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Volumn 40, Issue 8, 2012, Pages 1628-1640

Identification of the ortho-benzoquinone intermediate of 5-O-caffeoylquinic acid in vitro and in vivo: Comparison of bioactivation under normal and pathological situations

Author keywords

[No Author keywords available]

Indexed keywords

5 O CAFFEOYLQUINIC ACID DERIVATIVE; BENZOQUINONE DERIVATIVE; CARBONYL DERIVATIVE; CATECHOL METHYLTRANSFERASE; CHLOROGENIC ACID; CUMENE HYDROPEROXIDE; CYTOCHROME P450; CYTOCHROME P450 2E1; CYTOCHROME P450 3A4; DRUG METABOLITE; DRUG METABOLIZING ENZYME; GLUTATHIONE; GLUTATHIONE TRANSFERASE; MYELOPEROXIDASE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE; S ADENOSYLMETHIONINE; TOLCAPONE; UNCLASSIFIED DRUG;

EID: 84863913079     PISSN: 00909556     EISSN: 1521009X     Source Type: Journal    
DOI: 10.1124/dmd.112.045641     Document Type: Article
Times cited : (25)

References (37)
  • 1
    • 0033671475 scopus 로고    scopus 로고
    • Absorption of chlorogenic acid and caffeic acid in rats after oral administration
    • Azuma K, Ippoushi K, Nakayama M, Ito H, Higashio H, and Terao J (2000) Absorption of chlorogenic acid and caffeic acid in rats after oral administration. J Agric Food Chem 48:5496-5500.
    • (2000) J Agric Food Chem , vol.48 , pp. 5496-5500
    • Azuma, K.1    Ippoushi, K.2    Nakayama, M.3    Ito, H.4    Higashio, H.5    Terao, J.6
  • 2
    • 0013846203 scopus 로고
    • Chlorogenic acid: Further evidence for its antigenic and allergenic activity
    • Bariana DS, Krupey J, Scarpati LM, Freedman SO, and Sehon AH (1965) Chlorogenic acid: further evidence for its antigenic and allergenic activity. Nature 207:1155-1157.
    • (1965) Nature , vol.207 , pp. 1155-1157
    • Bariana, D.S.1    Krupey, J.2    Scarpati, L.M.3    Freedman, S.O.4    Sehon, A.H.5
  • 4
    • 79952851325 scopus 로고    scopus 로고
    • Role of catechol-O-methyltransferase in the disposition of luteolin in rats
    • Chen Z, Chen M, Pan H, Sun S, Li L, Zeng S, and Jiang H (2011) Role of catechol-O-methyltransferase in the disposition of luteolin in rats. Drug Metab Dispos 39:667-674.
    • (2011) Drug Metab Dispos , vol.39 , pp. 667-674
    • Chen, Z.1    Chen, M.2    Pan, H.3    Sun, S.4    Li, L.5    Zeng, S.6    Jiang, H.7
  • 5
    • 0034657786 scopus 로고    scopus 로고
    • Chlorogenic acids and other cinnamates - Nature, occurrence, dietary burden, absorption and metabolism
    • Clifford MN (2000) Chlorogenic acids and other cinnamates - nature, occurrence, dietary burden, absorption and metabolism. J Sci Food Agric 80:1033-1043.
    • (2000) J Sci Food Agric , vol.80 , pp. 1033-1043
    • Clifford, M.N.1
  • 7
    • 77958094800 scopus 로고    scopus 로고
    • Evidence for the bioactivation of 4-nonylphenol to quinone methide and ortho-benzoquinone metabolites in human liver microsomes
    • Deng P, Zhong D, Nan F, Liu S, Li D, Yuan T, Chen X, and Zheng J (2010) Evidence for the bioactivation of 4-nonylphenol to quinone methide and ortho-benzoquinone metabolites in human liver microsomes. Chem Res Toxicol 23:1617-1628.
    • (2010) Chem Res Toxicol , vol.23 , pp. 1617-1628
    • Deng, P.1    Zhong, D.2    Nan, F.3    Liu, S.4    Li, D.5    Yuan, T.6    Chen, X.7    Zheng, J.8
  • 8
    • 33750632133 scopus 로고    scopus 로고
    • Evaluation of the antiinflammatory, analgesic and antipyretic activities of the natural polyphenol chlorogenic acid
    • dos Santos MD, Almeida MC, Lopes NP, and de Souza GE (2006) Evaluation of the antiinflammatory, analgesic and antipyretic activities of the natural polyphenol chlorogenic acid. Biol Pharm Bull 29:2236-2240.
    • (2006) Biol Pharm Bull , vol.29 , pp. 2236-2240
    • Dos Santos, M.D.1    Almeida, M.C.2    Lopes, N.P.3    De Souza, G.E.4
  • 9
    • 33845271866 scopus 로고    scopus 로고
    • Chlorogenic acid is poorly absorbed, independently of the food matrix: A Caco-2 cells and rat chronic absorption study
    • Dupas C, Marsset Baglieri A, Ordonaud C, Tomé D, and Maillard MN (2006) Chlorogenic acid is poorly absorbed, independently of the food matrix: A Caco-2 cells and rat chronic absorption study. Mol Nutr Food Res 50:1053-1060.
    • (2006) Mol Nutr Food Res , vol.50 , pp. 1053-1060
    • Dupas, C.1    Marsset Baglieri, A.2    Ordonaud, C.3    Tomé, D.4    Maillard, M.N.5
  • 10
    • 0006006457 scopus 로고
    • Chlorogenic acid: An allergen in green coffee bean
    • Freedman SO, Krupey J, and Sehon AH (1961) Chlorogenic acid: an allergen in green coffee bean. Nature 192:241-243.
    • (1961) Nature , vol.192 , pp. 241-243
    • Freedman, S.O.1    Krupey, J.2    Sehon, A.H.3
  • 11
    • 41949122581 scopus 로고    scopus 로고
    • GM1-induced structural changes of bovine serum albumin after chemical and thermal disruption of the secondary structure: A spectroscopic comparison
    • Gayen A, Chatterjee C, and Mukhopadhyay C (2008) GM1-induced structural changes of bovine serum albumin after chemical and thermal disruption of the secondary structure: a spectroscopic comparison. Biomacromolecules 9:974-983.
    • (2008) Biomacromolecules , vol.9 , pp. 974-983
    • Gayen, A.1    Chatterjee, C.2    Mukhopadhyay, C.3
  • 12
    • 0021117986 scopus 로고
    • Nutritional consequences of the reactions between proteins and oxidized polyphenolic acids
    • Hurrell RF and Finot PA (1984) Nutritional consequences of the reactions between proteins and oxidized polyphenolic acids. Adv Exp Med Biol 177:423-435.
    • (1984) Adv Exp Med Biol , vol.177 , pp. 423-435
    • Hurrell, R.F.1    Finot, P.A.2
  • 13
    • 70349505771 scopus 로고    scopus 로고
    • Comments on serious anaphylaxis caused by nine Chinese herbal injections used to treat common colds and upper respiratory tract infections
    • Ji K, Chen J, Li M, Liu Z, Xia L, Wang C, Zhan Z, and Wu X (2009) Comments on serious anaphylaxis caused by nine Chinese herbal injections used to treat common colds and upper respiratory tract infections. Regul Toxicol Pharmacol 55:134-138.
    • (2009) Regul Toxicol Pharmacol , vol.55 , pp. 134-138
    • Ji, K.1    Chen, J.2    Li, M.3    Liu, Z.4    Xia, L.5    Wang, C.6    Zhan, Z.7    Wu, X.8
  • 15
    • 77952896934 scopus 로고    scopus 로고
    • How to distinguish between feruloyl quinic acids and isoferuloyl quinic acids by liquid chromatography/tandem mass spectrometry
    • Kuhnert N, Jaiswal R, Matei MF, Sovdat T, and Deshpande S (2010) How to distinguish between feruloyl quinic acids and isoferuloyl quinic acids by liquid chromatography/tandem mass spectrometry. Rapid Commun Mass Spectrom 24:1575-1582.
    • (2010) Rapid Commun Mass Spectrom , vol.24 , pp. 1575-1582
    • Kuhnert, N.1    Jaiswal, R.2    Matei, M.F.3    Sovdat, T.4    Deshpande, S.5
  • 17
    • 0034772876 scopus 로고    scopus 로고
    • Caffeic acid, chlorogenic acid, and dihydrocaffeic acid metabolism: Glutathione conjugate formation
    • Moridani MY, Scobie H, Jamshidzadeh A, Salehi P, and O'Brien PJ (2001) Caffeic acid, chlorogenic acid, and dihydrocaffeic acid metabolism: glutathione conjugate formation. Drug Metab Dispos 29:1432-1439.
    • (2001) Drug Metab Dispos , vol.29 , pp. 1432-1439
    • Moridani, M.Y.1    Scobie, H.2    Jamshidzadeh, A.3    Salehi, P.4    O'Brien, P.J.5
  • 18
    • 0037151241 scopus 로고    scopus 로고
    • Metabolism of caffeic acid by isolated rat hepatocytes and subcellular fractions
    • Moridani MY, Scobie H, and O'Brien PJ (2002) Metabolism of caffeic acid by isolated rat hepatocytes and subcellular fractions. Toxicol Lett 133:141-151.
    • (2002) Toxicol Lett , vol.133 , pp. 141-151
    • Moridani, M.Y.1    Scobie, H.2    O'Brien, P.J.3
  • 19
    • 0026040838 scopus 로고
    • Molecular mechanisms of quinone cytotoxicity
    • O'Brien PJ (1991) Molecular mechanisms of quinone cytotoxicity. Chem Biol Interact 80:1-41.
    • (1991) Chem Biol Interact , vol.80 , pp. 1-41
    • O'Brien, P.J.1
  • 20
    • 0141957596 scopus 로고    scopus 로고
    • Oxidative conjugation of chlorogenic acid with glutathione. Structural characterization of addition products and a new nitrite-Promoted pathway
    • Panzella L, Napolitano A, and d'Ischia M (2003) Oxidative conjugation of chlorogenic acid with glutathione. Structural characterization of addition products and a new nitrite-Promoted pathway. Bioorg Med Chem 11:4797-4805.
    • (2003) Bioorg Med Chem , vol.11 , pp. 4797-4805
    • Panzella, L.1    Napolitano, A.2    D'Ischia, M.3
  • 21
    • 77955012675 scopus 로고    scopus 로고
    • Comparative and combined effect of chlorogenic acid and tetrahydrocurcumin on antioxidant disparities in chemical induced experimental diabetes
    • Pari L, Karthikesan K, and Menon VP (2010) Comparative and combined effect of chlorogenic acid and tetrahydrocurcumin on antioxidant disparities in chemical induced experimental diabetes. Mol Cell Biochem 341:109-117.
    • (2010) Mol Cell Biochem , vol.341 , pp. 109-117
    • Pari, L.1    Karthikesan, K.2    Menon, V.P.3
  • 22
    • 33750564770 scopus 로고    scopus 로고
    • Reactions of myeloperoxidase-derived oxidants with biological substrates: Gaining chemical insight into human inflammatory diseases
    • Pattison DI and Davies MJ (2006) Reactions of myeloperoxidase-derived oxidants with biological substrates: gaining chemical insight into human inflammatory diseases. Curr Med Chem 13:3271-3290.
    • (2006) Curr Med Chem , vol.13 , pp. 3271-3290
    • Pattison, D.I.1    Davies, M.J.2
  • 23
    • 0033105118 scopus 로고    scopus 로고
    • Integrated cytochrome P450 reaction phenotyping: Attempting to bridge the gap between cDNA-expressed cytochromes P450 and native human liver microsomes
    • Rodrigues AD (1999) Integrated cytochrome P450 reaction phenotyping: attempting to bridge the gap between cDNA-expressed cytochromes P450 and native human liver microsomes. Biochem Pharmacol 57:465-480.
    • (1999) Biochem Pharmacol , vol.57 , pp. 465-480
    • Rodrigues, A.D.1
  • 25
    • 0033159195 scopus 로고    scopus 로고
    • Natural antioxidant, chlorogenic acid, protects against DNA breakage caused by monochloramine
    • Shibata H, Sakamoto Y, Oka M, and Kono Y (1999) Natural antioxidant, chlorogenic acid, protects against DNA breakage caused by monochloramine. Biosci Biotechnol Biochem 63:1295-1297.
    • (1999) Biosci Biotechnol Biochem , vol.63 , pp. 1295-1297
    • Shibata, H.1    Sakamoto, Y.2    Oka, M.3    Kono, Y.4
  • 26
    • 18944406318 scopus 로고    scopus 로고
    • Peroxidases: A role in the metabolism and side effects of drugs
    • Tafazoli S and O'Brien PJ (2005) Peroxidases: a role in the metabolism and side effects of drugs. Drug Discovery Today 10:617-625.
    • (2005) Drug Discovery Today , vol.10 , pp. 617-625
    • Tafazoli, S.1    O'Brien, P.J.2
  • 27
    • 18744364709 scopus 로고    scopus 로고
    • Oxidative stress mediated idiosyncratic drug toxicity
    • Tafazoli S, Spehar DD, and O'Brien PJ (2005) Oxidative stress mediated idiosyncratic drug toxicity. Drug Metab Rev 37:311-325.
    • (2005) Drug Metab Rev , vol.37 , pp. 311-325
    • Tafazoli, S.1    Spehar, D.D.2    O'Brien, P.J.3
  • 28
    • 0042858525 scopus 로고    scopus 로고
    • Conjugation of catechols by recombinant human sulfotransferases, UDP-glucuronosyltransferases, and soluble catechol O-methyltransferase: Structure-conjugation relationships and predictive models
    • Taskinen J, Ethell BT, Pihlavisto P, Hood AM, Burchell B, and Coughtrie MW (2003) Conjugation of catechols by recombinant human sulfotransferases, UDP-glucuronosyltransferases, and soluble catechol O-methyltransferase: structure-conjugation relationships and predictive models. Drug Metab Dispos 31:1187-1197.
    • (2003) Drug Metab Dispos , vol.31 , pp. 1187-1197
    • Taskinen, J.1    Ethell, B.T.2    Pihlavisto, P.3    Hood, A.M.4    Burchell, B.5    Coughtrie, M.W.6
  • 29
    • 38949104743 scopus 로고    scopus 로고
    • Idiosyncratic drug reactions: Past, present, and future
    • Uetrecht J (2008) Idiosyncratic drug reactions: past, present, and future. Chem Res Toxicol 21:84-92.
    • (2008) Chem Res Toxicol , vol.21 , pp. 84-92
    • Uetrecht, J.1
  • 30
    • 0031762781 scopus 로고    scopus 로고
    • Assessment of prooxidant activity of vitamin e in human low-density lipoprotein and plasma
    • Witting PK, Mohr D, and Stocker R (1999) Assessment of prooxidant activity of vitamin E in human low-density lipoprotein and plasma. Methods Enzymol 299:362-375.
    • (1999) Methods Enzymol , vol.299 , pp. 362-375
    • Witting, P.K.1    Mohr, D.2    Stocker, R.3
  • 31
    • 80054998073 scopus 로고    scopus 로고
    • Investigation of isomeric transformations of chlorogenic acid in buffers and biological matrixes by ultraperformance liquid chromatography coupled with hybrid quadrupole/ion mobility/orthogonal acceleration time-of-flight mass spectrometry
    • Xie C, Yu K, Zhong D, Yuan T, Ye F, Jarrell JA, Millar A, and Chen X (2011a) Investigation of isomeric transformations of chlorogenic acid in buffers and biological matrixes by ultraperformance liquid chromatography coupled with hybrid quadrupole/ion mobility/orthogonal acceleration time-of-flight mass spectrometry. J Agric Food Chem 59:11078-11087.
    • (2011) J Agric Food Chem , vol.59 , pp. 11078-11087
    • Xie, C.1    Yu, K.2    Zhong, D.3    Yuan, T.4    Ye, F.5    Jarrell, J.A.6    Millar, A.7    Chen, X.8
  • 32
    • 79551490786 scopus 로고    scopus 로고
    • Metabolites of injected chlorogenic acid in rats
    • Xie C, Zhong DF, and Chen XY (2011b) [Metabolites of injected chlorogenic acid in rats.] Yao Xue Xue Bao 46:88-95.
    • (2011) Yao Xue Xue Bao , vol.46 , pp. 88-95
    • Xie, C.1    Zhong, D.F.2    Chen, X.Y.3
  • 33
    • 77956898289 scopus 로고    scopus 로고
    • Protective effects of chlorogenic acid on acute hepatotoxicity induced by lipopolysaccharide in mice
    • Xu Y, Chen J, Yu X, Tao W, Jiang F, Yin Z, and Liu C (2010) Protective effects of chlorogenic acid on acute hepatotoxicity induced by lipopolysaccharide in mice. Inflamm Res 59:871-877.
    • (2010) Inflamm Res , vol.59 , pp. 871-877
    • Xu, Y.1    Chen, J.2    Yu, X.3    Tao, W.4    Jiang, F.5    Yin, Z.6    Liu, C.7
  • 34
    • 50049128215 scopus 로고    scopus 로고
    • Unbiased high-throughput screening of reactive metabolites on the linear ion trap mass spectrometer using polarity switch and mass tag triggered data-dependent acquisition
    • Yan Z, Caldwell GW, and Maher N (2008) Unbiased high-throughput screening of reactive metabolites on the linear ion trap mass spectrometer using polarity switch and mass tag triggered data-dependent acquisition. Anal Chem 80:6410-6422.
    • (2008) Anal Chem , vol.80 , pp. 6410-6422
    • Yan, Z.1    Caldwell, G.W.2    Maher, N.3
  • 35
    • 79551492071 scopus 로고    scopus 로고
    • Determination of six phendic acids in mailuoning injection by RP-HPLC
    • Zhang H, Li X, Zhou H, Xu X, and Chen W (2009) Determination of six phendic acids in mailuoning injection by RP-HPLC. Chin J Info TCM 16:54-56.
    • (2009) Chin J Info TCM , vol.16 , pp. 54-56
    • Zhang, H.1    Li, X.2    Zhou, H.3    Xu, X.4    Chen, W.5
  • 36
    • 84863914018 scopus 로고    scopus 로고
    • Determination of the content of chlorogenic acid in yinzhihuang injection by HPLC
    • Zhang N, Wang T, and Zhang H (2008) Determination of the content of chlorogenic acid in yinzhihuang injection by HPLC. Mod Med & Health 24:2553-2554.
    • (2008) Mod Med & Health , vol.24 , pp. 2553-2554
    • Zhang, N.1    Wang, T.2    Zhang, H.3
  • 37
    • 84863961510 scopus 로고    scopus 로고
    • Allergenicity assessment and comparison between chlorogenic acid and shuanghuanglian fenzhenji
    • Zhang R, Tang N, Lin H, Ma J, Xie C, and Chen X (2010) Allergenicity assessment and comparison between chlorogenic acid and shuanghuanglian fenzhenji. World Sci Technol 12:1005-1008.
    • (2010) World Sci Technol , vol.12 , pp. 1005-1008
    • Zhang, R.1    Tang, N.2    Lin, H.3    Ma, J.4    Xie, C.5    Chen, X.6


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