Enzymatic preparation of silybin phase II metabolites: Sulfation using aryl sulfotransferase from rat liver

Applied Microbiology and Biotechnology

Volumn 97, Issue 24, 2013, Pages 10391-10398

  Purchartová, Katerina ^a,c   Engels, Leonie ^b   Marhol, Petr ^a   Šulc, Miroslav ^a,c   Kuzma, Marek ^a   Slámová, Kristýna ^a   Elling, Lothar ^b   Kren, Vladimír ^a  

^a INSTITUTE OF MICROBIOLOGY   (Czech Republic)

^b RWTH AACHEN UNIVERSITY   (Germany)

^c CHARLES UNIVERSITY   (Czech Republic)

Author keywords

Aryl sulfotransferase; Biotransformation; Diastereoisomers; Rat liver; Silybin; Sulfation

Indexed keywords

ARYL SULFOTRANSFERASE; BIOTRANSFORMATION; DIASTEREOISOMERS; RAT LIVERS; SILYBIN; SULFATION;

ENZYMES; ESCHERICHIA COLI; PURIFICATION; RATS;

FLAVONOIDS;

20 O SILYBIN B SULFATE; ADENOSINE 3',5' DIPHOSPHATE; ARYL SULFOTRANSFERASE; ARYL SULFOTRANSFERASE IV; DRUG METABOLITE; LIVER ENZYME; PHOSPHATE; SILIBININ; SULFATE; UNCLASSIFIED DRUG;

COLIFORM BACTERIUM; ENZYME ACTIVITY; GENE EXPRESSION; METABOLITE; NUCLEAR MAGNETIC RESONANCE;

ANIMAL TISSUE; ARTICLE; BACTERIAL CELL; DIASTEREOISOMER; DRUG CONJUGATION; DRUG DETERMINATION; DRUG ISOLATION; DRUG STRUCTURE; DRUG SULFATION; ENZYME PURIFICATION; ESCHERICHIA COLI; LIVER; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; RAT; SOLID PHASE EXTRACTION; STRUCTURE ANALYSIS;

ESCHERICHIA COLI; MAMMALIA; RATTUS;

ANIMALS; ANTIOXIDANTS; ARYLSULFOTRANSFERASE; ESCHERICHIA COLI; LIVER; RATS; RECOMBINANT PROTEINS; SILYMARIN;

EID: 84892372798     PISSN: 01757598     EISSN: 14320614     Source Type: Journal    
DOI: 10.1007/s00253-013-4794-0     Document Type: Article

References (43)

1. Abourashed EA, Mikell JR, Khan IA (2012) Bioconversion of silybin to phase I and II microbial metabolites with retained antioxidant activity. Bioorg Med Chem 20:2784-2788
2. Agarwal C, Wadhwa R, Deep G, Biedermann D, Gažák R, Kffen V, Agarwal R (2013) Anti-cancer efficacy of silybin derivatives-a structure-activity relationship. PlosOne submitted
3. Baer-Dubowska W, Szaefer H, Krajka-Kuzniak V (1998) Inhibition of murine hepatic cytochrome P450 activities by natural and synthetic phenolic compounds. Xenobiotica 28:735-743
4. Bradford MM (1976) Rapid and sensitive method for quantification of microgram quantities of protein utilizing principle of protein-dye binding. Anal Biochem 72:248-254
5. Burkart MD, Wong CH (1999) A continuous assay for the spectrophotometric analysis of sulfotransferases using aryl sulfotransferase IV. Anal Biochem 274:131-137
6. Coughtrie MW, Sharp S, Maxwell K, Innes NP (1998) Biology and function of the reversible sulfation pathway catalyzed by human sulfotransferases and sulfates. Chem Biol Interact 109:3-27
7. De Groot H, Rauen U (1998) Tissue injury by reactive oxygen species and the protective effects of flavonoids. Fundam Clin Pharmacol 12:249-255
8. Dorai T, Aggarwal BB (2004) Role of chemopreventive agents in cancer therapy. Cancer Lett 215:129-140
9. Fiebrich F, Koch H (1979) Silymarin, an inhibitor of lipoxygenase. Experientia 35:1548-1560
10. Flora K, Hahn M, Rosen H, Benner K (1998) Milk thistle (Silybum marianum) for the therapy of liver diseases. Am J Gastroenterol 93:139-143
11. Fraschini F, Demartini G, Esposti D (2002) Pharmacology of silymarin. Clin Drug Invest 22:51-65
12. Gazák R, Walterová D, Kfen V (2007) Silybin and silymarin-new and emerging applications in medicine. Curr Med Chem 14:315-338
13. Goretti M, Branda E, Turchetti B, Cramarossa MR, Onofri A, Forti L, Buzzini P (2012) Response surface methodology as optimization strategy for asymmetric bioreduction of (4S) - (+)-carvone by Cryptococcus gastricus. Biores Technol 121:290-297
14. Gunaratna C, Zhang T (2003) Application of liquid chromatographyelectrospray ionization-ion trap mass spectrometry to investigate the metabolism of silibinin in human liver microsomes. J Chromatogr B Anal Technol Biomed Life Sci 794:303-310
15. Hahn G, Lehmann HD, Kürten M, Uebel H, Vogel G (1968) Zur Pharmakologie und Toxikologie von Silymarin, des antihepatotoxischen Wirkprinzips aus Silybum marianum (L.) Gaertn. Arzneimittel-Forsch 18:698-704
16. Jančová P, Anzenbacherová E, Papouš ková B, Lemr K, Luzná P, Veinlichová A, Anzenbacher P, Šimánek V (2007) Silybin is metabolized by cytochrome P450 2C8 in vitro. Drug Metab Dispos 35:2035-2039
17. Kauffmann FC, Whittaker M, Anundi I, Thurman RG (1991) Futile cycling of a sulfate conjugate by isolated hepatocytes. Mol Pharmacol 39:414-420
18. Kim N-C, Graf TN, Sparacino CM, Wani MC, Wall ME (2003) Complete isolation and characterization of silybins and isosilybins from milk thistle (Silybum marianum). Org Biomol Chem 1:1684-1689
19. Kfen V, Kubisch J, Sedmera P, Halada P, Pfikrylová V, Jegorov A, Cvak L, Gebhardt R, Ulrichová J, Šimánek V (1997) Glycosylation of silybin. J Chem Soc Perkin Trans 1:2467-2474
20. Kfen V, Ulrichová J, Kosina P, Stevenson D, Sedmera P, Pfikrylová V, Halada P, Šimánek V (2000) Chemoenzymatic preparation of silybin β-glucuronide and their biological evaluation. Drug Metab Dispos 28:1513-1517
21. Laemmli UK (1970) Cleavage of structural proteins during assembly of head of bacteriophage-T4. Nature 227:680-685
22. Lee D Y W, Liu Y (2003) Molecular structure and stereochemistry of silybin A, silybin B, isosilybin A, and isosilybin B, isolated from Silybum marianum (milk thistle). J Nat Prod 66:1171-1174
23. Lee N, Kim EJ, Kim BG (2012) Regioselective hydroxylation of transresveratrol via inhibition of tyrosinase from Streptomyces avermitilis MA4680. ACS Chem Biol 7:1687-1692
24. Mao SH, Hu XJ, Hua BY, Wang N, Liu XG, Lu FP (2012) 5a-Hydroxylation of a steroid (13-ethyl-gon-4-en-3, 17-dione) by Penicillium raistrickii in an ionic liquid/aqueous biphasic system. Biotechnol Lett 34:2113-2117
25. Marhol P, Hartog AF, van der Horst MA, Wever R, Purchartová K, Fuksová K, Kuzma M, Cvačka J, Kfen V (2013) Preparation of silybin and isosilybin sulfates by sulfotransferase from Desulfitobacterium hafniense. J Mol Catal B Enzymat 89:24-27
26. Miranda SR, Lee JK, Brouwer K L R, Wen ZM, Smith PC, Hawke RL (2008) Hepatic metabolism and biliary excretion of silymarin flavonolignans in isolated perfused rat livers: role of multidrug resistance-associated protein 2 (Abcc2). Drug Metab Dispos 36:2219-2226
27. Morazzoni P, Bombardelli E (1995) Silybum marianum (Carduus marianus). Fitoterapia 66:3-42
28. Neunzig I, Widjaja M, Dragan CA, Peters FT, Maurer HH, Bureik M (2012) Engineering of human CYP3A enzymes by combination of activating polymorphic variants. Appl Biochem Biotechnol 168:785-796
29. Pietrangelo A, Borella F, Casalgrandi G (1995) Antioxidant activity of silybin in vivo during long-term iron overload in rats. Gastroenterology 109:1941-1949
30. Schriewer H, Badde R, Roth G, Raven HM (1973) Antihepatotoxic effect of silymarin in thioacetamide-damaged liver. Arzneimittel-Forsch 23:160-161
31. Sekura RD, Jakoby WB (1981) Aryl sulfotransferase-IV from rat liver. Arch Biochem Biophys 211:352-359
32. Šimánek V, Kfen V, Ulrichová J, Vičar J, Cvak L (2000) "What is in the name...?" An appeal for a change of editorial policy. Hepatology 32:442-444
33. Strott CA (2002) Sulfonation and molecular action. Endocrin Rev 23:703-732
34. Tan E, Pang KS (2001) Sulfation is rate limiting in the futile cycling between estrone and estrone sulfate in enriched periportal and perivenous rat hepatocytes. Drug Metab Dispos 29:335-346
35. Vogel G, Tuchweber B, Trost W, Mengs U (1984) Protection by silibinin against Amanita phalloides intoxication in beagles. Toxicol Appl Pharmacol 73:355-362
36. Wagner H, Hörhammer L, Münster R (1968) Zur Chemie des Silymarins (Silybin), des Wirkprinzips der Früchte von Silybum marianum (L.) Gaertn. (Cardus marianus L.). Arzneimittel-Forsch 18:688-695
37. Wang LQ, James MO (2006) Inhibition of sulfotransferases by xenobiotics. Curr Drug Metab 7:83-104
38. Weyhenmeyer R, Mascher H, Birkmayer J (1992) Study on doselinearity of the pharmacokinetics of silibinin diastereomers using a new stereospecific assay. Int J Clin Pharmacol Ther Toxic 30:134-138
39. Wieland T, Faulstich H (1978) Amatoxins, phallotoxins, phallolysin, and antamanide: the biologically active components of poisonous Amanita mushrooms. CRC Crit Rev Biochem 78:185-260
40. Wieland T (1972) Struktur und Wirkung der Amatoxine. Naturwissen schaften 59:225-231
41. Wu JW, Lin LC, Hung SC, Chi CW, Tsai TH (2007) Analysis of silibinin in rat plasma and bile for hepatobiliary excretion and oral bioavailability application. J Pharm Biomed Anal 45:635-641
42. Yang YS, Marshall DA, McPhie P, Guo W X A, Xie XF, Chen X, Jakoby WB (1996) Two phenol sulfotransferase species from one cDNA: nature of the differences. Protein Expr Purif 8:423-429
43. Zarelli A, Sgambato A, Petito V, De Napoli L, Previtera L, Di Fabio G (2011) New C-23 modified of silybin and 2, 3-dehydrosilybin: synthesis and preliminary evaluation of antioxidant properties. Bioorg Med Chem Lett 21:4389-4392