Effects of phenolic acids on human phenolsulfotransferases in relation to their antioxidant activity

Journal of Agricultural and Food Chemistry

Volumn 51, Issue 5, 2003, Pages 1474-1479

  Yeh, Chi Tai ^a   Yen, Gow Chin ^a  

^a NATIONAL CHUNG HSING UNIVERSITY   (Taiwan)

Author keywords

Antioxidant activity; Human phenolsulfotransferases; Phenolic acids; Platelet

Indexed keywords

4 HYDROXYBENZOIC ACID; 6-HYDROXY-2,5,7,8-TETRAMETHYLCHROMAN-2-CARBOXYLIC ACID; ANTIOXIDANT; ARYL SULFOTRANSFERASE; CAFFEIC ACID; CHLOROGENIC ACID; CHROMAN DERIVATIVE; COUMARIC ACID; COUMARIN; FERULIC ACID; GALLIC ACID; GENTISIC ACID; HYDROXYBENZOIC ACID DERIVATIVE; MONOAMINE SULFATING PHENOL SULFOTRANSFERASE; MONOAMINE-SULFATING PHENOL SULFOTRANSFERASE; OXYGEN RADICAL; PARA COUMARIC ACID; PHENOL DERIVATIVE; PHENOLIC ACID; PROTOCATECHUIC ACID; REACTIVE OXYGEN METABOLITE; SINAPIC ACID; SULFATE; SULFOTRANSFERASE; SYRINGIC ACID; TROLOX C; UNCLASSIFIED DRUG; VANILLIC ACID;

ADULT; ANTIOXIDANT ACTIVITY; ARTICLE; BLOOD; CHEMISTRY; COMPARATIVE STUDY; CONJUGATION; CONTROLLED STUDY; ENZYME ACTIVATION; ENZYME ACTIVITY; ENZYMOLOGY; HUMAN; HUMAN CELL; SPECTROFLUOROMETRY; SULFATION; THROMBOCYTE;

ADULT; ANTIOXIDANTS; ARYLSULFOTRANSFERASE; BLOOD PLATELETS; CHROMANS; HUMANS; HYDROXYBENZOIC ACIDS; REACTIVE OXYGEN SPECIES; SPECTROMETRY, FLUORESCENCE; SULFOTRANSFERASES;

EID: 0037467073     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf0208132     Document Type: Article

References (28)

1. Brix, L. A.; Nicoll, R.; Zhu, X.; McManus, M. E. Structural and functional characterization of human sulfotransferases. Chem. Biol. Interact. 1998, 109, 123-127.
2. Coughtrie, M. C. H.; Sharp, S.; Maxwell, K.; Innes, N. P. Biology and function of the reversible sulfation pathway catalysed by human sulfotransferase and sulfatases. Chem. Biol. Interact. 1998, 109, 3-27.
3. Weinshilboum, R.; Aksoy, I. Sulfation pharmacogenetics in humans. Chem. Biol. Interact. 1994, 92, 233-237.
4. Brix, L. A.; Barnett, A. C.; Duggleby, R. G.; Leggett, B.; McManus, M. E. Analysis of the substrate specificity of human sulfotransferases SULT1A1 and SULT1A3:site-directed mutagenesis and kinetic studies. Biochemistry 1999, 38, 10474-10479.
5. Littlewood, J. T.; Glover, V.; Sandler, M. Red wine contains a potent inhibitor of phenolsulphotransferase. Br. J. Clin. Pharmacol. 1985, 19, 275-278.
6. Anderson, R. J.; Kudlacek, P. E.; Clemens, D. L. Sulfation of minoxidil by multiple human cytosolic sulfotransferases. Chem. Biol. Interact. 1998, 109, 53-67.
7. Weinshiboum, R. M. Phenol sulfotransferase in humans: properties, regulation and function. Fed. Proc. 1986, 45, 2223-2228.
8. Falany, C. N. Molecular enzymology of human liver cytosolic sulfotransferase. Trends Pharmacol. Sci. 1991, 12, 255-259.
9. Cao, G.; Sofic, E.; Prior, R. L. Antioxidant capacity of tea and common vegetables. J. Agric. Food Chem. 1996, 44, 3426- 3431.
10. Bagchi, D.; Hassoum, E.; Bagchi, M.; Stohs, S. Protective effects of antioxidants against Endrin-induced hepatic lipid/peroxidantion, DNA damage and excretion of urinary lipid metabolites. Free Radical Biol. Med. 1993, 15, 217-222.
11. Tanaka, T.; Kojima, T.; Kawamori, T.; Wang, A.; Suzui, M.; Okamoto, K.; Mori, H. Chemoprevention of diethynitro-samine- induced hepatocarcinogenesis by a simple phenolic acid protocatechuic acid in rats. Cancer Res. 1993, 53, 2775-2779.
12. Cao, G.; Alessio, H. M.; Culter, R. G. Oxygen-radical absorbance capacity assay for antioxidants. Free Radical Biol. Med. 1995, 14, 303-311.
13. Miller, N. J.; Rice-Evans, C. A.; Davies, M. J.; Gopinathan, V.; Milner, A. A novel method for measuring antioxidant capacity and its application to monitoring the antioxidant status in premature neonates. Clin. Sci. 1993, 84, 407-412.
14. Bradford, M. M. A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein- dye binding. Anal. Biochem. 1976, 72, 248-254.
15. Foldes, A.; Meek, J. L. Rat brain phenolsulfotransferase - partial purification and some properties. Biochim. Biophys. Acta 1973, 327, 365 -374.
16. Bamforth, K. J.; Jones, A. L.; Roberts, R. C.; Coughtrie, M. W. H. Common food additives are potent inhibitors of human liver 17α-ethinyloestradiol and dopamine sulphotransferases. Biochem. Pharmacol. 1993, 46, 1713-1720.
17. Cao, G.; Sofic, E.; Prior, R. L. Antioxidant and pro-oxidant behavior of flavonoids: structure-activity relationships. Free Radical Biol. Med. 1993, 22, 749-760.
18. Walle, T.; Eaton, E. A.; Walle, U. K. Quercetin, a potent and specific inhibitor of the human P-form phenolsulphotransferase. Biochem. Pharmacol. 1995, 50, 731 -734.
19. D'Aquino, M.; Buillion, C.; Chopra, M.; Devi, D.; Dunster, C.; James, G.; Niki, E.; Willson, R. Sulphydryl (thiyl) free radical formation, biochemically, by sonolysis, by radiolysis, and thermally: vitamin A, curcumin, muconic acid and related conjugated olefins as reference activity models. Methods Enzymol. 1994, 233, 34-36.
20. Aruoma, O. I. Antioxidant action of plant foods: use of oxidative DNA damage as a tool for studying antioxidant efficacy. Free Radical Res. 1999, 30, 419-427.
21. Hermann, M.; Kapiotis, S.; Hofbauer, R.; Seelos, Ch.; Held, I.; Gmeiner, B. Salicylate promotes myeloperoxidase- initiated LDL oxidation: Antagonization by its metabolite gentistic acid. Free Radical Biol. Med. 1999, 26, 1253-1260.
22. Serrano, A.; Palacios, C.; Roy, G.; Cespon, C.; Villar, M. L.; Nocito, M.; Porque, P. G. Derivates of gallic acid induce apoptosis in tumoral cell lines and inhibit lymphocyte proliferation. Arch. Biochem. Biophys. 1998, 350, 49-54.
23. Aejmelaeus, R.; Holm, P.; Kaukinen, U.; Metsä-Ketelä, T. J. A.; Laippala, P.; Hervonen, A. J. L.; Alho, H. R. O. Age-related changes in the peroxyl radical scavenging capacity of human plama. Free Radical Biol. Med. 1997, 23, 69-75.
24. Cao, G.; Verdon, C. P.; Wu, A. H. B.; Wang, H.; Prior, R. L. Automated oxygen radical absorbance capacity assay using the COBAS FARA II. Clin. Chem. 1997, 41, 1738-1744.
25. Kohen, R.; Beit-Yannai, E.; Berry, E. M.; Tirosh, O. Overall low molecular weight antioxidant activity of biological fluids and tissues by cyclic voltammetry. Methods Enzymol. 1999, 300, 285-296.
26. Humphrey, P. P. A.; Fenuik, W.; Perren, M. J.; Beresford, I. J. M.; Skingle, M.; Whalley, E. T. Serotonin and migraine. Ann. N.Y. Acad. Sci. 1990, 600, 587-600.
27. Friberg, L.; Olesen, J.; Iversen, H. K.; Sperling, B. Migraine pain associated with middle cerbral artery dilation: reversal by sumatriptan. Lancet 1991, 338, 13-17.
28. Mine, K.; Okada, M.; Mishima, N.; Fujiwara, M.; Nagakawa, T. Plasma-free and sulfoconjugated MHPG in major depressive disorders: Differences between responders to treatment and nonresponders. Biol. Psychiatry 1993, 34, 654-660.