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Volumn 39, Issue 6, 2013, Pages 644-651

Inhibition of hydroxycinnamic acid sulfation by flavonoids and their conjugated metabolites

Author keywords

Flavonoid conjugates; Flavonoids; Hydroxycinnamic acids; Sulfation

Indexed keywords

APIGENIN; CAFFEIC ACID; CATECHIN; COUMARIC ACID; DAIDZEIN; DIHYDROCAFFEIC ACID; DRUG METABOLITE; EPICATECHIN; FERULIC ACID; FLAVONOID; GENISTEIN; GLUCURONIDE; HESPERETIN; ISOFERULIC ACID; ISORHAMNETIN; KAEMPFEROL; LUTEOLIN; PHLORETIN; QUERCETIN; QUERCETIN 3 O GLUCURONIDE; QUERCETIN 3' O SULFATE; QUERCETIN 7 O GLUCURONIDE; UNCLASSIFIED DRUG;

EID: 84888137093     PISSN: 09516433     EISSN: 18728081     Source Type: Journal    
DOI: 10.1002/biof.1127     Document Type: Article
Times cited : (19)

References (24)
  • 1
    • 37549062630 scopus 로고    scopus 로고
    • Transport and metabolism of ferulic acid through the colonic epithelium
    • Poquet, L., Clifford, M. N., and Williamson, G. (2008) Transport and metabolism of ferulic acid through the colonic epithelium. Drug Metab. Dispos. 36, 190-197.
    • (2008) Drug Metab. Dispos. , vol.36 , pp. 190-197
    • Poquet, L.1    Clifford, M.N.2    Williamson, G.3
  • 2
    • 39149093653 scopus 로고    scopus 로고
    • Investigation of the metabolic fate of dihydrocaffeic acid
    • Poquet, L., Clifford, M. N., and Williamson, G. (2008) Investigation of the metabolic fate of dihydrocaffeic acid. Biochem. Pharmacol. 75, 1218-1229.
    • (2008) Biochem. Pharmacol. , vol.75 , pp. 1218-1229
    • Poquet, L.1    Clifford, M.N.2    Williamson, G.3
  • 3
    • 67650802353 scopus 로고    scopus 로고
    • Metabolite profiling of hydroxycinnamate derivatives in plasma and urine after the ingestion of coffee by humans: identification of biomarkers of coffee consumption
    • Stalmach, A., Mullen, W., Barron, D., Uchida, K., Yokota, T., et al. (2009) Metabolite profiling of hydroxycinnamate derivatives in plasma and urine after the ingestion of coffee by humans: identification of biomarkers of coffee consumption. Drug Metab. Dispos. 37, 1749-1758.
    • (2009) Drug Metab. Dispos. , vol.37 , pp. 1749-1758
    • Stalmach, A.1    Mullen, W.2    Barron, D.3    Uchida, K.4    Yokota, T.5
  • 4
    • 77958151737 scopus 로고    scopus 로고
    • In vitro and in vivo conjugation of dietary hydroxycinnamic acids by UDP-glucuronosyltransferases and sulfotransferases in humans
    • Wong, C. C., Meinl, W., Glatt, H. R., Barron, D., Stalmach, A., et al. (2009) In vitro and in vivo conjugation of dietary hydroxycinnamic acids by UDP-glucuronosyltransferases and sulfotransferases in humans. J. Nutr. Biochem. 21, 1060-1068.
    • (2009) J. Nutr. Biochem. , vol.21 , pp. 1060-1068
    • Wong, C.C.1    Meinl, W.2    Glatt, H.R.3    Barron, D.4    Stalmach, A.5
  • 5
    • 79957960590 scopus 로고    scopus 로고
    • First chemical synthesis and in vitro characterization of the potential human metabolites 5-O-feruloylquinic acid 4′-sulfate and 4′-O-glucuronide
    • Menozzi-Smarrito, C., Wong, C. C., Meinl, W., Glatt, H., Fumeaux, R., et al. (2011) First chemical synthesis and in vitro characterization of the potential human metabolites 5-O-feruloylquinic acid 4′-sulfate and 4′-O-glucuronide. J. Agric. Food Chem. 59, 5671-5676.
    • (2011) J. Agric. Food Chem. , vol.59 , pp. 5671-5676
    • Menozzi-Smarrito, C.1    Wong, C.C.2    Meinl, W.3    Glatt, H.4    Fumeaux, R.5
  • 6
    • 79956110490 scopus 로고    scopus 로고
    • Interaction of hydroxycinnamic acids and their conjugates with organic anion transporters and ATP-binding cassette transporters
    • Wong, C. C., Barron, D., Orfila, C., Dionisi, F., Krajcsi, P., et al. (2011) Interaction of hydroxycinnamic acids and their conjugates with organic anion transporters and ATP-binding cassette transporters. Mol. Nutr. Food Res. 55, 979-988.
    • (2011) Mol. Nutr. Food Res. , vol.55 , pp. 979-988
    • Wong, C.C.1    Barron, D.2    Orfila, C.3    Dionisi, F.4    Krajcsi, P.5
  • 7
    • 84871348237 scopus 로고    scopus 로고
    • Antioxidant activity of phenolic acids and their metabolites: synthesis and antioxidant properties of the sulfate derivatives of ferulic and caffeic acids and of the acyl glucuronide of ferulic acid
    • Piazzon, A., Vrhovsek, U., Masuero, D., Mattivi, F., Mandoj, F., et al. (2012) Antioxidant activity of phenolic acids and their metabolites: synthesis and antioxidant properties of the sulfate derivatives of ferulic and caffeic acids and of the acyl glucuronide of ferulic acid. J. Agric. Food Chem. 60, 12312-12323.
    • (2012) J. Agric. Food Chem. , vol.60 , pp. 12312-12323
    • Piazzon, A.1    Vrhovsek, U.2    Masuero, D.3    Mattivi, F.4    Mandoj, F.5
  • 8
    • 0030022005 scopus 로고    scopus 로고
    • Flavonoids, potent inhibitors of the human P-form phenolsulfotransferase. Potential role in drug metabolism and chemoprevention
    • Eaton, E. A., Walle, U. K., Lewis, A. J., Hudson, T., Wilson, A. A., et al. (1996) Flavonoids, potent inhibitors of the human P-form phenolsulfotransferase. Potential role in drug metabolism and chemoprevention. Drug Metab. Dispos. 24, 232-237.
    • (1996) Drug Metab. Dispos. , vol.24 , pp. 232-237
    • Eaton, E.A.1    Walle, U.K.2    Lewis, A.J.3    Hudson, T.4    Wilson, A.A.5
  • 9
    • 0036269922 scopus 로고    scopus 로고
    • Inhibition of phenol sulfotransferase (SULT1A1) by quercetin in human adult and foetal livers
    • De Santi, C., Pietrabissa, A., Mosca, F., Rane, A., and Pacifici, G. M. (2002) Inhibition of phenol sulfotransferase (SULT1A1) by quercetin in human adult and foetal livers. Xenobiotica. 32, 363-368.
    • (2002) Xenobiotica. , vol.32 , pp. 363-368
    • De Santi, C.1    Pietrabissa, A.2    Mosca, F.3    Rane, A.4    Pacifici, G.M.5
  • 11
    • 13844281685 scopus 로고    scopus 로고
    • Bioavailability and bioefficacy of polyphenols in humans. I. Review of 97 bioavailability studies
    • Manach, C., Williamson, G., Morand, C., Scalbert, A., and Remesy, C. (2005) Bioavailability and bioefficacy of polyphenols in humans. I. Review of 97 bioavailability studies. Am. J. Clin. Nutr. 81, 230S-242S.
    • (2005) Am. J. Clin. Nutr. , vol.81
    • Manach, C.1    Williamson, G.2    Morand, C.3    Scalbert, A.4    Remesy, C.5
  • 12
    • 78049322870 scopus 로고    scopus 로고
    • First synthesis, characterization, and evidence for the presence of hydroxycinnamic acid sulfate and glucuronide conjugates in human biological fluids as a result of coffee consumption
    • Fumeaux, R., Menozzi-Smarrito, C., Stalmach, A., Munari, C., Kraehenbuehl, K., et al. (2010) First synthesis, characterization, and evidence for the presence of hydroxycinnamic acid sulfate and glucuronide conjugates in human biological fluids as a result of coffee consumption. Org. Biomol. Chem. 8, 5199-5211.
    • (2010) Org. Biomol. Chem. , vol.8 , pp. 5199-5211
    • Fumeaux, R.1    Menozzi-Smarrito, C.2    Stalmach, A.3    Munari, C.4    Kraehenbuehl, K.5
  • 13
    • 0034672514 scopus 로고    scopus 로고
    • Conjugation position of quercetin glucuronides and effect on biological activity
    • Day, A. J., Bao, Y. P., Morgan, M. R. A., and Williamson, G. (2000) Conjugation position of quercetin glucuronides and effect on biological activity. Free Radical Bio. Med. 29, 1234-1243.
    • (2000) Free Radical Bio. Med. , vol.29 , pp. 1234-1243
    • Day, A.J.1    Bao, Y.P.2    Morgan, M.R.A.3    Williamson, G.4
  • 14
    • 79952575127 scopus 로고    scopus 로고
    • Flavonoid conjugates interact with organic anion transporters (OATs) and attenuate cytotoxicity of adefovir mediated by organic anion transporter 1 (OAT1/SLC22A6)
    • Wong, C. C., Botting, N. P., Orfila, C., Al-Maharik, N., and Williamson, G. (2011) Flavonoid conjugates interact with organic anion transporters (OATs) and attenuate cytotoxicity of adefovir mediated by organic anion transporter 1 (OAT1/SLC22A6). Biochem. Pharmacol. 81, 942-949.
    • (2011) Biochem. Pharmacol. , vol.81 , pp. 942-949
    • Wong, C.C.1    Botting, N.P.2    Orfila, C.3    Al-Maharik, N.4    Williamson, G.5
  • 15
    • 0035692180 scopus 로고    scopus 로고
    • Human metabolism of dietary flavonoids: identification of plasma metabolites of quercetin
    • Day, A. J., Mellon, F., Barron, D., Sarrazin, G., Morgan, M. R. A., et al. (2001) Human metabolism of dietary flavonoids: identification of plasma metabolites of quercetin. Free Radical Res. 35, 941-952.
    • (2001) Free Radical Res. , vol.35 , pp. 941-952
    • Day, A.J.1    Mellon, F.2    Barron, D.3    Sarrazin, G.4    Morgan, M.R.A.5
  • 16
    • 84864122633 scopus 로고    scopus 로고
    • Carrier-mediated transport of quercetin conjugates: involvement of organic anion transporters and organic anion transporting polypeptides
    • Wong, C. C., Akiyama, Y., Abe, T., Lippiat, J. D., Orfila, C., et al. (2012) Carrier-mediated transport of quercetin conjugates: involvement of organic anion transporters and organic anion transporting polypeptides. Biochem. Pharmacol. 84, 564-570.
    • (2012) Biochem. Pharmacol. , vol.84 , pp. 564-570
    • Wong, C.C.1    Akiyama, Y.2    Abe, T.3    Lippiat, J.D.4    Orfila, C.5
  • 17
    • 0037300834 scopus 로고    scopus 로고
    • Metabolism of quercetin-7- and quercetin-3-glucuronides by an in vitro hepatic model: the role of human beta-glucuronidase, sulfotransferase, catechol-O-methyltransferase and multi-resistant protein 2 (MRP2) in flavonoid metabolism
    • O'Leary, K. A., Day, A. J., Needs, P. W., Mellon, F. A., O'Brien, N. M., et al. (2003) Metabolism of quercetin-7- and quercetin-3-glucuronides by an in vitro hepatic model: the role of human beta-glucuronidase, sulfotransferase, catechol-O-methyltransferase and multi-resistant protein 2 (MRP2) in flavonoid metabolism. Biochem. Pharmacol. 65, 479-491.
    • (2003) Biochem. Pharmacol. , vol.65 , pp. 479-491
    • O'Leary, K.A.1    Day, A.J.2    Needs, P.W.3    Mellon, F.A.4    O'Brien, N.M.5
  • 18
    • 1942472986 scopus 로고    scopus 로고
    • Phytoestrogens are potent inhibitors of estrogen sulfation: implications for breast cancer risk and treatment
    • Harris, R. M., Wood, D. M., Bottomley, L., Blagg, S., Owen, K., et al. (2004) Phytoestrogens are potent inhibitors of estrogen sulfation: implications for breast cancer risk and treatment. J. Clin. Endocrinol. Metab. 89, 1779-1787.
    • (2004) J. Clin. Endocrinol. Metab. , vol.89 , pp. 1779-1787
    • Harris, R.M.1    Wood, D.M.2    Bottomley, L.3    Blagg, S.4    Owen, K.5
  • 19
    • 0037518134 scopus 로고    scopus 로고
    • Absorption/metabolism of sulforaphane and quercetin, and regulation of phase II enzymes, in human jejunum in vivo
    • Petri, N., Tannergren, C., Holst, B., Mellon, F. A., Bao, Y., et al. (2003) Absorption/metabolism of sulforaphane and quercetin, and regulation of phase II enzymes, in human jejunum in vivo. Drug Metab. Dispos. 31, 805-813.
    • (2003) Drug Metab. Dispos. , vol.31 , pp. 805-813
    • Petri, N.1    Tannergren, C.2    Holst, B.3    Mellon, F.A.4    Bao, Y.5
  • 20
    • 34147147914 scopus 로고    scopus 로고
    • Isoflavonoid glucosides are deconjugated and absorbed in the small intestine of human subjects with ileostomies
    • Walsh, K. R., Haak, S. J., Bohn, T., Tian, Q., Schwartz, S. J., et al. (2007) Isoflavonoid glucosides are deconjugated and absorbed in the small intestine of human subjects with ileostomies. Am. J. Clin. Nutr. 85, 1050-1056.
    • (2007) Am. J. Clin. Nutr. , vol.85 , pp. 1050-1056
    • Walsh, K.R.1    Haak, S.J.2    Bohn, T.3    Tian, Q.4    Schwartz, S.J.5
  • 21
    • 49449085678 scopus 로고    scopus 로고
    • Bioavailability of polyphenon E flavan-3-ols in humans with an ileostomy
    • Auger, C., Mullen, W., Hara, Y., and Crozier, A. (2008) Bioavailability of polyphenon E flavan-3-ols in humans with an ileostomy. J. Nutr. 138, 1535S-1542S.
    • (2008) J. Nutr. , vol.138
    • Auger, C.1    Mullen, W.2    Hara, Y.3    Crozier, A.4
  • 22
    • 0033863355 scopus 로고    scopus 로고
    • Dietary intake and bioavailability of polyphenols
    • Scalbert, A., and Williamson, G. (2000) Dietary intake and bioavailability of polyphenols. J. Nutr. 130, 2073S-2085S.
    • (2000) J. Nutr. , vol.130
    • Scalbert, A.1    Williamson, G.2
  • 23
    • 34547169521 scopus 로고    scopus 로고
    • Expression of thirty-six drug transporter genes in human intestine, liver, kidney, and organotypic cell lines
    • Hilgendorf, C., Ahlin, G., Seithel, A., Artursson, P., Ungell, A. L., et al. (2007) Expression of thirty-six drug transporter genes in human intestine, liver, kidney, and organotypic cell lines. Drug Metab. Dispos. 35, 1333-1340.
    • (2007) Drug Metab. Dispos. , vol.35 , pp. 1333-1340
    • Hilgendorf, C.1    Ahlin, G.2    Seithel, A.3    Artursson, P.4    Ungell, A.L.5
  • 24
    • 13844281685 scopus 로고    scopus 로고
    • Bioavailability and bioefficacy of polyphenols in humans. I. Review of 97 bioavailability studies
    • Manach, C., Williamson, G., Morand, C., Scalbert, A., and Rémésy, C. (2005) Bioavailability and bioefficacy of polyphenols in humans. I. Review of 97 bioavailability studies. Am. J. Clin. Nutr. 81, 2305-2425.
    • (2005) Am. J. Clin. Nutr. , vol.81 , pp. 2305-2425
    • Manach, C.1    Williamson, G.2    Morand, C.3    Scalbert, A.4    Rémésy, C.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.