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Volumn 70, Issue 1, 2013, Pages 155-162

Synthesis and Nrf2-inducing activity of the isothiocyanates iberverin, iberin and cheirolin

Author keywords

Cheirolin; Chemical isothiocyanate synthesis; Iberin; Iberverin; Nrf2

Indexed keywords

CHEIROLIN; GLUTAMATE CYSTEINE LIGASE; HEME OXYGENASE 1; IBERIN; IBERVERIN; ISOTHIOCYANIC ACID DERIVATIVE; KELCH LIKE ECH ASSOCIATED PROTEIN 1; MESSENGER RNA; SULFORAPHANE; TRANSCRIPTION FACTOR NRF2; UNCLASSIFIED DRUG;

EID: 84875157012     PISSN: 10436618     EISSN: 10961186     Source Type: Journal    
DOI: 10.1016/j.phrs.2013.01.011     Document Type: Article
Times cited : (29)

References (38)
  • 2
    • 0028326168 scopus 로고
    • Anticarcinogenic activities of organic isothiocyanates: Chemistry and mechanisms
    • Y. Zhang, and P. Talalay Anticarcinogenic activities of organic isothiocyanates: chemistry and mechanisms Cancer Research 54 1994 1976s 1981s
    • (1994) Cancer Research , vol.54
    • Zhang, Y.1    Talalay, P.2
  • 4
    • 0035808553 scopus 로고    scopus 로고
    • The chemical diversity and distribution of glucosinolates and isothiocyanates among plants
    • J.W. Fahey, A.T. Zalcmann, and P. Talalay The chemical diversity and distribution of glucosinolates and isothiocyanates among plants Phytochemistry 56 2001 5 51
    • (2001) Phytochemistry , vol.56 , pp. 5-51
    • Fahey, J.W.1    Zalcmann, A.T.2    Talalay, P.3
  • 7
    • 0029411321 scopus 로고
    • Parallel induction of heme oxygenase-1 and chemoprotective phase 2 enzymes by electrophiles and antioxidants: Regulation by upstream antioxidant-responsive elements (are)
    • T. Prestera, P. Talalay, J. Alam, Y.I. Ahn, P.J. Lee, and A.M. Choi Parallel induction of heme oxygenase-1 and chemoprotective phase 2 enzymes by electrophiles and antioxidants: regulation by upstream antioxidant-responsive elements (are) Molecular Medicine 1 1995 827 837
    • (1995) Molecular Medicine , vol.1 , pp. 827-837
    • Prestera, T.1    Talalay, P.2    Alam, J.3    Ahn, Y.I.4    Lee, P.J.5    Choi, A.M.6
  • 9
    • 0028061444 scopus 로고
    • Isolation of nf-e2-related factor 2 (nrf2), a nf-e2-like basic leucine zipper transcriptional activator that binds to the tandem nf-e2/ap1 repeat of the beta-globin locus control region
    • P. Moi, K. Chan, I. Asunis, A. Cao, and Y.W. Kan Isolation of nf-e2-related factor 2 (nrf2), a nf-e2-like basic leucine zipper transcriptional activator that binds to the tandem nf-e2/ap1 repeat of the beta-globin locus control region Proceedings of the National Academy of Sciences of the United States of America 91 1994 9926 9930
    • (1994) Proceedings of the National Academy of Sciences of the United States of America , vol.91 , pp. 9926-9930
    • Moi, P.1    Chan, K.2    Asunis, I.3    Cao, A.4    Kan, Y.W.5
  • 10
    • 33747606306 scopus 로고    scopus 로고
    • Structure of the keap1: Nrf2 interface provides mechanistic insight into nrf2 signaling
    • S.C. Lo, X. Li, M.T. Henzl, L.J. Beamer, and M. Hannink Structure of the keap1: Nrf2 interface provides mechanistic insight into nrf2 signaling EMBO Journal 25 2006 3605 3617
    • (2006) EMBO Journal , vol.25 , pp. 3605-3617
    • Lo, S.C.1    Li, X.2    Henzl, M.T.3    Beamer, L.J.4    Hannink, M.5
  • 11
    • 0003047154 scopus 로고
    • Purification of the omega-(methylsulfinyl)alkyl glucosinolate hydrolysis products: 1-isothiocyanato-3-(methylsulfinyl)propane, 1-isothiocyanato-4- (methylsulfinyl)butane, 4-(methylsulfinyl)butanenitrile, and 5-(methylsulfinyl)pentanenitrile from broccoli and lesquerella fendleri
    • A.M.S. Kore, and G.F.M.A. Wallig Purification of the omega- (methylsulfinyl)alkyl glucosinolate hydrolysis products: 1-isothiocyanato-3- (methylsulfinyl)propane, 1-isothiocyanato-4-(methylsulfinyl)butane, 4-(methylsulfinyl)butanenitrile, and 5-(methylsulfinyl)pentanenitrile from broccoli and lesquerella fendleri Journal of Agricultural and Food Chemistry 1993 89 95
    • (1993) Journal of Agricultural and Food Chemistry , pp. 89-95
    • Kore, A.M.S.1    Wallig, G.F.M.A.2
  • 12
    • 0034691291 scopus 로고    scopus 로고
    • Hydrolysis of glucosinolates using nylon-immobilized myrosinase to produce pure bioactive molecules
    • O. Leoni, R. Iori, and S. Palmieri Hydrolysis of glucosinolates using nylon-immobilized myrosinase to produce pure bioactive molecules Biotechnology and bioengineering 68 2000 660 664
    • (2000) Biotechnology and Bioengineering , vol.68 , pp. 660-664
    • Leoni, O.1    Iori, R.2    Palmieri, S.3
  • 13
    • 13944260838 scopus 로고    scopus 로고
    • Glucosinolate hydrolysis products from various plant sources: Ph effects, isolation, and purification
    • S.F. Vaughn, and M.A. Berhow Glucosinolate hydrolysis products from various plant sources: Ph effects, isolation, and purification Industrial Crops and Products 2005 193 202
    • (2005) Industrial Crops and Products , pp. 193-202
    • Vaughn, S.F.1    Berhow, M.A.2
  • 14
    • 33745401980 scopus 로고    scopus 로고
    • Purification of major glucosinolates from brassicaceae seeds and preparation of isothiocyanate and amine metabolites
    • L. Song, R. Iori, and P.J. Thornalley Purification of major glucosinolates from brassicaceae seeds and preparation of isothiocyanate and amine metabolites Journal of the Science of Food and Agriculture 2006 1271 1280
    • (2006) Journal of the Science of Food and Agriculture , pp. 1271-1280
    • Song, L.1    Iori, R.2    Thornalley, P.J.3
  • 15
    • 62349106315 scopus 로고    scopus 로고
    • Dietary intake of individual glucosinolates in participants of the epic-Heidelberg cohort study
    • A. Steinbrecher, and J. Linseisen Dietary intake of individual glucosinolates in participants of the epic-Heidelberg cohort study Annals of Nutrition and Metabolism 54 2009 87 96
    • (2009) Annals of Nutrition and Metabolism , vol.54 , pp. 87-96
    • Steinbrecher, A.1    Linseisen, J.2
  • 16
    • 9744283511 scopus 로고    scopus 로고
    • Transcription factor nrf2 is essential for induction of nad(p)h:Quinone oxidoreductase 1, glutathione s-transferases, and glutamate cysteine ligase by broccoli seeds and isothiocyanates
    • G.K. McWalter, L.G. Higgins, L.I. McLellan, C.J. Henderson, L. Song, and P.J. Thornalley Transcription factor nrf2 is essential for induction of nad(p)h:Quinone oxidoreductase 1, glutathione s-transferases, and glutamate cysteine ligase by broccoli seeds and isothiocyanates Journal of Nutrition 134 2004 3499S 3506S
    • (2004) Journal of Nutrition , vol.134
    • McWalter, G.K.1    Higgins, L.G.2    McLellan, L.I.3    Henderson, C.J.4    Song, L.5    Thornalley, P.J.6
  • 18
    • 0032948428 scopus 로고    scopus 로고
    • Conversion of glucosinolates to isothiocyanates in humans after ingestion of cooked watercress
    • S.M. Getahun, and F.L. Chung Conversion of glucosinolates to isothiocyanates in humans after ingestion of cooked watercress Cancer Epidemiology, Biomarkers and Prevention 8 1999 447 451
    • (1999) Cancer Epidemiology, Biomarkers and Prevention , vol.8 , pp. 447-451
    • Getahun, S.M.1    Chung, F.L.2
  • 20
    • 0008783678 scopus 로고
    • Isothiocyanates. 12. 3-Methylthiopropyl isothiocyanate (ibervirin), a new naturally occurring mustard oil
    • A. Kjaer, R. Gmelin, and I. Larsen Isothiocyanates. 12. 3-Methylthiopropyl isothiocyanate (ibervirin), a new naturally occurring mustard oil Acta Chemica Scandinavica 9 1955 1143 1147
    • (1955) Acta Chemica Scandinavica , vol.9 , pp. 1143-1147
    • Kjaer, A.1    Gmelin, R.2    Larsen, I.3
  • 21
    • 84875149406 scopus 로고
    • Isothiocyanates. 6. A synthesis of cheiroline (gamma- methylsulphonylpropyl isothiocyanate)
    • A. Kjaer, F. Marcus, and J. Conti Isothiocyanates. 6. A synthesis of cheiroline (gamma-methylsulphonylpropyl isothiocyanate) Acta Chemica Scandinavica 7 1953 1370 1374
    • (1953) Acta Chemica Scandinavica , vol.7 , pp. 1370-1374
    • Kjaer, A.1    Marcus, F.2    Conti, J.3
  • 22
    • 0029156562 scopus 로고
    • Biotransformation of organic sulfides. 7. Formation of chiral isothiocyanato sulfoxides and related-compounds by microbial biotransformation
    • H.L. Holland, F.M. Brown, B.G. Larsen, and M. Zabic Biotransformation of organic sulfides. 7. Formation of chiral isothiocyanato sulfoxides and related-compounds by microbial biotransformation Tetrahedron-Asymmetry 6 1995 1569 1574
    • (1995) Tetrahedron-Asymmetry , vol.6 , pp. 1569-1574
    • Holland, H.L.1    Brown, F.M.2    Larsen, B.G.3    Zabic, M.4
  • 23
    • 43149121599 scopus 로고    scopus 로고
    • Identification, synthesis, and enzymology of non-natural glucosinolate chemopreventive candidates
    • J.R. Mays, R.L.W. Roska, S. Sarfaraz, H. Mukhtar, and S.R. Rajski Identification, synthesis, and enzymology of non-natural glucosinolate chemopreventive candidates Chembiochem 9 2008 729 747
    • (2008) Chembiochem , vol.9 , pp. 729-747
    • Mays, J.R.1    Roska, R.L.W.2    Sarfaraz, S.3    Mukhtar, H.4    Rajski, S.R.5
  • 24
    • 0021990499 scopus 로고
    • Toxicity determined in vitro by morphological alterations and neutral red absorption
    • E. Borenfreund, and J.A. Puerner Toxicity determined in vitro by morphological alterations and neutral red absorption Toxicology Letters 24 1985 119 124
    • (1985) Toxicology Letters , vol.24 , pp. 119-124
    • Borenfreund, E.1    Puerner, J.A.2
  • 25
    • 0035964432 scopus 로고    scopus 로고
    • Effect of benzoyl peroxide on antioxidant status, nf-kappab activity and interleukin-1 alpha gene expression in human keratinocytes
    • G. Valacchi, G. Rimbach, C. Saliou, S.U. Weber, and L. Packer Effect of benzoyl peroxide on antioxidant status, nf-kappab activity and interleukin-1 alpha gene expression in human keratinocytes Toxicology 165 2001 225 234
    • (2001) Toxicology , vol.165 , pp. 225-234
    • Valacchi, G.1    Rimbach, G.2    Saliou, C.3    Weber, S.U.4    Packer, L.5
  • 26
    • 74949124720 scopus 로고    scopus 로고
    • Sulforaphane but not ascorbigen, indole-3-carbinole and ascorbic acid activates the transcription factor nrf2 and induces phase-2 and antioxidant enzymes in human keratinocytes in culture
    • A.E. Wagner, I. Ernst, R. Iori, C. Desel, and G. Rimbach Sulforaphane but not ascorbigen, indole-3-carbinole and ascorbic acid activates the transcription factor nrf2 and induces phase-2 and antioxidant enzymes in human keratinocytes in culture Experimental Dermatology 19 2010 137 144
    • (2010) Experimental Dermatology , vol.19 , pp. 137-144
    • Wagner, A.E.1    Ernst, I.2    Iori, R.3    Desel, C.4    Rimbach, G.5
  • 28
    • 84856227947 scopus 로고    scopus 로고
    • Hormetics: Dietary triggers of an adaptive stress response
    • M. Birringer Hormetics: dietary triggers of an adaptive stress response Pharmaceutical Research 28 2011 2680 2694
    • (2011) Pharmaceutical Research , vol.28 , pp. 2680-2694
    • Birringer, M.1
  • 31
    • 0026033907 scopus 로고
    • Induction of heme oxygenase: A general response to oxidant stress in cultured mammalian cells
    • L.A. Applegate, P. Luscher, and R.M. Tyrrell Induction of heme oxygenase: a general response to oxidant stress in cultured mammalian cells Cancer Research 51 1991 974 978
    • (1991) Cancer Research , vol.51 , pp. 974-978
    • Applegate, L.A.1    Luscher, P.2    Tyrrell, R.M.3
  • 33
    • 84862689618 scopus 로고    scopus 로고
    • Structural influence of isothiocyanates on expression of cytochrome p450, phase ii enzymes, and activation of nrf2 in primary rat hepatocytes
    • M. La Marca, P. Beffy, C. Della Croce, P.G. Gervasi, R. Iori, and E. Puccinelli Structural influence of isothiocyanates on expression of cytochrome p450, phase ii enzymes, and activation of nrf2 in primary rat hepatocytes Food and Chemical Toxicology 50 2012 2822 2830
    • (2012) Food and Chemical Toxicology , vol.50 , pp. 2822-2830
    • La Marca, M.1    Beffy, P.2    Della Croce, C.3    Gervasi, P.G.4    Iori, R.5    Puccinelli, E.6
  • 34
    • 67651165192 scopus 로고    scopus 로고
    • D,l-Sulforaphane causes transcriptional repression of androgen receptor in human prostate cancer cells
    • S.H. Kim, and S.V. Singh d,l-Sulforaphane causes transcriptional repression of androgen receptor in human prostate cancer cells Molecular Cancer Therapeutics 8 2009 1946 1954
    • (2009) Molecular Cancer Therapeutics , vol.8 , pp. 1946-1954
    • Kim, S.H.1    Singh, S.V.2
  • 35
    • 1842588301 scopus 로고    scopus 로고
    • Induction of phase ii detoxification enzymes in rats by plant-derived isothiocyanates: Comparison of allyl isothiocyanate with sulforaphane and related compounds
    • R. Munday, and C.M. Munday Induction of phase ii detoxification enzymes in rats by plant-derived isothiocyanates: comparison of allyl isothiocyanate with sulforaphane and related compounds Journal of Agricultural and Food Chemistry 52 2004 1867 1871
    • (2004) Journal of Agricultural and Food Chemistry , vol.52 , pp. 1867-1871
    • Munday, R.1    Munday, C.M.2
  • 37
    • 0030781225 scopus 로고    scopus 로고
    • Biotransformation of the naturally occurring isothiocyanate sulforaphane in the rat: Identification of phase i metabolites and glutathione conjugates
    • K. Kassahun, M. Davis, P. Hu, B. Martin, and T. Baillie Biotransformation of the naturally occurring isothiocyanate sulforaphane in the rat: identification of phase i metabolites and glutathione conjugates Chemical Research in Toxicology 10 1997 1228 1233
    • (1997) Chemical Research in Toxicology , vol.10 , pp. 1228-1233
    • Kassahun, K.1    Davis, M.2    Hu, P.3    Martin, B.4    Baillie, T.5
  • 38
    • 69049120201 scopus 로고    scopus 로고
    • Repeated intake of broccoli does not lead to higher plasma levels of sulforaphane in human volunteers
    • N. Hanlon, N. Coldham, A. Gielbert, M.J. Sauer, and C. Ioannides Repeated intake of broccoli does not lead to higher plasma levels of sulforaphane in human volunteers Cancer Letters 284 2009 15 20
    • (2009) Cancer Letters , vol.284 , pp. 15-20
    • Hanlon, N.1    Coldham, N.2    Gielbert, A.3    Sauer, M.J.4    Ioannides, C.5


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