104048, Study No. T5407.380, Microbiological Associates, Inc., Rockville, MD, unpublished report to the Flavor and Extract Manufacturers Association of the USA, Washington, DC.
    • (1987) Unscheduled DNA Synthesis in Rat Primary Hepatocytes Test Article Anethole Lot No. 104048
  • 47
    • 84904707530 scopus 로고
    • Recherche d′une eventuelle potentilaite genotoxique du p-methoxy-propenylbenzene par la technique du micronucleus chez la souris, unpublished report of C.E.R.T.I. submitted to WHO by Pernod Ricard
    • Siou, G., Lerond-Conan, L., El Haitem, M., and Lancrampe, M. (1984) Recherche d′une eventuelle potentilaite genotoxique du p-methoxy-propenylbenzene par la technique du micronucleus chez la souris, unpublished report of C.E.R.T.I., submitted to WHO by Pernod Ricard.
    • (1984)
    • Siou, G.1    Lerond-Conan, L.2    El Haitem, M.3    Lancrampe, M.4
  • 48
    • 0030040885 scopus 로고    scopus 로고
    • Anti-genotoxic effects in mice after the interaction between coffee and dietary constituents
    • Abraham, S. K. (1996) Anti-genotoxic effects in mice after the interaction between coffee and dietary constituents Food Chem. Toxicol. 34, 15-20
    • (1996) Food Chem. Toxicol. , vol.34 , pp. 15-20
    • Abraham, S.K.1
  • 49
    • 0029133499 scopus 로고
    • Influence of anethole treatment on the tumour induced by Ehrlich ascites carcinoma cells in paw of Swiss albino mice
    • Al-Harbi, M. M., Qureshi, S., Raza, M., Ahmed, M. M., and Giangreco, A. B. (1995) Influence of anethole treatment on the tumour induced by Ehrlich ascites carcinoma cells in paw of Swiss albino mice Eur. J. Cancer Pre. 4, 307-318
    • (1995) Eur. J. Cancer Pre. , vol.4 , pp. 307-318
    • Al-Harbi, M.M.1    Qureshi, S.2    Raza, M.3    Ahmed, M.M.4    Giangreco, A.B.5
  • 50
    • 77049091176 scopus 로고
    • NTP, National Toxicology Program, NTP TR 223, NTP Publication Number 84-1779, National Toxicology Program, Research Triangle Park, NC
    • NTP, National Toxicology Program (1983) Carcinogenesis Studies of Eugenol (CAS No. 97-53-0) in F344/N rats and B6C3F1 mice (feed studies), NTP TR 223, NTP Publication Number 84-1779, National Toxicology Program, Research Triangle Park, NC.
    • (1983) Carcinogenesis Studies of Eugenol (CAS No. 97-53-0) in F344/N Rats and B6C3F1 Mice (Feed Studies)
  • 52
    • 84904708902 scopus 로고
    • JECFA (Joint FAO/WHO Expert Committee on Food Additives), WHO Food Additives Series 17, WHO, Geneva, Switzerland
    • JECFA (Joint FAO/WHO Expert Committee on Food Additives) (1982) Toxicological Evaluation of Certain Veterinary Drug Residues in Food, WHO Food Additives Series 17, WHO, Geneva, Switzerland.
    • (1982) Toxicological Evaluation of Certain Veterinary Drug Residues in Food
  • 53
    • 0003794616 scopus 로고    scopus 로고
    • JECFA (Joint FAO/WHO Expert Committee on Food Additives), WHO Food Additives Series 56, pp, WHO, Geneva, Switzerland
    • JECFA (Joint FAO/WHO Expert Committee on Food Additives) (2006) Safety Evaluation of Certain Food Additives, WHO Food Additives Series 56, pp 155-161, WHO, Geneva, Switzerland.
    • (2006) Safety Evaluation of Certain Food Additives , pp. 155-161
  • 54
    • 85078382555 scopus 로고    scopus 로고
    • Conclusion on the peer review of the pesticide risk assessment of the active substance eugenol
    • EFSA (European Food Safety Authority). DOI: 10.2903/j.efsa.2012.2914
    • EFSA (European Food Safety Authority) (2012) Conclusion on the peer review of the pesticide risk assessment of the active substance eugenol. EFSA J. DOI: 10.2903/j.efsa.2012.2914.
    • (2012) EFSA J.
  • 56
    • 0023235633 scopus 로고
    • Induction of forestomach lesions in rats by oral administrations of naturally occurring antioxidants for 4 weeks
    • Hirose, M. A., Imaida, K., Kagawa, M., Tsuda, H., and Ito, N. (1987) Induction of forestomach lesions in rats by oral administrations of naturally occurring antioxidants for 4 weeks Jpn. J. Cancer Res. 78, 317-321
    • (1987) Jpn. J. Cancer Res. , vol.78 , pp. 317-321
    • Hirose, M.A.1    Imaida, K.2    Kagawa, M.3    Tsuda, H.4    Ito, N.5
  • 61
    • 0016346972 scopus 로고
    • The metabolism of safrole and 2′,3′-epoxysafrole in the rat and guinea pig
    • Stillwell, W. G., Carman, M. J., Bell, L., and Horning, M. G. (1974) The metabolism of safrole and 2′,3′-epoxysafrole in the rat and guinea pig Drug Metab. Dispos. 2, 489-498
    • (1974) Drug Metab. Dispos. , vol.2 , pp. 489-498
    • Stillwell, W.G.1    Carman, M.J.2    Bell, L.3    Horning, M.G.4
  • 62
    • 0017365837 scopus 로고
    • Absorption, metabolism and excretion of safrole in the rat and man
    • Benedetti, M. S., Malnoë, A., and Broillet, A. L. (1977) Absorption, metabolism and excretion of safrole in the rat and man Toxicology 7, 69-83
    • (1977) Toxicology , vol.7 , pp. 69-83
    • Benedetti, M.S.1    Malnoë, A.2    Broillet, A.L.3
  • 63
    • 0015895662 scopus 로고
    • Metabolism of alkenebenzene derivatives in the rat I. P-Methoxyallylbenzene (estragole) and p-methoxypropenylbenzene (anethole)
    • Solheim, E. and Scheline, R. R. (1973) Metabolism of alkenebenzene derivatives in the rat I. p-Methoxyallylbenzene (estragole) and p-methoxypropenylbenzene (anethole) Xenobiotica 3, 493-510
    • (1973) Xenobiotica , vol.3 , pp. 493-510
    • Solheim, E.1    Scheline, R.R.2
  • 64
    • 0023543566 scopus 로고
    • Metabolism of estragole in rat and mouse and influence of dose size on excretion of the proximate carcinogen 1′-hydroxyestragole
    • Anthony, A., Caldwell, J., Hutt, A. J., and Smith, R. L. (1987) Metabolism of estragole in rat and mouse and influence of dose size on excretion of the proximate carcinogen 1′-hydroxyestragole Food Chem. Toxicol. 25, 799-806
    • (1987) Food Chem. Toxicol. , vol.25 , pp. 799-806
    • Anthony, A.1    Caldwell, J.2    Hutt, A.J.3    Smith, R.L.4
  • 65
    • 67650727414 scopus 로고    scopus 로고
    • Use of physiologically based biokinetic (PBBK) modeling to study estragole bioactivation and detoxification in humans as compared with male rats
    • Punt, A., Paini, A., Boersma, M. G., Freidig, A. P., Delatour, T., Scholz, G., Schilter, B., Van Bladeren, P. J., and Rietjens, I. M. C. M. (2009) Use of physiologically based biokinetic (PBBK) modeling to study estragole bioactivation and detoxification in humans as compared with male rats Toxicol. Sci. 110, 255-269
    • (2009) Toxicol. Sci. , vol.110 , pp. 255-269
    • Punt, A.1    Paini, A.2    Boersma, M.G.3    Freidig, A.P.4    Delatour, T.5    Scholz, G.6    Schilter, B.7    Van Bladeren, P.J.8    Rietjens, I.M.C.M.9
  • 66
    • 84859958511 scopus 로고    scopus 로고
    • Physiologically based kinetic modeling of bioactivation and detoxification of the alkenylbenzene methyleugenol in human as compared to rat
    • Al-Subeihi, A. A. A., Spenkelink, B., Punt, A., Boersma, M. G., Van Bladeren, P. J., and Rietjens, I. M. C. M. (2012) Physiologically based kinetic modeling of bioactivation and detoxification of the alkenylbenzene methyleugenol in human as compared to rat Toxicol. Appl. Pharmacol. 260, 271-284
    • (2012) Toxicol. Appl. Pharmacol. , vol.260 , pp. 271-284
    • Al-Subeihi, A.A.A.1    Spenkelink, B.2    Punt, A.3    Boersma, M.G.4    Van Bladeren, P.J.5    Rietjens, I.M.C.M.6
  • 67
    • 84865377799 scopus 로고    scopus 로고
    • Physiologically based biokinetic (PBBK) modeling of safrole bioactivation and detoxification in human as compared with rat
    • Martati, E., Boersma, M. G., Spenkelink, A., Khadka, D. B., Punt, A., Van Bladeren, P. J., and Rietjens, I. M. C. M. (2012) Physiologically based biokinetic (PBBK) modeling of safrole bioactivation and detoxification in human as compared with rat Toxicol. Sci. 12, 301-316
    • (2012) Toxicol. Sci. , vol.12 , pp. 301-316
    • Martati, E.1    Boersma, M.G.2    Spenkelink, A.3    Khadka, D.B.4    Punt, A.5    Van Bladeren, P.J.6    Rietjens, I.M.C.M.7
  • 68
    • 0019421614 scopus 로고
    • Dose dependent conversion of estragole in the rat and mouse to the carcinogenic metabolite, 1′-hydroxyestragole
    • Zangouras, A., Caldwell, J., Hutt, A. J., and Smith, R. L. (1981) Dose dependent conversion of estragole in the rat and mouse to the carcinogenic metabolite, 1′-hydroxyestragole Biochem. Pharmacol. 30, 1383-1386
    • (1981) Biochem. Pharmacol. , vol.30 , pp. 1383-1386
    • Zangouras, A.1    Caldwell, J.2    Hutt, A.J.3    Smith, R.L.4
  • 69
    • 0020966109 scopus 로고
    • The metabolism of p-propylanisole in the rat and mouse and its variation with dose
    • Sangster, S. A., Caldwell, J., Hutt, A. J., and Smith, R. L. (1983) The metabolism of p-propylanisole in the rat and mouse and its variation with dose Food Chem. Toxicol. 21, 263-271
    • (1983) Food Chem. Toxicol. , vol.21 , pp. 263-271
    • Sangster, S.A.1    Caldwell, J.2    Hutt, A.J.3    Smith, R.L.4
  • 70
    • 0026683699 scopus 로고
    • Hydrolysis of the 2′,3′-allylic epoxides of allylbenzene, estragole, eugenol, and safrole by both microsomal and cytosolic epoxide hydrolases
    • Luo, G., Qato, M. K., and Guenthner, T. M. (1992) Hydrolysis of the 2′,3′-allylic epoxides of allylbenzene, estragole, eugenol, and safrole by both microsomal and cytosolic epoxide hydrolases Drug Metab. Dispos. 20, 440-445
    • (1992) Drug Metab. Dispos. , vol.20 , pp. 440-445
    • Luo, G.1    Qato, M.K.2    Guenthner, T.M.3
  • 71
    • 0028861306 scopus 로고
    • Metabolism of allylbenzene 2′,3′-oxide and estragole 2′,3′-oxide in the isolated perfused rat liver
    • Luo, G. and Guenthner, T. M. (1995) Metabolism of allylbenzene 2′,3′-oxide and estragole 2′,3′-oxide in the isolated perfused rat liver J. Pharmacol. Exp. Ther. 272, 588-596
    • (1995) J. Pharmacol. Exp. Ther. , vol.272 , pp. 588-596
    • Luo, G.1    Guenthner, T.M.2
  • 72
    • 0035819912 scopus 로고    scopus 로고
    • Investigation of the role of the 2′,3′-epoxidation pathway in the bioactivation and genotoxicity of dietary allylbenzene analogs
    • Guenthner, T. M. and Luo, G. (2001) Investigation of the role of the 2′,3′-epoxidation pathway in the bioactivation and genotoxicity of dietary allylbenzene analogs Toxicology 160, 47-58
    • (2001) Toxicology , vol.160 , pp. 47-58
    • Guenthner, T.M.1    Luo, G.2
  • 73
    • 0019788152 scopus 로고
    • Safrole: Its metabolism, carcinogenicity and interactions with cytochrome P-450
    • Ioannides, C., Delaforge, M., and Parke, D. V. (1981) Safrole: Its metabolism, carcinogenicity and interactions with cytochrome P-450 Food Cosmet. Toxicol. 19, 657-666
    • (1981) Food Cosmet. Toxicol. , vol.19 , pp. 657-666
    • Ioannides, C.1    Delaforge, M.2    Parke, D.V.3
  • 75
    • 0019378206 scopus 로고
    • Structures of the DNA adducts formed in mouse liver after administration of the proximate hepatocarcinogen 1′-hydroxyestragole
    • Phillips, D. H., Miller, J. A., Miller, E. C., and Adams, B. (1981) Structures of the DNA adducts formed in mouse liver after administration of the proximate hepatocarcinogen 1′-hydroxyestragole Cancer Res. 41, 176-186
    • (1981) Cancer Res. , vol.41 , pp. 176-186
    • Phillips, D.H.1    Miller, J.A.2    Miller, E.C.3    Adams, B.4
  • 76
    • 0020595109 scopus 로고
    • The metabolic activation and nucleic acid adducts of naturally-occuring carcinogens: Recent results with ethyl carbamate and the spice flavors safrole and estragole
    • Miller, J. A. and Miller, E. C. (1983) The metabolic activation and nucleic acid adducts of naturally-occuring carcinogens: Recent results with ethyl carbamate and the spice flavors safrole and estragole Br. J. Cancer 48, 1-15
    • (1983) Br. J. Cancer , vol.48 , pp. 1-15
    • Miller, J.A.1    Miller, E.C.2
  • 77
    • 0021173863 scopus 로고
    • Characterization of the biliary and urinary glutathione and N-acetylcysteine metabolites of the hepatic carcinogen 1′-hydroxysafrole and its 1′-oxo metabolite in rats and mice
    • Fennell, T. R., Miller, J. A., and Miller, E. C. (1984) Characterization of the biliary and urinary glutathione and N-acetylcysteine metabolites of the hepatic carcinogen 1′-hydroxysafrole and its 1′-oxo metabolite in rats and mice Cancer Res. 44, 3231-3240
    • (1984) Cancer Res. , vol.44 , pp. 3231-3240
    • Fennell, T.R.1    Miller, J.A.2    Miller, E.C.3
  • 78
    • 79954479248 scopus 로고    scopus 로고
    • Detection and quantification of specific DNA adducts by liquid chromatography-tandem mass spectrometry in the livers of rats given estragole at the carcinogenic dose
    • Ishii, Y., Suzuki, Y., Hibi, D., Jin, M., Fukuhara, K., Umemura, T., and Nishikawa, A. (2011) Detection and quantification of specific DNA adducts by liquid chromatography-tandem mass spectrometry in the livers of rats given estragole at the carcinogenic dose Chem. Res. Toxicol. 24, 532-541
    • (2011) Chem. Res. Toxicol. , vol.24 , pp. 532-541
    • Ishii, Y.1    Suzuki, Y.2    Hibi, D.3    Jin, M.4    Fukuhara, K.5    Umemura, T.6    Nishikawa, A.7
  • 79
    • 34547641946 scopus 로고    scopus 로고
    • Tandem mass spectrometry analysis of N 2-(trans -isoestragole-3′-yl)-2′deoxyguanosime as a strategy to study species differences in sulfotransferase conversion of the proximate carcinogen 1′-hydroxyestragole
    • Punt, A., Delatour, T., Scholz, G., Schilter, B., van Bladeren, P. J., and Rietjens, I. M. C. M. (2007) Tandem mass spectrometry analysis of N 2-(trans -isoestragole-3′-yl)-2′deoxyguanosime as a strategy to study species differences in sulfotransferase conversion of the proximate carcinogen 1′-hydroxyestragole Chem. Res. Toxicol. 20, 991-998
    • (2007) Chem. Res. Toxicol. , vol.20 , pp. 991-998
    • Punt, A.1    Delatour, T.2    Scholz, G.3    Schilter, B.4    Van Bladeren, P.J.5    Rietjens, I.M.C.M.6
  • 80
    • 30444457731 scopus 로고    scopus 로고
    • Mechanism studies on the CSI reaction with allyl ethers by varying p-substituent
    • Jung, Y. H. and Kim, J. D. (2003) Mechanism studies on the CSI reaction with allyl ethers by varying p-substituent Arch. Pharmacal. Res. 26, 667-678
    • (2003) Arch. Pharmacal. Res. , vol.26 , pp. 667-678
    • Jung, Y.H.1    Kim, J.D.2
  • 81
    • 84877106342 scopus 로고    scopus 로고
    • Abundance of DNA adducts of methyleugenol, a rodent hepatocarcinogen, in human liver samples
    • Herrmann, K., Schumacher, F., Engst, W., Appel, K. E., Klein, K., Zanger, U. M., and Glatt, H. (2013) Abundance of DNA adducts of methyleugenol, a rodent hepatocarcinogen, in human liver samples Carcinogenesis 34, 1025-1030
    • (2013) Carcinogenesis , vol.34 , pp. 1025-1030
    • Herrmann, K.1    Schumacher, F.2    Engst, W.3    Appel, K.E.4    Klein, K.5    Zanger, U.M.6    Glatt, H.7
  • 82
    • 0023619038 scopus 로고
    • The metabolic disposition of [methoxy-14C]-labelled trans -anethole, estragole and p-propylanisole in human volunteers
    • Sangster, S. A., Caldwell, J., Hutt, A. J., Anthony, A., and Smith, R. L. (1987) The metabolic disposition of [methoxy-14C]-labelled trans -anethole, estragole and p-propylanisole in human volunteers Xenobiotica 17, 1223-1232
    • (1987) Xenobiotica , vol.17 , pp. 1223-1232
    • Sangster, S.A.1    Caldwell, J.2    Hutt, A.J.3    Anthony, A.4    Smith, R.L.5
  • 83
    • 33746309901 scopus 로고    scopus 로고
    • Abuse of nutmeg (Myristica fragrans Houtt.): Studies on the metabolism and the toxicologic detection of its ingredients elemicin, myristicin, and safrole in rat and human urine using gas chromatography/mass spectrometry
    • Beyer, J., Ehlers, D., and Maurer, H. H. (2006) Abuse of nutmeg (Myristica fragrans Houtt.): studies on the metabolism and the toxicologic detection of its ingredients elemicin, myristicin, and safrole in rat and human urine using gas chromatography/mass spectrometry Ther. Drug Monit. 28, 568-575
    • (2006) Ther. Drug Monit. , vol.28 , pp. 568-575
    • Beyer, J.1    Ehlers, D.2    Maurer, H.H.3
  • 85
    • 0027326903 scopus 로고
    • Formation and persistence of safrole-DNA adducts over a 10,000-fold dose range in mouse liver
    • Gupta, K. P., van Golen, K. L., Putman, K. L., and Randerath, K. (1993) Formation and persistence of safrole-DNA adducts over a 10,000-fold dose range in mouse liver Carcinogenesis 14, 1517-1521
    • (1993) Carcinogenesis , vol.14 , pp. 1517-1521
    • Gupta, K.P.1    Van Golen, K.L.2    Putman, K.L.3    Randerath, K.4
  • 86
    • 76749144742 scopus 로고    scopus 로고
    • In-silico methods for physiologically based biokinetic models describing bioactivation and detoxification of coumarin and estragole: Implications for risk assessment
    • Rietjens, I. M. C. M., Punt, A., Schilter, B., Scholz, G., Delatour, T., and van Bladeren, P. J. (2010) In-silico methods for physiologically based biokinetic models describing bioactivation and detoxification of coumarin and estragole: Implications for risk assessment Mol. Nutr. Food Res. 54, 195-207
    • (2010) Mol. Nutr. Food Res. , vol.54 , pp. 195-207
    • Rietjens, I.M.C.M.1    Punt, A.2    Schilter, B.3    Scholz, G.4    Delatour, T.5    Van Bladeren, P.J.6
  • 87
    • 77952546103 scopus 로고    scopus 로고
    • A physiologically based biodynamic (PBBD) model for estragole DNA binding in rat liver based on in vitro kinetic data and estragole DNA adduct formation in rat primary hepatocytes
    • Paini, A., Punt, A., Viton, F., Scholz, G., Delatour, T., Marin-Kuan, M., Schilter, B., van Bladeren, P. J., and Rietjens, I. M. C. M. (2010) A physiologically based biodynamic (PBBD) model for estragole DNA binding in rat liver based on in vitro kinetic data and estragole DNA adduct formation in rat primary hepatocytes Toxicol. Appl. Pharmacol. 245, 57-66
    • (2010) Toxicol. Appl. Pharmacol. , vol.245 , pp. 57-66
    • Paini, A.1    Punt, A.2    Viton, F.3    Scholz, G.4    Delatour, T.5    Marin-Kuan, M.6    Schilter, B.7    Van Bladeren, P.J.8    Rietjens, I.M.C.M.9
  • 90
    • 0024510193 scopus 로고
    • Histopathological evaluation of proliferative liver lesions in rats fed trans -anethole in chronic studies
    • Newberne, P. M., Carlton, W. W., and Brown, W. R. (1989) Histopathological evaluation of proliferative liver lesions in rats fed trans -anethole in chronic studies Food Chem. Toxicol. 27, 21-26
    • (1989) Food Chem. Toxicol. , vol.27 , pp. 21-26
    • Newberne, P.M.1    Carlton, W.W.2    Brown, W.R.3
  • 91
    • 0023888902 scopus 로고
    • Influence of dose size on the disposition of trans -[methoxy- 14C]anethole in human volunteers
    • Caldwell, J. and Sutton, J. D. (1988) Influence of dose size on the disposition of trans -[methoxy-14C]anethole in human volunteers Food Chem. Toxicol. 26, 87-91
    • (1988) Food Chem. Toxicol. , vol.26 , pp. 87-91
    • Caldwell, J.1    Sutton, J.D.2
  • 92
    • 0017286721 scopus 로고
    • Metabolism of alkenebenzene derivatives in the rat. II. Eugenol and isoeugenol methyl ethers
    • Solheim, E. and Scheline, R. R. (1976) Metabolism of alkenebenzene derivatives in the rat. II. Eugenol and isoeugenol methyl ethers Xenobiotica 6, 137-150
    • (1976) Xenobiotica , vol.6 , pp. 137-150
    • Solheim, E.1    Scheline, R.R.2
  • 93
    • 0030035224 scopus 로고    scopus 로고
    • Pathways of metabolism of [1′-14C] trans -anethole in the rat and mouse
    • Bounds, S. V. and Caldwell, J. (1996) Pathways of metabolism of [1′-14C] trans -anethole in the rat and mouse Drug Metab. Dispos. 24, 717-724
    • (1996) Drug Metab. Dispos. , vol.24 , pp. 717-724
    • Bounds, S.V.1    Caldwell, J.2
  • 95
    • 84904601464 scopus 로고
    • Ph.D. Thesis submitted for the degree of Doctor of Philosophy in the University of London, unpublished work
    • Sutton, J. D. (1986) Metabolic Studies of Eugenol in Relation to Its Safety Evaluation, Ph.D. Thesis submitted for the degree of Doctor of Philosophy in the University of London, unpublished work.
    • (1986) Metabolic Studies of Eugenol in Relation to Its Safety Evaluation
    • Sutton, J.D.1
  • 96
    • 0021923439 scopus 로고
    • Dose-dependent variation in the disposition of eugenol in the rat
    • Sutton, J. D., Sangster, S., and Caldwell, J. (1985) Dose-dependent variation in the disposition of eugenol in the rat Biochem. Pharmacol. 34, 465-466
    • (1985) Biochem. Pharmacol. , vol.34 , pp. 465-466
    • Sutton, J.D.1    Sangster, S.2    Caldwell, J.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.