Bulletin of the Korean Chemical Society

  • 제30권7호
  • /
  • Pages.1489-1496
  • /
  • 2009
  • /
  • 0253-2964(pISSN)
  • /
  • 1229-5949(eISSN)
대한화학회 (Korean Chemical Society)
권호 표지
DOI QR코드

DOI QR Code

Determination of Adrenosterone and its Metabolites in Human Urine by LC/APCI/MS and GC/MS

  • 발행 : 2009.07.20
PDF 다운로드
⟨ 이전 논문 다음 논문 ⟩

초록

This study was done for the determination and excretion profile of adrenosterone and its metabolites in human urine using both liquid chromatography with atmospheric pressure chemical ionization mass spectrometry and gas chromatography with mass spectrometry. Adrenosterone and its two metabolites were detected in human urine after administration a healthy volunteer with 75 mg of adrenosterone. We found that adrenosterone-M1 ($C_{19}H_{26}O_3$) was a reduction and adrenosterone-M2 ($C_{19}H_{26}O_4$) was a hydroxylation at C-ring, which did not know the exact position of the C-ring. The adrenosterone parent was detected by GC/TOF-MS, but not detected by LC/APCI/MS because of low intensity. Adrenosterone and its two metabolites were excreted as their glucuronided fractions. The recovery of this method ranged from 100.7 to 118.4% and the reproducibility and accuracy test were 85.5 to 112.0% and 1.1 to 8.4%, respectively. The excretion studies showed that adrenosterone and its metabolites were detectable in human urine during a 48 h period after oral administration, with maximum level of excretion at 4.1 h. The glucuro-/sulfaconjugated ratio of adrenosterone, M1 and M2 was 0.73 ${\pm}$ 0.03, 0.96 ${\pm}$ 0.06 and 0.89 ${\pm}$ 0.03 (n = 6), respectively. The amounts of adrenosterone excreted in urine were 14.75 ng for 48 h. Also, the maximum level of androsterone and 11$\beta$-hydroxy androsterone, which were endogenous steroids, were reached 4.1 h after the oral administration of adrenosterone.

키워드

참고문헌

  1. Nasrollah, T.; Shahidi, M. D. Clin. Ther. 2001, 23, 1355 https://doi.org/10.1016/S0149-2918(01)80114-4
  2. Kintz, P. Legal Med. 2003, 5, S29 https://doi.org/10.1016/S1344-6223(02)00085-8
  3. Cellotti, F.; Negri Cesi, P.; Steroid Biochem. Mol. Biol. 1992, 43, 469 https://doi.org/10.1016/0960-0760(92)90085-W
  4. Maravelias, C.; Dona, A.; Stefanidou, M.; Spiliopoulou, G. Toxicol Lett. 2005, 158, 167 https://doi.org/10.1016/j.toxlet.2005.06.005
  5. Delbeke, F. T.; Van Eenoo, P.; Van Thuyne, W. J. Steroid Biochem. Mol. Biol. 2003, 83, 245
  6. WADA, The World Anti-Doping Agency, Prohibited list of substances, 2005
  7. Reichstein, T. Helv. Chim. Acta 1936, 19, 29 https://doi.org/10.1002/hlca.19360190108
  8. Gavaco, J. E. B.; Van Blijswijk, B.; Leatherland, J. F.; Goos, H. J. T.; Schulz, R.W. Cell Tissue Res. 1999, 38, 2834
  9. Thevis, M.; Opfermann, G.; Schmickler, H.;Schӓnzer, W. J. Mass Spectrom. 2001, 36,159 https://doi.org/10.1002/jms.117
  10. Lone, K. P.; Matty, A. J. J. Fish Biol. 1981, 18, 353 https://doi.org/10.1111/j.1095-8649.1981.tb03777.x
  11. Yoshihama, M.; Tamura, K.; Nakakoshi, M.; Nakamura, J.; Fujise, N.; Kawanishi, G. J. Mass Spectrom. 2001, 36, 159 https://doi.org/10.1002/jms.117
  12. Delahaut, Ph.; Jacquemin, P.; Colemonts, Y.; Dubois, M.; De Graeve, J.; Deluyker, H. J. Chromatogr. B 1997, 696, 203 https://doi.org/10.1016/S0378-4347(97)00222-3
  13. Palermo, M.; Gomez-Sanchez, C.; Roitman, E.; Shacklenton, C. H. Steroids 1996, 61, 583. https://doi.org/10.1016/S0039-128X(96)00118-9
  14. Kohler, K.; Parr, M. K.; Opfermann, G.; Thevis, M.; Schlorer, N.; Marner, F. J.; Schӓnzer, W. Steroids 2007, 72, 278 https://doi.org/10.1016/j.steroids.2006.11.018
  15. Van Puymbroeck, M.; Leyssens, L.; Vanderzande, D.; Gelan, J.; Raus, J. Analyst 1998, 123, 2449 https://doi.org/10.1039/a805009k
  16. Raffaelli, A.; Saba, A.; Vignali, E.; Marcocci, C.; Alvadori, P. J. Chromatogr. B 2006, 830, 278 https://doi.org/10.1016/j.jchromb.2005.11.011
  17. Deventer, K.; Van Eenoo, P.; Mikulcikova, P.; Van Thuyne, W.; Delbeke, F. T. J. Chromatogr. B 2005, 828, 21 https://doi.org/10.1016/j.jchromb.2005.08.024
  18. Mckinney, A. R.; Suann, C. J.; Dunstan, A. J.; Mulley, S. L.; Ridley, D. D.; Stenhouse, A. M. J. Chromatogr. B 2004, 811, 75 https://doi.org/10.1016/S1570-0232(04)00634-8
  19. Tubaro, M.; Fedrigo, M. A.; Cativiela, C.; Jimenez, A. L.; Traldi, P. Rapid Commun. Mass Spectrom. 2003, 17, 107 https://doi.org/10.1002/rcm.879
  20. Schanzer, W.; Donike, M. Anal. Chim. Acta 1993, 275, 23 https://doi.org/10.1016/0003-2670(93)80274-O
  21. Hintikka, L.; Kuuranne, T.; Aitio, O.; Thevis, M.; Schӓnzer, W.; Kosstiainen, R. Steroids 2008, 73, 257 https://doi.org/10.1016/j.steroids.2007.10.008
  22. Bizec, B. L.; Courant, F.; Gaudin, I.; Bichon, E.; Destres, B.; Schilt, R.; Draisci, R.; Monteau, F.; Andre, F. Steroids 2006, 71, 1078 https://doi.org/10.1016/j.steroids.2006.09.009
  23. Parr, M.; Zapp, J.; Becker, M.; Opfermann, G.; Bartz, U.; Schӓnzer, W. Steroids 2007, 72, 545 https://doi.org/10.1016/j.steroids.2007.03.006
  24. Torrado, S.; Segura, J.; Farre, M.; Ventura, R. Steroids 2008, 73, 751 https://doi.org/10.1016/j.steroids.2008.02.012
  25. Deventer, K.; Van Eenoo, P.; Mikulčíková, P.; Van Thuyne, W.; Delbeke, F. T. J. Chromatogr. B 2005, 828, 21 https://doi.org/10.1016/j.jchromb.2005.08.024
  26. Buiarelli, F.; Cartoni, G. P.; Coccioli, F.; Giannetti, L.; Merolle, M.; Terracciano, A. Anal. Chim. Acta 2005, 552, 116 https://doi.org/10.1016/j.aca.2005.06.071
  27. Lee, S. H.; Choi, M. H.; Kim, K.; Chung, B. C. J. Kor. Chem. Soc. 1997, 41, 406
  28. Norli, M. R.; Esbensen, F.; Westad, K.; Birkeland, I.; Hemmnnersbach, P. J. Steroid Biochem. Molec. Biol. 1995, 54, 83 https://doi.org/10.1016/0960-0760(95)00114-F
  29. Donike, M.; Geyer, H.; Kraft, M.; Rauth, S. International Athletic Foundation; 1990; p 107

피인용 문헌

  1. Metabolism of anabolic steroids and their relevance to drug detection in horseracing vol.2, pp.6, 2010, https://doi.org/10.4155/bio.10.57
  2. Highly sensitive and selective analysis of urinary steroids by comprehensive two-dimensional gas chromatography combined with positive chemical ionization quadrupole mass spectrometry vol.137, pp.13, 2012, https://doi.org/10.1039/c2an35087d
  3. Current literature in mass spectrometry vol.45, pp.1, 2010, https://doi.org/10.1002/jms.1643
  4. Feasibility of gas chromatography-microchip atmospheric pressure photoionization-mass spectrometry in analysis of anabolic steroids vol.1217, pp.52, 2009, https://doi.org/10.1016/j.chroma.2010.10.074
  5. A Validated TLC-Densitometric Method for the Determination of Mesterolone in Bulk Material and in Tablets vol.2015, pp.None, 2009, https://doi.org/10.1155/2015/230104