메뉴 건너뛰기




Volumn 9, Issue 4, 2012, Pages 862-873

SULT1A3-mediated regiospecific 7-O-sulfation of flavonoids in caco-2 cells can be explained by the relevant molecular docking studies

Author keywords

Caco 2; flavonoids; molecular docking; SULT1A3

Indexed keywords

APIGENIN; FLAVANONE; FLAVONE; FLAVONOID; FLAVONOL; GENISTEIN; GLUCURONOSYLTRANSFERASE; NARINGENIN; PHLORETIN;

EID: 84859369611     PISSN: 15438384     EISSN: 15438392     Source Type: Journal    
DOI: 10.1021/mp200400s     Document Type: Article
Times cited : (30)

References (33)
  • 1
    • 33845705480 scopus 로고    scopus 로고
    • Dietary polyphenolic phytochemicals - Promising cancer chemopreventive agents in humans? A review of their clinical properties
    • DOI 10.1002/ijc.22419
    • Thomasset, S. C.; Berry, D. P.; Garcea, G.; Marczylo, T.; Steward, W. P.; Gescher, A. J. Dietary polyphenolic phytochemicals-promising cancer chemopreventive agents in humans? A review of their clinical properties Int. J. Cancer 2007, 120, 451-8 (Pubitemid 44969013)
    • (2007) International Journal of Cancer , vol.120 , Issue.3 , pp. 451-458
    • Thomasset, S.C.1    Berry, D.P.2    Garcea, G.3    Marczylo, T.4    Steward, W.P.5    Gescher, A.J.6
  • 2
    • 50449111165 scopus 로고    scopus 로고
    • Update on uses and properties of citrus flavonoids: New findings in anticancer, cardiovascular, and anti-inflammatory activity
    • Benavente-Garcia, O.; Castillo, J. Update on uses and properties of citrus flavonoids: new findings in anticancer, cardiovascular, and anti-inflammatory activity J. Agric. Food Chem. 2008, 56, 6185-205
    • (2008) J. Agric. Food Chem. , vol.56 , pp. 6185-6205
    • Benavente-Garcia, O.1    Castillo, J.2
  • 3
    • 46349111961 scopus 로고    scopus 로고
    • Effect of a prodrug of the green tea polyphenol (-)-epigallocatechin-3- gallate on the growth of androgen-independent prostate cancer in vivo
    • DOI 10.1080/01635580801947674, PII 794506453
    • Lee, S. C.; Chan, W. K.; Lee, T. W.; Lam, W. H.; Wang, X.; Chan, T. H.; Wong, Y. C. Effect of a prodrug of the green tea polyphenol (-)- epigallocatechin-3-gallate on the growth of androgen-independent prostate cancer in vivo Nutr. Cancer 2008, 60, 483-91 (Pubitemid 351918537)
    • (2008) Nutrition and Cancer , vol.60 , Issue.4 , pp. 483-491
    • Lee, S.-C.1    Chan, W.-K.2    Lee, T.-W.3    Lam, W.-H.4    Wang, X.5    Chan, T.-H.6    Wong, Y.-C.7
  • 4
    • 0034950281 scopus 로고    scopus 로고
    • Induction of UDP-glucuronosyltransferase UGT1A1 by the flavonoid chrysin in Caco-2 cells - Potential role in carcinogen bioinactivation
    • DOI 10.1023/A:1011019417236
    • Galijatovic, A.; Otake, Y.; Walle, U. K.; Walle, T. Induction of UDP-glucuronosyltransferase UGT1A1 by the flavonoid chrysin in Caco-2 cells-potential role in carcinogen bioinactivation Pharm. Res. 2001, 18, 374-9 (Pubitemid 32595827)
    • (2001) Pharmaceutical Research , vol.18 , Issue.3 , pp. 374-379
    • Galijatovic, A.1    Otake, Y.2    Walle, U.K.3    Walle, T.4
  • 5
    • 37549032699 scopus 로고    scopus 로고
    • Disposition of flavonoids via enteric recycling: Enzyme stability affects characterization of prunetin glucuronidation across species, organs, and UGT isoforms
    • Joseph, T. B.; Wang, S. W.; Liu, X.; Kulkarni, K. H.; Wang, J.; Xu, H.; Hu, M. Disposition of flavonoids via enteric recycling: enzyme stability affects characterization of prunetin glucuronidation across species, organs, and UGT isoforms Mol. Pharmaceutics 2007, 4, 883-94
    • (2007) Mol. Pharmaceutics , vol.4 , pp. 883-894
    • Joseph, T.B.1    Wang, S.W.2    Liu, X.3    Kulkarni, K.H.4    Wang, J.5    Xu, H.6    Hu, M.7
  • 7
    • 0036400016 scopus 로고    scopus 로고
    • Dietary flavonoids: Bioavailability, metabolic effects, and safety
    • DOI 10.1146/annurev.nutr.22.111401.144957
    • Ross, J. A.; Kasum, C. M. Dietary flavonoids: bioavailability, metabolic effects, and safety Annu. Rev. Nutr. 2002, 22, 19-34 (Pubitemid 35221452)
    • (2002) Annual Review of Nutrition , vol.22 , pp. 19-34
    • Ross, J.A.1    Kasum, C.M.2
  • 9
    • 0033858417 scopus 로고    scopus 로고
    • Accumulation of quercetin conjugates in blood plasma after the short-term ingestion of onion by women
    • Moon, J. H.; Nakata, R.; Oshima, S.; Inakuma, T.; Terao, J. Accumulation of quercetin conjugates in blood plasma after the short-term ingestion of onion by women Am. J. Physiol. 2000, 279, R461-7
    • (2000) Am. J. Physiol. , vol.279 , pp. 461-467
    • Moon, J.H.1    Nakata, R.2    Oshima, S.3    Inakuma, T.4    Terao, J.5
  • 12
    • 23744515308 scopus 로고    scopus 로고
    • Crystal structure of human sulfotransferase SULT1A3 in complex with dopamine and 3′-phosphoadenosine 5′-phosphate
    • DOI 10.1016/j.bbrc.2005.07.091, PII S0006291X05015135
    • Lu, J. H.; Li, H. T.; Liu, M. C.; Zhang, J. P.; Li, M.; An, X. M.; Chang, W. R. Crystal structure of human sulfotransferase SULT1A3 in complex with dopamine and 3′-phosphoadenosine 5′-phosphate Biochem. Biophys. Res. Commun. 2005, 335, 417-23 (Pubitemid 41140239)
    • (2005) Biochemical and Biophysical Research Communications , vol.335 , Issue.2 , pp. 417-423
    • Lu, J.-H.1    Li, H.-T.2    Liu, M.-C.3    Zhang, J.-P.4    Li, M.5    An, X.-M.6    Chang, W.-R.7
  • 13
    • 38749138122 scopus 로고    scopus 로고
    • Sulfotransferase forms expressed in human intestinal Caco-2 and TC7 cells at varying stages of differentiation and role in benzo[a]pyrene metabolism
    • DOI 10.1124/dmd.107.018036
    • Meinl, W.; Ebert, B.; Glatt, H.; Lampen, A. Sulfotransferase forms expressed in human intestinal Caco-2 and TC7 cells at varying stages of differentiation and role in benzo[a]pyrene metabolism Drug Metab. Dispos. 2008, 36, 276-83 (Pubitemid 351185739)
    • (2008) Drug Metabolism and Disposition , vol.36 , Issue.2 , pp. 276-283
    • Meinl, W.1    Ebert, B.2    Glatt, H.3    Lampen, A.4
  • 14
    • 0037371414 scopus 로고    scopus 로고
    • Metabolism of flavonoids via enteric recycling: Role of intestinal disposition
    • DOI 10.1124/jpet.102.046409
    • Chen, J.; Lin, H.; Hu, M. Metabolism of flavonoids via enteric recycling: role of intestinal disposition J. Pharmacol. Exp. Ther. 2003, 304, 1228-35 (Pubitemid 36254436)
    • (2003) Journal of Pharmacology and Experimental Therapeutics , vol.304 , Issue.3 , pp. 1228-1235
    • Chen, J.1    Lin, H.2    Hu, M.3
  • 15
    • 0141742373 scopus 로고    scopus 로고
    • Metabolism of flavonoids via enteric recycling: Mechanistic studies of disposition of apigenin in the Caco-2 cell culture model
    • DOI 10.1124/jpet.103.053496
    • Hu, M.; Chen, J.; Lin, H. Metabolism of flavonoids via enteric recycling: mechanistic studies of disposition of apigenin in the Caco-2 cell culture model J. Pharmacol. Exp. Ther. 2003, 307, 314-21 (Pubitemid 37151923)
    • (2003) Journal of Pharmacology and Experimental Therapeutics , vol.307 , Issue.1 , pp. 314-321
    • Hu, M.1    Chen, J.2    Lin, H.3
  • 16
    • 0036302957 scopus 로고    scopus 로고
    • Unique uptake and transport of isoflavone aglycones by human intestinal Caco-2 cells: Comparison of isoflavonoids and flavonoids
    • Murota, K.; Shimizu, S.; Miyamoto, S.; Izumi, T.; Obata, A.; Kikuchi, M.; Terao, J. Unique uptake and transport of isoflavone aglycones by human intestinal caco-2 cells: comparison of isoflavonoids and flavonoids J. Nutr. 2002, 132, 1956-61 (Pubitemid 34742884)
    • (2002) Journal of Nutrition , vol.132 , Issue.7 , pp. 1956-1961
    • Murota, K.1    Shimizu, S.2    Miyamoto, S.3    Izumi, T.4    Obata, A.5    Kikuchi, M.6    Terao, J.7
  • 17
    • 4544247421 scopus 로고    scopus 로고
    • Interactions between sulforaphane and apigenin in the induction of UGT1A1 and GSTA1 in CaCo-2 cells
    • DOI 10.1093/carcin/bgh169
    • Svehlikova, V.; Wang, S.; Jakubikova, J.; Williamson, G.; Mithen, R.; Bao, Y. Interactions between sulforaphane and apigenin in the induction of UGT1A1 and GSTA1 in CaCo-2 cells Carcinogenesis 2004, 25, 1629-37 (Pubitemid 39214305)
    • (2004) Carcinogenesis , vol.25 , Issue.9 , pp. 1629-1637
    • Svehlikova, V.1    Wang, S.2    Jakubikova, J.3    Williamson, G.4    Mithen, R.5    Bao, Y.6
  • 18
    • 0036238982 scopus 로고    scopus 로고
    • Induction of human UDP-glucuronosyltransferase UGT1A1 by flavonoids - Structural requirements
    • DOI 10.1124/dmd.30.5.564
    • Walle, U. K.; Walle, T. Induction of human UDP-glucuronosyltransferase UGT1A1 by flavonoids-structural requirements Drug Metab. Dispos. 2002, 30, 564-9 (Pubitemid 34456979)
    • (2002) Drug Metabolism and Disposition , vol.30 , Issue.5 , pp. 564-569
    • Walle, U.K.1    Walle, T.2
  • 19
    • 0043127383 scopus 로고    scopus 로고
    • Effect of the flavonoids biochanin A and silymarin on the P-glycoprotein-mediated transport of digoxin and vinblastine in human intestinal Caco-2 cells
    • DOI 10.1023/A:1025044913766
    • Zhang, S.; Morris, M. E. Effect of the flavonoids biochanin A and silymarin on the P-glycoprotein-mediated transport of digoxin and vinblastine in human intestinal Caco-2 cells Pharm. Res. 2003, 20, 1184-91 (Pubitemid 36951843)
    • (2003) Pharmaceutical Research , vol.20 , Issue.8 , pp. 1184-1191
    • Zhang, S.1    Morris, M.E.2
  • 20
    • 12144271052 scopus 로고    scopus 로고
    • Absorption and metabolism of genistein and its five isoflavone analogs in the human intestinal Caco-2 model
    • DOI 10.1007/s00280-004-0842-x
    • Chen, J.; Lin, H.; Hu, M. Absorption and metabolism of genistein and its five isoflavone analogs in the human intestinal Caco-2 model Cancer Chemother. Pharmacol. 2005, 55, 159-69 (Pubitemid 40110059)
    • (2005) Cancer Chemotherapy and Pharmacology , vol.55 , Issue.2 , pp. 159-169
    • Chen, J.1    Lin, H.2    Hu, M.3
  • 21
    • 70350049066 scopus 로고    scopus 로고
    • Structure and concentration changes affect characterization of UGT isoform-specific metabolism of isoflavones
    • Tang, L.; Singh, R.; Liu, Z.; Hu, M. Structure and concentration changes affect characterization of UGT isoform-specific metabolism of isoflavones Mol. Pharmaceutics 2009, 6, 1466-82
    • (2009) Mol. Pharmaceutics , vol.6 , pp. 1466-1482
    • Tang, L.1    Singh, R.2    Liu, Z.3    Hu, M.4
  • 22
    • 77953245569 scopus 로고    scopus 로고
    • Use of glucuronidation fingerprinting to describe and predict mono- and dihydroxyflavone metabolism by recombinant UGT isoforms and human intestinal and liver microsomes
    • Tang, L.; Ye, L.; Singh, R.; Wu, B.; Lv, C.; Zhao, J.; Liu, Z.; Hu, M. Use of glucuronidation fingerprinting to describe and predict mono- and dihydroxyflavone metabolism by recombinant UGT isoforms and human intestinal and liver microsomes Mol. Pharmaceutics 2010, 7, 664-79
    • (2010) Mol. Pharmaceutics , vol.7 , pp. 664-679
    • Tang, L.1    Ye, L.2    Singh, R.3    Wu, B.4    Lv, C.5    Zhao, J.6    Liu, Z.7    Hu, M.8
  • 23
    • 33751113603 scopus 로고    scopus 로고
    • Disposition of flavonoids via enteric recycling: Structural effects and lack of correlations between in vitro and in situ metabolic properties
    • DOI 10.1124/dmd.106.009910
    • Wang, S. W.; Chen, J.; Jia, X.; Tam, V. H.; Hu, M. Disposition of flavonoids via enteric recycling: structural effects and lack of correlations between in vitro and in situ metabolic properties Drug Metab. Dispos. 2006, 34, 1837-48 (Pubitemid 44771711)
    • (2006) Drug Metabolism and Disposition , vol.34 , Issue.11 , pp. 1837-1848
    • Wang, S.W.J.1    Chen, J.2    Jia, X.3    Tam, V.H.4    Hu, M.5
  • 24
    • 66149158179 scopus 로고    scopus 로고
    • Sulfation of dietary flavonoids by human sulfotransferases
    • Huang, C.; Chen, Y.; Zhou, T.; Chen, G. Sulfation of dietary flavonoids by human sulfotransferases Xenobiotica 2009, 39, 312-22
    • (2009) Xenobiotica , vol.39 , pp. 312-322
    • Huang, C.1    Chen, Y.2    Zhou, T.3    Chen, G.4
  • 25
    • 77956261020 scopus 로고    scopus 로고
    • Identification of the position of mono-O-glucuronide of flavones and flavonols by analyzing shift in online UV spectrum (lambdamax) generated from an online diode array detector
    • Singh, R.; Wu, B.; Tang, L.; Liu, Z.; Hu, M. Identification of the position of mono-O-glucuronide of flavones and flavonols by analyzing shift in online UV spectrum (lambdamax) generated from an online diode array detector J. Agric. Food Chem. 2010, 58, 9384-95
    • (2010) J. Agric. Food Chem. , vol.58 , pp. 9384-9395
    • Singh, R.1    Wu, B.2    Tang, L.3    Liu, Z.4    Hu, M.5
  • 26
    • 0034607796 scopus 로고    scopus 로고
    • Mutational analysis of the substrate binding/catalytic domains of human M form and P form phenol sulfotransferases
    • DOI 10.1074/jbc.275.18.13460
    • Liu, M. C.; Suiko, M.; Sakakibara, Y. Mutational analysis of the substrate binding/catalytic domains of human M form and P form phenol sulfotransferases J. Biol. Chem. 2000, 275, 13460-4 (Pubitemid 30257410)
    • (2000) Journal of Biological Chemistry , vol.275 , Issue.18 , pp. 13460-13464
    • Liu, M.-C.1    Suiko, M.2    Sakakibara, Y.3
  • 27
    • 0033051339 scopus 로고    scopus 로고
    • Transport of the flavonoid chrysin and its conjugated metabolites by the human intestinal cell line Caco-2
    • DOI 10.1016/S0006-2952(99)00133-1, PII S0006295299001331
    • Walle, U. K.; Galijatovic, A.; Walle, T. Transport of the flavonoid chrysin and its conjugated metabolites by the human intestinal cell line Caco-2 Biochem. Pharmacol. 1999, 58, 431-8 (Pubitemid 29281542)
    • (1999) Biochemical Pharmacology , vol.58 , Issue.3 , pp. 431-438
    • Kristina Walle, U.1    Galijatovic, A.2    Walle, T.3
  • 28
    • 34249297623 scopus 로고    scopus 로고
    • Mechanistic study on the intestinal absorption and disposition of baicalein
    • DOI 10.1016/j.ejps.2007.04.001, PII S0928098707000814
    • Zhang, L.; Lin, G.; Kovacs, B.; Jani, M.; Krajcsi, P.; Zuo, Z. Mechanistic study on the intestinal absorption and disposition of baicalein Eur. J. Pharm. Sci. 2007, 31, 221-31 (Pubitemid 46818982)
    • (2007) European Journal of Pharmaceutical Sciences , vol.31 , Issue.3-4 , pp. 221-231
    • Zhang, L.1    Lin, G.2    Kovacs, B.3    Jani, M.4    Krajcsi, P.5    Zuo, Z.6
  • 29
    • 70350319524 scopus 로고    scopus 로고
    • Quantitative evaluation of the expression and activity of five major sulfotransferases (SULTs) in human tissues: The SULT "pie"
    • Riches, Z.; Stanley, E. L.; Bloomer, J. C.; Coughtrie, M. W. Quantitative evaluation of the expression and activity of five major sulfotransferases (SULTs) in human tissues: the SULT "pie" Drug Metab. Dispos. 2009, 37, 2255-61
    • (2009) Drug Metab. Dispos. , vol.37 , pp. 2255-2261
    • Riches, Z.1    Stanley, E.L.2    Bloomer, J.C.3    Coughtrie, M.W.4
  • 30
    • 34249799590 scopus 로고    scopus 로고
    • Identification and localization of soluble sulfotransferases in the human gastrointestinal tract
    • DOI 10.1042/BJ20061431
    • Teubner, W.; Meinl, W.; Florian, S.; Kretzschmar, M.; Glatt, H. Identification and localization of soluble sulfotransferases in the human gastrointestinal tract Biochem. J. 2007, 404, 207-15 (Pubitemid 46849592)
    • (2007) Biochemical Journal , vol.404 , Issue.2 , pp. 207-215
    • Teubner, W.1    Meinl, W.2    Florian, S.3    Kretzschmar, M.4    Glatt, H.5
  • 31
    • 34250777414 scopus 로고    scopus 로고
    • Regioselective sulfonation of dopamine by SULT1A3 in vitro provides a molecular explanation for the preponderance of dopamine-3-O-sulfate in human blood circulation
    • DOI 10.1016/j.bcp.2007.05.003, PII S0006295207002948
    • Itaaho, K.; Alakurtti, S.; Yli-Kauhaluoma, J.; Taskinen, J.; Coughtrie, M. W.; Kostiainen, R. Regioselective sulfonation of dopamine by SULT1A3 in vitro provides a molecular explanation for the preponderance of dopamine-3-O-sulfate in human blood circulation Biochem. Pharmacol. 2007, 74, 504-10 (Pubitemid 46963238)
    • (2007) Biochemical Pharmacology , vol.74 , Issue.3 , pp. 504-510
    • Itaaho, K.1    Alakurtti, S.2    Yli-Kauhaluoma, J.3    Taskinen, J.4    Coughtrie, M.W.H.5    Kostiainen, R.6
  • 32
    • 0033621476 scopus 로고    scopus 로고
    • X-ray crystal structure of human dopamine sulfotransferase, SULT1A3. Molecular modeling and quantitative structure-activity relationship analysis demonstrate a molecular basis for sulfotransferase substrate specificity
    • DOI 10.1074/jbc.274.53.37862
    • Dajani, R.; Cleasby, A.; Neu, M.; Wonacott, A. J.; Jhoti, H.; Hood, A. M.; Modi, S.; Hersey, A.; Taskinen, J.; Cooke, R. M.; Manchee, G. R.; Coughtrie, M. W. H. X-ray crystal structure of human dopamine sulfotransferase, SULT1A3. Molecular modeling and quantitative structure-activity relationship analysis demonstrate a molecular basis for sulfotransferase substrate specificity J. Biol. Chem. 1999, 274, 37862-8 (Pubitemid 30026852)
    • (1999) Journal of Biological Chemistry , vol.274 , Issue.53 , pp. 37862-37868
    • Dajani, R.1    Cleasby, A.2    Margarete, N.3    Wonacott, A.J.4    Jhoti, H.5    Hood, A.M.6    Modi, S.7    Hersey, A.8    Taskinen, J.9    Cooke, R.M.10    Manchee, G.R.11    Coughtrie, M.W.H.12
  • 33
    • 77952323519 scopus 로고    scopus 로고
    • Simultaneous determination of genistein and its four phase II metabolites in blood by a sensitive and robust UPLC-MS/MS method: Application to an oral bioavailability study of genistein in mice
    • Yang, Z.; Zhu, W.; Gao, S.; Xu, H.; Wu, B.; Kulkarni, K.; Singh, R.; Tang, L.; Hu, M. Simultaneous determination of genistein and its four phase II metabolites in blood by a sensitive and robust UPLC-MS/MS method: Application to an oral bioavailability study of genistein in mice J. Pharm. Biomed. Anal. 2010, 53, 81-9
    • (2010) J. Pharm. Biomed. Anal. , vol.53 , pp. 81-89
    • Yang, Z.1    Zhu, W.2    Gao, S.3    Xu, H.4    Wu, B.5    Kulkarni, K.6    Singh, R.7    Tang, L.8    Hu, M.9


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.