Transformation of steroids by Bacillus strains isolated from the foregut of water beetles (Coleoptera:Dytiscidae): I. Metabolism of androst-4-en- 3,17-dione (AD)

Journal of Steroid Biochemistry and Molecular Biology

Volumn 67, Issue 5-6, 1998, Pages 451-465

  Schaaf, O ^a   Dettner, K ^a  

^a UNIVERSITY OF BAYREUTH   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

5ALPHA ANDROSTANE DERIVATIVE; ANDROSTENEDIONE; ANDROSTENEDIONE DERIVATIVE; OXOSTEROID; TRIMETHYLSILYL DERIVATIVE;

ARTICLE; BACILLUS; BEETLE; HYDROXYLATION; INTESTINE; MASS SPECTROMETRY; NONHUMAN; OXIDATION; REDUCTION; STEROID METABOLISM;

ANDROSTANES; ANDROSTENEDIONE; ANIMALS; BACILLUS; BEETLES; BIOTRANSFORMATION; CHROMATOGRAPHY, GAS; DIGESTIVE SYSTEM; HYDROXYSTEROIDS; INDICATORS AND REAGENTS; MOLECULAR STRUCTURE;

EID: 0032448469     PISSN: 09600760     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-0760(98)00137-X     Document Type: Article

References (44)

1. 1. Schildknecht H., Das Arsenal der Schwimmkäfer: Sexualhormone und "Antibiotica". Nachr. Chem. Techn. 16 (1968) 311-312.
2. 2. Dettner K., Ecological and phylogenetic significance of defensive compounds from pygidial glands of Hydradephaga (Coleoptera). Proc. Acad. Natl. Sci. Phil 137 (1985) 156-171.
3. 3. Blum, M. S., Chemical Defenses of Arthropods. Academic Press, New York, 1981.
4. 4. Swevers L., Lambert J. G. D. and De Loof A., Synthesis and metabolism of vertebrate-type steroids by tissues of insects: a critical evaluation. Experientia 47 (1991) 687-698.
5. 5. Svoboda J, A., Kaplanis J. N., Robbins W. E. and Thompson M. J., Recent developments in insect steroid metabolism. A. Rev. Entomol. 20 (1975) 205-220.
6. 6. Chapman J. C., Lockley W. J. S., Rees H. H. and Goodwin Tr.W., Stereochemistry of olefinic bond formation in defensive steroids of Acilius sulcatus (Dytiscidae). Eur. J. Biochem. 81 (1977) 293-298.
7. 7. Joshi M. and Agarwal H. C., Site of cholesterol absorption in some insects. J. Insect Physiol. 23 (1977) 403-404.
8. 8. Schaaf O. and Dettner K., Microbial diversity of aerobic heterotrophic bacteria inside the foregut of two tyrphophilous water beetle species (Coleoptera:Dytiscidae). Microbiol. Res. 152 (1997) 57-64.
9. 9. Horning M. G., Moss A. M. and Horning E. C., Formation and gas-liquid Chromatographic behavior of isometric steroid ketone methoxime derivatives. Anal. Biochem. 22 (1968) 284-294.
10. 10. Lisboa B. P. and Plasse J.-CI., Studies on the metabolism of steroids in the foetus - metabolism of 4-androstene-3,17-dione by human foetal-liver microsomes. Eur. J. Biochem. 31 (1972) 378-385.
11. 11. Houghton E., Grainger L., Dumasia M. C. and Teale P., Application of gas chromatography/mass spectrometry to steroid analysis in equine sports: problems with enzyme hydrolysis. Org. Mass Spectrom. 27 (1992) 1061-1070.
12. 4-steroids in rat liver microsomes. Eur. J. Biochem. 12 (1970) 369-374.
13. 13. Gustafsson J.-Å. and Lisboa B. P., Biosynthesis of 6β-hydroxytestosterone from testosterone by human fetal liver microsomes. Steroids 12 (1968) 555-563.
14. 14. Brooks, C. J. W. and Middleditch, B. S., Some aspects of mass spectrometry in steroid analysis. In: Modern Methods of Steroid Analysis, ed. E. Heftmann. Academic Press, New York, 1973, pp. 139-198.
15. 15. Gazdar A. F., Oie H. K., Shackleton C. H. L., Chen T. R., Triche T. J., Myers Ch.E., Chrousos G. P., Brennan M. F., Stein C. A. and La Rocca R. V., Establishment and characterization of a human adrenocortical carcinoma cell line that expresses multiple pathways of steroid biosynthesis. Cancer Res. 50 (1990) 5488-5496.
16. 16. Waxman D. J., Ko A. and Walsh Chr., Regioselectivity and stereoselectivity of androgen hydroxylations catalyzed by cytochrome P-450 isozymes purified from phenobarbital-induced rat liver. J. Biol. Chem. 258 (1983) 11937-11947.
17. 17. Brooks C. J. W., Horning E. C. and Young M. S., Characterization of sterols by gas chromatography-mass spectrometry of the trimethylsilyl ethers. Lipids 3 (1968) 394-402.
18. 18. Allen J. G., Thomas G. H., Brooks C. J. W. and Knights B. A., The determination of stereochemistry at C-5 of 3,6-dioxygenated steroids. Steroids 13 (1969) 133-142.
19. 19. Obermann H., Spiteller-Friedmann M. and Spiteller G., Zur Lokalisierung funktioneller Gruppen in Steroiden mit Hilfe der Massenspektrometrie. I. Ketosteroide. Chem. Ber. 103 (1970) 1497-1511.
20. 3 steroids by thin-layer and gas-liquid chromatography and mass spectrometry. J. Chromatogr. 140 (1977) 229-244.
21. 21. Hammerschmidt F. J. and Spiteller G., Zur Lokalisierung funktioneller Gruppen mit Hilfe der Massenspektrometrie -IX: 17β-Hydroxy-androstan-3,6-dione, 3-Hydroxy-androstan-6,17-dione und 3,17β-Dihydroxy-androstan-6-one. Tetrahedron 29 (1973) 3995-4001.
22. 19 steroids in faeces from germfree rats. Eur. J. Biochem. 6 (1968) 227-235.
23. + ion in the mass spectra of trimethylsilyl ethers of dehydroepiandrosterone and related compounds. J. Org. Chem. 37 (1972) 3365.
24. 24. Yoshihama M., Microbial hydroxylation of steroid hormones and their pharmaceutical applications. Yukijirushi Nyugyo Kenkyusho hokoku 99 (1993) 1-70.
25. 25. Sjövall J. and Axelson M., Newer approaches to the isolation, identification, and quantitation of steroids in biological materials. Vitam. Horm. 39 (1982) 31-144.
26. 19-steroids in rat liver - 1. hydroxylation of testosterone in rat liver microsomes. Eur. J. Biochem. 4 (1968) 496-505.
27. 27. Lisboa B. P. and Gustafsson J.-Å., Biosynthesis of 6β-and 6α-hydroxyprogesterone in the human foetal liver. Eur. J. Biochem. 9 (1969) 503-506.
28. 19 steroids in rat liver - 2. Biosynthesis of hydroxylated derivatives of 17β-hydroxy-5α-androstan-3-one in rat liver microsomes. Eur. J. Biochem. 5 (1968) 437-443.
29. 29. Capek, A., Hanc, O. and Tadra, M., Microbial Transformations of Steroids. Academia, Prague, 1966.
30. 30. Charney, W. and Herzog, H. L., Microbial Transformations of Steroids. Academic Press, New York, 1967.
31. 31. Smith L. L., Microbiological reactions with steroids. Terpenoids and steroids 4 (1974) 394-530.
32. 32. Mahato Sh.B. and Mukherjee A., Steroid transformations by microorganisms. Phytochemistry 23 (1984) 2131-2154.
33. 33. Mahato Sh.B. and Banerjee S., Steroid transformations by microorganisms-II. Phytochemistry 24 (1985) 1403-1421.
34. 34. Mahato Sh.B., Banerjee S. and Podder S., Steroid transformations by microorganisms - III. Phytochemistry 28 (1989) 7-40.
35. 35. Mahato Sh.B. and Majumdar I., Current trends in microbial steroid biotransformation. Phytochemistry 34 (1993) 883-898.
36. meg. J. Biol. Chem. 254 (1979) 5264-5271.
37. 37. Rauschenbach R., Isernhagen M., Noeske-Jungblut Chr., Boidol W. and Siewert G., Cloning sequencing and expression of the gene for cytochrome P450meg, the steroid-15β-monooxygenase from Bacillus megaterium ATCC 13368. Mol. Gen. Genet. 241 (1993) 170-176.
38. 38. Sideso O., Smith K. E., Welch S. G. and Williams R. A. D., Thermostable cytochrome P450 steroid hydroxylase from a thermophilic bacillus strain. Biochem. Soc. Trans. 25 (1997) 17S.
39. 39. Wilson J. E., Ober R. E. and Vestling C. S., Hydroxylation of deoxycorticosterone by Bacillus cereus, strain T. Arch. Biochem. Biophys. 114 (1966) 166-177.
40. 40. Smith K. E., Williams R. A. D. and Sideso O., Transformation of progesterone by a thermophilic bacillus. FEMS Microbiol. Lett. 92 (1992) 29-34.
41. 41. Mahato Sh.B., Banerjee S. and Sahu N. P., Metabolism of progesterone and testosterone by a Bacillus sp. Steroids 43 (1984) 545-558.
42. 42. Mahato Sh.B. and Banerjee S., Metabolism of 17-hydroxyprogesterone by a Bacillus species. Biochem. J. 239 (1986) 473-476.
43. 43. Mahato Sh.B. and Banerjee S., Metabolism of 11-deoxycortisol by a Bacillus species. J. Steroid Biochem. 25 (1986) 995-999.
44. 44. Mahato Sh.B., Banerjee S. and Mazumder I., Metabolism of progesterone by a Bacillus species. J. Chem. Res. (S) 0 (1989) 184-185.