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Volumn 28, Issue 9, 2015, Pages 1760-1773

Hepatic Metabolism of Carcinogenic β-Asarone

Author keywords

[No Author keywords available]

Indexed keywords

AROCLOR 1254; BETA ASARONE; CYTOCHROME P450; SULFOTRANSFERASE; ANISOLE DERIVATIVE; ASARONE; CARCINOGEN;

EID: 84941966067     PISSN: 0893228X     EISSN: 15205010     Source Type: Journal    
DOI: 10.1021/acs.chemrestox.5b00223     Document Type: Article
Times cited : (45)

References (44)
  • 1
    • 84877927370 scopus 로고    scopus 로고
    • Molecular and chemical profiling of sweet flag (Acorus calamus L.) germplasm from India
    • Rana, T. S., Mahar, K. S., Pandey, M. M., Srivastava, S. K., and Rawat, A. K. (2013) Molecular and chemical profiling of sweet flag (Acorus calamus L.) germplasm from India Physiol. Mol. Biol. Plants 19, 231-237 10.1007/s12298-013-0164-8
    • (2013) Physiol. Mol. Biol. Plants , vol.19 , pp. 231-237
    • Rana, T.S.1    Mahar, K.S.2    Pandey, M.M.3    Srivastava, S.K.4    Rawat, A.K.5
  • 2
    • 84883233958 scopus 로고    scopus 로고
    • Chemical compositions, phytotoxicity, and biological activities of Acorus calamus essential oils from Nepal
    • Satyal, P., Paudel, P., Poudel, A., Dosoky, N. S., Moriarity, D. M., Vogler, B., and Setzer, W. N. (2013) Chemical compositions, phytotoxicity, and biological activities of Acorus calamus essential oils from Nepal Nat. Prod. Commun. 8, 1179-1181
    • (2013) Nat. Prod. Commun. , vol.8 , pp. 1179-1181
    • Satyal, P.1    Paudel, P.2    Poudel, A.3    Dosoky, N.S.4    Moriarity, D.M.5    Vogler, B.6    Setzer, W.N.7
  • 3
    • 84896490225 scopus 로고    scopus 로고
    • An overview on traditional uses and pharmacological profile of Acorus calamus Linn. (Sweet flag) and other Acorus species
    • Rajput, S. B., Tonge, M. B., and Karuppayil, S. M. (2014) An overview on traditional uses and pharmacological profile of Acorus calamus Linn. (Sweet flag) and other Acorus species Phytomedicine 21, 268-276 10.1016/j.phymed.2013.09.020
    • (2014) Phytomedicine , vol.21 , pp. 268-276
    • Rajput, S.B.1    Tonge, M.B.2    Karuppayil, S.M.3
  • 4
    • 34848853246 scopus 로고    scopus 로고
    • Acorus calamus: Scientific Validation of Ayurvedic Tradition from Natural Resources
    • Mukherjee, P. K., Kumar, V., Mal, M., and Houghton, P. J. (2007) Acorus calamus: Scientific Validation of Ayurvedic Tradition from Natural Resources Pharm. Biol. 45, 651-666 10.1080/13880200701538724
    • (2007) Pharm. Biol. , vol.45 , pp. 651-666
    • Mukherjee, P.K.1    Kumar, V.2    Mal, M.3    Houghton, P.J.4
  • 5
    • 34250368093 scopus 로고    scopus 로고
    • In vitro Acetylcholinesterase Inhibitory Activity of the Essential Oil from Acorus calamus and its Main Constituents
    • Mukherjee, P. K., Kumar, V., Mal, M., and Houghton, P. J. (2007) In vitro Acetylcholinesterase Inhibitory Activity of the Essential Oil from Acorus calamus and its Main Constituents Planta Med. 73, 283-285 10.1055/s-2007-967114
    • (2007) Planta Med. , vol.73 , pp. 283-285
    • Mukherjee, P.K.1    Kumar, V.2    Mal, M.3    Houghton, P.J.4
  • 7
    • 74549139705 scopus 로고    scopus 로고
    • Bioanalytical Investigation of Aasarone in Connection with Acorus calamus Oil Intoxications
    • Björnstad, K., Helander, A., Hultén, P., and Beck, O. (2009) Bioanalytical Investigation of Aasarone in Connection with Acorus calamus Oil Intoxications J. Anal. Toxicol. 33, 604-609 10.1093/jat/33.9.604
    • (2009) J. Anal. Toxicol. , vol.33 , pp. 604-609
    • Björnstad, K.1    Helander, A.2    Hultén, P.3    Beck, O.4
  • 10
    • 84871284915 scopus 로고    scopus 로고
    • Analysis of transformation and excretion of β-asarone in rabbits with GC-MS
    • Fang, Y. Q., Shi, C., Liu, L., and Fang, R. M. (2012) Analysis of transformation and excretion of β-asarone in rabbits with GC-MS Eur. J. Drug Metab. Pharmacokinet. 37, 187-190 10.1007/s13318-012-0083-z
    • (2012) Eur. J. Drug Metab. Pharmacokinet. , vol.37 , pp. 187-190
    • Fang, Y.Q.1    Shi, C.2    Liu, L.3    Fang, R.M.4
  • 11
    • 84860647087 scopus 로고    scopus 로고
    • Pharmacokinetics of β-asarone in rabbit blood, hippocampus, cortex, brain stem, thalamus and cerebellum
    • Fang, Y. Q., Shi, C., Liu, L., and Fang, R. M. (2012) Pharmacokinetics of β-asarone in rabbit blood, hippocampus, cortex, brain stem, thalamus and cerebellum Pharmazie 67, 120-123 10.1691/ph.2012.1100
    • (2012) Pharmazie , vol.67 , pp. 120-123
    • Fang, Y.Q.1    Shi, C.2    Liu, L.3    Fang, R.M.4
  • 12
    • 84890061380 scopus 로고    scopus 로고
    • Simultaneous Determination of Volatile Constituents from Acorus tatarinowii Schott in Rat Plasma by Gas Chromatography-Mass Spectrometry with Selective Ion Monitoring and Application in Pharmacokinetic Study
    • Meng, X., Zhao, X., Wang, S., Jia, P., Bai, Y., Liao, S., and Zheng, X. (2013) Simultaneous Determination of Volatile Constituents from Acorus tatarinowii Schott in Rat Plasma by Gas Chromatography-Mass Spectrometry with Selective Ion Monitoring and Application in Pharmacokinetic Study J. Anal. Methods Chem. 2013, 1-7 10.1155/2013/949830
    • (2013) J. Anal. Methods Chem. , vol.2013 , pp. 1-7
    • Meng, X.1    Zhao, X.2    Wang, S.3    Jia, P.4    Bai, Y.5    Liao, S.6    Zheng, X.7
  • 13
    • 0023241740 scopus 로고
    • Structure-Activity Studies of the Hepatocarcinogenicities of Alkenylbenzene Derivatives Related to Estragole and Safrole on Administration to Preweanling Male C57BL/6J × 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 × C3H/HeJ F1 mice Cancer Res. 47, 2275-2278
    • (1987) Cancer Res. , vol.47 , pp. 2275-2278
    • Wiseman, R.W.1    Miller, E.C.2    Miller, J.A.3    Liem, A.4
  • 14
    • 0003520236 scopus 로고
    • JECFA (Joint FAO/WHO Expert Committee on Food Additives) (), WHO Technical Report Series No. 669, pp, WHO, Geneva, Switzerland.
    • JECFA (Joint FAO/WHO Expert Committee on Food Additives) (1981) Toxicological Evaluation of Certain Food Additives, WHO Technical Report Series No. 669, pp 33-44, WHO, Geneva, Switzerland.
    • (1981) Toxicological Evaluation of Certain Food Additives , pp. 33-44
  • 15
    • 84862556638 scopus 로고    scopus 로고
    • Levels of Genotoxic and Carcinogenic Compounds in Plant Food Supplements and Associated Risk Assessment
    • van den Berg, S. J., Restani, P., Boersma, M. G., Delmulle, L., and Rietjens, I. M. (2011) Levels of Genotoxic and Carcinogenic Compounds in Plant Food Supplements and Associated Risk Assessment Food Nutr. Sci. 2, 989-1010 10.4236/fns.2011.29134
    • (2011) Food Nutr. Sci. , vol.2 , pp. 989-1010
    • Van Den Berg, S.J.1    Restani, P.2    Boersma, M.G.3    Delmulle, L.4    Rietjens, I.M.5
  • 17
    • 84941985893 scopus 로고    scopus 로고
    • SCF (Scientific Committee on Food) () Opinion of the Scientific Committee on Food on the Presence of β-Asarone in Flavourings and Other Food Ingredients with Flavouring Properties, SCF/CS/FLAV/FLAVOUR/9-en.pdf. ADD1 Final, available online at.
    • SCF (Scientific Committee on Food) (2002) Opinion of the Scientific Committee on Food on the Presence of β-Asarone in Flavourings and Other Food Ingredients with Flavouring Properties, SCF/CS/FLAV/FLAVOUR/9 ADD1 Final, available online at http://ec.europa.eu/food/fs/sc/scf/out111
    • (2002)
  • 19
    • 0020576244 scopus 로고
    • Mutagenicity testing of β-asarone and commercial calamus drugs with Salmonella typhimurium
    • Göggelmann, W. and Schimmer, O. (1983) Mutagenicity testing of β-asarone and commercial calamus drugs with Salmonella typhimurium Mutat. Res. Lett. 121, 191-194 10.1016/0165-7992(83)90202-6
    • (1983) Mutat. Res. Lett. , vol.121 , pp. 191-194
    • Göggelmann, W.1    Schimmer, O.2
  • 20
    • 84941962003 scopus 로고
    • Genotoxic activity of β-asarone and commercial calamus drugs
    • Abel, G. and Göggelmann, W. (1986) Genotoxic activity of β-asarone and commercial calamus drugs Mutat. Res., Environ. Mutagen. Relat. Subj. 164, 287 10.1016/0165-1161(86)90126-3
    • (1986) Mutat. Res., Environ. Mutagen. Relat. Subj. , vol.164 , pp. 287
    • Abel, G.1    Göggelmann, W.2
  • 21
    • 0028178150 scopus 로고
    • Genotoxicity of the Alkenylbenzenes α- And β-Asarone, Myristicin and Elimicin as Determined by the UDS Assay in Cultured Rat Hepatocytes
    • Hasheminejad, G. and Caldwell, J. (1994) Genotoxicity of the Alkenylbenzenes α- and β-Asarone, Myristicin and Elimicin as Determined by the UDS Assay in Cultured Rat Hepatocytes Food Chem. Toxicol. 32, 223-231 10.1016/0278-6915(94)90194-5
    • (1994) Food Chem. Toxicol. , vol.32 , pp. 223-231
    • Hasheminejad, G.1    Caldwell, J.2
  • 22
    • 0035061234 scopus 로고    scopus 로고
    • Micronucleus Formation in Human Lymphocytes and in the Metabolically Competent Human Hepatoma Cell Line Hep-G2: Results with 15 Naturally Occurring Substances
    • Kevekordes, S., Spielberger, J., Burghaus, C. M., Birkenkamp, P., Zietz, B., Paufler, P., Diez, M., Bolten, C., and Dunkelberg, H. (2001) Micronucleus Formation in Human Lymphocytes and in the Metabolically Competent Human Hepatoma Cell Line Hep-G2: Results with 15 Naturally Occurring Substances Anticancer Res. 21, 461-469
    • (2001) Anticancer Res. , vol.21 , pp. 461-469
    • Kevekordes, S.1    Spielberger, J.2    Burghaus, C.M.3    Birkenkamp, P.4    Zietz, B.5    Paufler, P.6    Diez, M.7    Bolten, C.8    Dunkelberg, H.9
  • 23
    • 84866524791 scopus 로고    scopus 로고
    • Comparative Study of the Cytotoxicity and Genotoxicity of Alpha- and Beta-Asarone
    • Unger, P. and Melzig, M. F. (2012) Comparative Study of the Cytotoxicity and Genotoxicity of Alpha- and Beta-Asarone Sci. Pharm. 80, 663-668 10.3797/scipharm.1204-21
    • (2012) Sci. Pharm. , vol.80 , pp. 663-668
    • Unger, P.1    Melzig, M.F.2
  • 24
    • 0023359755 scopus 로고
    • Chromosome Damaging Effect on Human Lymphocytes by β-Asarone /Chromosomenschädigende Wirkung von beta-Asaron in menschlichen Lymphocyten
    • Abel, G. (1987) Chromosome Damaging Effect on Human Lymphocytes by β-Asarone /Chromosomenschädigende Wirkung von beta-Asaron in menschlichen Lymphocyten Planta Med. 53, 251-253 10.1055/s-2006-962694
    • (1987) Planta Med. , vol.53 , pp. 251-253
    • Abel, G.1
  • 26
    • 84941985894 scopus 로고    scopus 로고
    • Regulation (EC) No. 1334/2008 of the European Parliament and of the Council of 16 December 2008 on Flavourings and Certain Food Ingredients with Flavouring Properties for Use in and on Foods and Amending Council Regulation (EEC) No 1601/91, Regulations (EC) No. 2232/96 and (EC) No. 110/2008 and Directive 2000/13/EC, available online at.
    • Regulation (EC) No. 1334/2008 of the European Parliament and of the Council of 16 December 2008 on Flavourings and Certain Food Ingredients with Flavouring Properties for Use in and on Foods and Amending Council Regulation (EEC) No 1601/91, Regulations (EC) No. 2232/96 and (EC) No. 110/2008 and Directive 2000/13/EC, available online at http://eur-lex.europa.eu/legal-content/EN/TXT/?uri=celex:32008R1334.
  • 27
    • 84941985895 scopus 로고    scopus 로고
    • COE (Committee of Experts on Flavouring Substances of the Council of Europe) () The 1st Report on Active Principles Constituents of Toxicological Concern) Contained in Natural Sources of Flavourings, available online at.
    • COE (Committee of Experts on Flavouring Substances of the Council of Europe) (2005) The 1st Report on Active Principles (Constituents of Toxicological Concern) Contained in Natural Sources of Flavourings, available online at http://www.coe.int/t/e/social-cohesion/soc%2Dsp/public-health/flavouring-substances/Active%20principles.pdf.
    • (2005)
  • 28
    • 80052013370 scopus 로고    scopus 로고
    • Metabolism of Methylisoeugenol in Liver Microsomes of Human, Rat, and Bovine Origin
    • Cartus, A. T., Merz, K. H., and Schrenk, D. (2011) Metabolism of Methylisoeugenol in Liver Microsomes of Human, Rat, and Bovine Origin Drug Metab. Dispos. 39, 1727-1733 10.1124/dmd.111.038851
    • (2011) Drug Metab. Dispos. , vol.39 , pp. 1727-1733
    • Cartus, A.T.1    Merz, K.H.2    Schrenk, D.3
  • 29
    • 0022383140 scopus 로고
    • Metabolism of 2-Methylnaphthalene by Rat and Rainbow Trout Hepatic Microsomes and Purified Cytochromes P-450
    • Melancon, M. J., Williams, D. E., Buhler, D. R., and Lech, J. J. (1985) Metabolism of 2-Methylnaphthalene by Rat and Rainbow Trout Hepatic Microsomes and Purified Cytochromes P-450 Drug Metab. Dispos. 13, 542-547
    • (1985) Drug Metab. Dispos. , vol.13 , pp. 542-547
    • Melancon, M.J.1    Williams, D.E.2    Buhler, D.R.3    Lech, J.J.4
  • 30
    • 0017184389 scopus 로고
    • A Rapid and Sensitive Method for the Quantitation of Microgram Quantities of Protein Utilizing the Principle of Protein-Dye Binding
    • Bradford, M. M. (1976) A Rapid and Sensitive Method for the Quantitation of Microgram Quantities of Protein Utilizing the Principle of Protein-Dye Binding Anal. Biochem. 72, 248-254 10.1016/0003-2697(76)90527-3
    • (1976) Anal. Biochem. , vol.72 , pp. 248-254
    • Bradford, M.M.1
  • 31
    • 0000622703 scopus 로고
    • A new Cytochrome in Liver Microsomes
    • Omura, T. and Sato, R. (1962) A new Cytochrome in Liver Microsomes J. Biol. Chem. 239, 2370-2385
    • (1962) J. Biol. Chem. , vol.239 , pp. 2370-2385
    • Omura, T.1    Sato, R.2
  • 32
    • 0036201594 scopus 로고    scopus 로고
    • Atypical Kinetic Profiles in Drug Metabolism Reactions
    • Hutzler, J. M. and Tracy, T. S. (2002) Atypical Kinetic Profiles in Drug Metabolism Reactions Drug Metab. Dispos. 30, 355-362 10.1124/dmd.30.4.355
    • (2002) Drug Metab. Dispos. , vol.30 , pp. 355-362
    • Hutzler, J.M.1    Tracy, T.S.2
  • 33
    • 0038532316 scopus 로고    scopus 로고
    • The Effect of Incubation Conditions on the Enzyme Kinetics of UDP-Glucuronosyltransferases
    • Soars, M. G., Ring, B. J., and Wrighton, S. A. (2003) The Effect of Incubation Conditions on the Enzyme Kinetics of UDP-Glucuronosyltransferases Drug Metab. Dispos. 31, 762-767 10.1124/dmd.31.6.762
    • (2003) Drug Metab. Dispos. , vol.31 , pp. 762-767
    • Soars, M.G.1    Ring, B.J.2    Wrighton, S.A.3
  • 35
    • 0032441633 scopus 로고    scopus 로고
    • Stereochemistry of the Biotransformation of 1-Hexene and 2-Methyl-1-hexene with Rat Liver Microsomes and Purified P450s of Rats and Humans
    • Chiappe, C., De Rubertis, A., Amato, G., and Gervasi, P. G. (1998) Stereochemistry of the Biotransformation of 1-Hexene and 2-Methyl-1-hexene with Rat Liver Microsomes and Purified P450s of Rats and Humans Chem. Res. Toxicol. 11, 1487-1493 10.1021/tx980170d
    • (1998) Chem. Res. Toxicol. , vol.11 , pp. 1487-1493
    • Chiappe, C.1    De Rubertis, A.2    Amato, G.3    Gervasi, P.G.4
  • 36
    • 0034999950 scopus 로고    scopus 로고
    • Stereochemical Aspects in the 4-Vinylcyclohexene Biotransformation with Rat Liver Microsomes and Purified P450s. Monoepoxides and Diols
    • Chiappe, C., De Rubertis, A., De Carlo, M., Amato, G., and Gervasi, P. G. (2001) Stereochemical Aspects in the 4-Vinylcyclohexene Biotransformation with Rat Liver Microsomes and Purified P450s. Monoepoxides and Diols Chem. Res. Toxicol. 14, 492-499 10.1021/tx000255q
    • (2001) Chem. Res. Toxicol. , vol.14 , pp. 492-499
    • Chiappe, C.1    De Rubertis, A.2    De Carlo, M.3    Amato, G.4    Gervasi, P.G.5
  • 37
    • 0034629436 scopus 로고    scopus 로고
    • Spontaneous Hydrolysis Reactions of cis- and trans-β-Methyl-4-methoxystyrene Oxides (Anethole Oxides): Buildup of trans-Anethole Oxide as an Intermediate in the Spontaneous Reaction of cis-Anethole Oxide
    • Mohan, R. S., Gavardinas, K., Kyere, S., and Whalen, D. L. (2000) Spontaneous Hydrolysis Reactions of cis- and trans-β-Methyl-4-methoxystyrene Oxides (Anethole Oxides): Buildup of trans-Anethole Oxide as an Intermediate in the Spontaneous Reaction of cis-Anethole Oxide J. Org. Chem. 65, 1407-1413 10.1021/jo991521b
    • (2000) J. Org. Chem. , vol.65 , pp. 1407-1413
    • Mohan, R.S.1    Gavardinas, K.2    Kyere, S.3    Whalen, D.L.4
  • 38
    • 0032799750 scopus 로고    scopus 로고
    • New studies on trans-anethole oxide and trans-asarone oxide
    • Kim, S. G., Liem, A., Stewart, B. C., and Miller, J. A. (1999) New studies on trans-anethole oxide and trans-asarone oxide Carcinogenesis 20, 1303-1307 10.1093/carcin/20.7.1303
    • (1999) Carcinogenesis , vol.20 , pp. 1303-1307
    • Kim, S.G.1    Liem, A.2    Stewart, B.C.3    Miller, J.A.4
  • 39
    • 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 10.3109/00498257609151624
    • (1976) Xenobiotica , vol.6 , pp. 137-150
    • Solheim, E.1    Scheline, R.R.2
  • 40
    • 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 10.3109/00498257309151538
    • (1973) Xenobiotica , vol.3 , pp. 493-510
    • Solheim, E.1    Scheline, R.R.2
  • 41
    • 0018955455 scopus 로고
    • Metabolism of lkenebenzene derivatives in the rat. III. Elemicin and isoelemicin
    • Solheim, E. and Scheline, R. R. (1980) Metabolism of lkenebenzene derivatives in the rat. III. Elemicin and isoelemicin Xenobiotica 10, 371-380 10.3109/00498258009033770
    • (1980) Xenobiotica , vol.10 , pp. 371-380
    • Solheim, E.1    Scheline, R.R.2
  • 43
    • 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., and Caldwell, J. (1990) 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 10.1016/0278-6915(90)90152-D
    • (1990) Food Chem. Toxicol. , vol.28 , pp. 537-542
    • Howes, A.J.1    Chan, V.S.2    Caldwell, J.3
  • 44
    • 0028869545 scopus 로고
    • Genotoxicity of trans-anethole in vitro
    • Gorelick, N. J. (1995) Genotoxicity of trans-anethole in vitro Mutat. Res., Fundam. Mol. Mech. Mutagen. 326, 199-209 10.1016/0027-5107(94)00173-3
    • (1995) Mutat. Res., Fundam. Mol. Mech. Mutagen. , vol.326 , pp. 199-209
    • Gorelick, N.J.1


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