4-Methylsulfanyl-3-butenyl isothiocyanate derived from glucoraphasatin is a potent inducer of rat hepatic phase II enzymes and a potential chemopreventive agent

Archives of Toxicology

Volumn 86, Issue 2, 2012, Pages 183-194

  Abdull Razis, Ahmed Faizal ^a   De Nicola, Gina Rosalinda ^b   Pagnotta, Eleonora ^b   Iori, Renato ^b   Ioannides, Costas ^a  

^a UNIVERSITY OF SURREY   (United Kingdom)

^b ISTITUTO NAZIONALE DELLA NUTRIZIONE   (Italy)

Author keywords

Chemoprevention; Cruciferous vegetables; Glucoraphasatin; Glucosinolates; Isothiocyanates

Indexed keywords

4 METHYLSULFANYL 3 BUTENYL ISOTHIOCYANATE; CYTOCHROME P450 1A1; CYTOCHROME P450 1A2; CYTOCHROME P450 1B1; EPOXIDE HYDROLASE; ETHOXYRESORUFIN; GLUCORAPHASATIN; GLUCOSINOLATE; GLUCURONOSYLTRANSFERASE; GLUTATHIONE; GLUTATHIONE TRANSFERASE; ISOTHIOCYANIC ACID DERIVATIVE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE (PHOSPHATE) DEHYDROGENASE (QUINONE); THIOGLUCOSIDASE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL TISSUE; ANTINEOPLASTIC ACTIVITY; APOPTOSIS; ARTICLE; CONCENTRATION RESPONSE; CONTROLLED STUDY; DEALKYLATION; DETOXIFICATION; DRUG STRUCTURE; ENZYME ACTIVITY; ENZYME INDUCTION; INCUBATION TIME; LIVER SLICE; MALE; NONHUMAN; PRIORITY JOURNAL; PROTEIN EXPRESSION; RAT; SINAPIS ALBA;

ANIMALS; ANTICARCINOGENIC AGENTS; BRASSICACEAE; ENZYME INDUCTION; GLUCOSINOLATES; GLYCOSIDE HYDROLASES; ISOTHIOCYANATES; LIVER; LIVER NEOPLASMS; METABOLIC DETOXICATION, DRUG; PLANT EXTRACTS; RATS; SINAPIS;

RAPHANUS SATIVUS VAR. NIGER; RATTUS; SINAPIS ALBA;

EID: 84856955584     PISSN: 03405761     EISSN: 14320738     Source Type: Journal    
DOI: 10.1007/s00204-011-0750-x     Document Type: Article

References (50)

1. AF Abdull Razis M Bagatta GR De Nicola R Iori C Ioannides 2010 Intact glucosinolates modulate hepatic cytochrome P450 and phase II conjugation activities and may contribute directly to the chemopreventive activity of cruciferous vegetables Toxicology 277 74 85 20833222 1:CAS:528: DC%2BC3cXhtlShurzL 10.1016/j.tox.2010.08.080
2. AF Abdull Razis M Bagatta GR De Nicola R Iori C Ioannides 2010 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 71 298 305 20638746 10.1016/j.lungcan.2010.06.015
3. AF Abdull Razis M Bagatta GR De Nicola R Iori C Ioannides 2011 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 Arch Toxicol 85 919 927 21132492 1:CAS:528: DC%2BC3cXhsFWlsrjP 10.1007/s00204-010-0629-2
4. TPH Akerboom H Sies 1981 Assay of glutathione, glutathione disulfide, and glutathione mixed disulfides in biological samples Meth Enzymol 7 373 382 10.1016/S0076-6879(81)77050-2
5. 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)
6. 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)
7. J Barillari R Cervellati M Paolini A Tatibouët P Rollin R Iori 2005 Isolation of 4-methylthio-3-butenyl glucosinolate from Raphanus sativus sprouts (Kaiware-daikon) and its redox properties J Agric Food Chem 53 9890 9896 16366671 1:CAS:528:DC%2BD2MXht1Gju73J 10.1021/jf051465h (Pubitemid 43081194)
8. J Barillari R Cervellati S Costa MC Guerra E Speroni A Utan R Iori 2006 Antioxidant and Choleretic properties of Raphanus sativus L. sprout (Kaiware Daikon) extract J Agric Food Chem 54 9443 9778 10.1021/jf061838u (Pubitemid 46158969)
9. A Bhattacharya L Tang F Geng JD Paonessa SC Chen MKK Wong Y Zhang 2010 Inhibition of bladder cancer development by allyl isothiocyanate Carcinogenesis 31 281 286 19955395 1:CAS:528:DC%2BC3cXhsVWjurc%3D 10.1093/carcin/bgp303
10. RM Bheemreddy EH Jeffery 2007 The metabolic fate of purified glucoraphanin in F344 rats J Agric Food Chem 55 2861 2866 17367161 1:CAS:528:DC%2BD2sXivF2jt7Y%3D 10.1021/jf0633544 (Pubitemid 46668290)
11. Bock KW (2006) UDP-Glucuronosyltransferases. In: Ioannides C (ed) Enzyme systems that metabolise drugs and other xenobiotics. Wiley, Chichester, pp 281-318
12. 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 1:CAS:528:DyaE2cXls1equ74%3D 10.1111/j.1432-1033.1974.tb03638.x
13. 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 1:CAS:528:DyaE28XksVehtrY%3D 10.1016/0003- 2697(76)90527-3
14. MD Burke RT Mayer 1974 Ethoxyresorufin: direct fluorimetric assay of a microsomal O-dealkylation which is preferentially inducible by 3-methylcholanthrene Drug Met Disp 2 583 588 1:CAS:528:DyaE2MXhtVOqtLw%3D
15. MD Burke RT Mayer 1983 Differential effects of phenobarbitone and 3-methylcholanthrene induction on the hepatic microsomal and cytochrome P450 binding of phenoxazone and a homologous series of its n-alkyl ethers (alkoxyresorufins) Chem Biol Inter 45 243 258 1:CAS:528:DyaL3sXlvVKqu7k%3D 10.1016/0009-2797(83)90072-8 (Pubitemid 13039225)
16. 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 Analysis 52 544 549 1:CAS:528:DC%2BC3cXjt1Kjsbw%3D 10.1016/j.jpba.2010.01.020
17. PM Dansette GC DuBois DM Jerina 1979 Continuous fluorometric assay of epoxide hydratase activity Anal Biochem 97 340 345 525797 1:CAS:528: DyaE1MXmtVKis70%3D 10.1016/0003-2697(79)90083-6 (Pubitemid 10240162)
18. M Decker M Arand A Cronin 2009 Mammalian epoxide hydrolases in xenobiotic metabolism Arch Toxicol 83 297 318 19340413 1:CAS:528:DC%2BD1MXjvFeisbo%3D 10.1007/s00204-009-0416-0
19. 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 1:CAS:528:DC%2BD2cXislSntA%3D%3D 10.1207/S15327914NC4602-15 (Pubitemid 37500513)
20. EEC Regulation No 1861/90 (1990) Enclosure VII, Office. J Eur Commun L170:27-34
21. WH Habig MJ Pabst WB Jakoby 1974 Glutathione S-transferase, the first enzymic step in mercapturic acid formation J Biol Chem 249 7130 7139 4436300 1:CAS:528:DyaE2MXltlahtg%3D%3D
22. P Hanlon DM Webber DM Barnes 2007 Aqueous extract from Spanish black radish (Raphanus sativus L. Var. Niger) induces detoxification enzymes in the HepG2 human hepatoma cell line J Agric Food Chem 55 6439 6446 17616135 1:CAS:528:DC%2BD2sXns1Cksb4%3D 10.1021/jf070530f (Pubitemid 47280015)
23. 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 1:CAS:528:DC%2BD1cXptlaqurw%3D 10.1021/jf801456h
24. N Hanlon N Coldham MJ Sauer C Ioannides 2008 Up-regulation of the CYP1 family in rat and human liver by the aliphatic isothiocyanates erucin and sulforaphane Toxicology 252 92 98 18773935 1:CAS:528:DC%2BD1cXht1ens7fF 10.1016/j.tox.2008.08.002
25. 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 Nutr 99 559 564 17868493 1:CAS:528:DC%2BD1cXivFektbc%3D 10.1017/ S0007114507824093 (Pubitemid 351223423)
26. N Hanlon N Coldham MJ Sauer C Ioannides 2009 Modulation of rat pulmonary carcinogen-metabolising enzyme systems by the isothiocyanates erucin and sulforaphane Chem-Biol Inter 177 115 120 1:CAS:528:DC%2BD1cXhsFagurnO 10.1016/j.cbi.2008.08.015
27. 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 1:CAS:528:DyaK1MXotlKqtQ%3D%3D 10.1080/004982599238786 (Pubitemid 29050388)
28. JD Hayes MO Kelleher IM Eggleston 2008 The cancer chemopreventive actions of phytochemicals derived from glucosinolates Eur J Nutr 47 73 88 18458837 1:CAS:528:DC%2BD1cXntl2rur4%3D 10.1007/s00394-008-2009-8 (Pubitemid 351644183)
29. B Holst G Williamson 2004 A critical review of the bioavailability of glucosinolates and related compounds Nat Prod Rep 21 425 447 15162227 1:CAS:528:DC%2BD2cXlvVagsLk%3D 10.1039/b204039p (Pubitemid 38865722)
30. C Ioannides DFV Lewis 2004 Cytochromes P450 in the bioactivation of chemicals Curr Topics Med Chem 4 1767 1788 1:CAS:528:DC%2BD2cXhtVKmsbnO 10.2174/1568026043387188 (Pubitemid 39662666)
31. MA Joseph KB Moysich JL Freudenheim PG Shields ED Bowman Y Zhang JR Marshall CB Ambrosone 2004 Cruciferous vegetables, genetic polymorphisms in glutathione S-transferases M1 and T1, and prostate cancer risk Nutr Cancer 50 206 213 15623468 1:CAS:528:DC%2BD2MXht1Kis74%3D 10.1207/s15327914nc5002-11
32. 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 1:CAS:528: DC%2BD1cXhsVajtLrE 10.1016/j.fct.2008.09.046
33. 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 1:CAS:528: DC%2BC3cXjtFKhs7Y%3D 10.1002/mnfr.200900090
34. N Konsue C Ioannides 2010 Modulation of carcinogen-metabolising cytochromes P450 in human liver by the chemopreventive phytochemical phenethyl isothiocyanate, a constituent of cruciferous vegetables Toxicology 268 184 190 20025923 1:CAS:528:DC%2BC3cXit1Omsrc%3D 10.1016/j.tox.2009.12.011
35. 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 1:CAS:528:DC%2BC3cXjtFKhs7Y%3D 10.1002/mnfr.200900090
36. TK Lam L Gallicchio K Lindsley M Shiels E Hammond X Tao L Chen KA Robinson LE Caulfield JG Herman E Guallar AJ Alberg 2009 Cruciferous vegetable consumption and lung cancer risk: a systematic review Cancer Epidemiol Biomarkers Prev 18 184 195 19124497 1:CAS:528:DC%2BD1MXhvFersQ%3D%3D 10.1158/1055-9965.EPI-08-0710
37. S Montaut J Barillari R Iori P Rollin 2010 Glucoraphasatin: chemistry, occurrence, and biological properties Phytochemistry 71 6 12 19896154 1:CAS:528:DC%2BD1MXhsFyks7zI 10.1016/j.phytochem.2009.09.021
38. A Papi M Orlandi G Bartolini J Barillari R Iori M Paolini F Ferroni MG Fumo GF Pedulli L Valgimigli 2008 Cytotoxic and antioxidant activit of 4-methylthio-3-butenyl isothiocyanate from Raphanus Sativus L. (Kaiware Daikon) sprouts J Agric Food Chem 56 875 883 18189352 1:CAS:528:DC%2BD1cXlsl2mtQ%3D%3D 10.1021/jf073123c (Pubitemid 351300258)
39. A Pessina RM Thomas S Palmieri PL Luisi 1990 An improved method for the purification of myrosinase and its physicochemical characterization Arch Biochem Biophys 280 383 389 2369130 1:CAS:528:DyaK3cXkvFekt7w%3D 10.1016/0003-9861(90) 90346-Z (Pubitemid 20221980)
40. HJ Prohaska AB Santamaria 1988 Direct measurement of NAD(P)H:quinone reductase from cells cultured in microtiter wells: a screening assay for anticarcinogenic enzyme inducers Anal Biochem 169 328 336 10.1016/0003-2697(88) 90292-8 (Pubitemid 18081406)
41. Sherratt PJ, Hayes JD (2002) Glutathione S-transferases. In: Ioannides C (ed) Enzyme systems that metabolise drugs and other xenobiotics. Wiley, Chichester, pp 319-352
42. K Singletary C MacDonald 2000 Inhibition of benzo[a]pyrene and 1, 6-dinitropyrene-DNA adduct formation in mammary epithelial cells by dibenzoylmethatne and sulforaphane Cancer Lett 155 47 54 10814878 1:CAS:528:DC%2BD3cXjt1ejsLg%3D 10.1016/S0304-3835(00)00412-2 (Pubitemid 30256223)
43. P Talalay JW Fahey 2001 Phytochemicals form Cruciferous plants protect against cancer by modulating carcinogen metabolism J Nutr 131 3027S 3033S 11694642 1:CAS:528:DC%2BD3MXosVGit7g%3D (Pubitemid 33070774)
44. 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
45. 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 1:CAS:528:DC%2BD38Xos1SnsA%3D%3D 10.1093/carcin/22.12.1987 (Pubitemid 34065393)
46. 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 1:CAS:528:DC%2BD2MXhtFant7rO 10.1002/ijc.21191 (Pubitemid 41429558)
47. 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 10.1016/j.mrfmmm.2004.04.017 (Pubitemid 39345403)
48. 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)
49. H Zhao HB Grossman LM Hernandez CP Dinney X Wu 2007 Dietary isothiocyanates, GSTM1, GSTT1, NAT2 polymorphisms and bladder cancer risk Int J Cancer 120 2208 2213 17290402 1:CAS:528:DC%2BD2sXkt1Oiu74%3D 10.1002/ijc.22549 (Pubitemid 46555860)
50. SF Zhou B Wang LP Yang JP Liu 2009 Sttructure, function, regulation and polymorphism of human cytochrome P450 1A2 Drug Metab Rev 42 268 354 10.3109/03602530903286476