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Volumn 28, Issue 5, 2015, Pages 989-996

Oxidative Transformation of Demethoxy- and Bisdemethoxycurcumin: Products, Mechanism of Formation, and Poisoning of Human Topoisomerase IIα

Author keywords

[No Author keywords available]

Indexed keywords

CURCUMIN; DEMETHOXYCURCUMIN; DIDEMETHOXYCURCUMIN; DNA TOPOISOMERASE (ATP HYDROLYSING); DNA TOPOISOMERASE IIALPHA; HORSERADISH PEROXIDASE; HYDROGEN PEROXIDE; POTASSIUM FERRICYANIDE; TURMERIC; UNCLASSIFIED DRUG; BIS(4-HYDROXYCINNAMOYL)METHANE; DNA BINDING PROTEIN; DNA TOPOISOMERASE II ALPHA; EPOXIDE; PLANT EXTRACT; TUMOR ANTIGEN; TURMERIC EXTRACT;

EID: 84929590403     PISSN: 0893228X     EISSN: 15205010     Source Type: Journal    
DOI: 10.1021/acs.chemrestox.5b00009     Document Type: Article
Times cited : (65)

References (43)
  • 3
    • 84877285857 scopus 로고    scopus 로고
    • New perspectives of curcumin in cancer prevention
    • Park, W., Amin, A. R., Chen, Z. G., and Shin, D. M. (2013) New perspectives of curcumin in cancer prevention Cancer Prev. Res. 6, 387 - 400
    • (2013) Cancer Prev. Res. , vol.6 , pp. 387-400
    • Park, W.1    Amin, A.R.2    Chen, Z.G.3    Shin, D.M.4
  • 5
    • 84891613383 scopus 로고    scopus 로고
    • The molecular basis for the pharmacokinetics and pharmacodynamics of curcumin and its metabolites in relation to cancer
    • Heger, M., van Golen, R. F., Broekgaarden, M., and Michel, M. C. (2014) The molecular basis for the pharmacokinetics and pharmacodynamics of curcumin and its metabolites in relation to cancer Pharmacol. Rev. 66, 222 - 307
    • (2014) Pharmacol. Rev. , vol.66 , pp. 222-307
    • Heger, M.1    Van Golen, R.F.2    Broekgaarden, M.3    Michel, M.C.4
  • 7
    • 79952253826 scopus 로고    scopus 로고
    • Efficacy and safety of Meriva(R), a curcumin-phosphatidylcholine complex, during extended administration in osteoarthritis patients
    • Belcaro, G., Cesarone, M. R., Dugall, M., Pellegrini, L., Ledda, A., Grossi, M. G., Togni, S., and Appendino, G. (2010) Efficacy and safety of Meriva(R), a curcumin-phosphatidylcholine complex, during extended administration in osteoarthritis patients Altern. Med. Rev. 15, 337 - 344
    • (2010) Altern. Med. Rev. , vol.15 , pp. 337-344
    • Belcaro, G.1    Cesarone, M.R.2    Dugall, M.3    Pellegrini, L.4    Ledda, A.5    Grossi, M.G.6    Togni, S.7    Appendino, G.8
  • 9
    • 77953615306 scopus 로고    scopus 로고
    • Curcumin as a therapeutic agent: The evidence from in vitro, animal and human studies
    • Epstein, J., Sanderson, I. R., and Macdonald, T. T. (2010) Curcumin as a therapeutic agent: the evidence from in vitro, animal and human studies Br. J. Nutr. 103, 1545 - 1557
    • (2010) Br. J. Nutr. , vol.103 , pp. 1545-1557
    • Epstein, J.1    Sanderson, I.R.2    MacDonald, T.T.3
  • 10
    • 0022066944 scopus 로고
    • Studies on curcumin and curcuminoids. VI. Kinetics of curcumin degradation in aqueous solution
    • Tonnesen, H. H. and Karlsen, J. (1985) Studies on curcumin and curcuminoids. VI. Kinetics of curcumin degradation in aqueous solution Z. Lebensm.-Unters. Forsch. 180, 402 - 404
    • (1985) Z. Lebensm.-Unters. Forsch. , vol.180 , pp. 402-404
    • Tonnesen, H.H.1    Karlsen, J.2
  • 11
    • 0030839940 scopus 로고    scopus 로고
    • Stability of curcumin in buffer solutions and characterization of its degradation products
    • Wang, Y. J., Pan, M. H., Cheng, A. L., Lin, L. I., Ho, Y. S., Hsieh, C. Y., and Lin, J. K. (1997) Stability of curcumin in buffer solutions and characterization of its degradation products J. Pharm. Biomed. Anal. 15, 1867 - 1876
    • (1997) J. Pharm. Biomed. Anal. , vol.15 , pp. 1867-1876
    • Wang, Y.J.1    Pan, M.H.2    Cheng, A.L.3    Lin, L.I.4    Ho, Y.S.5    Hsieh, C.Y.6    Lin, J.K.7
  • 12
    • 0037290321 scopus 로고    scopus 로고
    • Studies on the stability of turmeric constituents
    • Pfeiffer, E., Hoehle, S. I., Solyom, A. M., and Metzler, M. (2003) Studies on the stability of turmeric constituents J. Food Eng. 56, 257 - 259
    • (2003) J. Food Eng. , vol.56 , pp. 257-259
    • Pfeiffer, E.1    Hoehle, S.I.2    Solyom, A.M.3    Metzler, M.4
  • 13
    • 78651401023 scopus 로고    scopus 로고
    • Autoxidative and cyclooxygenase-2 catalyzed transformation of the dietary chemopreventive agent curcumin
    • Griesser, M., Pistis, V., Suzuki, T., Tejera, N., Pratt, D. A., and Schneider, C. (2011) Autoxidative and cyclooxygenase-2 catalyzed transformation of the dietary chemopreventive agent curcumin J. Biol. Chem. 286, 1114 - 1124
    • (2011) J. Biol. Chem. , vol.286 , pp. 1114-1124
    • Griesser, M.1    Pistis, V.2    Suzuki, T.3    Tejera, N.4    Pratt, D.A.5    Schneider, C.6
  • 14
    • 84863090612 scopus 로고    scopus 로고
    • Vanillin and ferulic acid: Not the major degradation products of curcumin
    • Gordon, O. N. and Schneider, C. (2012) Vanillin and ferulic acid: not the major degradation products of curcumin Trends Mol. Med. 18, 361 - 363
    • (2012) Trends Mol. Med. , vol.18 , pp. 361-363
    • Gordon, O.N.1    Schneider, C.2
  • 15
    • 84872119769 scopus 로고    scopus 로고
    • Oxidative metabolites of curcumin poison human type II topoisomerases
    • Ketron, A. C., Gordon, O. N., Schneider, C., and Osheroff, N. (2013) Oxidative metabolites of curcumin poison human type II topoisomerases Biochemistry 52, 221 - 227
    • (2013) Biochemistry , vol.52 , pp. 221-227
    • Ketron, A.C.1    Gordon, O.N.2    Schneider, C.3    Osheroff, N.4
  • 16
    • 84929096317 scopus 로고    scopus 로고
    • Unraveling curcumin degradation. Autoxidation proceeds through spiroepoxide and vinylether intermediates en route to the main bicyclopentadione
    • Gordon, O. N., Luis, P. B., Sintim, H. O., and Schneider, C. (2015) Unraveling curcumin degradation. Autoxidation proceeds through spiroepoxide and vinylether intermediates en route to the main bicyclopentadione J. Biol. Chem. 290, 4817 - 4828
    • (2015) J. Biol. Chem. , vol.290 , pp. 4817-4828
    • Gordon, O.N.1    Luis, P.B.2    Sintim, H.O.3    Schneider, C.4
  • 17
    • 84982364659 scopus 로고
    • A synthesis of curcumin and related compounds
    • Pabon, H. J. J. (1964) A synthesis of curcumin and related compounds Recl. Trav. Chim. Pays-Bas 83, 379 - 386
    • (1964) Recl. Trav. Chim. Pays-Bas , vol.83 , pp. 379-386
    • Pabon, H.J.J.1
  • 18
    • 84890560570 scopus 로고    scopus 로고
    • Facile synthesis of deuterated and [14C]labeled analogs of vanillin and curcumin for use as mechanistic and analytical tools
    • Gordon, O. N., Graham, L. A., and Schneider, C. (2013) Facile synthesis of deuterated and [14C]labeled analogs of vanillin and curcumin for use as mechanistic and analytical tools J. Labelled Compd. Radiopharm. 56, 696 - 699
    • (2013) J. Labelled Compd. Radiopharm. , vol.56 , pp. 696-699
    • Gordon, O.N.1    Graham, L.A.2    Schneider, C.3
  • 19
    • 0032504157 scopus 로고    scopus 로고
    • Merbarone inhibits the catalytic activity of human topoisomerase IIalpha by blocking DNA cleavage
    • Fortune, J. M. and Osheroff, N. (1998) Merbarone inhibits the catalytic activity of human topoisomerase IIalpha by blocking DNA cleavage J. Biol. Chem. 273, 17643 - 17650
    • (1998) J. Biol. Chem. , vol.273 , pp. 17643-17650
    • Fortune, J.M.1    Osheroff, N.2
  • 20
    • 0024519424 scopus 로고
    • Inducible overexpression, purification, and active site mapping of DNA topoisomerase II from the yeast Saccharomyces cerevisiae
    • Worland, S. T. and Wang, J. C. (1989) Inducible overexpression, purification, and active site mapping of DNA topoisomerase II from the yeast Saccharomyces cerevisiae J. Biol. Chem. 264, 4412 - 4416
    • (1989) J. Biol. Chem. , vol.264 , pp. 4412-4416
    • Worland, S.T.1    Wang, J.C.2
  • 21
    • 0027275284 scopus 로고
    • Use of yeast in the study of anticancer drugs targeting DNA topoisomerases: Expression of a functional recombinant human DNA topoisomerase II alpha in yeast
    • Wasserman, R. A., Austin, C. A., Fisher, L. M., and Wang, J. C. (1993) Use of yeast in the study of anticancer drugs targeting DNA topoisomerases: expression of a functional recombinant human DNA topoisomerase II alpha in yeast Cancer Res. 53, 3591 - 3596
    • (1993) Cancer Res , vol.53 , pp. 3591-3596
    • Wasserman, R.A.1    Austin, C.A.2    Fisher, L.M.3    Wang, J.C.4
  • 22
    • 0030958484 scopus 로고    scopus 로고
    • Spontaneous DNA lesions poison human topoisomerase IIalpha and stimulate cleavage proximal to leukemic 11q23 chromosomal breakpoints
    • Kingma, P. S., Greider, C. A., and Osheroff, N. (1997) Spontaneous DNA lesions poison human topoisomerase IIalpha and stimulate cleavage proximal to leukemic 11q23 chromosomal breakpoints Biochemistry 36, 5934 - 5939
    • (1997) Biochemistry , vol.36 , pp. 5934-5939
    • Kingma, P.S.1    Greider, C.A.2    Osheroff, N.3
  • 23
    • 63349086953 scopus 로고    scopus 로고
    • The DNA cleavage reaction of topoisomerase II: Wolf in sheep's clothing
    • Deweese, J. E. and Osheroff, N. (2009) The DNA cleavage reaction of topoisomerase II: wolf in sheep's clothing Nucleic Acids Res. 37, 738 - 748
    • (2009) Nucleic Acids Res , vol.37 , pp. 738-748
    • Deweese, J.E.1    Osheroff, N.2
  • 24
    • 64649105115 scopus 로고    scopus 로고
    • DNA topoisomerase II and its growing repertoire of biological functions
    • Nitiss, J. L. (2009) DNA topoisomerase II and its growing repertoire of biological functions Nat. Rev. Cancer 9, 327 - 337
    • (2009) Nat. Rev. Cancer , vol.9 , pp. 327-337
    • Nitiss, J.L.1
  • 25
    • 64649090292 scopus 로고    scopus 로고
    • Targeting DNA topoisomerase II in cancer chemotherapy
    • Nitiss, J. L. (2009) Targeting DNA topoisomerase II in cancer chemotherapy Nat. Rev. Cancer 9, 338 - 350
    • (2009) Nat. Rev. Cancer , vol.9 , pp. 338-350
    • Nitiss, J.L.1
  • 26
    • 84872547120 scopus 로고    scopus 로고
    • Drugging topoisomerases: Lessons and challenges
    • Pommier, Y. (2013) Drugging topoisomerases: lessons and challenges ACS Chem. Biol. 8, 82 - 95
    • (2013) ACS Chem. Biol. , vol.8 , pp. 82-95
    • Pommier, Y.1
  • 28
    • 84896699533 scopus 로고    scopus 로고
    • Phytochemicals as anticancer and chemopreventive topoisomerase II poisons
    • Ketron, A. C. and Osheroff, N. (2014) Phytochemicals as anticancer and chemopreventive topoisomerase II poisons Phytochem. Rev. 13, 19 - 35
    • (2014) Phytochem. Rev. , vol.13 , pp. 19-35
    • Ketron, A.C.1    Osheroff, N.2
  • 29
    • 0001394917 scopus 로고
    • Studies on curcumin and curcuminoids. V. Alkaline degradation of curcumin
    • Tonnesen, H. H. and Karlsen, J. (1985) Studies on curcumin and curcuminoids. V. Alkaline degradation of curcumin Z. Lebensm.-Unters. Forsch. 180, 132 - 134
    • (1985) Z. Lebensm.-Unters. Forsch. , vol.180 , pp. 132-134
    • Tonnesen, H.H.1    Karlsen, J.2
  • 30
    • 4344694589 scopus 로고    scopus 로고
    • Abnormal solvent effects on hydrogen atom abstraction. 2. Resolution of the curcumin antioxidant controversy. The role of sequential proton loss electron transfer
    • Litwinienko, G. and Ingold, K. U. (2004) Abnormal solvent effects on hydrogen atom abstraction. 2. Resolution of the curcumin antioxidant controversy. The role of sequential proton loss electron transfer J. Org. Chem. 69, 5888 - 5896
    • (2004) J. Org. Chem. , vol.69 , pp. 5888-5896
    • Litwinienko, G.1    Ingold, K.U.2
  • 31
    • 34247143185 scopus 로고    scopus 로고
    • Solvent effects on the rates and mechanisms of reaction of phenols with free radicals
    • Litwinienko, G. and Ingold, K. U. (2007) Solvent effects on the rates and mechanisms of reaction of phenols with free radicals Acc. Chem. Res. 40, 222 - 230
    • (2007) Acc. Chem. Res. , vol.40 , pp. 222-230
    • Litwinienko, G.1    Ingold, K.U.2
  • 34
    • 0028800250 scopus 로고
    • Effects of curcumin, demethoxycurcumin, bisdemethoxycurcumin and tetrahydrocurcumin on 12- O -tetradecanoylphorbol-13-acetate-induced tumor promotion
    • Huang, M. T., Ma, W., Lu, Y. P., Chang, R. L., Fisher, C., Manchand, P. S., Newmark, H. L., and Conney, A. H. (1995) Effects of curcumin, demethoxycurcumin, bisdemethoxycurcumin and tetrahydrocurcumin on 12- O -tetradecanoylphorbol-13-acetate-induced tumor promotion Carcinogenesis 16, 2493 - 2497
    • (1995) Carcinogenesis , vol.16 , pp. 2493-2497
    • Huang, M.T.1    Ma, W.2    Lu, Y.P.3    Chang, R.L.4    Fisher, C.5    Manchand, P.S.6    Newmark, H.L.7    Conney, A.H.8
  • 35
    • 0029947057 scopus 로고    scopus 로고
    • Effects of the phytochemicals, curcumin and quercetin, upon azoxymethane-induced colon cancer and 7,12-dimethylbenz[ a ]anthracene-induced mammary cancer in rats
    • Pereira, M. A., Grubbs, C. J., Barnes, L. H., Li, H., Olson, G. R., Eto, I., Juliana, M., Whitaker, L. M., Kelloff, G. J., Steele, V. E., and Lubet, R. A. (1996) Effects of the phytochemicals, curcumin and quercetin, upon azoxymethane-induced colon cancer and 7,12-dimethylbenz[ a ]anthracene-induced mammary cancer in rats Carcinogenesis 17, 1305 - 1311
    • (1996) Carcinogenesis , vol.17 , pp. 1305-1311
    • Pereira, M.A.1    Grubbs, C.J.2    Barnes, L.H.3    Li, H.4    Olson, G.R.5    Eto, I.6    Juliana, M.7    Whitaker, L.M.8    Kelloff, G.J.9    Steele, V.E.10    Lubet, R.A.11
  • 36
    • 84887978737 scopus 로고    scopus 로고
    • Bioactivity of turmeric-derived curcuminoids and related metabolites in breast cancer
    • Wright, L. E., Frye, J. B., Gorti, B., Timmermann, B. N., and Funk, J. L. (2013) Bioactivity of turmeric-derived curcuminoids and related metabolites in breast cancer Curr. Pharm. Des. 19, 6218 - 6225
    • (2013) Curr. Pharm. Des. , vol.19 , pp. 6218-6225
    • Wright, L.E.1    Frye, J.B.2    Gorti, B.3    Timmermann, B.N.4    Funk, J.L.5
  • 38
    • 0033161171 scopus 로고    scopus 로고
    • Epidemiology of digestive tract cancers in India. V. Large and small bowel
    • Mohandas, K. M. and Desai, D. C. (1999) Epidemiology of digestive tract cancers in India. V. Large and small bowel Ind. J. Gastroenterol. 18, 118 - 121
    • (1999) Ind. J. Gastroenterol. , vol.18 , pp. 118-121
    • Mohandas, K.M.1    Desai, D.C.2
  • 39
  • 40
    • 0036708902 scopus 로고    scopus 로고
    • Antioxidants and oxidants regulated signal transduction pathways
    • Owuor, E. D. and Kong, A. N. (2002) Antioxidants and oxidants regulated signal transduction pathways Biochem. Pharmacol. 64, 765 - 770
    • (2002) Biochem. Pharmacol. , vol.64 , pp. 765-770
    • Owuor, E.D.1    Kong, A.N.2
  • 41
    • 47849083585 scopus 로고    scopus 로고
    • Nrf2 signaling: An adaptive response pathway for protection against environmental toxic insults
    • Osburn, W. O. and Kensler, T. W. (2008) Nrf2 signaling: an adaptive response pathway for protection against environmental toxic insults Mutat. Res. 659, 31 - 39
    • (2008) Mutat. Res. , vol.659 , pp. 31-39
    • Osburn, W.O.1    Kensler, T.W.2
  • 42
    • 56349116715 scopus 로고    scopus 로고
    • Natural derivatives of curcumin attenuate the Wnt/beta-catenin pathway through down-regulation of the transcriptional coactivator p300
    • Ryu, M. J., Cho, M., Song, J. Y., Yun, Y. S., Choi, I. W., Kim, D. E., Park, B. S., and Oh, S. (2008) Natural derivatives of curcumin attenuate the Wnt/beta-catenin pathway through down-regulation of the transcriptional coactivator p300 Biochem. Biophys. Res. Commun. 377, 1304 - 1308
    • (2008) Biochem. Biophys. Res. Commun. , vol.377 , pp. 1304-1308
    • Ryu, M.J.1    Cho, M.2    Song, J.Y.3    Yun, Y.S.4    Choi, I.W.5    Kim, D.E.6    Park, B.S.7    Oh, S.8
  • 43
    • 84883454684 scopus 로고    scopus 로고
    • Demethoxycurcumin, a major active curcuminoid from Curcuma longa, suppresses balloon injury induced vascular smooth muscle cell migration and neointima formation: An in vitro and in vivo study
    • Sheu, M. J., Lin, H. Y., Yang, Y. H., Chou, C. J., Chien, Y. C., Wu, T. S., and Wu, C. H. (2013) Demethoxycurcumin, a major active curcuminoid from Curcuma longa, suppresses balloon injury induced vascular smooth muscle cell migration and neointima formation: an in vitro and in vivo study Mol. Nutr. Food Res. 57, 1586 - 1597
    • (2013) Mol. Nutr. Food Res. , vol.57 , pp. 1586-1597
    • Sheu, M.J.1    Lin, H.Y.2    Yang, Y.H.3    Chou, C.J.4    Chien, Y.C.5    Wu, T.S.6    Wu, C.H.7


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