Sulfation of dietary flavonoids by human sulfotransferases

References

• Actis-Goretta L, Ottaviani JI, Fraga CG. 2006. Inhibition of angiotensin converting enzyme activity by flavanol-rich foods. J Agric Food Chem 54(1):229–234.
   PubMedGoogle Scholar
• Arlt VM, Glatt H, Muckel E, Pabel U, Sorg BL, Schmeiser HH, Phillips DH. 2002. Metabolic activation of the environmental contaminant 3-nitrobenzanthrone by human acetyltransferases and sulfotransferase. Carcinogenesis 23(11):1937–1945.
   PubMedGoogle Scholar
• Aust S, Jaeger W, Klimpfinger M, Mayer K, Baravalle G, Ekmekcioglu C, Thalhammer T. 2005a. Biotransformation of melatonin in human breast cancer cell lines: role of sulfotransferase 1A1. J Pineal Res 39(3):276–282.
   PubMedGoogle Scholar
• Aust S, Obrist P, Klimpfinger M, Tucek G, Jager W, Thalhammer T. 2005b. Altered expression of the hormone- and xenobiotic-metabolizing sulfotransferase enzymes 1A2 and 1C1 in malignant breast tissue. Int J Oncol 26(4):1079–1085.
   PubMedGoogle Scholar
• Borradaile NM, Carroll KK, Kurowska EM. 1999. Regulation of HepG2 cell apolipoprotein B metabolism by the citrus flavanones hesperetin and naringenin. Lipids 34(6):591–598.
   PubMedGoogle Scholar
• Chen CL, Yu G, Venkatachalam TK, Uckun FM. 2002. Metabolism of stavudine-5´-[p-bromophenyl methoxyalaninyl phosphate], stampidine, in mice, dogs, and cats. Drug Metab Dispos 30(12):1523–1531.
   PubMedGoogle Scholar
• Chen G, Battaglia E, Senay C, Falany CN, Radominska-Pandya A. 1999. Photoaffinity labeling probe for the substrate binding site of human phenol sulfotransferase (SULT1A1): 7-azido-4-methylcoumarin. Protein Sci 8(10):2151–2157.
   PubMedGoogle Scholar
• Chen G, Chen X. 2003. Arginine residues in the active site of human phenol sulfotransferase (SULT1A1). J Biol Chem 278(38):36358–36364.
   PubMedGoogle Scholar
• Chen G, Rabjohn PA, York JL, Wooldridge C, Zhang D, Falany CN, Radominska-Pandya A. 2000. Carboxyl residues in the active site of human phenol sulfotransferase (SULT1A1). Biochemistry 39(51):16000–16007.
   PubMedGoogle Scholar
• Chen G, Zhang D, Jing N, Yin S, Falany CN, Radominska-Pandya A. 2003. Human gastrointestinal sulfotransferases: identification and distribution. Toxicol Appl Pharmacol 187(3):186–197.
   PubMedGoogle Scholar
• Cho J. 2006. Antioxidant and neuroprotective effects of hesperidin and its aglycone hesperetin. Arch Pharm Res 29(8):699–706.
   PubMedGoogle Scholar
• Chou HC, Lang NP, Kadlubar FF. 1995. Metabolic activation of N-hydroxy arylamines and N-hydroxy heterocyclic amines by human sulfotransferase(s). Cancer Res 55(3):525–529.
   PubMedGoogle Scholar
• De Santi C, Pietrabissa A, Mosca F, Rane A, Pacifici GM. 2002. Inhibition of phenol sulfotransferase (SULT1A1) by quercetin in human adult and foetal livers. Xenobiotica 32(5):363–368.
   PubMedGoogle Scholar
• Eaton EA, Walle UK, Lewis AJ, Hudson T, Wilson AA, Walle T. 1996. Flavonoids, potent inhibitors of the human P-form phenolsulfotransferase. Potential role in drug metabolism and chemoprevention. Drug Metab Dispos 24(2):232–237.
   PubMedGoogle Scholar
• Falany CN, Zhuang W, Falany JL. 1994. Characterization of expressed human phenol-sulfating phenol sulfotransferase: effect of mutating cys70 on activity and thermostability. Chem Biol Interact 92(1–3):57–66.
   PubMedGoogle Scholar
• Fink BN, Steck SE, Wolff MS, Britton JA, Kabat GC, Schroeder JC, Teitelbaum SL, Neugut AI, Gammon MD. 2007. Dietary flavonoid intake and breast cancer risk among women on Long Island. Am J Epidemiol 165(5):514–523.
   PubMedGoogle Scholar
• Fisher ND, Hollenberg NK. 2005. Flavanols for cardiovascular health: the science behind the sweetness. J Hypertens 23(8):1453–1459.
   PubMedGoogle Scholar
• Fisher ND, Hughes M, Gerhard-Herman M, Hollenberg NK. 2003. Flavanol-rich cocoa induces nitric-oxide-dependent vasodilation in healthy humans. J Hypertens 21(12):2281–2286.
   PubMedGoogle Scholar
• Frydoonfar HR, McGrath DR, Spigelman AD. 2003. The variable effect on proliferation of a colon cancer cell line by the citrus fruit flavonoid Naringenin. Colorectal Dis 5(2):149–152.
   PubMedGoogle Scholar
• Gardana C, Guarnieri S, Riso P, Simonetti P, Porrini M. 2007. Flavanone plasma pharmacokinetics from blood orange juice in human subjects. Br J Nutr 98(1):165–172.
   PubMedGoogle Scholar
• Ghazali RA, Waring RH. 1999. The effects of flavonoids on human phenolsulphotransferases: potential in drug metabolism and chemoprevention. Life Sci 65(16):1625–1632.
   PubMedGoogle Scholar
• Gibb C, Glover V, Sandler M. 1987. In vitro inhibition of phenolsulphotransferase by food and drink constituents. Biochem Pharmacol 36(14):2325–2330.
   PubMedGoogle Scholar
• Harnly JM, Doherty RF, Beecher GR, Holden JM, Haytowitz DB, Bhagwat S, Gebhardt S. 2006. Flavonoid content of U.S. fruits, vegetables, and nuts. J Agric Food Chem 54(26):9966–9977.
   PubMedGoogle Scholar
• Harris RM, Wood DM, Bottomley L, Blagg S, Owen K, Hughes PJ, Waring RH, Kirk CJ. 2004. Phytoestrogens are potent inhibitors of estrogen sulfation: implications for breast cancer risk and treatment. J Clin Endocrinol Metab 89(4):1779–1787.
   PubMedGoogle Scholar
• Henning SM, Fajardo-Lira C, Lee HW, Youssefian AA, Go VL, Heber D. 2003. Catechin content of 18 teas and a green tea extract supplement correlates with the antioxidant capacity. Nutr Cancer 45(2):226–235.
   PubMedGoogle Scholar
• Heptinstall S, May J, Fox S, Kwik-Uribe C, Zhao L. 2006. Cocoa flavanols and platelet and leukocyte function: recent in vitro and ex vivo studies in healthy adults. J Cardiovasc Pharmacol 47 Suppl. 2:S197–205; discussion S6–9.
   Google Scholar
• Her C, Aksoy IA, Kimura S, Brandriff BF, Wasmuth JJ, Weinshilboum RM. 1995. Human estrogen sulfotransferase gene (STE): cloning, structure, and chromosomal localization. Genomics 29(1):16–23.
   PubMedGoogle Scholar
• Hollman PC, Katan MB. 1999. Health effects and bioavailability of dietary flavonols. Free Radic Res 31 Suppl.:S75–S80.
   PubMedGoogle Scholar
• Jenner AM, Rafter J, Halliwell B. 2005. Human fecal water content of phenolics: the extent of colonic exposure to aromatic compounds. Free Radic Biol Med 38(6):763–772.
   PubMedGoogle Scholar
• Justesen U, Knuthsen P, Leth T. 1998. Quantitative analysis of flavonols, flavones, and flavanones in fruits, vegetables and beverages by high-performance liquid chromatography with photo-diode array and mass spectrometric detection. J Chromatogr A 799(1–2):101–110.
   PubMedGoogle Scholar
• Kanaze FI, Bounartzi MI, Georgarakis M, Niopas I. 2007. Pharmacokinetics of the citrus flavanone aglycones hesperetin and naringenin after single oral administration in human subjects. Eur J Clin Nutr 61(4):472–477.
   PubMedGoogle Scholar
• Khokhar S, Magnusdottir SG. 2002. Total phenol, catechin, and caffeine contents of teas commonly consumed in the United kingdom. J Agric Food Chem 50(3):565–570.
   PubMedGoogle Scholar
• Kim HK, Jeon WK, Ko BS. 2001. Flavanone glycosides from Citrus junos and their anti-influenza virus activity. Planta Med 67(6):548–549.
   PubMedGoogle Scholar
• Kren V, Martinkova L. 2001. Glycosides in medicine: ‘the role of glycosidic residue in biological activity’. Curr Med Chem 8(11):1303–1328.
   PubMedGoogle Scholar
• Lin J, Zhang SM, Wu K, Willett WC, Fuchs CS, Giovannucci E. 2006. Flavonoid intake and colorectal cancer risk in men and women. Am J Epidemiol 164(7):644–651.
   PubMedGoogle Scholar
• Lu JH, Li HT, Liu MC, Zhang JP, Li M, An XM, Chang WR. 2005. Crystal structure of human sulfotransferase SULT1A3 in complex with dopamine and 3´-phosphoadenosine 5´-phosphate. Biochem Biophys Res Commun 335(2):417–423.
   PubMedGoogle Scholar
• Marchetti F, De Santi C, Vietri M, Pietrabissa A, Spisni R, Mosca F, Pacifici GM. 2001. Differential inhibition of human liver and duodenum sulphotransferase activities by quercetin, a flavonoid present in vegetables, fruit and wine. Xenobiotica 31(12):841–847.
   PubMedGoogle Scholar
• Mateus N, Silva AM, Santos-Buelga C, Rivas-Gonzalo JC, de Freitas V. 2002. Identification of anthocyanin-flavanol pigments in red wines by NMR and mass spectrometry. J Agric Food Chem 50(7):2110–2116.
   PubMedGoogle Scholar
• Meerman JH, Van de Poll ML. 1994. Metabolic activation routes of arylamines and their genotoxic effects. Environ Health Perspect 102Suppl. 6:153–159.
   PubMedGoogle Scholar
• Meinl W, Meerman JH, Glatt H. 2002. Differential activation of promutagens by alloenzymes of human sulfotransferase 1A2 expressed in Salmonella typhimurium. Pharmacogenetics 12(9):677–689.
   PubMedGoogle Scholar
• Mesia-Vela S, Kauffman FC. 2003. Inhibition of rat liver sulfotransferases SULT1A1 and SULT2A1 and glucuronosyltransferase by dietary flavonoids. Xenobiotica 33(12):1211–1220.
   PubMedGoogle Scholar
• Miller JA. 1994. Sulfonation in chemical carcinogenesis – history and present status. Chem Biol Interact 92(1–3):329–341.
   PubMedGoogle Scholar
• Miyake Y, Minato K, Fukumoto S, Yamamoto K, Oya-Ito T, Kawakishi S, Osawa T. 2003. New potent antioxidative hydroxyflavanones produced with Aspergillus saitoi from flavanone glycoside in citrus fruit. Biosci Biotechnol Biochem 67(7):1443–1450.
   PubMedGoogle Scholar
• Nair HK, Rao KV, Aalinkeel R, Mahajan S, Chawda R, Schwartz SA. 2004. Inhibition of prostate cancer cell colony formation by the flavonoid quercetin correlates with modulation of specific regulatory genes. Clin Diagn Lab Immunol 11(1):63–69.
   PubMedGoogle Scholar
• Ohkimoto K, Liu MY, Suiko M, Sakakibara Y, Liu MC. 2004. Characterization of a zebrafish estrogen-sulfating cytosolic sulfotransferase: inhibitory effects and mechanism of action of phytoestrogens. Chem Biol Interact 147(1):1–7.
   PubMedGoogle Scholar
• O’Leary KA, Day AJ, Needs PW, Mellon FA, O’Brien NM, Williamson G. 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(3):479–491.
   PubMedGoogle Scholar
• Otterness DM, Wieben ED, Wood TC, Watson WG, Madden BJ, McCormick DJ, Weinshilboum RM. 1992. Human liver dehydroepiandrosterone sulfotransferase: molecular cloning and expression of cDNA. Mol Pharmacol 41(5):865–872.
   PubMedGoogle Scholar
• Pacifici GM. 2004. Inhibition of human liver and duodenum sulfotransferases by drugs and dietary chemicals: a review of the literature. Int J Clin Pharmacol Ther 42(9):488–495.
   PubMedGoogle Scholar
• Park SH, Park EK, Kim DH. 2005. Passive cutaneous anaphylaxis- inhibitory activity of flavanones from Citrus unshiu and Poncirus trifoliata. Planta Med 71(1):24–27.
   PubMedGoogle Scholar
• Pearson DA, Paglieroni TG, Rein D, Wun T, Schramm DD, Wang JF, Holt RR, Gosselin R, Schmitz HH, Keen CL. 2002. The effects of flavanol-rich cocoa and aspirin on ex vivo platelet function. Thromb Res 106(4–5):191–197.
   PubMedGoogle Scholar
• Pezzato E, Sartor L, Dell’Aica I, Dittadi R, Gion M, Belluco C, Lise M, Garbisa S. 2004. Prostate carcinoma and green tea: PSA-triggered basement membrane degradation and MMP-2 activation are inhibited by (–)epigallocatechin-3-gallate. Int J Cancer 112(5):787–792.
   PubMedGoogle Scholar
• Radominska-Pandya A, Little JM, Pandya JT, Tephly TR, King CD, Barone GW, Raufman JP. 1998. UDP-glucuronosyltransferases in human intestinal mucosa. Biochim Biophys Acta 1394(2–3):199–208.
   PubMedGoogle Scholar
• Radominska-Pyrek A, Zimniak P, Irshaid YM, Lester R, Tephly TR, St Pyrek J. 1987. Glucuronidation of 6 alpha-hydroxy bile acids by human liver microsomes. J Clin Invest 80(1):234–241.
   PubMedGoogle Scholar
• Scholz EP, Zitron E, Kiesecker C, Thomas D, Kathofer S, Kreuzer J, Bauer A, Katus HA, Remppis A, Karle CA, Greten J. 2006. Orange flavonoid hesperetin modulates cardiac hERG potassium channel via binding to amino acid F656. Nutr Metab Cardiovasc Dis.
   PubMedGoogle Scholar
• Schroeter H, Heiss C, Balzer J, Kleinbongard P, Keen CL, Hollenberg NK, Sies H, Kwik-Uribe C, Schmitz HH, Kelm M. 2006. (–)-Epicatechin mediates beneficial effects of flavanol-rich cocoa on vascular function in humans. Proc Natl Acad Sci USA 103(4):1024–1029.
   PubMedGoogle Scholar
• Sehm J, Polster J, Pfaffl MW. 2005. Effects of varied EGCG and (+)-catechin concentrations on proinflammatory cytokines mrna expression in cona-stimulated primary white blood cell cultures. J Agric Food Chem 53(17):6907–6911.
   PubMedGoogle Scholar
• Selmi C, Mao TK, Keen CL, Schmitz HH, Eric Gershwin M. 2006. The anti-inflammatory properties of cocoa flavanols. J Cardiovasc Pharmacol 47 Suppl. 2:S163–S171; discussion S72–S76.
   PubMedGoogle Scholar
• Silberberg M, Gil-Izquierdo A, Combaret L, Remesy C, Scalbert A, Morand C. 2006. Flavanone metabolism in healthy and tumor-bearing rats. Biomed Pharmacother 60(9):529–535.
   PubMedGoogle Scholar
• Stampfer MJ, Colditz GA, Willett WC, Manson JE, Rosner B, Speizer FE, Hennekens CH. 1991. Postmenopausal estrogen therapy and cardiovascular disease. Ten-year follow-up from the nurses’ health study. N Engl J Med 325(11):756–762.
   PubMed Web of Science ®Google Scholar
• Steffen Y, Schewe T, Sies H. 2005. Epicatechin protects endothelial cells against oxidized LDL and maintains NO synthase. Biochem Biophys Res Commun 331(4):1277–1283.
   PubMedGoogle Scholar
• Terao J. 1999. Dietary flavonoids as antioxidants in vivo: conjugated metabolites of (–)-epicatechin and quercetin participate in antioxidative defense in blood plasma. J Med Invest 46(3–4):159–168.
   PubMedGoogle Scholar
• Torres JL, Bobet R. 2001. New flavanol derivatives from grape (Vitis vinifera) byproducts. Antioxidant aminoethylthio-flavan-3-ol conjugates from a polymeric waste fraction used as a source of flavanols. J Agric Food Chem 49(10):4627–4634.
   PubMedGoogle Scholar
• Vaidyanathan JB, Walle T. 2002. Glucuronidation and sulfation of the tea flavonoid (–)-epicatechin by the human and rat enzymes. Drug Metab Dispos 30(8):897–903.
   PubMedGoogle Scholar
• Veluri R, Weir TL, Bais HP, Stermitz FR, Vivanco JM. 2004. Phytotoxic and antimicrobial activities of catechin derivatives. J Agric Food Chem 52(5):1077–1082.
   PubMedGoogle Scholar
• Vietri M, Pietrabissa A, Spisni R, Mosca F, Pacifici GM. 2002. 7-OH-flavone is sulfated in the human liver and duodenum, whereas 5-OH-flavone and 3-OH-flavone are potent inhibitors of SULT1A1 activity and 7-OH-flavone sulfation rate. Xenobiotica 32(7):563–571.
   PubMedGoogle Scholar
• Wakazono H, Gardner I, Eliasson E, Coughtrie MW, Kenna JG, Caldwell J. 1998. Immunochemical identification of hepatic protein adducts derived from estragole. Chem Res Toxicol 11(8):863–872.
   PubMedGoogle Scholar
• Walle T, Eaton EA, Walle UK. 1995. Quercetin, a potent and specific inhibitor of the human P-form phenosulfotransferase. Biochem Pharmacol 50(5):731–734.
   PubMed Web of Science ®Google Scholar
• Waring RH, Ayers S, Gescher AJ, Glatt HR, Meinl W, Jarratt P, Kirk CJ, Pettitt T, Rea D, Harris RM. 2008. Phytoestrogens and xenoestrogens: the contribution of diet and environment to endocrine disruption. J Steroid Biochem Mol Biol 108(3–5):213–220.
   PubMedGoogle Scholar
• Yang SH, Tao J, Liu XF, Guo DA, Zheng JH. 2006. [Effects of carbon source and nitrogen source on callus growth and flavonoid content in Glycyrrhiza uralensis]. Zhongguo Zhong Yao Za Zhi 31(22):1857–1859.
   PubMedGoogle Scholar
• Zhu QY, Schramm DD, Gross HB, Holt RR, Kim SH, Yamaguchi T, Kwik-Uribe CL, Keen CL. 2005. Influence of cocoa flavanols and procyanidins on free radical-induced human erythrocyte hemolysis. Clin Dev Immunol 12(1):27–34.
   PubMedGoogle Scholar