Effect of resveratrol on 17β-estradiol sulfation by human hepatic and jejunal S9 and recombinant sulfotransferase 1E1

Drug Metabolism and Disposition

Volumn 36, Issue 1, 2008, Pages 129-136

  Furimsky, Anna M ^a   Green, Carol E ^a   Hunt Sharp, Lewanne E ^a   Catz, Paul ^a   Adjei, Araba A ^b   Parman, Toufan ^a   Kapetanovic, Izet M ^c   Weinshilboum, Richard M ^d   Iyer, Lalitha V ^a  

^a SRI INTERNATIONAL   (United States)

^b MAYO GRADUATE SCHOOL   (United States)

^c ROSWELL PARK CANCER INSTITUTE   (United States)

^d NATIONAL CANCER INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIESTROGEN; ESTRADIOL; ESTROGEN; PHYTOESTROGEN; RESVERATROL; SULFOTRANSFERASE; SULFOTRANSFERASE 1E1; UNCLASSIFIED DRUG; ARYL SULFOTRANSFERASE; ESTRONE SULFOTRANSFERASE; RECOMBINANT PROTEIN; STILBENE DERIVATIVE; SULFATE; SULT1A1 PROTEIN, HUMAN;

ARTICLE; CONJUGATION; DRUG INHIBITION; DRUG METABOLISM; ESTROGEN BLOOD LEVEL; HOMEOSTASIS; HUMAN; HUMAN TISSUE; JEJUNUM; LIVER; PRIORITY JOURNAL; SULFONATION; DRUG EFFECT; FEMALE; LIVER MICROSOME; MALE; METABOLISM; MICROSOME;

ARYLSULFOTRANSFERASE; ESTRADIOL; FEMALE; HUMANS; JEJUNUM; LIVER; MALE; MICROSOMES; MICROSOMES, LIVER; PHYTOESTROGENS; RECOMBINANT PROTEINS; STILBENES; SULFATES; SULFOTRANSFERASES;

EID: 37549003662     PISSN: 00909556     EISSN: 1521009X     Source Type: Journal    
DOI: 10.1124/dmd.107.016725     Document Type: Article

References (43)

1. Adjei AA, Thomae BA, Prondzinski JL, Eckloff BW, Wieben ED, and Weinshilboum RM (2003) Human estrogen sulfotransferase (SULT1E1) pharmacogenomics: gene resequencing and functional genomics. Br J Pharmacol 139:1373-1382.
2. Adjei AA and Weinshilboum RM (2002) Catecholestrogen sulfation: possible role in carcinogenesis. Biochem Biophys Res Commun 292:402-408.
3. Aumont V, Krisa S, Battaglia E, Netter P, Richard T, Merillon JM, Magdalou J, and Sabolovic N (2001) Regioselective and stereospecific glucuronidation of trans- and cis-resveratrol in human. Arch Biochem Biophys 393:281-289.
4. Aziz MH, Kumar R, and Ahmad N (2003) Cancer chemoprevention by resveratrol: in vitro and in vivo studies and the underlying mechanisms (Review). Int J Oncol 23:17-28.
5. Baur JA, Pearson KJ, Price NL, Jamieson HA, Lerin C, Kalra A, Prabhu VV, Allard JS, Lopez-Lluch G, Lewis K, et al. (2006) Resveratrol improves health and survival of mice on a high-calorie diet. Nature 444:337-342.
6. Baur JA and Sinclair DA (2006) Therapeutic potential of resveratrol: the in vivo evidence. Nat Rev Drug Discov 5:493-506.
7. Bhat KPL, Kosmeder JW 2nd, and Pezzuto JM (2001) Biological effects of resveratrol. Antioxid Redox Signal 3:1041-1064.
8. Boocock DJ, Faust GE, Patel KR, Schinas AM, Brown VA, Ducharme MP, Booth TD, Crowell JA, Perloff M, Gescher AJ, et al. (2007) Phase I dose escalation pharmacokinetic study in healthy volunteers of resveratrol, a potential cancer chemopreventive agent. Cancer Epidemiol Biomarkers Prev 16:1246-1252.
9. Brill SS, Furimsky AM, Ho MN, Furniss MJ, Li Y, Green AG, Bradford WW, Green CE, Kapetanovic IM, and Iyer LV (2006) Glucuronidation of trans-resveratrol by human liver and intestinal microsomes and UGT isoforms. J Pharm Pharmacol 58:469-479.
10. Cavalieri E, Chakravarti D, Guttenplan J, Hart E, Ingle J, Jankowiak R, Muti P, Rogan E, Russo J, Santen R, et al. (2006) Catechol estrogen quinones as initiators of breast and other human cancers: implications for biomarkers of susceptibility and cancer prevention. Biochim Biophys Acta 1766:63-78.
11. Chen G, Zhang D, Jing N, Yin S, Falany CN, and Radominska-Pandya A (2003) Human gastrointestinal sulfotransferases: identification and distribution. Toxicol Appl Pharmacol 187:186-197.
12. Coughtrie MW (2002) Sulfation through the looking glass - recent advances in sulfotransferase research for the curious. Pharmacogenomics J 2:297-308.
13. De Santi C, Pietrabissa A, Spisni R, Mosca F, and Pacifici GM (2000a) Sulphation of resveratrol, a natural compound present in wine, and its inhibition by natural flavonoids. Xenobiotica 30:857-866.
14. De Santi C, Pietrabissa A, Spisni R, Mosca F, and Pacifici GM (2000b) Sulphation of resveratrol, a natural product present in grapes and wine, in the human liver and duodenum. Xenobiotica 30:609-617.
15. Falany JL, Macrina N, and Falany CN (2002) Regulation of MCF-7 breast cancer cell growth by β-estradiol sulfation. Breast Cancer Res Treat 74:167-176.
16. Furimsky AM, Sharp LE, Bettridge A, Kapetanovic IM, Green CE, and Iyer LV (2006) Inhibition of human hepatic and jejunal estradiol sulfation by resveratrol and piceatannol (Abstract). FASEB J 20:A264.
17. Gamage N, Barnett A, Hempel N, Duggleby RG, Windmill KF, Martin JL, and McManus ME (2006) Human sulfotransferases and their role in chemical metabolism. Toxicol Sci 90:5-22.
18. Garvin S, Ollinger K, and Dabrosin C (2006) Resveratrol induces apoptosis and inhibits angiogenesis in human breast cancer xenografts in vivo. Cancer Lett 231:113-122.
19. Gehm BD, McAndrews JM, Chien PY, and Jameson JL (1997) Resveratrol, a polyphenolic compound found in grapes and wine, is an agonist for the estrogen receptor. Proc Natl Acad Sci U S A 94:14138-14143.
20. Gescher AJ and Steward WP (2003) Relationship between mechanisms, bioavailibility, and preclinical chemopreventive efficacy of resveratrol: a conundrum. Cancer Epidemiol Biomarkers Prev 12:953-957.
21. Her C, Szumlanski C, Aksoy IA, and Weinshilboum RM (1996) Human jejunal estrogen sulfotransferase and dehydroepiandrosterone sulfotransferase: immunochemical characterization of individual variation. Drug Metab Dispos 24:1328-1335.
22. Kester MH, van Dijk CH, Tibboel D, Hood AM, Rose NJ, Meinl W, Pabel U, Glatt H, Falany CN, Coughtrie MW, et al. (1999) Sulfation of thyroid hormone by estrogen sulfotransferase. J Clin Endocrinol Metab 84:2577-2580.
23. Kopp P (1998) Resveratrol, a phytoestrogen found in red wine: a possible explanation for the conundrum of the 'French paradox'? Eur J Endocrinol 138:619-620.
24. Matsuoka A, Takeshita K, Furuta A, Ozaki M, Fukuhara K, and Miyata N (2002) The 4′-hydroxy group is responsible for the in vitro cytogenetic activity of resveratrol. Mutat Res 521:29-35.
25. Miksits M, Maier-Salamon A, Aust S, Thalhammer T, Reznicek G, Kunert O, Haslinger E, Szekeres T, and Jaeger W (2005) Sulfation of resveratrol in human liver: evidence of a major role for the sulfotransferases SULT1A1 and SULT1E1. Xenobiotica 35:1101-1119.
26. Miller WR and O'Neill JS (1990) The significance of steroid metabolism in human cancer. J Steroid Biochem Mol Biol 37:317-325.
27. Nagar S, Walther S, and Blanchard RL (2006) Sulfotransferase (SULT) 1A1 polymorphic variants *1, *2, and *3 are associated with altered enzymatic activity, cellular phenotype, and protein degradation. Mol Pharmacol 69:2084-2092.
28. Nath SS, Ho MN, Furniss MJ, Sharp LE, Green AG, Bradford WW, Green CE, Swezey R, Kapetanovic IM, and Iyer LV (2004) In vitro metabolism and drug interaction studies with trans-resveratrol (Abstract). Drug Metab. Rev 36:153.
29. Nishiyama T, Ogura K, Nakano H, Kaku T, Takahashi E, Ohkubo Y, Sekine K, Hiratsuka A, Kadota S, and Watabe T (2002) Sulfation of environmental estrogens by cytosolic human sulfotransferases. Drug Metab Pharmacokinet 17:221-228.
30. Nowell S, Green B, Tang YM, Wiese R, and Kadlubar FF (2005) Examination of human tissue cytosols for expression of sulfotransferase isoform 1A2 (SULT1A2) using a SULT1A2-specific antibody. Mol Pharmacol 67:394-399.
31. Otake Y, Nolan AL, Walle UK, and Walle T (2000) Quercetin and resveratrol potently reduce estrogen sulfotransferase activity in normal human mammary epithelial cells. J Steroid Biochem Mol Biol 73:265-270.
32. Piver B, Fer M, Vitrac X, Merillon JM, Dreano Y, Berthou F, and Lucas D (2004) Involvement of cytochrome P450 1A2 in the biotransformation of trans-resveratrol in human liver microsomes. Biochem Pharmacol 68:773-782.
33. Potter GA, Patterson LH, Wanogho E, Perry PJ, Butler PC, Ijaz T, Ruparelia KC, Lamb JH, Farmer PB, Stanley LA, et al. (2002) The cancer preventative agent resveratrol is converted to the anticancer agent piceatannol by the cytochrome P450 enzyme CYP1B1. Br J Cancer 86:774-778.
34. Schrag ML, Cui D, Rushmore TH, Shou M, Ma B, and Rodrigues AD (2004) Sulfotransferase 1E1 is a low km isoform mediating the 3-O-sulfation of ethinyl estradiol. Drug Metab Dispos 32:1299-1303.
35. Senafi SB, Clarke DJ, and Burchell B (1994) Investigation of the substrate specificity of a cloned expressed human bilirubin UDP- glucuronosyltransferase: UDP-sugar specificity and involvement in steroid and xenobiotic glucuronidation. Biochem J 303 (Pt 1):233-240.
36. Suzuki T, Miki Y, Nakata T, Shiotsu Y, Akinaga S, Inoue K, Ishida T, Kimura M, Moriya T, and Sasano H (2003) Steroid sulfatase and estrogen sulfotransferase in normal human tissue and breast carcinoma. J Steroid Biochem Mol Biol 86:449-454.
37. Teubner W, Meinl W, Florian S, Kretzschmar M, and Glatt H (2007) Identification and localization of soluble sulfotransferases in the human gastrointestinal tract. Biochem J 404:207-215.
38. Thakkar K, Geahlen RL, and CushmanM(1993) Synthesis and protein-tyrosine kinase inhibitory activity of polyhydroxylated stilbene analogues of piceatannol. J Med Chem 36:2950-2955.
39. Walle T, Hsieh F, DeLegge MH, Oatis JE Jr, and Walle UK (2004) High absorption but very low bioavailability of oral resveratrol in humans. Drug Metab Dispos 32:1377-1382.
40. Wenzel E and Somoza V (2005) Metabolism and bioavailability of trans-resveratrol. Mol Nutr Food Res 49:472-481.
41. Yasuda S, Suiko M, and Liu MC (2005) Oral contraceptives as substrates and inhibitors for human cytosolic SULTs. J Biochem (Tokyo) 137:401-406.
42. Yu C, Shin YG, Chow A, Li Y, Kosmeder JW, Lee YS, Hirschelman WH, Pezzuto JM, Mehta RG, and van Breemen RB (2002) Human, rat, and mouse metabolism of resveratrol. Pharmacol Res 19:1907-1914.
43. Zhang H, Varlamova O, Vargas FM, Falany CN, and Leyh TS (1998) Sulfuryl transfer: the catalytic mechanism of human estrogen sulfotransferase. J Biol Chem 273:10888-10892.