The identification of novel steroid N-acetylglucosaminides in the urine of pregnant women

Journal of Steroid Biochemistry and Molecular Biology

Volumn 58, Issue 5-6, 1996, Pages 585-598

  Meng, L J ^a   Griffiths, W J ^a   Sjovall J ^a  

^a KAROLINSKA INSTITUTE   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

N ACETYLGLUCOSAMINE; PREGNANEDIOL; PREGNANETRIOL; PROGESTERONE;

ARTICLE; CHEMISTRY; CHROMATOGRAPHY; FEMALE; HUMAN; ISOLATION AND PURIFICATION; METABOLISM; PREGNANCY; URINE;

ACETYLGLUCOSAMINE; CHROMATOGRAPHY; FEMALE; HUMANS; PREGNANCY; PREGNANEDIOL; PREGNANETRIOL; PROGESTERONE;

EID: 0030203363     PISSN: 09600760     EISSN: None     Source Type: Journal    
DOI: 10.1016/0960-0760(96)00080-5     Document Type: Article

References (32)

1. Layne D. S.: New metabolic conjugates of steroids. In Metabolic Conjugation and Metabolic Hydrolysis (Edited by J. Fishman). Academic Press, New York, Vol. 1 (1970) pp. 21-52.
2. Musey P. I., Wright K., Preedy J. R. K. and Collins D.C.: Formation and metabolism of steroid conjugates: effect of conjugation on excretion and tissue distribution. In Steroid Biochemistry (Edited by R. Hobkirk). CRC Press, Boca Raton, Vol. II (1979) pp. 82-131.
3. Arcos M. and Lieberman S.: 5-Pregnene-3β,20α-diol-3-sulfate-20-(2′-acetamido-2′- deoxy-α-D-glucoside) and 5-pregnene-3β,20α-diol-3,20-disulfate. Two novel urinary conjugates. Biochemistry 6 (1967) 2032-2039.
4. Matsui M. and Fukushima D. K.: On the configuration of naturally occurring steroid N-acetylglucosaminides. Biochemistry 8 (1969) 2997-3000.
5. Marschall H.-U., Egestad B., Matern H., Matern S. and Sjövall J.: N-Acetylglucosaminides: a new type of bile acid conjugate in man. J. Biol. Chem. 264 (1989) 12989-12993.
6. Marschall H.-U., Matern H., Wietholtz H., Egestad B., Matern S. and Sjövall J.: Bile acid N-acetylglucosaminidation. In vivo and in vitro evidence for a selective conjugation reaction of 7β-hydroxylated bile acids in humans. J. Clin. Invest. 89 (1992) 1981-1987.
7. Marschall H.-U., Griffiths W. J., Zhang J., Wietholtz H., Matern H., Matern S. and Sjövall J.: Position of conjugation of bile acids with glucose and N-acetylglucosamine in vitro. J. Lipid Res. 35 (1995) 1599-1610.
8. Anderson R. A., Baillie T. A., Axelson M., Cronholm T., Sjövall K. and Sjövall J.: Stable isotope studies on steroid metabolism and kinetics: sulfates of 3α-hydroxy-5α-pregnane derivatives in human pregnancy. Steroids 55 (1990) 443-457.
9. Sjövall J. and Axelson M.: Newer approaches to the isolation, identification, and quantitation of steroids in biological materials. Vitam. Horm. 39 (1982) 31-144.
10. Baillie T. A., Curstedt T., Sjövall K. and Sjövall J.: Production rates and metabolism of sulphates of 3β-hydroxy-5α-pregnane derivatives in pregnant women. J. Steroid Biochem. 13 (1980) 1473-1488.
11. Mumma R. O., Hoiberg C. P. and Weber II W. W.: Preparation of sulfate esters. The synthesis of steroids sulfates by a dicyclohexylcarbodiimide-mediated sulfation. Steroids 14 (1969) 67-73.
12. Carlström K. and Sköldefors H.: Determination of total oestrone in peripheral serum from non-pregnant humans. J. Steroid Biochem. 8 (1977) 1127-1128.
13. Axelson M., Sahlberg B.-L. and Sjövall J.: Analysis of profiles of conjugated steroids in urine by ion-exchange separation and gas chromatography-mass spectrometry. J. Chromatogr. Biomed. Appl. 244 (1981) 355-370.
14. Bremmelgaard A. and Sjövall J.: Hydroxylation of cholic, chenodeoxycholic, and deoxycholic acids in patients with intrahepatic cholestasis. J. Lipid Res. 21 (1980) 1072-1081.
15. Hirano Y., Miyazaki H., Higashidate S. and Nakayama F.: Analysis of 3-sulfated and non-sulfated bile acids by one-step solvolysis and high performance liquid chromatography. J. Lipid Res. 28 (1987) 1524-1529.
16. 27-steroid dehydrogenase deficiency: effects of chenodeoxycholic acid treatment. J. Lipid. Res. 32 (1991) 829-841.
17. Tomer K. B., Jensen N. J. and Gross M. L.: Fast atom bombardment and tandem mass spectrometry for determining structural modification of fatty acids. Analyt. Chem. 58 (1986) 2429-2433.
18. Adams J.: Charge-remote fragmentation: analytical applications and fundamental studies. Mass Spectrom. Rev. 9 (1990) 141-186.
19. Gross M. L.: Charge-remote fragmentation: method, mechanism and applications. Int. J. Mass Spectrom. Ion Processes 118 (1992) 137-165.
20. Tomer K. B. and Gross M. L.: Fast atom bombardment and tandem mass spectrometry for structure determination: remote site fragmentation of steroid conjugates and bile salts. Org. Mass Spectrom. 15 (1988) 89-98.
21. Griffiths W. J., Zhang J. and Sjövall J.: Charge-remote fragmentation of bile acids derivatized with amino-sulphonic acids. Rapid Commun. Mass Spectrom. 7 (1993) 235-240.
22. Li S.-C. and Li Y.-T.: Studies on the glycosidases of jack bean meal. 3. Crystallization and properties of beta-N-acetyl-hexosaminidase. J. Biol. Chem. 245 (1970) 5153-5160.
23. DeJongh D. C., Radford T., Hribar J. D., Hanessian S., Bieber M., Dawson G. and Sweeley C. C.: Analysis of trimethylsilyl derivatives of carbohydrates by gas chromatography and mass spectrometry. J. Am. Chem. Soc. 91 (1969) 1728-1740.
24. Coduti P. L. and Bush C. A.: Structure determination of N-acetyl amino sugar derivatives and disaccharides by gas chromatography and mass spectroscopy. Analyt. Biochem. 78 (1977) 21-38.
25. Baillie T. A., Eriksson H., Herz J. E. and Sjövall J.: Specific deuterium labelling and computerized gas chromatography-mass spectrometry in studies on the metabolism in vivo of a steroid sulphate in the rat. Eur. J. Biochem. 55 (1975) 157-165.
26. Axelson M. and Sahlberg B.-L.: Group separation and gas chromatography-mass spectrometry of conjugated steroids in plasma. J. Steroid Biochem. 18 (1983) 313-321.
27. 35S in a woman. J. Clin. Endocr. Metab. 29 (1969) 615-637.
28. Cable R. G., Jirku H. and Levitz M.: Transfer of N-acetylglucosamine from undine diphosphate N-acetylglucosamine to 3,15α-dihydroxyestra-1,3,5(10)-trien-17-one by human adult and fetal kidney homogenate. Biochemistry 9 (1970) 4587-4593.
29. Matern H., Bolz R., Marschall H.-U., Sjövall J. and Matern S.: Bile acid N-acetylglucosaminides. Formation by microsomal N-acetylglucosaminyltransferases in human liver and kidney. FEBS Lett. 270 (1990) 11-14.
30. Solomon S. and Fuchs F.: Progesterone and related neutral steroids. In Endocrinology of Pregnancy (Edited by F. Fuchs and A. Klopper). Harper and Row, New York (1971) pp. 66-100.
31. 21 steroids in faeces from pregnant women. Eur. J. Biochem. 12 (1970) 520-526.
32. Martin F., Peltonen J., Laatikainen T., Pulkkinen M. and Adlercreutz H.: Excretion of progesterone metabolites and estriol in faeces from pregnant women during ampicillin administration. J. Steroid Biochem. 6 (1975) 1339-1346.