메뉴 건너뛰기




Volumn 88, Issue 3, 2014, Pages 823-836

A secondary metabolite of Brassicales, 1-methoxy-3-indolylmethyl glucosinolate, as well as its degradation product, 1-methoxy-3-indolylmethyl alcohol, forms DNA adducts in the mouse, but in varying tissues and cells

Author keywords

DNA adducts; Glucosinolates; Immunohistochemistry; Sulphotransferase; UPLC MS MS

Indexed keywords

1 METHOXY 3 INDOLYLMETHYL ALCOHOL; 1 METHOXY 3 INDOLYLMETHYL GLUCOSINOLATE; ALCOHOL DERIVATIVE; GLUCOSINOLATE; GLYCOGEN; PROTEIN P21; PROTEIN P53; THIOGLUCOSIDASE; UNCLASSIFIED DRUG; 1-METHOXY-3-INDOLYLMETHYLGLUCOSINOLATE; 2'-DEOXYADENOSINE; DEOXYADENOSINE DERIVATIVE; DNA ADDUCT; INDOLE DERIVATIVE; N-METHOXYINDOLE-3-CARBINOL;

EID: 84896735727     PISSN: 03405761     EISSN: 14320738     Source Type: Journal    
DOI: 10.1007/s00204-013-1149-7     Document Type: Article
Times cited : (21)

References (31)
  • 1
    • 79953749694 scopus 로고    scopus 로고
    • Hepatocyte turnover and regeneration: Virtually a virtuoso performance
    • 1:CAS:528:DC%2BC3MXktl2jtLg%3D 21480343 10.1002/hep.24252
    • Alison MR, Lin W-R (2011) Hepatocyte turnover and regeneration: virtually a virtuoso performance. Hepatology 53:1393-1396
    • (2011) Hepatology , vol.53 , pp. 1393-1396
    • Alison, M.R.1    Lin, W.-R.2
  • 2
    • 33748750527 scopus 로고    scopus 로고
    • Tissue distribution and ontogeny of sulfotransferase enzymes in mice
    • 1:CAS:528:DC%2BD28Xps1yhu78%3D 16807285 10.1093/toxsci/kfl050
    • Alnouti Y, Klaassen CD (2006) Tissue distribution and ontogeny of sulfotransferase enzymes in mice. Toxicol Sci 93:242-255
    • (2006) Toxicol Sci , vol.93 , pp. 242-255
    • Alnouti, Y.1    Klaassen, C.D.2
  • 3
    • 79955609668 scopus 로고    scopus 로고
    • Identification of glucosinolate congeners able to form DNA adducts and to induce mutations upon activation by myrosinase
    • 1:CAS:528:DC%2BC3MXlsFKgsLY%3D 21213326 10.1002/mnfr.201000352
    • Baasanjav-Gerber C, Monien BH, Mewis I, Schreiner M, Barillari J, Iori R, Glatt H (2011) Identification of glucosinolate congeners able to form DNA adducts and to induce mutations upon activation by myrosinase. Mol Nutr Food Res 55:783-792
    • (2011) Mol Nutr Food Res , vol.55 , pp. 783-792
    • Baasanjav-Gerber, C.1    Monien, B.H.2    Mewis, I.3    Schreiner, M.4    Barillari, J.5    Iori, R.6    Glatt, H.7
  • 4
    • 34247626240 scopus 로고    scopus 로고
    • The metabolic fate of purified glucoraphanin in F344 rats
    • 1:CAS:528:DC%2BD2sXivF2jt7Y%3D 17367161 10.1021/jf0633544
    • Bheemreddy RM, Jeffery EH (2007) The metabolic fate of purified glucoraphanin in F344 rats. J Agric Food Chem 55:2861-2866
    • (2007) J Agric Food Chem , vol.55 , pp. 2861-2866
    • Bheemreddy, R.M.1    Jeffery, E.H.2
  • 5
    • 1642268315 scopus 로고    scopus 로고
    • A proposed nomenclature system for the cytosolic sulfotransferase (SULT) superfamily
    • 1:CAS:528:DC%2BD2cXjt1Kjs78%3D 15167709 10.1097/00008571-200403000-00009
    • Blanchard RL, Freimuth RR, Buck J, Weinshilboum RM, Coughtrie MH (2004) A proposed nomenclature system for the cytosolic sulfotransferase (SULT) superfamily. Pharmacogenetics 14:199-211
    • (2004) Pharmacogenetics , vol.14 , pp. 199-211
    • Blanchard, R.L.1    Freimuth, R.R.2    Buck, J.3    Weinshilboum, R.M.4    Coughtrie, M.H.5
  • 6
    • 80755168366 scopus 로고    scopus 로고
    • Altered tissue distribution of 2-amino-1-methyl-6-phenylimidazo[4,5-b] pyridine-DNA adducts in mice transgenic for human sulfotransferases 1A1 and 1A2
    • 1:CAS:528:DC%2BC3MXhtlyqur7J 21900212 10.1093/carcin/bgr204
    • Dobbernack G, Meinl W, Schade N, Florian S, Wend K, Voigt I, Himmelbauer H, Gross M, Liehr T, Glatt H (2011) Altered tissue distribution of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine-DNA adducts in mice transgenic for human sulfotransferases 1A1 and 1A2. Carcinogenesis 32:1734-1740
    • (2011) Carcinogenesis , vol.32 , pp. 1734-1740
    • Dobbernack, G.1    Meinl, W.2    Schade, N.3    Florian, S.4    Wend, K.5    Voigt, I.6    Himmelbauer, H.7    Gross, M.8    Liehr, T.9    Glatt, H.10
  • 7
    • 0035313091 scopus 로고    scopus 로고
    • Formation of allyl isothiocyanate from sinigrin in the digestive tract of rats monoassociated with a human colonic strain of Bacteroides thetaiotaomicron
    • 1:CAS:528:DC%2BD3MXisVWgtro%3D 11287153 10.1111/j.1574-6968.2001.tb10589. x
    • Elfoul L, Rabot S, Khelifa N, Quinsac A, Duguay A, Rimbault A (2001) Formation of allyl isothiocyanate from sinigrin in the digestive tract of rats monoassociated with a human colonic strain of Bacteroides thetaiotaomicron. FEMS Microbiol Lett 197:99-103
    • (2001) FEMS Microbiol Lett , vol.197 , pp. 99-103
    • Elfoul, L.1    Rabot, S.2    Khelifa, N.3    Quinsac, A.4    Duguay, A.5    Rimbault, A.6
  • 8
    • 0001042792 scopus 로고
    • Synthesis of 11 benzylic sulfate esters, their bacterial mutagenicity and its modulation by chloride, bromide and acetate anions
    • Enders N, Seidel A, Monnerjahn S, Glatt H (1993) Synthesis of 11 benzylic sulfate esters, their bacterial mutagenicity and its modulation by chloride, bromide and acetate anions. Polycycl Aromat Compds 3:887s-894s
    • (1993) Polycycl Aromat Compds , vol.3
    • Enders, N.1    Seidel, A.2    Monnerjahn, S.3    Glatt, H.4
  • 9
    • 0032948428 scopus 로고    scopus 로고
    • Conversion of glucosinolates to isothiocyanates in humans after ingestion of cooked watercress
    • 1:CAS:528:DyaK1MXjs1yitr0%3D 10350441
    • Getahun SM, Chung FL (1999) Conversion of glucosinolates to isothiocyanates in humans after ingestion of cooked watercress. Cancer Epidemiol Biomarkers Prev 8:447-451
    • (1999) Cancer Epidemiol Biomarkers Prev , vol.8 , pp. 447-451
    • Getahun, S.M.1    Chung, F.L.2
  • 10
    • 0034534841 scopus 로고    scopus 로고
    • Sulfotransferases in the bioactivation of xenobiotics
    • 1:CAS:528:DC%2BD3MXitlOmsg%3D%3D 11154739 10.1016/S0009-2797(00)00202-7
    • Glatt H (2000) Sulfotransferases in the bioactivation of xenobiotics. Chem-Biol Interact 129:141-170
    • (2000) Chem-Biol Interact , vol.129 , pp. 141-170
    • Glatt, H.1
  • 11
    • 0025175960 scopus 로고
    • Sulfotransferase-mediated chlorination of 1-hydroxymethylpyrene to a mutagen capable of penetrating indicator cells
    • 1:CAS:528:DyaK3MXktVaqs7w%3D 1568025 2272332 10.1289/ehp.908843
    • Glatt H, Henschler R, Phillips DH, Blake JW, Steinberg P, Seidel A, Oesch F (1990) Sulfotransferase-mediated chlorination of 1-hydroxymethylpyrene to a mutagen capable of penetrating indicator cells. Environ Health Perspect 88:43-48
    • (1990) Environ Health Perspect , vol.88 , pp. 43-48
    • Glatt, H.1    Henschler, R.2    Phillips, D.H.3    Blake, J.W.4    Steinberg, P.5    Seidel, A.6    Oesch, F.7
  • 12
    • 0035479494 scopus 로고    scopus 로고
    • Human cytosolic sulphotransferases: Genetics, characteristics, toxicological aspects
    • 1:CAS:528:DC%2BD3MXmsFeltbw%3D 11535246 10.1016/S0027-5107(01)00207-X
    • Glatt H, Boeing H, Engelke CEH, Kuhlow A, Ma L, Pabel U, Pomplun D, Teubner W, Meinl W (2001) Human cytosolic sulphotransferases: genetics, characteristics, toxicological aspects. Mutat Res 482:27-40
    • (2001) Mutat Res , vol.482 , pp. 27-40
    • Glatt, H.1    Boeing, H.2    Engelke, C.E.H.3    Kuhlow, A.4    Ma, L.5    Pabel, U.6    Pomplun, D.7    Teubner, W.8    Meinl, W.9
  • 13
    • 79955625686 scopus 로고    scopus 로고
    • 1-Methoxy-3-indolylmethyl glucosinolate, a potent genotoxicant in bacterial and mammalian cells: Mechanisms of bioactivation
    • 1:CAS:528:DC%2BC3MXntVyhsrY%3D 20846518 10.1016/j.cbi.2010.09.009
    • Glatt H, Baasanjav-Gerber C, Schumacher F, Monien BH, Schreiner M, Frank H, Seidel A, Engst W (2011) 1-Methoxy-3-indolylmethyl glucosinolate, a potent genotoxicant in bacterial and mammalian cells: mechanisms of bioactivation. Chem-Biol Interact 192:81-86
    • (2011) Chem-Biol Interact , vol.192 , pp. 81-86
    • Glatt, H.1    Baasanjav-Gerber, C.2    Schumacher, F.3    Monien, B.H.4    Schreiner, M.5    Frank, H.6    Seidel, A.7    Engst, W.8
  • 14
    • 0027346285 scopus 로고
    • 32P-postlabelling analysis of bulky aromatic adducts
    • 1:CAS:528:DyaK2cXpvVGkug%3D%3D 8225473
    • 32P-postlabelling analysis of bulky aromatic adducts. IARC Sci Publ 124:11-23
    • (1993) IARC Sci Publ , vol.124 , pp. 11-23
    • Gupta, R.C.1
  • 15
    • 37049068013 scopus 로고
    • Chemistry of indole glucosinolates: Intermediacy of indol-3-ylmethyl isothiocyanates in the enzymic hydrolysis of indole glucosinolates
    • 10.1039/p19900002273
    • Hanley AB, Parsley KR, Lewis JA, Fenwick GR (1990) Chemistry of indole glucosinolates: intermediacy of indol-3-ylmethyl isothiocyanates in the enzymic hydrolysis of indole glucosinolates. J Chem Soc Perkin Trans 1:2273-2276
    • (1990) J Chem Soc Perkin Trans , vol.1 , pp. 2273-2276
    • Hanley, A.B.1    Parsley, K.R.2    Lewis, J.A.3    Fenwick, G.R.4
  • 16
    • 3042783575 scopus 로고    scopus 로고
    • A critical review of the bioavailability of glucosinolates and related compounds
    • 1:CAS:528:DC%2BD2cXlvVagsLk%3D 15162227 10.1039/b204039p
    • Holst B, Williamson G (2004) A critical review of the bioavailability of glucosinolates and related compounds. Nat Prod Rep 21:425-447
    • (2004) Nat Prod Rep , vol.21 , pp. 425-447
    • Holst, B.1    Williamson, G.2
  • 17
    • 0343517520 scopus 로고    scopus 로고
    • Genotoxic effects of allyl isothiocyanate (AITC) and phenethyl isothiocyanate (PEITC)
    • 1:CAS:528:DC%2BD3cXlsFeqt7o%3D 10936231 10.1016/S0009-2797(00)00178-2
    • Kassie F, Knasmüller S (2000) Genotoxic effects of allyl isothiocyanate (AITC) and phenethyl isothiocyanate (PEITC). Chem-Biol Interact 127:163-180
    • (2000) Chem-Biol Interact , vol.127 , pp. 163-180
    • Kassie, F.1    Knasmüller, S.2
  • 18
    • 0032728663 scopus 로고    scopus 로고
    • Genotoxic effects of benzyl isothiocyanate, a natural chemopreventive agent
    • 1:CAS:528:DyaK1MXnvV2htr4%3D 10567035 10.1093/mutage/14.6.595
    • Kassie F, Pool-Zobel B, Parzefall W, Knasmüller S (1999) Genotoxic effects of benzyl isothiocyanate, a natural chemopreventive agent. Mutagenesis 14:595-603
    • (1999) Mutagenesis , vol.14 , pp. 595-603
    • Kassie, F.1    Pool-Zobel, B.2    Parzefall, W.3    Knasmüller, S.4
  • 19
    • 0036309574 scopus 로고    scopus 로고
    • Metabolism of sinigrin (2-propenyl glucosinolate) by the human colonic microflora in a dynamic in vitro large-intestinal model
    • 1:CAS:528:DC%2BD38Xlt1Knurg%3D 12082023 10.1093/carcin/23.6.1009
    • Krul C, Humblot C, Philippe C, Vermeulen M, van Nuenen M, Havenaar R, Rabot S (2002) Metabolism of sinigrin (2-propenyl glucosinolate) by the human colonic microflora in a dynamic in vitro large-intestinal model. Carcinogenesis 23:1009-1016
    • (2002) Carcinogenesis , vol.23 , pp. 1009-1016
    • Krul, C.1    Humblot, C.2    Philippe, C.3    Vermeulen, M.4    Van Nuenen, M.5    Havenaar, R.6    Rabot, S.7
  • 20
    • 79953295413 scopus 로고    scopus 로고
    • Glucoraphanin hydrolysis by microbiota in the rat cecum results in sulforaphane absorption
    • 1:CAS:528:DC%2BC3MXktV2gsQ%3D%3D 21776467 10.1039/c0fo00110d
    • Lai RH, Miller MJ, Jeffery E (2010) Glucoraphanin hydrolysis by microbiota in the rat cecum results in sulforaphane absorption. Food Funct 1:161-166
    • (2010) Food Funct , vol.1 , pp. 161-166
    • Lai, R.H.1    Miller, M.J.2    Jeffery, E.3
  • 21
    • 0030355238 scopus 로고    scopus 로고
    • Benzylic sulphuric acid esters react with diverse functional groups and often form secondary reactive species
    • 1:CAS:528:DyaK2sXjtFyisr8%3D 10.1080/10406639608544685
    • Landsiedel R, Engst W, Scholtyssek M, Seidel A, Glatt H (1996) Benzylic sulphuric acid esters react with diverse functional groups and often form secondary reactive species. Polycycl Aromat Compds 11:341-348
    • (1996) Polycycl Aromat Compds , vol.11 , pp. 341-348
    • Landsiedel, R.1    Engst, W.2    Scholtyssek, M.3    Seidel, A.4    Glatt, H.5
  • 22
    • 26944435924 scopus 로고    scopus 로고
    • Major signaling pathways modulate Arabidopsis glucosinolate accumulation and response to both phloem-feeding and chewing insects
    • 1:CAS:528:DC%2BD2MXmtVejsbw%3D 1150428 15923339 10.1104/pp.104.053389
    • Mewis I, Appel HM, Hom A, Raina R, Schultz JC (2005) Major signaling pathways modulate Arabidopsis glucosinolate accumulation and response to both phloem-feeding and chewing insects. Plant Physiol 138:1149-1162
    • (2005) Plant Physiol , vol.138 , pp. 1149-1162
    • Mewis, I.1    Appel, H.M.2    Hom, A.3    Raina, R.4    Schultz, J.C.5
  • 23
    • 84866350709 scopus 로고    scopus 로고
    • UV-B irradiation changes specifically the secondary metabolite profile in broccoli sprouts: Induced signaling overlaps with defense response to biotic stressors
    • 1:CAS:528:DC%2BC38XhtlKktrfL 22773681 10.1093/pcp/pcs096
    • Mewis I, Schreiner M, Nguyen CN, Krumbein A, Ulrichs C, Lohse M, Zrenner R (2012) UV-B irradiation changes specifically the secondary metabolite profile in broccoli sprouts: induced signaling overlaps with defense response to biotic stressors. Plant Cell Physiol 53:1546-1560
    • (2012) Plant Cell Physiol , vol.53 , pp. 1546-1560
    • Mewis, I.1    Schreiner, M.2    Nguyen, C.N.3    Krumbein, A.4    Ulrichs, C.5    Lohse, M.6    Zrenner, R.7
  • 24
    • 0019222505 scopus 로고
    • Quantitation of benzo[a]pyrene-deoxyguanosine adducts by radioimmunoassay
    • 1:CAS:528:DyaL3cXhsVWntbw%3D 7356524
    • Poirier MC, Santella R, Weinstein IB, Grunberger D, Yuspa SH (1980) Quantitation of benzo[a]pyrene-deoxyguanosine adducts by radioimmunoassay. Cancer Res 40:412-416
    • (1980) Cancer Res , vol.40 , pp. 412-416
    • Poirier, M.C.1    Santella, R.2    Weinstein, I.B.3    Grunberger, D.4    Yuspa, S.H.5
  • 26
    • 84863970194 scopus 로고    scopus 로고
    • Detection of DNA adducts originating from 1-methoxy-3-indolylmethyl glucosinolate using isotope-dilution UPLC-ESI-MS/MS
    • 1:CAS:528:DC%2BC38XoslGiu7k%3D 22816785 10.1021/ac301436q
    • Schumacher F, Engst W, Monien BH, Florian S, Schnapper A, Steinhauser L, Albert K, Frank H, Seidel A, Glatt H (2012) Detection of DNA adducts originating from 1-methoxy-3-indolylmethyl glucosinolate using isotope-dilution UPLC-ESI-MS/MS. Anal Chem 84:6256-6262
    • (2012) Anal Chem , vol.84 , pp. 6256-6262
    • Schumacher, F.1    Engst, W.2    Monien, B.H.3    Florian, S.4    Schnapper, A.5    Steinhauser, L.6    Albert, K.7    Frank, H.8    Seidel, A.9    Glatt, H.10
  • 27
    • 84872855761 scopus 로고    scopus 로고
    • Optimized enzymatic hydrolysis of DNA for LC-MS/MS analyses of adducts of 1-methoxy-3-indolylmethyl glucosinolate and methyleugenol
    • 1:CAS:528:DC%2BC3sXhtlert70%3D 23142629 10.1016/j.ab.2012.11.001
    • Schumacher F, Herrmann K, Florian S, Engst W, Glatt H (2013) Optimized enzymatic hydrolysis of DNA for LC-MS/MS analyses of adducts of 1-methoxy-3-indolylmethyl glucosinolate and methyleugenol. Anal Biochem 434:4-11
    • (2013) Anal Biochem , vol.434 , pp. 4-11
    • Schumacher, F.1    Herrmann, K.2    Florian, S.3    Engst, W.4    Glatt, H.5
  • 28
    • 62349106315 scopus 로고    scopus 로고
    • Dietary intake of individual glucosinolates in participants of the EPIC-Heidelberg cohort study
    • 1:CAS:528:DC%2BD1MXlvFWmtr0%3D 19295191 10.1159/000209266
    • Steinbrecher A, Linseisen J (2009) Dietary intake of individual glucosinolates in participants of the EPIC-Heidelberg cohort study. Ann Nutr Metab 54:87-96
    • (2009) Ann Nutr Metab , vol.54 , pp. 87-96
    • Steinbrecher, A.1    Linseisen, J.2
  • 30
    • 84880733311 scopus 로고    scopus 로고
    • Induced production of 1-methoxy-indol-3-ylmethyl glucosinolate by jasmonic acid and methyl jasmonate in sprouts and leaves of pak choi (Brassica rapa ssp. Chinensis)
    • 1:CAS:528:DC%2BC3sXht12msb3M 3742284 23873294 10.3390/ijms140714996
    • Wiesner M, Hanschen FS, Schreiner M, Glatt H, Zrenner R (2013a) Induced production of 1-methoxy-indol-3-ylmethyl glucosinolate by jasmonic acid and methyl jasmonate in sprouts and leaves of pak choi (Brassica rapa ssp. chinensis). Int J Mol Sci 14:14996-15016
    • (2013) Int J Mol Sci , vol.14 , pp. 14996-15016
    • Wiesner, M.1    Hanschen, F.S.2    Schreiner, M.3    Glatt, H.4    Zrenner, R.5
  • 31
    • 84874607823 scopus 로고    scopus 로고
    • Genotypic variation of the glucosinolate profile in pak choi (Brassica rapa ssp. Chinensis)
    • 1:CAS:528:DC%2BC3sXhsVelsLc%3D 23350944 10.1021/jf303970k
    • Wiesner M, Zrenner R, Krumbein A, Glatt H, Schreiner M (2013b) Genotypic variation of the glucosinolate profile in pak choi (Brassica rapa ssp. chinensis). J Agric Food Chem 61:1943-1953
    • (2013) J Agric Food Chem , vol.61 , pp. 1943-1953
    • Wiesner, M.1    Zrenner, R.2    Krumbein, A.3    Glatt, H.4    Schreiner, M.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.