Metabolism of the 16-androstene steroids in primary cultured porcine hepatocytes

Journal of Steroid Biochemistry and Molecular Biology

Volumn 96, Issue 1, 2005, Pages 79-87

  Sinclair, P A ^a   Hancock, S ^a   Gilmore, W J ^a   Squires, E J ^a  

^a UNIVERSITY OF GUELPH   (Canada)

Author keywords

Androstenone; Glucuronyltransferase; Porcine hepatocytes; Sulfotransferase

Indexed keywords

ANDROSTANE DERIVATIVE;

ANIMAL CELL; ARTICLE; CONTROLLED STUDY; HYDROXYLATION; LIVER; LIVER CELL; NONHUMAN; SOLID PHASE EXTRACTION; STEROID BINDING;

ANDROSTENES; ANIMALS; CELLS, CULTURED; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; HEPATOCYTES; KINETICS; SWINE;

SUIDAE;

EID: 23144440211     PISSN: 09600760     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jsbmb.2005.01.030     Document Type: Article

References (56)

1. W.D. Booth Changes with age in the occurrence of C19 steroids in the testis and submaxillary gland of the boar J. Reprod. Fertil. 42 3 1975 459 472
2. W.D. Booth, and C. Polge The occurrence of C19 steroids in testicular tissue and submaxillary glands of intersex pigs in relation to morphological characteristics J. Reprod. Fertil. 46 1 1976 115 121
3. D.B. Gower 16-Unsaturated C 19 steroids. A review of their chemistry, biochemistry and possible physiological role J. Steroid Biochem. 3 1 1972 45 103
4. R.L.S. Patterson 5a-Androst-16-ene-3-one: compound responsible for taint in boar fat J. Sci. Food Agric. 19 1968 31 41
5. F.J. Gasparini, R.B. Hochberg, and S. Lieberman Biosynthesis of steroid sulfates by the boar testes Biochemistry 15 18 1976 3969 3975
6. H.S. Tan, and J.I. Raeside Developmental patterns of plasma dehydroepiandrosterone sulfate and testosterone in male pigs Anim. Reprod. Sci. 3 1980 73 81
7. P.A. Sinclair, and E.J. Squires Testicular sulfoconjugation of the 16-androstene steroids by hydroxysteroid sulfotransferase: Its effect on the concentrations of 5α-androstenone in plasma and fat of the mature domestic boar J. Anim. Sci. 83 2 2005 358 365
8. J.I. Raeside, and R.L. Renaud Estrogen and androgen production by purified Leydig cells of mature boars Biol. Reprod. 28 3 1983 727 733
9. R. Hobkirk Steroid sulfotransferases and steroid sulfate sulfatases: characteristics and biological roles Can. J. Biochem. Cell Biol. 63 11 1985 1127 1144
10. R. Hobkirk, R. Renaud, and J.I. Raeside Partial characterization of steroid sulfohydrolase and steroid sulfotransferase activities in purified porcine Leydig cells J. Steroid Biochem. 32 3 1989 387 392
11. K.D. Roberts, and S. Lieberman The biochemistry of the 3b-hydroxy-dela-5 steroid sulftes S. Bernstein S. Solomon Chemical and Biological Aspects of Steroid Conjugation 1970 Springer-Verlag New York 291 320
12. J. Babol, E.J. Squires, and K. Lundstrom Relationship between metabolism of androstenone and skatole in intact male pigs J. Anim. Sci. 77 1 1999 84 92
13. J.I. Mason, D.S. Keeney, I.M. Bird, W.E. Rainey, K. Morohashi, S. Leers-Sucheta, and M.H. Melner The regulation of 3 beta-hydroxysteroid dehydrogenase expression Steroids 62 1 1997 164 168
14. T.M. Penning, M.J. Bennett, S. Smith-Hoog, B.P. Schlegel, J.M. Jez, and M. Lewis Structure and function of 3 alpha-hydroxysteroid dehydrogenase Steroids 62 1 1997 101 111
15. E.C. Pirog, and D.C. Collins Metabolism of dihydrotestosterone in human liver: importance of 3alpha- and 3beta-hydroxysteroid dehydrogenase J. Clin. Endocrinol. Metab. 84 9 1999 3217 3221
16. D.B. Gower, and R.L. Patterson Identification of C19-16-unsaturated steroids in boar urine and spermatic vein plasma by combined gas chromatography and mass spectrometry J. Endocrinol. 47 3 1970 365 368
17. D.B. Gower, F.A. Harrison, and R.B. Heap The identification of C19-16-unsaturated steroids and estimation of 17-oxosteroids in boar spermativ vein plasma and urine J. Endocrinol. 47 3 1970 357 365
18. D. Turgeon, J.S. Carrier, E. Levesque, D.W. Hum, and A. Belanger Relative enzymatic activity, protein stability, and tissue distribution of human steroid-metabolizing UGT2B subfamily members Endocrinology 142 2 2001 778 787
19. P.I. Mackenzie, L. Rodbourne, and S. Stranks Steroid UDP glucuronosyltransferases J. Steroid Biochem. Mol. Biol. 43 1992 1105
20. D.W. Hum, A. Belanger, E. Levesque, O. Barbier, M. Beaulieu, C. Albert, M. Vallee, C. Guillemette, A. Tchernof, D. Turgeon, and S. Dubois Characterization of UDP-glucuronosyltransferases active on steroid hormones J. Steroid Biochem. Mol. Biol. 69 1-6 1999 413 423
21. H. Sato, O. Koiwai, K. Tanabe, and S. Kashiwamata Isolation and sequencing of rat liver bilirubin UDP-glucuronosyltransferase cDNA: possible alternate splicing of a common primary transcript Biochem. Biophys. Res. Commun. 169 1 1990 260 264
22. P.I. Mackenzie, B. Mojarrabi, R. Meech, and A. Hansen Steroid UDP glucuronosyltransferases: characterization and regulation J. Endocrinol. 150 Suppl. 1996 S79 S86
23. P.I. Mackenzie, I.S. Owens, B. Burchell, K.W. Bock, A. Bairoch, A. Belanger, S. Fournel-Gigleux, M. Green, D.W. Hum, T. Iyanagi, D. Lancet, P. Louisot, J. Magdalou, J.R. Chowdhury, J.K. Ritter, H. Schachter, T.R. Tephly, K.F. Tipton, and D.W. Nebert The UDP glycosyltransferase gene superfamily: recommended nomenclature update based on evolutionary divergence Pharmacogenetics 7 4 1997 255 269
24. H.J. Makin, and D. Turgeon The chemistry of the steroids Clin. Endocr. Metab. 1 1972 333 364
25. D.W. Nebert Drug-metabolizing enzymes in ligand-modulated transcription Biochem. Pharmacol. 47 1 1994 25 37
26. J.I. Raeside, H.L. Christie, and R.L. Renaud Androgen and estrogen metabolism in the reproductive tract and accessory sex glands of the domestic boar (Sus scrofa) Biol. Reprod. 61 5 1999 1242 1248
27. P.A. Sinclair, E.J. Squires, J.I. Raeside, J.H. Britt, and V.G. Hedgpeth The effect of early postnatal treatment with a gonadotropin-releasing hormone agonist on the developmental profiles of testicular steroid hormones in the intact male pig J. Anim. Sci. 79 4 2001 1003 1010
28. P.A. Sinclair, E.J. Squires, and J.I. Raeside Early postnatal plasma concentrations of testicular steroid hormones, pubertal development, and carcass leanness as potential indicators of boar taint in market weight intact male pigs J. Anim. Sci. 79 7 2001 1868 1876
29. W.J. Gilmore, and G.M. Kirby Endoplasmic reticulum stress due to altered cellular redox status positively regulates murine hepatic CYP2A5 expression J. Pharmacol. Exp. Ther. 308 2 2004 600 608
30. M. Matsui, M. Takahashi, and H. Homma Inhibition of rat liver hydroxysteroid sulfotransferase activity by alkylamines Biochem. Pharmacol. 46 3 1993 465 470
31. J.I. Raeside, R.L. Renaud, and H.L. Christie Postnatal decline in gonadal secretion of dehydroepiandrosterone and 3 beta-hydroxyandrosta-5,7-dien-17-one in the newborn foal J. Endocrinol. 155 2 1997 277 282
32. J.I. Raeside, H.L. Christie, and R.L. Renaud Metabolism of oestrone and oestradiol-17beta to conjugated steroids by the accessory sex glands of the male pig J. Endocrinol. 163 1 1999 49 53
33. M.W. Khalil, and V. Lawson Steroids in porcine follicular fluid: analysis by HPLC, capillary CG and capillary CG/MS after purification on SEP-PAK C18 and ion exchange chromatography Steroids 41 4 1983 549 566
34. M.W. Khalil, B. Strutt, D. Vachon, and D.W. Killinger Metabolism of dehydroepiandrosterone by cultured human adipose stromal cells: identification of 7 alpha-hydroxydehydroepiandrosterone as a major metabolite using high performance liquid chromatography and mass spectrometry J. Steroid Biochem. Mol. Biol. 46 5 1993 585 595
35. T.K. Kwan, M.A. Kraevskaya, H.L. Makin, D.J. Trafford, and D.B. Gower Use of gas chromatographic-mass spectrometric techniques in studies of androst-16-ene and androgen biosynthesis in human testis; cytosolic specific binding of 5alpha-androst-16-en-3-one J. Steroid Biochem. Mol. Biol. 60 1-2 1997 137 146
36. T.K. Kwan, D.B. Gower, D.J. Trafford, and H.J. Makin Gas chromatographic/mass spectrometric characteristics of 16-androstenes, saturated analogues and their derivatives Biol. Mass Spectrom. 21 1992 160 164
37. P.A. Sinclair, E.J. Squires, J.I. Raeside, R. Renaud, Synthesis of free and sulphoconjugated 16-androstene steroids by the Leydig cells of the mature domestic boar, J. Steroid Biochem. Mol. Biol. 96 (2) (2005), in press.
38. D.S. Keeney, D. Naville, L. Milewich, A. Bartke, and J.I. Mason Multiple isoforms of 3 beta-hydroxysteroid dehydrogenase/delta 5 → 4-isomerase in mouse tissues: male-specific isoforms are expressed in the gonads and liver Endocrinology 133 1 1993 39 45
39. W.L. Miller Molecular biology of steroid hormone synthesis Endocr. Rev. 9 3 1988 295 318
40. D.W. Russell, and J.D. Wilson Steroid 5 alpha-reductase: two genes/two enzymes Annu. Rev. Biochem. 63 1994 25 61
41. Y. Jin, and T.M. Penning Steroid 5alpha-reductases and 3alpha-hydroxysteroid dehydrogenases: key enzymes in androgen metabolism Best Pract. Res. Clin. Endocrinol. Metab. 15 1 2001 79 94
42. G.M. Cooke, F. Pothier, and B.D. Murphy The effects of progesterone, 4,16-androstadien-3-one and MK-434 on the kinetics of pig testis microsomal testosterone-4-ene-5alpha-reductase activity J. Steroid Biochem. Mol. Biol. 60 5-6 1997 353 359
43. D.B. Gower Steroid catabolism and urinary excretion H.J. Makin The Biochemistry of Steroid Hormones 1984 Blackwell Scientific Publications Oxford 349 408
44. P.D. Josephy Cytochrome P-450 P.D. Josephy B. Mannervik P. Ortiz DeMontellano Molecular Toxicology 1997 Oxford University Press New York 209 252
45. C.P. Martucci, and J. Fishman P450 enzymes of estrogen metabolism Pharmacol. Ther. 57 2-3 1993 237 257
46. C. Austin, and J. Ellis Microbial pathways leading to steroidal malodour in the axilla J. Steroid Biochem. Mol. Biol. 87 1 2003 105 110
47. D. Kouretas, S. Voyatzi, D. Sahpazidou, K. Lazopoulos, and O. Antonoglou Enzymatic conversion of dihydrotestosterone from 3-keto to 3-enol form in the rat prostate Anticancer Res. 16 5A 1996 2843 2848
48. Z. Drmanovic, S. Voyatzi, D. Kouretas, D. Sahpazidou, A. Papageorgiou, and O. Antonoglou Albumin possesses intrinsic enolase activity towards dihydrotestosterone which can differentiate benign from malignant breast tumors Anticancer Res. 19 5B 1999 4113 4124
49. Z. Duanmu, D. Locke, J. Smigelski, W. Wu, M.S. Dahn, C.N. Falany, T.A. Kocarek, and M. Runge-Morris Effects of dexamethasone on aryl (SULT1A1)- and hydroxysteroid (SULT2A1)-sulfotransferase gene expression in primary cultured human hepatocytes Drug Metab. Dispos. 30 9 2002 997 1004
50. L. Liu, E.L. LeCluyse, J. Liu, and C.D. Klaassen Sulfotransferase gene expression in primary cultures of rat hepatocytes Biochem. Pharmacol. 52 10 1996 1621 1630
51. S. Sharp, E.V. Barker, M.W. Coughtrie, P.R. Lowenstein, and R. Hume Immunochemical characterisation of a dehydroepiandrosterone sulfotransferase in rats and humans Eur. J. Biochem. 211 3 1993 539 548
52. C.N. Falany, M.E. Vazquez, and J.M. Kalb Purification and characterization of human liver dehydroepiandrosterone sulphotransferase Biochem. J. 260 3 1989 641 646
53. S.A. Strott Steroid sulfotranferases Endocr. Rev. 17 6 1996 670 697
54. A. Belanger, D.W. Hum, M. Beaulieu, E. Levesque, C. Guillemette, A. Tchernof, G. Belanger, D. Turgeon, and S. Dubois Characterization and regulation of UDP-glucuronosyltransferases in steroid target tissues J. Steroid Biochem. Mol. Biol. 65 1-6 1998 301 310
55. D.G. Munroe, and P.L. Chang Tissue-specific expression of human arylsulfatase-C isozymes and steroid sulfatase Am. J. Hum. Genet. 40 2 1987 102 114
56. H.L. Bradlow The hydrolysis of steroid conjugates S. Bernstein S. Solomon Chemical and Biological Aspects of Steroid Conjugation 1970 Springer-Verlag New York 131 181