Degradation of the acyl side chain of the steroid compound cholate in Pseudomonas sp. strain chol1 proceeds via an aldehyde intermediate

Journal of Bacteriology

Volumn 195, Issue 3, 2013, Pages 585-595

  Holert, Johannes ^a   Kulić, Žarko ^b   Yücel, Onur ^a   Suvekbala, Vemparthan ^b   Suter, Marc J F ^c   Möller, Heiko M ^b   Philipp, Bodo ^a  

^a UNIVERSITY OF MÜNSTER   (Germany)

^b UNIVERSITY OF KONSTANZ   (Germany)

^c SWISS FEDERAL INSTITUTE OF AQUATIC SCIENCE AND TECHNOLOGY   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

(22) 7ALPHA,12ALPHA DIHYDROXY 3 OXOCHOLA 1,4,22 TRIENE 24 OATE; 7ALPHA,12ALPHA DIHYDROXY 3 OXOPREGNA 1,4 DIENE 20S CARBALDEHYDE; 7ALPHA,12BETA DIHYDROXY ANDROSTA 1,4 DIENE 3,17 DIONE; ADENOSINE TRIPHOSPHATE; ALDEHYDE; CELL EXTRACT; CHOLIC ACID; COENZYME A; NICOTINAMIDE ADENINE DINUCLEOTIDE; STEROID; UNCLASSIFIED DRUG;

ARTICLE; BACTERIAL STRAIN; ENZYME ASSAY; ENZYME MECHANISM; ENZYME SUBSTRATE; FATTY ACID OXIDATION; IN VITRO STUDY; NONHUMAN; PRIORITY JOURNAL; PROTEIN DEGRADATION; PROTEIN STRUCTURE; PSEUDOMONAS;

ADENOSINE TRIPHOSPHATE; ALDEHYDE-LYASES; ALDEHYDES; CATALYSIS; CHOLATES; COENZYME A; GENE EXPRESSION REGULATION, BACTERIAL; GENE EXPRESSION REGULATION, ENZYMOLOGIC; MOLECULAR STRUCTURE; NAD; NADP; OXIDATION-REDUCTION; PSEUDOMONAS;

EID: 84873026357     PISSN: 00219193     EISSN: 10985530     Source Type: Journal    
DOI: 10.1128/JB.01961-12     Document Type: Article

References (36)

1. Bortolini O, Medici A, Poli S. 1997. Biotransformations on steroid nucleus of bile acids. Steroids 62:564-577.
2. Donova MV, Egorova OV. 2012. Microbial steroid transformations: current state and prospects. Appl. Microbiol. Biotechnol. 94:1423-1447.
3. Mahato SB, Garai S. 1997. Advances in microbial steroid biotransformation. Steroids 62:332-345.
4. Silva CP, Otero M, Esteves V. 2012. Processes for the elimination of estrogenic steroid hormones from water: a review. Environ. Pollut. 165: 38-58.
5. Hayakawa S. 1982. Microbial transformation of bile acids. A unified scheme for bile acid degradation and hydroxylation of bile acids. Z Allg. Mikrobiol. 22:309-326.
6. Horinouchi M, Hayashi T, Kudo T. 2012. Steroid degradation in Comamonas testosteroni. J. Steroid Biochem. Mol. Biol. 129:4-14.
7. Kieslich K. 1985. Microbial side-chain degradation of sterols. J. Basic Microbiol. 25:461-474.
8. Philipp B. 2011. Bacterial degradation of bile salts. Appl. Microbiol. Biotechnol. 89:903-915.
9. Yam KC, Okamoto S, Roberts JN, Eltis LD. 2011. Adventures in Rhodococcus- from steroids to explosives. Can. J. Microbiol. 57:155-168.
10. Petrusma M, Hessels G, Dijkhuizen L, Van Der Geize R. 2011. Multiplicity of 3-ketosteroid-9α-hydroxylase enzymes in Rhodococcus rhodochrous DSM43269 for specific degradation of different classes of steroids. J. Bacteriol. 193:3931-3940.
11. Dresen C, Lin L, D'Angelo I, Tocheva E, Strynadka N, Eltis L. 2010. A flavin-dependent monooxygenase from Mycobacterium tuberculosis involved in cholesterol catabolism. J. Biol. Chem. 285:22264-22275.
12. Yam K, D'Angelo I, Kalscheuer R, Zhu H, Wang J, Snieckus V, Ly L, Converse P, Jacobs W, Jr, Strynadka N. 2009. Studies of a ring-cleaving dioxygenase illuminate the role of cholesterol metabolism in the pathogenesis of Mycobacterium tuberculosis. PLoS Pathog. 5:e1000344. doi:10 .1371/journal.ppat.1000344.
13. Lack NA, Yam KC, Lowe ED, Horsman GP, Owen RL, Sim E, Eltis LD. 2010. Characterization of a carbon-carbon hydrolase from Mycobacterium tuberculosis involved in cholesterol metabolism. J. Biol. Chem. 285:434-443.
14. Swain K, Casabon I, Eltis LD, Mohn WW. 28 September 2012. Two transporters essential for the reassimilation of novel cholate metabolites by Rhodococcus jostii RHA1. J. Bacteriol. doi:10.1128/JB.01167-12.
15. Philipp B, Erdbrink H, Suter MJ, Schink B. 2006. Degradation of and sensitivity to cholate in Pseudomonas sp. strain Chol1. Arch. Microbiol. 185:192-201.
16. Hofmann AF, Mysels KJ. 1987. Bile salts as biological surfactants. Colloids Surf. 30:145-173.
17. Ridlon J, Kang D, Hylemon P. 2006. Bile salt biotransformations by human intestinal bacteria. J. Lipid Res. 47:241-259.
18. Birkenmaier A, Möller H, Philipp B. 2011. Identification of a thiolase gene essential for β-oxidation of the acyl side chain of the steroid compound cholate in Pseudomonas sp. strain Chol1. FEMS Microbiol. Lett. 318:123-130.
19. Birkenmaier A, Holert J, Erdbrink H, Möller HM, Friemel A, Schoenenberger R, Suter MJ, Klebensberger J, Philipp B. 2007. Biochemical and genetic investigation of initial reactions in aerobic degradation of the bile acid cholate in Pseudomonas sp. strain Chol1. J. Bacteriol. 189:7165-7173.
20. Jagmann N, Brachvogel H, Philipp B. 2010. Parasitic growth of Pseudomonas aeruginosa in co-culture with the chitinolytic bacterium Aeromonas hydrophila. Environ. Microbiol. 12:1787-1802.
21. Tenneson M, Baty J, Bilton R, Mason A. 1979. The degradation of cholic acid by Pseudomonas sp. NCIB 10590. Biochem. J. 184:613-618.
22. Hwang T, Shaka A. 1995. Water suppression that works. Excitation sculpting using arbitrary wave-forms and pulsed-field gradients. J. Magn. Reson. 112:275-279.
23. Textor S, Wendisch V, Graaf A, Müller U, Linder M, Linder D, Buckel W. 1997. Propionate oxidation in Escherichia coli: evidence for operation of a methylcitrate cycle in bacteria. Arch. Microbiol. 168:428-436.
24. Griffin JE, Pandey AK, Gilmore SA, Mizrahi V, McKinney JD, Bertozzi CR, Sassetti CM. 2012. Cholesterol catabolism by Mycobacterium tuberculosis requires transcriptional and metabolic adaptations. Chem. Biol. 19:218-227.
25. Thomas ST, VanderVen BC, Sherman DR, Russell DG, Sampson NS. 2011. Pathway profiling in Mycobacterium tuberculosis: elucidation of cholesterol- derived catabolite and enzymes that catalyze its metabolism. J. Biol. Chem. 286:43668-43678.
26. Wilbrink MH, Van Der Geize R, Dijkhuizen L. 2012. Molecular characterization of ltp3 and ltp4, essential for C24-branched chain sterol side chain degradation in Rhodococcus rhodochrous DSM43269. Microbiology doi:10.1099/mic.0.059501-0.
27. Plaggenborg R, Steinbüchel A, Priefert H. 2001. The coenzyme A-dependent, non-beta-oxidation pathway and not direct deacetylation is the major route for ferulic acid degradation in Delftia acidovorans. FEMS Microbiol. Lett. 205:9-16.
28. Narbad A, Gasson MJ. 1998. Metabolism of ferulic acid via vanillin using a novel CoA-dependent pathway in a newly-isolated strain of Pseudomonas fluorescens. Microbiology 144:1397-1405.
29. Overhage J, Priefert H, Steinbüchel A. 1999. Biochemical and genetic analyses of ferulic acid catabolism in Pseudomonas sp. strain HR199. Appl. Environ. Microbiol. 65:4837-4847.
30. Holert J, Alam I, Larsen M, Antunes A, Bajic V, Stingl U, Philipp B. 2013. Genome sequence of Pseudomonas sp. strain Chol1, a model organism for the degradation of bile salts and other steroid compounds. Genome Announc. doi:10.1128/genomeA.00014-12.
31. Ghisla S, Thorpe C. 2004. Acyl-CoA dehydrogenases. Eur. J. Biochem. 271:494-508.
32. Horinouchi M, Hayashi T, Koshino H, Malon M, Yamamoto T, Kudo T. 2008. Identification of genes involved in inversion of stereochemistry of a C-12 hydroxyl group in the catabolism of cholic acid by Comamonas testosteroni TA441. J. Bacteriol. 190:5545-5554.
33. Mohn WW, Wilbrink MH, Casabon I, Stewart GR, Liu J, van der Geize R, Eltis LD. 28 September 2012. A gene cluster encoding cholate catabolism in Rhodococcus spp. J. Bacteriol. doi:10.1128/JB.01169-12.
34. Pollock SB, Kent SBH. 2011. An investigation into the origin of the dramatically reduced reactivity of peptide-prolyl-thioesters in native chemical ligation. Chem. Commun. (Camb.) 47:2342-2344.
35. Fujimoto Y, Chen C, Szeleczky Z, Ditullio D, Sih C. 1982. Microbial degradation of the phytosterol side chain. I. Enzymic conversion of 3-oxo- 24-ethylcholest-4-en-26-oic acid into 3-oxochol-4-en-24-oic acid and androst-4-ene-3,17-dione. J. Am. Chem. Soc. 104:4718-4720.
36. Lee K, Park H. 1991. The conversion of lithocholic acid into 5β- androstan-3,17-dione in the cell-free system of Mycobacterium sp. NRRL B-3805. Arch. Pharm. Res. 14:261-265.