Metabolism of the carcinogen alpha-asarone in liver microsomes

Food and Chemical Toxicology

Volumn 87, Issue , 2016, Pages 103-112

  Cartus, Alexander T ^a   Schrenk, Dieter ^a  

^a University of Koblenz Landau   (Germany)

Author keywords

Alkenylbenzene; Asarone; Carcinogenicity; Liver microsomes; Metabolism; Phenylpropanoid

Indexed keywords

ALCOHOL; ALPHA ASARONE; CARCINOGEN; ANISOLE DERIVATIVE; ASARONE;

ACORUS CALAMUS; ANIMAL CELL; ARTICLE; BOVINE; CHEMICAL STRUCTURE; CONCENTRATION (PARAMETERS); CONTROLLED STUDY; DEMETHYLATION; ELECTROSPRAY MASS SPECTROMETRY; EPOXIDATION; GENOTOXICITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN CELL; HYDROLYSIS; HYDROXYLATION; LIQUID CHROMATOGRAPHY; LIVER MICROSOME METABOLISM; NONHUMAN; PIG; RAT; SPECIES DIFFERENCE; TANDEM MASS SPECTROMETRY; TOXICOKINETICS; ANIMAL; CHEMISTRY; FEMALE; KINETICS; LIVER MICROSOME; MALE; METABOLISM; MOUSE; WISTAR RAT;

ANIMALS; ANISOLES; CATTLE; FEMALE; HUMANS; KINETICS; MALE; MICE; MICROSOMES, LIVER; MOLECULAR STRUCTURE; RATS; RATS, WISTAR; SPECIES SPECIFICITY; SWINE;

EID: 84954114945     PISSN: 02786915     EISSN: 18736351     Source Type: Journal    
DOI: 10.1016/j.fct.2015.11.021     Document Type: Article

References (42)

1. Belova L.F., Alibekov S.D., Baginskaia A.I., Sokolov S., Pokrovskaia G.V. Asarone and its biological properties. Farmakol. Toksikol. 1985, 48:17-20.
2. Bradford M.M. A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal. Biochem. 1976, 72:248-254.
3. Cartus A.T., Merz K.H., Schrenk D. Metabolism of methylisoeugenol in liver microsomes of human, rat, and bovine origin. Drug Metab. Dispos. 2011, 39:1727-1733.
4. Cartus A.T., Herrmann K., Weishaupt L.W., Merz K.H., Engst W., Glatt H., Schrenk D. Metabolism of methyleugenol in liver microsomes and primary hepatocytes: pattern of metabolites, cytotoxicity, and DNA-adduct formation. Toxicol. Sci. 2012, 129:21-34.
5. Cartus A.T., Stegmüller S., Simson N., Wahl A., Neef S., Kelm H., Schrenk D. Hepatic Metabolism of Carcinogenic beta-Asarone. Chem. Res. Toxicol. 2015, 28:1760-1773.
6. 21CFR189, Code of Federal Regulations Title 21: Food and Drugs: Chapter I: Food and Drug Administration, Department of Health and Human Services (Continued) Part 189: Substances Prohibited from Use in Human Food 2003, vol. 3:571-572. Food and Drug Administration, Washington, DC.
7. Chamorro G., Salazar M., Salazar S. Dominant lethal effects in male and female Wistar rats after shortterm alpha-asarone treatment. Toxicol. Lett. 1996, 67. Suppl. 1.
8. Chamorro G., Garduño L., Martínez E., Madrigal E., Tamariz J., Salazar M. Dominant lethal study of alpha-asarone in male mice. Toxicol. Lett. 1998, 99:71-77.
9. 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" 2005, online available at:. http://www.coe.int/t/e/social_cohesion/soc%2Dsp/public_health/flavouring_substances/Active%20principles.pdf.
10. de Visser S.P., Kumar D., Shaik S. How do aldehyde side products occur during alkene epoxidation by cytochrome P450? Theory reveals a state-specific multi-state scenario where the high-spin component leads to all side products. J. Inorg. Biochem. 2004, 98:1183-1193.
11. EC, 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. Online available at:. http://eur-lex.europa.eu/legal-content/EN/TXT/?uri=celex:32008R1334.
12. Gorelick N.J. Genotoxicity of trans-anethole in vitro. Mutat. Res. 1995, 326:199-209.
13. Hasheminejad G., Caldwell J. Genotoxicity of the alkenylbenzenes α- and β-asarone, Myristicin and Elimicin as determined by the UDS assay in cultured rat hepatocytes. Food Chem. Toxicol. 1994, 32:223-231.
14. Hsia M.T.S., Adamovics J.A., Kreamer B.L. Microbial mutagenicity studies of insect growth regulators and other potential insecticidal compounds in Salmonella typhimurium. Chemosphere 1979, 8:521-529.
15. HMPC, Committee on Herbal Medicinal Products Evaluation of Medicines for Human Use, Public Statement on the Use of Herbal Medicinal Products Containing Asarone, European Medicines Agency (EMEA), London 2005, Doc Ref: EMEA/HMPC/139215/2005.
16. JECFA Joint FAO/WHO Expert Committee on Food Additives, Toxicological Evaluation of Certain Food Additives 1981, 33-44. WHO Tech Rep Ser No. 669.
17. Jin Z., Qin W., Chen X. Mutagenicity of alpha-asarone from Acorus Calamus and its metabolic pathway in vitro. Zhejiang Yike Daxue Xuebao 1982, 11:1-3. 25.
18. Kim S.G., Liem A., Stewart B.C., Miller J.A. New studies on trans-anethole oxide and trans-asarone oxide. Carcinogenesis 1999, 20:1303-1307.
19. Kim B.W., Koppula S., Kumar H., Park J.Y., Kim I.W., More S.V., Kim I.S., Han S.D., Kim S.K., Yoon S.H., Choi D.K. α-Asarone attenuates microglia-mediated neuroinflammation by inhibiting NF kappa B activation and mitigates MPTP-induced behavioral deficits in a mouse model of Parkinson's disease. Neuropharmacology 2015, 97:46-57.
20. Krahulcova A. Chromosome numbers in selected monocotyledons. Perslia Praha 2003, 75:97-113.
21. Marczewska J., Drozd E., Anuszewska E., Chilmonczyk Z., Łozowicka B. Assessment of the genotoxic activity of alpha-asarone and its derivatives in the comet assay. Acta Pol. Pharm. 2013, 70:349-354.
22. Melancon M.J., Williams D.E., Buhler D.R., Lech J.J. Metabolism of 2-methylnaphthalene by rat and rainbow trout hepatic microsomes and purified cytochromes P-450. Drug Metab. Dispos. 1985, 13:542-547.
23. Meng X., Zhao X., Wang S., Jia P., Bai Y., Liao S., Zheng X. 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, 2013:949830.
24. Morales-Ramírez P., Madrigal-Bujaidar E., Mercader-Martínez J., Cassini M., González G., Chamorro-Cevallos G., Salazar-Jacobo M. Sister-chromatid exchange induction produced by in vivo and in vitro exposure to alpha-asarone. Mutat. Res. 1992, 279:269-273.
25. Mukherjee P.K., Kumar V., Mal M., Houghton P.J. Acorus calamus: scientific validation of ayurvedic tradition from natural resources. Pharm. Biol. 2007, 45:651-666.
26. Mukherjee P.K., Rai S., Kumar V., Mukherjee K., Hylands P., Hider R. Plants of Indian origin in drug discovery. Expert Opin. Drug Discov. 2007, 2:633-657.
27. National Toxicology Program (NTP) Toxicology and carcinogenesis studies of isoeugenol (CAS No. 97-54-1) in F344/N rats and B6C3F1 mice (gavage studies). Natl. Toxicol. Program Tech. Rep. Ser. 2010, 551:1-178.
28. Newberne P., Smith R.L., Doull J., Goodman J.I., Munro I.C., Portoghese P.S., Wagner B.M., Weil C.S., Woods L.A., Adams T.B., Lucas C.D., Ford R.A. The FEMA GRAS assessment of trans-anethole used as a flavouring substance. Flavour and Extract Manufacturer's Association. Food Chem. Toxicol. 1999, 37:789-811.
29. Omura T., Sato R. The carbon monoxide-bindung pigment of liver microsomes. II. Solubilization, purification and properties. J. Biol. Chem. 1964, 239:2379-2385.
30. Rajput S.B., Tonge M.B., Karuppayil S.M. An overview on traditional uses and pharmacological profile of Acorus calamus Linn. (Sweet flag) and other Acorus species. Phytomedicine 2014, 21:268-276.
31. Rana T.S., Mahar K.S., Pandey M.M., Srivastava S.K., Rawat A.K. Molecular and chemical profiling of 'sweet flag' (Acorus calamus L.) germplasm from India. Physiol. Mol. Biol. Plants 2013, 19:231-237.
32. Rietjens I.M., Cohen S.M., Fukushima S., Gooderham N.J., Hecht S., Marnett L.J., Smith R.L., Adams T.B., Bastaki M., Harman C.G., Taylor S.V. Impact of structural and metabolic variations on the toxicity and carcinogenicity of hydroxy- and alkoxy-substituted allyl- and propenylbenzenes. Chem. Res. Toxicol. 2014, 27:1092-1103.
33. Salazar M., Salazar S., Ulloa V., Mendoza T., Pages N., Chamoro G. Teratogenic action of alpha-asarone in the mouse. J. Toxicol. Clin. Exp. 1992, 12:149-154.
34. Satyal P., Paudel P., Poudel A., Dosoky N.S., Moriarity D.M., Vogler B., Setzer W.N. Chemical compositions, phytotoxicity, and biological activities of Acorus calamus essential oils from Nepal. Nat. Prod. Commun. 2013, 8:1179-1181.
35. 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 ADD1 Final 2002, online available at:. http://ec.europa.eu/food/fs/sc/scf/out111_en.pdf.
36. Shin J.W., Cheong Y.J., Koo Y.M., Kim S., Noh C.K., Son Y.H., Kang C., Sohn N.W. α-asarone ameliorates memory deficit in lipopolysaccharide-treated mice via suppression of pro-inflammatory cytokines and microglial activation. Biomol. Ther. Seoul. 2014, 22:17-26.
37. 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.
38. Solheim E., Scheline R.R. Metabolism of alkenebenzene derivatives in the rat. II. Eugenol and isoeugenol methyl ethers. Xenobiotica 1976, 6:137-150.
39. Taylor J.M., Jones W.I., Hagan E.C., Gross M.A., Davis D.A., Cook E.L. Toxicity of oil of calamus (Jammus variety). Toxicol. Appl. Pharmacol. 1967, 10:405.
40. van den Berg S.J., Restani P., Boersma M.G., Delmulle L., Rietjens I.M. Levels of genotoxic and carcinogenic compounds in plant food supplements and associated risk assessment. Food Nutr. Sci. 2011, 2:989-1010.
41. 1 mice. Cancer Res. 1987, 47:2275-2278.
42. Zuba D., Byrska B. Alpha- and beta-asarone in herbal medicinal products. A case study. Forensic Sci. Int. 2012, 30(223):e5-9. 10.1016/j.forsciint.2012.08.015.