Microbial side-chain degradation of ergosterol and its 3-substituted derivatives: A new route for obtaining of deltanoids

Steroids

Volumn 75, Issue 10, 2010, Pages 653-658

  Dovbnya, Dmitry V ^a   Egorova, Olga V ^a   Donova, Marina V ^a  

^a SKRYABIN INSTITUTE OF BIOCHEMISTRY AND PHYSIOLOGY OF MICROORGANISMS   (Russian Federation)

Author keywords

Bioconversion; Deltanoids; Ergosterol; Mycobacterium; Sterol side chain degradation

Indexed keywords

11BETA HYDROXYANDROSTENEDIONE; 3 METHOXYMETHOXY ANDROSTA 5,7 DIENE 17 ONE; 3(OR 17)BETA HYDROXYSTEROID DEHYDROGENASE; 3BETA METHOXYMETHOXY ERGOSTA 5,7,22 TRIENE; ANDROSTA 1,4 ENE 3,17 DIONE; ANDROSTERONE DERIVATIVE; CHOLEST 5 EN 3 ONE; ERGOSTEROL; ERGOSTEROL 3 ACETATE; ERGOSTEROL 3BETA HYDROXYL; ISOFLAVONE DERIVATIVE; LITHOCHOLIC ACID; O METHOXYMETHYL ERGOSTEROL; PRASTERONE; STEROL DERIVATIVE; UNCLASSIFIED DRUG; ANDROSTENEDIOL DERIVATIVE; GAMMA-SITOSTEROL; SITOSTEROL DERIVATIVE;

ARTICLE; BIOTRANSFORMATION; MASS SPECTROMETRY; MICROBIAL DEGRADATION; MYCOBACTERIUM; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; CHEMISTRY; METABOLISM; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; THIN LAYER CHROMATOGRAPHY;

ANDROSTENEDIOLS; CHROMATOGRAPHY, THIN LAYER; ERGOSTEROL; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; MOLECULAR STRUCTURE; MYCOBACTERIUM; SITOSTEROLS;

MYCOBACTERIUM; MYCOBACTERIUM SP.;

EID: 77954309292     PISSN: 0039128X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.steroids.2010.04.001     Document Type: Article

References (29)

1. A.W. Norman Pleiotropic actions of 1α,25-dihydroxyvitamin D3: an overview J Nutr 125 1995 1687S 1689S
2. S.E. Brown Vitamin D and fracture reduction: an evaluation of the existing research Altern Med Rev 13 2008 21 33
3. E.S. Agoston Anticancer Agents Med Chem 6 2006 53 71
4. T. Gulliford, J. English, K.W. Colston, P. Menday, S. Moller, and R.C. Coombes A phase I study of the vitamin D analogue EB 1089 in patients with advanced breast and colorectal cancer Br J Cancer 78 1998 6 13
5. A.F. Gombart, Q.T. Luong, and H.P. Koeffler Vitamin D compounds: activity against microbes and cancer Anticancer Res 26 2006 2531 2542
6. Steinmeyer A, Kirsch G, Neef G, Schwarz K, Thieroff-Ekerdt R, Wiesinger H, et al. Vitamin D derivatives with carbo- or heterocyclic substituents at C-25, a process for their production, intermediate products and their use for producing medicaments. US Patent 6,600,058; 2003.
7. A.U. Siddiqui, W.K. Wilson, S. Swaminathan, and G.J. Schroepfer Jr. Efficient preparation of steroidal 5,7-dienes of high purity Chem Phys Lipids 63 1992 115 129
8. R.M. Moriarty, and D. Albinescu Synthesis of 1α-hydroxyvitamin D5 using a modified two wavelength photolysis for vitamin D formation J Org Chem 70 2005 7624 7628
9. I. Cornella, R.M. Suárez, A. Mouriño, J.P. Sestelo, and L.A. Sarandeses Stereoselective convergent synthesis of 24-substituted metabolites and analogues of vitamin D J Steroid Biochem Mol Biol 89-90 2004 19 23
10. U. Groth, N. Richter, and A. Kalogerakis Synthesis of (3S)-hydroxyandrosta-5,7-diene-17-ones via intramolecular cobalt-mediated [2 + 2 + 2] cycloaddition Synlett 6 2006 905 908
11. M. Okabe, R.-C. Sun, M. Scalone, C.H. Jubilian, and S.D. Hutchings Synthesis of 25-hydroxycholecalcifer-16-en-23-ynol: a potential antipsoriatic agent J Org Chem 60 1995 767 771
12. M.A. Zmijewski, W. Li, J.K. Zjawiony, T.W. Sweatman, J. Chen, and D.D. Miller Synthesis and photo-conversion of androsta- and pregna-5,7-dienes to vitamin D3-like derivatives Photochem Photobiol Sci 7 2008 1570 1576
13. T.G. Lobastova, S.M. Khomutov, L.L. Vasiljeva, M.A. Lapitskaya, K.K. Pivnitsky, and M.V. Donova Synthesis of 3β-hydroxy-androsta-5,7-dien-17-one from 3β-hydroxyandrost-5-en-17-one via microbial 7α-hydroxylation Steroids 74 2009 233 237
14. M.M. Klimashina, I.V. Viktorovskii, N.P. Mikhailova, and K.A. V'iunov Analysis of the products of ergosta-7,22-dien-3β-ol biotransformation by a Nocardia erythropolis culture Appl Biochem Microbiol 24 1988 647 652
15. Weber A, Kennecke M, Process for the production of 4-androstene-3,17- dione and 1,4-androstadiene-3,17-dione from ergosterol with Mycobacterium. US Patent 5,516,649; 1996.
16. Weber A, Kennekke M, Neef G. Process for the production of 20-methyl-5,7-pregnadiene-3β,21-diol derivatives using mycobacterium. US Patent 5,429,934; 1995.
17. Donova MV, Dovbnya DV, Kalinichenko AN, Vagabova LM, Arinbasarova AY, Morozova ZV, et al. Method for production of androst-4-ene-3,17-dione. RF Patent 20,779,258; 1997.
18. M.V. Donova, V.M. Nikolayeva, D.V. Dovbnya, S.A. Gulevskaya, and N.E. Suzina Methyl-β-cyclodextrin alters growth, activity and cell envelope features of sterol transforming mycobacteria Microbiology 153 2007 1981 1992
19. O.V. Egorova, S.A. Gulevskaya, I.F. Puntus, A.E. Filonov, and M.V. Donova Production of androstenedione using mutants of Mycobacterium sp J Chem Technol Biotechnol 77 2002 141 147
20. M.A. Quail, and S.L. Kelly Isolation and investigation of sterols from yeast I.H. Evans, Methods in molecular biology 1996 Humana Press Totowa 123 131
21. M.V. Donova Transformation of steroids by actinobacteria: a review Appl Biochem Microbiol 43 2007 1 14
22. L. Pollegioni, L. Piubelli, and G. Molla Cholesterol oxidase: biotechnological applications FEBS J 276 2009 6857 6870
23. W.M. Keung Dietary estrogenic isoflavones are potent inhibitors of β-hydroxysteroid dehydrogenase of P. testosteronii Biochem Biophys Res Commun 215 1995 1137 1144
24. A. Elalami, J. Kreit, A. Filali-Malfout, J. Boudrant, and P.R.P. Germain Characterization of a secreted cholesterol oxidase from Rhodococcus sp. GKI (CIP 105335) World J Microbiol Biotechnol 15 1999 579 585
25. I.B. Ivshina, GrishkoVV, NogovitsinaEM, T.P. Kukina, and G.A. Tolstikov Bioconversion of β-sitosterol and its esters by actinobacteria of the genus Rhodococcus Appl Biochem Microbiol 41 2005 626 633
26. A. Szentirmai Microbial physiology of side-chain degradation of steroids J Ind Microbiol 6 1999 101 116
27. D.V. Dovbnya, S.M. Khomutov, V.M. Nikolaeva, and M.V. Donova CD-medium control of microbial sterol sidechain cleavage J.J.T. Labandeira, J.L.V. Jato, Proceedings of 9th international symposium on cyclodextrins 1999 Kluwer Academic Publishers New York 395 398
28. Z. Wang, F. Zhao, D. Chen, and D. Li Cloud point system as a tool to improve the efficiency of biotransformation Enzyme Microb Technol 36 2005 589 594
29. Gates S, Loria RM. Compositions for regulation of immune response. US Patent 5,776,921; 1998.