Induction of epoxide hydrolase and glucuronosyl transferase by isothiocyanates and intact glucosinolates in precision-cut rat liver slices: Importance of side-chain substituent and chirality

Archives of Toxicology

Volumn 85, Issue 8, 2011, Pages 919-927

  Abdull Razis, Ahmad Faizal ^a   Bagatta, Manuela ^b   De Nicola, Gina Rosalinda ^b   Iori, Renato ^b   Ioannides, Costas ^a  

^a UNIVERSITY OF SURREY   (United Kingdom)

^b ISTITUTO NAZIONALE DELLA NUTRIZIONE   (Italy)

Author keywords

Erucin; Glucoraphanin; Glucosinolates; Isothiocyanates; Phenethyl isothiocyanate; Sulforaphane

Indexed keywords

EPOXIDE HYDROLASE; ERUCIN; GLUCOSINOLATE; GLUCURONOSYLTRANSFERASE; ISOTHIOCYANIC ACID; ISOTHIOCYANIC ACID DERIVATIVE; PHENETHYL ISOTHIOCYANATE; SULFORAPHANE;

ANIMAL TISSUE; ARTICLE; CHIRALITY; CONCENTRATION RESPONSE; CONTROLLED STUDY; ENANTIOMER; ENZYME ACTIVITY; ENZYME INDUCTION; FOOD COMPOSITION; GLUCURONIDATION; IMMUNOCHEMISTRY; LIVER SLICE; MALE; NONHUMAN; PRIORITY JOURNAL; PROTEIN EXPRESSION; RAT; STRUCTURE ACTIVITY RELATION; UPREGULATION;

ANIMALS; DOSE-RESPONSE RELATIONSHIP, DRUG; ENZYME INDUCTION; EPOXIDE HYDROLASES; GLUCOSE; GLUCOSINOLATES; GLUCURONOSYLTRANSFERASE; IMIDOESTERS; ISOTHIOCYANATES; LIVER; MALE; RATS; RATS, WISTAR; STEREOISOMERISM; SULFIDES; THIOCYANATES;

RATTUS;

EID: 80052746485     PISSN: 03405761     EISSN: 14320738     Source Type: Journal    
DOI: 10.1007/s00204-010-0629-2     Document Type: Article

References (35)

1. Abdull Razis AF, Iori R, Ioannides C (2010a) The natural chemopreventive phytochemical R-sulforaphane is a far more potent inducer of the carcinogen-detoxifying enzyme systems in rat liver and lung than the S-isomer. Intern J Cancer (in press)
2. Abdull Razis AF, Bagatta M, De Nicola GR, Iori R, Ioannides C (2010b) Up-regulation of cytochrome P450 and phase II enzyme systems in rat precision-cut rat lung slices by the intact glucosinolates, glucoraphanin and glucoerucin. Lung Cancer (in press). doi: 10.1016/j.lungcan.2010.06.015
3. Abdull Razis AF, Bagatta M, De Nicola GR, Iori R, Ioannides C (2010c) Intact glucosinolates modulate hepatic cytochrome P450 and phase II conjugation activities and can contribute directly to the chemopreventive activity of cruciferous vegetables. Toxicology 277:74-85
4. CB Ambrosone SE McCann JL Freudenheim JR Marshall Y Zhang PG Shields 2004 Breast cancer risk in premenopausal women is inversely associated with consumption of broccoli, a source of isothiocyanates, but is not modified by GST genotype J Nutr 134 1134 1138 15113959 1:CAS:528:DC%2BD2cXjvFGqurg%3D (Pubitemid 38619952)
5. JR Bacon G Williamson RC Garner G Lappin S Langouët Y Bao 2003 Sulforaphane and quercetin modulate PhIP-DNA adduct formation in human HepG2 cells and hepatocytes Carcinogenesis 24 1909 1911 10.1093/carcin/bgg157 (Pubitemid 38008530)
6. RM Bheemreddy EH Jeffery 2007 The metabolic fate of purified glucoraphanin in F344 rats J Agric Food Chem 55 2861 2866 17367161 10.1021/jf0633544 1:CAS:528:DC%2BD2sXivF2jt7Y%3D (Pubitemid 46668290)
7. Bock KW (2006) UDP-Glucuronosyltransferases. In: Ioannides C (ed) Enzyme systems that metabolise drugs and other xenobiotics. Wiley, Chichester, pp 281-318
8. KW Bock IN White 1974 UDP-glucuronyltransferase in perfused rat liver in microsomes: influence of phenobarbital and 3-methylcholanthrene Eur J Biochem 46 451 459 4212510 10.1111/j.1432-1033.1974.tb03638.x 1:CAS:528:DyaE2cXls1equ74%3D
9. MM Bradford 1976 A rapid and sensitive method for the quantitation of microgram quantities of protein utilising the principle of protein-dye binding Anal Biochem 72 248 254 942051 10.1016/0003-2697(76)90527-3 1:CAS:528: DyaE28XksVehtrY%3D
10. MJ Cwik H Wu M Muzzio DL McCormick I Kapetanovic 2010 Direct quantitation of glucoraphanin in dog and rat plasma by LC-MS/MS J Pharmaceut Biomed Anal 52 544 549 10.1016/j.jpba.2010.01.020 1:CAS:528:DC%2BC3cXjt1Kjsbw%3D
11. PM Dansette GC DuBois DM Jerina 1979 Continuous fluorometric assay of epoxide hydratase activity Anal Biochem 97 340 345 525797 10.1016/0003-2697(79) 90083-6 1:CAS:528:DyaE1MXmtVKis70%3D (Pubitemid 10240162)
12. M Decker M Arand A Cronin 2009 Mammalian epoxide hydrolases in xenobiotic metabolism Arch Toxicol 83 297 318 19340413 10.1007/s00204-009-0416-0 1:CAS:528:DC%2BD1MXjvFeisbo%3D
13. KH Dingley EA Ubick ML Chiarappa-Zucca S Nowell S Abel SE Ebeler AE Mitchell SA Burns FM Steinberg AJ Clifford 2003 Effect of dietary constituents with chemopreventive potential on adduct formation of a low dose of the heterocyclic amines PhIP and IQ and phase II enzymes Nutr Cancer 46 212 221 14690798 10.1207/S15327914NC4602-15 1:CAS:528:DC%2BD2cXislSntA%3D%3D (Pubitemid 37500513)
14. SM Getahun FL Chung 1999 Conversion of isothiocyanates in humans after ingestion of cooked watercress Cancer Epidemiol Biomarkers Prev 8 447 451 10350441 1:CAS:528:DyaK1MXjs1yitr0%3D (Pubitemid 29230550)
15. N Hanlon M Okpara N Coldham MJ Sauer C Ioannides 2008 Modulation of rat hepatic and pulmonary cytochromes P450 and Phase II enzyme systems by erucin, an isothiocyanate structurally related to sulforaphane J Agric Food Chem 56 7866 7871 18680373 10.1021/jf801456h 1:CAS:528:DC%2BD1cXptlaqurw%3D
16. N Hanlon N Coldham A Gielbert N Kuhnert MJ Sauer LJ King C Ioannides 2008 Absolute bioavailability and dose-dependent pharmacokinetic behaviour of dietary doses of the chemopreventive isothiocyanate sulforaphane in the rat Br J Nut 99 559 564 10.1017/S0007114507824093 1:CAS:528:DC%2BD1cXivFektbc%3D (Pubitemid 351223423)
17. N Hanlon CL Poynton N Coldham MJ Sauer C Ioannides 2009 The aliphatic isothiocyanates erucin and sulforaphane do not effectively up-regulate NAD(P)H: quinone oxidoreductase (NQO1) in human liver compared with rat Molec Nutr Food Res 53 836 844 10.1002/mnfr.200800292 1:CAS:528:DC%2BD1MXpsV2lur0%3D
18. N Hanlon N Coldham A Gielbert MJ Sauer C Ioannides 2009 Repeated intake of broccoli does not lead to higher plasma levels of sulforaphane in human volunteers Cancer Lett 284 15 20 19409695 10.1016/j.canlet.2009.04.004 1:CAS:528:DC%2BD1MXhtVKlsLjF
19. E Hashemi M Dobrota C Till C Ioannides 1999 Structural and functional integrity of precision-cut liver slices in xenobiotic metabolism: a comparison of the dynamic organ and multiwell plate culture procedures Xenobiotica 29 11 25 10078837 10.1080/004982599238786 1:CAS:528:DyaK1MXotlKqtQ%3D%3D (Pubitemid 29050388)
20. JD Hayes MO Kelleher IM Eggleston 2008 The cancer chemopreventive actions of phytochemicals derived from glucosinolates Eur J Nutr 47 73 88 18458837 10.1007/s00394-008-2009-8 1:CAS:528:DC%2BD1cXntl2rur4%3D (Pubitemid 351644183)
21. SS Hecht SG Carmella SE Murphy 1999 Effects of watercress consumption on urinary metabolites of nicotine smokers Cancer Epidemiol Biomarkers Prev 8 907 913 10548320 1:CAS:528:DyaK1MXns1CrtLk%3D (Pubitemid 29508727)
22. N Konsue C Ioannides 2008 Tissue differences in the modulation of rat cytochromes P450 and phase II conjugation systems by dietary doses of phenethyl isothiocyanate Food Chem Toxicol 46 3677 3683 18929617 10.1016/j.fct.2008.09.046 1:CAS:528:DC%2BD1cXhsVajtLrE
23. N Konsue C Ioannides 2010 Differential response of four human livers to modulation of phase II enzyme systems by the chemopreventive phytochemical phenethyl isothiocyanate Molec Nut Food Res 54 426 432 10.1002/mnfr.200900090 1:CAS:528:DC%2BC3cXjtFKhs7Y%3D
24. N Konsue J Kirkpatrick N Kuhnert LJ King C Ioannides 2010 Repeated oral administration modulates the pharmacokinetic behaviour of the chemopreventive agent phenethyl isothiocyanate in rats Molec Nut Food Res 54 426 432 10.1002/mnfr.200900090 1:CAS:528:DC%2BC3cXjtFKhs7Y%3D
25. SL Navarro S Peterson C Chen KW Makar Y Schwarz IB King SS Li M Kestin JW Lampe 2009 Cruciferous vegetable feeding alters UGT1A1 activity: diet- and genotype-dependent changes in serum bilirubin in a feeding trial Cancer Prev Res 2 345 352 10.1158/1940-6207.CAPR-08-0178 1:CAS:528:DC%2BC3cXptFKgu70%3D
26. K Singletary C MacDonald 2000 Inhibition of benzo[a]pyrene and 1, 6-dinitropyrene-DNA adduct formation in mammary epithelial cells by dibenzoylmethane and sulforaphane Cancer Lett 155 47 54 10814878 10.1016/S0304-3835(00)00412-2 1:CAS:528:DC%2BD3cXjt1ejsLg%3D (Pubitemid 30256223)
27. A Steinbrecher L Linseisen 2009 Dietary intake of individual glucosinolates in participants of the EIPC-Heidelberg cohort study Ann Nutr Metab 54 87 96 19295191 10.1159/000209266 1:CAS:528:DC%2BD1MXlvFWmtr0%3D
28. L Tang GR Zirpoli K Guru KB Moyisch Y Zhang CB Ambrosone SE McCann 2008 Consumption of raw cruciferous vegetables is inversely associated with bladder cancer risk Cancer Epidemiol Biomarkers Prev 17 938 944 18398034 10.1158/1055-9965.EPI-07-2502 1:CAS:528:DC%2BD1cXkslGqurs%3D (Pubitemid 351536426)
29. R Verkerk M Schreiner A Krumbein E Ciska B Holst I Rowland R De Schrijver M Hansen C Gerhäuser R Mithen M Dekker 2009 Glucosinolates in Brassica vegetables: the influence of the food supply chain on intake, bioavailability and human health Mol Nutr Food Res 53 S219 S265 19035553 10.1002/mnfr.200800065
30. M Visentin A Tava R Iori S Palmieri 1992 Isolation and Identification of trans-4-(methylthio)-3-butenyl-glucosinolate from radish roots (Raphanus sativus L.) J Agri Food Chem 40 1687 1691 10.1021/jf00021a041 1:CAS:528: DyaK38XlsV2mtb4%3D
31. G Walters PJ Young C Agus MG Knize AR Boobis NJ Gooderham BG Lake 2004 Cruciferous vegetable consumption alters the metabolism of the dietary carcinogen 2-amino-1-methyl-6-phenylimidazo(4, 5-b)pyridine (PhIP) in humans Carcinogenesis 25 1659 1669 15073045 10.1093/carcin/bgh164 1:CAS:528: DC%2BD2cXntFaiuro%3D (Pubitemid 39214308)
32. L Ye Y Zhang 2001 Total intracellular accumulation levels of dietary isothiocyanates determine the activity in elevation of cellular glutathione and phase 2 detoxication enzymes Carcinogenesis 22 1987 1992 11751429 10.1093/carcin/22.12.1987 1:CAS:528:DC%2BD38Xos1SnsA%3D%3D (Pubitemid 34065393)
33. V Yoxall P Kentish N Coldham N Kuhnert MJ Sauer C Ioannides 2005 Modulation of hepatic cytochromes P450 and phase II enzymes by dietary doses of sulforaphane in rats: Implications for its chemopreventive activity Int J Cancer 117 356 362 15906351 10.1002/ijc.21191 1:CAS:528:DC%2BD2MXhtFant7rO (Pubitemid 41429558)
34. Y Zhang 2004 Cancer-preventive isothiocyanates: measurement of human exposure and mechanism of action Mut Res 555 173 190 1:CAS:528: DC%2BD2cXot12gs7o%3D (Pubitemid 39345403)
35. Y Zhang EC Callaway 2002 High cellular accumulation of sulphoraphane, a dietary anticarcinogen, is followed by rapid transporter-mediated export as a glutathione conjugate Biochem J 364 301 307 11988104 1:CAS:528: DC%2BD38XktFWhs7Y%3D (Pubitemid 34538974)