Sulfation of resveratrol in human liver: Evidence of a major role for the sulfotransferases SULT1A1 and SULT1E1

References

• Andlauer W, Kolb J, Siebert K, Furst P. Assessment of resveratrol bioavailability in the perfused small intestine of the rat. Drugs under Experimental and Clinical Research 2000; 26: 47–55
   PubMedGoogle Scholar
• Anderson RJ, Kudlacek PE, Clemens DL. Sulfation of minoxidil by multiple human cytosolic sulfotransferases. Chemico-Biological Interations 1998; 109: 53–67
   PubMed Web of Science ®Google Scholar
• Aumont V, Krisa S, Battaglia E, Netter P, Richard T, Merillon JM, Magdalou J, Sabolovic N. Regioselective and stereospecific glucuronidation of trans- and cis-resveratrol in human. Archives of Biochemistry and Biophysics 2001; 393: 281–289
   PubMed Web of Science ®Google Scholar
• Banoglu E. Current status of the cytosolic sulfotransferases in the metabolic activation of promutagens and procarcinogens. Current Drug Metabolism 2000; 1: 1–30
   PubMed Web of Science ®Google Scholar
• Bertelli AAE, Giovannini L, Gianessi D, Migliori M, Bernini W, Fregoni M, Bertelli A. Antiplatelet activity of synthetic and natural Resveratrol in red wine. International Journal of Tissue Reactions 1995; 17: 1–3
   PubMedGoogle Scholar
• Bradford MM. A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein–dye binding. Analytical Biochemistry 1976; 72: 248–254
   PubMed Web of Science ®Google Scholar
• Chen CK, Pace-Asciak CR. Vasorelaxing activity of resveratrol and quercetin in isolated rat aorta. General Pharmacology 1996; 27: 363–366
   PubMedGoogle Scholar
• Constant J. Alcohol, ischemic heart disease, and the French paradox. Coronary Artery Disease 1997; 8: 645–649
   PubMed Web of Science ®Google Scholar
• Debella A, Haslinger E, Kunert O, Michl G, Abebe D. Steroidal saponins from Asparagus africanus. Phytochemistry 1999; 51: 1069–1075
   PubMed Web of Science ®Google Scholar
• De Santi C, Pietrabissa A, Spisni R, Mosca F, Pacifici GM. Sulphation of resveratrol, a natural compound present in grapes and wine, in the human liver and duodenum. Xenobiotica 2000a; 30: 609–617
   PubMed Web of Science ®Google Scholar
• De Santi C, Pietrabissa A, Spisni R, Mosca F, Pacifici GM. Sulphation of resveratrol, a natural compound present in wine, and its inhibition by natural flavonoids. Xenobiotica 2000b; 30: 857–866
   PubMed Web of Science ®Google Scholar
• Dickinson RG, King AR, Kelly MA, Kaltashov IA, Fenselau C. Excretion of 3-hydroxy-diflunisal as a monosulphate conjugate — identification using ESI-MS. Journal of Pharmaceutical Biomedical Analysis 1994; 12: 1075–1078
   PubMed Web of Science ®Google Scholar
• Dooley TP, Haldeman-Cahill R, Joiner J, Wiborn TW. Expression profiling of human sulfotransferase and sulfatase gene superfamilies in epithelial tissues and cultured cells. Biochemical and Biophysical Research Communications 2000; 277: 236–245
   PubMed Web of Science ®Google Scholar
• Falany CN, Wheeler J, Oh TS, Falany JL. Steroid sulfation by expressed human cytosolic sulfotransferases. Journal of Steroid Biochemistry and Molecular Biology 1994; 48: 369–375
   PubMed Web of Science ®Google Scholar
• Frémont L, Belguendouz L, Delpal S. Antioxidant activity of resveratrol and alcohol-free wine polyphenols related to LDL oxidation and polyunsaturated fatty acids. Life Sciences 1999; 64: 2511–2521
   PubMed Web of Science ®Google Scholar
• Frémont L. Biological effects of resveratrol. Life Sciences 2000; 66: 663–673
   PubMed Web of Science ®Google Scholar
• Garay RP, Rosati C, Fanous K, Allard M, Morin E, Lamiable D, Vistelle R. Evidence for (+)-cicletanine sulfate as an active natriuretic metabolite of cicletanine in the rat. European Journal of Pharmacology 1995; 274: 175–180
   PubMed Web of Science ®Google Scholar
• Gehm BD, Mcandrews JM, Chien PY, Jameson JL. Resveratrol, a polyphenolic compound found in grapes and wine, is an agonist for the estrogen receptor. Proceedings of the National Academy of Sciences, USA, 1997. 94: 14138–14143
   Google Scholar
• Gescher AJ, Steward WP. Relationship between mechanisms, bioavailibility, and preclinical chemopreventive efficacy of resveratrol: a conundrum. Cancer Epidemiology Biomarkers and Prevention 2003; 12: 953–957
   PubMed Web of Science ®Google Scholar
• Glatt H. Sulfotransferases in the bioactivation of xenobiotics. Chemico-Biological Interactions 2000; 129: 141–170
   PubMed Web of Science ®Google Scholar
• Glatt M. Sulphotransferases. Enzyme systems that metabolise drugs and other xenobiotics, C Ioannides. Wiley, Chichester 2002; 353–439
   Google Scholar
• Horvath Z, Saiko P, Illmer C, Madlener S, Hoechtl T, Bauer W, Erker T, Jaeger W, Fritzer-Szekeres M, Szekeres T. Synergistic action of resveratrol, an ingredient of wine, with Arc-C and tiazofurin in HL-60 human promyelocytic leukemia cells. Experimental Hematology 2005; 33: 329–335
   PubMed Web of Science ®Google Scholar
• Hutzler JM, Tracy TS. Atypical kinetic profiles in drug metabolism reactions. Drug Metabolism and Disposition 2002; 30: 355–362
   PubMed Web of Science ®Google Scholar
• Jang M, Cai L, Udeani GO, Slowing KV, Thomas CF, Beecher CW, Fong HH, Farnsworth NR, Kinghorn AD, Mehta RG, Moon RC, Pezzuto JM. Cancer chemopreventive activity of resveratrol, a natural product derived from grapes. Science 1997; 275: 218–220
   PubMed Web of Science ®Google Scholar
• Kaldas MI, Walle UK, Walle T. Resveratrol transport and metabolism by human intestinal Caco-2 cells. Journal of Pharmacy and Pharmacology 2003; 55: 307–312
   PubMed Web of Science ®Google Scholar
• Kim HJ, Cho JH, Klaassen CD. Depletion of hepatic 3′-phosphoadenosine 5′-phosphosulfate (PAPS) and sulfate in rats by xenobiotics that are sulfated. Journal of Pharmacology and Experimental Therapeutics 1995; 275: 654–658
   PubMed Web of Science ®Google Scholar
• Leilich G, Knauf H, Mutschler E, Volger KD. Influence of triamterene and hydroxytriamterene sulfuric acid ester on diuresis and saluresis in rats after oral and intravenous application. Arzneimittelforschung 1980; 30: 949–953
   PubMed Web of Science ®Google Scholar
• Leonard SS, Xia C, Jiang BH, Stinefelt B, Klandorf H, Harris GK, Shi X. Resveratrol scavenges reactive oxygen species and effects radical-induced cellular responses. Biochemical and Biophysical Research Communications 2003; 309: 1017–1026
   PubMed Web of Science ®Google Scholar
• Marier JF, Vachon P, Gritsas A, Zhang J, Moreau JP, Ducharme MP. Metabolism and disposition of resveratrol in rats: Extent of absorption, glucuronidation, and enterohepatic recirculation evidence by a linked-rat model. Journal of Pharmacology and Experimental Therapeutics 2002; 302: 369–373
   PubMed Web of Science ®Google Scholar
• Meng X, Maliakal P, Lu H, Lee MJ, Yang CS. Urinary and plasma levels of resveratrol and quercetin in humans, mice, and rats after ingestion of pure compounds and grape juice. Journal of Agricultural and Food Chemistry 2004; 52: 935–942
   PubMed Web of Science ®Google Scholar
• Morris ME, Hansel SB. High-performance liquid chromatographic analysis of p-nitrophenol and its conjugates in biological samples. Journal of Chromatography B 1990; 532: 285–293
   Web of Science ®Google Scholar
• Murias M, Handler N, Erker T, Pleban K, Ecker G, Saiko P, Szekeres T, Jäger W. Resveratrol analogues as selective cyclooxygenase-2 inhibitors: synthesis and structure-activity relationship. Bioorganic and Medicinal Chemistry 2004; 12: 5571–5578
   PubMed Web of Science ®Google Scholar
• Murias M, Jaeger W, Handler N, Erker T, Horvath Z, Szekeres T, Nohl H, Gille L. Antioxidant, prooxidant and cytotoxic activity of hydroxylated resveratrol analogues: structure–activity relationship. Biochemical Pharmacology 2005; 69: 903–912
   PubMed Web of Science ®Google Scholar
• Nakano H, Ogura K, Takahashi E, Harada T, Nishiyama T, Muro K, Hiratsuka A, Kadota S, Watabe T. Regioselective monosulfation and disulfation of the phytoestrogens daidzein and genistein by human liver sulfotransferases. Drug Metabolism and Pharmacokinetics 2004; 19: 216–226
   PubMedGoogle Scholar
• Nowell S, Green B, Tang YM, Wiese R, Kadlubar FF. Examination of human tissue cytosols for expression of sulfotransferase isoform 1A2 (SULT1A2) using a SULT1A2-specific antibody. Molecular Pharmacology 2005; 67: 394–399
   PubMed Web of Science ®Google Scholar
• Pasqualini JR, Chetrite GS. Recent insight on the control of enzymes involved in estrogen formation and transformation in human breast cancer. Journal of Steroid Biochemistry and Molecular Biology 2005; 93: 221–236
   PubMed Web of Science ®Google Scholar
• Raftogianis RB, Wood TC, Weinshilboum RM. Human phenol sulfotransferases SULT1A2 and SULT1A1. Genetic polymorphisms, allozyme properties, and human liver genotype-phenotype correlations. Biochemical Pharmacology 1999; 58: 605–616
   PubMed Web of Science ®Google Scholar
• Richard K, Hume R, Kaptein E, Stanley EL, Visser TJ, Coughtire MW. Sulfation of thyroid hormone and dopamine during human development: ontogeny of phenol sulfotransferases and arylsulfatase in liver, lung, and brain. Journal of Clinical Endocrinology and Metabolsim 2001; 86: 2734–2742
   PubMed Web of Science ®Google Scholar
• Taskinen J, Ethell BT, Pihlavisto P, Hood AM, Burchell B, Coughtrie MW. Conjugation of catechols by recombinant human sulfotransferases, UDP-glucuronosyltransferases, and soluble catechol O-methyltransferase: structure–conjugation relationships and predictive models. Drug Metabolism and Disposition 2003; 31: 1187–1197
   PubMed Web of Science ®Google Scholar
• Thomas NL, Coughtrie MW. Sulfation of apomorphine by human sulfotransferases: evidence of a major role for the polymorphic phenol sulfotransferase, SULT1A1. Xenobiotica 2003; 33: 1139–1148
   PubMed Web of Science ®Google Scholar
• Tsan MF, White JE, Maheshwari JG, Chikkappa G. Anti-leukemia effect of resveratrol. Leukemia and Lymphoma 2002; 43: 983–987
   PubMed Web of Science ®Google Scholar
• Urpi-Sarda M, Jauregui O, Lamuela-Raventos RM, Jaeger W, Miksits M, Covas MI, Andres-Lacueva C. Uptake of diet resveratrol into the human low-density lipoprotein. Identification and quantification of resveratrol metabolites by liquid chromatography coupled with tandem mass spectrometry. Analytical Chemistry 2005; 77: 3149–3155
   PubMed Web of Science ®Google Scholar
• Vos RM, Krebbers SF, Verhoeven CH, Delbressine LP. The in vivo human metabolism of tibolone. Drug Metabolism and Disposition 2002; 30: 106–112
   PubMed Web of Science ®Google Scholar
• Walle T, Hsieh F, Delegge MH, Oatis JE, Walle UK. High absorption but very low bioavailability of oral resveratrol in humans. Drug Metabolism and Disposition 2004; 32: 1377–1382
   PubMed Web of Science ®Google Scholar
• Wu JM, Wang ZR, Hsieh TC, Bruder JL, Zou JG, Huang YZ. Mechanisms of cardioprotection by resveratrol, a phenolic antioxidant present in red wine. International Journal of Molecular Medicine 2001; 8: 3–17
   PubMed Web of Science ®Google Scholar
• Yu C, Shin YG, Chow A, Li Y, Kosmeder JW, Lee YS, Hirschelman WH, Pezzuto JM, Mehta RG, Van Breeman RB. Human, rat, and mouse metabolism of resveratrol. Pharmaceutical Research 2002; 19: 1907–1914
   PubMed Web of Science ®Google Scholar
• Zou JG, Huang YZ, Chen Q, Wei EH, Hsieh TC, Wu JM. Resveratrol inhibits copper ion-induced and azo compound-initiated oxidative modification of human low density lipoprotein. IUBMB Life 1999; 47: 1089–1096
   Google Scholar
• Zuckerman A, Bolan E, De Paulis T, Schmidt D, Spector S, Pasternak GW. Pharmacological characterization of morphine-6-sulfate and codeine-6-sulfate. Brain Research 1999; 842: 1–5
   PubMed Web of Science ®Google Scholar