Baeyer-Villiger oxidation of DHEA, pregnenolone, and androstenedione by Penicillium lilacinum AM111

Steroids

Volumn 73, Issue 14, 2008, Pages 1441-1445

  Kołek, Teresa ^a   Szpineter, Anna ^a   Świzdor, Alina ^a  

^a WROC AW UNIVERSITY OF ENVIRONMENTAL AND LIFE SCIENCES   (Poland)

Author keywords

Baeyer Villiger oxidation; Biotransformation; DHEA; Penicillium lilacinum; Pregnenolone; Steroidal lactones

Indexed keywords

3 BETA HYDROXY 17 ALPHA OXA DEXTRO HOMO ANDROST 5 EN 17 ONE; ANDROSTENEDIONE; PRASTERONE; PREGNENOLONE; TESTOLOLACTONE; UNCLASSIFIED DRUG;

ARTICLE; BAEYER VILLIGER REACTION; CHEMICAL REACTION; DRUG IDENTIFICATION; DRUG ISOLATION; DRUG STRUCTURE; NONHUMAN; OXIDATION; PENICILLIUM; PENICILLIUM LILACINUM;

ANDROSTENEDIONE; BIOTRANSFORMATION; DEHYDROEPIANDROSTERONE; MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION-REDUCTION; PENICILLIUM; PREGNENOLONE; TESTOLACTONE;

PENICILLIUM LILACINUM;

EID: 55549111846     PISSN: 0039128X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.steroids.2008.07.008     Document Type: Article

References (40)

1. Mao Q., Lu S.-F., and Simon N.G. Dehydroepiandrosterone and its metabolites: differential effects on androgen receptor tracking and transcriptional activity. J Steroid Biochem Mol Biol 99 (2006) 50-58
2. Muller C., Pompon D., Urban P., and Morfin R. Inter-conversion of 7α- and 7β-hydroxy- dehydroepiandrosterone by the human 11β-hydroxysteroid dehydrogenase type 1. J Steroid Biochem Mol Biol 99 (2006) 215-222
3. Marwah A., Gomez F.E., Marwah P., Ntambi J.M., Fox B.G., and Lardy H. Redox reaction of dehydroepiandrosterone and its metabolites in differentiating 3T3-L1 adipocytes: a liquid chromatographic-mass spectrometric study. Arch Biochem Biophys 456 (2006) 1-7
4. Tang W., Eggertsen, Chiang J.Y.L., and Norlin M. Estrogen mediated regulation of CYP7B1: a possible role for controling DHEA levels in human tissues. J Steroid Biochem Mol Biol 100 (2006) 42-51
5. Chalbot S., and Morfin R. Neurosteroids: metabolism in human intestine microsomes. Steroids 70 (2005) 319-326
6. Kim S.-B., Chalbot S., Pompon D., Jo D.-H., and Morfin R. The human cytochrome P4507B1: catalytic activity studies. J Steroid Biochem Mol Biol 92 (2004) 383-389
7. Zenk J.L., Frestedt J.L., and Kuskowski A. HUM5007, a novel combination of thermogenic compounds, and 3-acetyl-7-oxo-dehydroepiandrosterone: each increases the resting metabolic rate of overweight adults. J Nutr Biochem 18 (2007) 629-634
8. Jellinck P.H., Croft G., McEvans B.S., Gottfried-Blackmore A., Jones G., Byford V., et al. Metabolism of dehydroepiandrosterone by rodent brain cell lines: relationship between 7-hydroxylation and aromatization. J Steroid Biochem Mol Biol 93 (2005) 81-86
9. Jellinck P.H., Kaufmann M., Gottfried-Blackmore A., Croft G., Byford V., McEvans B.S., et al. Dehydroepiandrosterone (DHEA) metabolism in brain: identification by liquid chromatography/mass spectrometry of the delta-4-isomer of DHEA and related steroid formed from androstenedione by mouse BV2 microglia. J Steroid Biochem Mol Biol 98 (2006) 41-47
10. Jellinck P.H., Kaufmann M., Gottfried-Blackmore A., McEvans B.S., Jones G., and Bulloch K. Selective conversion by microglia of dehydroepiandrosterone to 5-androstenediol-a steroid with inherent estrogenic properties. J Steroid Biochem Mol Biol 107 (2007) 156-162
11. Lardy H. A postulated role for 16α-hydroxydehydroepiandrosterone in the prevention of respiratory distress syndrome. Med Hypotheses 66 (2006) 107-109
12. Morfin M., and Courchay G. Pregnenolone and dehydroepiandrosterone as precursors of native 7-hydroxylated metabolites which increase the immune response in mice. J Steroid Biochem Mol Biol 50 (1994) 91-100
13. Lardy H., Marwah A., and Marwah P. Transformation of DHEA and its metabolites by rat liver. Lipids 37 (2002) 1187-1191
14. Dodson R.M., Nicholson R.T., and Muir R.D. Microbial transformations IV. The oxidation of dehydroepiandrosterone at C-7. J Am Chem Soc 81 (1959) 6295-6297
15. Defaye G., Luche M.J., and Chambaz E.M. Microbiological 7- and 15-hydroxylation of 19 steroids. J Steroid Biochem 9 (1978) 331-336
16. Crabb T.A., Dawson P.J., and Williams R.O. Microbial transformations. Part 3. The oxidation of androstene derivatives with Cunninghamella elegans. J Chem Soc Perkin Trans I (1980) 2535-2541
17. Madyastha K.M., and Joseph T. Transformation of dehydroepiandrosterone and pregnenolone by Mucor piriformis. Appl Microbiol Biotechnol 44 (1995) 339-343
18. Cottilon A.-C., and Morfin R. Transformation of 3-hydroxy-steroids by Fusarium moniliforme 7α-hydroxylase. J Steroid Biochem Mol Biol 68 (1999) 229-237
19. Wilson M.R., Gallimore W.A., and Reese P.B. Steroid transformation with Fusarium oxysporum var. cubense and Colletotrichum musae. Steroids 64 (1999) 834-843
20. Kołek T. Biotransformation XLVII: transformations of 5-ene steroids in Fusarium culmorum culture. J Steroid Biochem Mol Biol 71 (1999) 83-90
21. Romano A., Romano D., Ragg E., Costantino F., Lenna R., Gandolfi R., et al. Steroid hydroxylation with Botryodiplodia malorum and Colletotrichum lini. Steroids 71 (2006) 429-434
22. Hunter A.C., Mills P.W., Dedi C., and Dodd H.T. Predominant allylic hydroxylation at carbons 6 and 7 of 4 and 5-ene functionalized steroids by thermophilic fungus Rhizomucor tauricus IMI23312. J Steroid Biochem Mol Biol 108 (2008) 155-163
23. Holland H.L., Dore S., Xu W., and Brown F.M. Formation of 5-steroids by biotransformation involving the 5 reductase activity of Penicillium decumbens. Steroids 59 (1994) 642-647
24. Holland H.L., Nguyen D.H., and Pearson N.M. Bioconversion of corticosteroids by Penicillium decumbens ATCC 10436. Steroids 60 (1995) 646-649
25. Irrgang S., Schlosser D., and Schmauder H.-P. The steroid 15-hydroxylase of Penicillium raistrickii I 477 is inducible. Biotechnol Lett 14 (1992) 33-38
26. Irrgang S., Schlosser D., and Fritsche W. Involvement of cytochrome P-450 in the hydroxylation of 13-ethyl-gone-4-ene-3,17-dione by Penicillium raistrickii. J Steroid Biochem Mol Biol 60 (1997) 339-346
27. Fried J., Thoma R.W., and Klingsberg A. Oxidation of steroids by microorganisms. III. Side chain degradation, ring D-cleavage and dehydrogenation in ring A. J Am Chem Soc 75 (1953) 5764-5765
28. Prairie R.L., and Talalay P. Enzymatic formation of testololactone. Biochemistry 2 (1963) 203-208
29. Viola F., Caputo O., Balliano G., Delprino L., and Cattel L. Side chain degradation and microbial reduction of different steroids by Aspergillus aureogulgens. J Steroid Biochem 19 (1983) 1451-1458
30. Bartmańska A., Dmochowska-Gładysz J., and Huszcza E. Steroids' transformations in Penicillium notatum culture. Steroids 70 (2005) 193-198
31. Liu H.-M., Li H., Shan L., and Wu J. Synthesis of steroidal lactones by Penicillim citreo-viride. Steroids 71 (2006) 931-934
32. Sebek O.K., Reineke L.M., and Peterson D.H. Intermediates in the metabolism of steroids by Penicillium lilacinum. J Bacteriol 83 (1962) 1327-1331
33. Holland H.L. Organic synthesis with oxidative enzymes (1992), Verlag Chemie, Weinheim p. 241-54
34. Hanson J.R., and Hunter A.C. The hydroxylation of steroidal D lactones by Cephalosporium aphidicola. Phytochemistry 49 (1998) 2349-2353
35. Hunter A.C., and Carragher N.E. Flexibility of the endogenous progesterone lactonisation pathway in Aspergillus tamarii KITA: transformation of a series of cortical steroid analogues. J Steroid Biochem Mol Biol 87 (2003) 301-308
36. Fonken G.S., Murray H.C., and Reineke L.M. Pathway of progesterone oxidation by Cladosporium resinae. J Am Chem Soc 82 (1960) 5507-5508
37. Brodie A.M.H., and Njar V.C.O. Aromatase inhibitors in advanced breast cancer: mechanism of action and clinical implications. J Steroid Biochem Mol Biol 66 (1998) 1-10
38. Braustein G.D. Aromatase and gynecomastia. Endocr-Relat Cancer 6 (1999) 315-324
39. Baran J.C. The synthesis, stereochemistry, and biology of 16-hetero and 17-oxa-d-homo steroids. J Med Chem 10 (1967) 1039-1047
40. Djurendić E.A., Sakač M.N., Zaviš M.P., Gaković A.R., Čanadi J.J., Andrić S.A., et al. Synthesis and biological evaluation of some new A,B-ring modified steroidal D-lactones. Steroids 73 (2008) 681-688