Efficient biotransformation of cholesterol to androsta-1,4-diene-3,17-dione by a newly isolated actinomycete Gordonia neofelifaecis

World Journal of Microbiology and Biotechnology

Volumn 27, Issue 4, 2011, Pages 759-765

  Liu, Yuchang ^a   Chen, Guiying ^a   Ge, Fanglan ^a   Li, Wei ^a   Zeng, Lihua ^a   Cao, Weiguo ^b  

^a SICHUAN NORMAL UNIVERSITY   (China)

^b CLEMSON UNIVERSITY   (United States)

Author keywords

Androsta 1,4 diene 3,17 dione; Gordonia neofelifaecis; Side chain cleavage of cholesterol

Indexed keywords

ANDROSTA-1,4-DIENE-3,17-DIONE; CONVERSION RATES; GORDONIA; GORDONIA NEOFELIFAECIS; INDUSTRIAL PRODUCTION; QUANTITATIVE ANALYSIS; SIDE-CHAIN; SIDE-CHAIN CLEAVAGE OF CHOLESTEROL;

BIOCONVERSION; METABOLISM; METABOLITES; OLEFINS;

CHOLESTEROL;

ACTINOBACTERIA; BACTERIA (MICROORGANISMS); GORDONIA (ACTINOMYCETE); NEOFELIS NEBULOSA;

EID: 79952572495     PISSN: 09593993     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11274-010-0513-5     Document Type: Article

References (27)

1. Ahmad S, Roy PK, Khan AW, Basu SK, Johri BN (1991) Microbial transformation of sterols to C19 steroids by Rhodococcus equi. World J Microbiol Biotechnol 7: 557-561.
2. Al-Aboudi A, Mohammad MY, Musharraf SG, Choudhary MI (2008) Microbial transformation of testosterone by Rhizopus stolonifer and Fusarium lini. Nat Prod Res 22: 1498-1509.
3. Allain CC, Poon LS, Chan CSG, Richmond W, Fu PC (1974) Enzymatic determination of total serum cholesterol. Clin Chem 20: 470-475.
4. Arima K, Nakamatsu W, Beppu T (1978) Microbial production of 3- oxobisnorchola-1, 4-dien-22-oic acid. Agric Biol Chem 42: 411-416.
5. Barton HRD, Lester DJ, Ley SV (1980) Dehydrogenation of steroidal and triterpenoid ketones using benzeneseleninic anhydride. J Chem Soc Perkin Trans 1: 2209-2212.
6. Buchanan RE, Gibbons NE (1974) Bergey's manual of determinative bacteriology, 8th edn. Williams and Wilkins Co, Baltimore, pp 290-340.
7. Chiang YR, Ismail W, Müller M, Fuchs G (2007) Initial steps in the anoxic metabolism of cholesterol by the denitrifying Sterolibacterium denitrificans. J Biol Chem 282: 13240-13249.
8. Dogra N, Qazi G (2001) Steroid biotransformation by different strains of Micrococcus sp. Folia Microbiol 46: 17-20.
9. Faramarzi MA, Yazdi MT, Jahandar H, Amini M, Monsef-Esfahani HR (2006) Studies on the microbial transformation of androsta-1, 4-diene-3 17-dione with Acremonium strictum. J Ind Microbiol Biotechnol 33: 725-733.
10. Hiraishi A, Shin YK, Ueda Y, Sugiyama J (1994) Automated sequencing of PCR-amplified 16S rRNA on 'Hydrolink' gels. J Microbiol Methods 19: 145-154.
11. Iida M, Murohisa I, Yoneyama A, Iizuka H (1985) Microbiological production of 20-carboxy-pregna-1, 4-dien-3-one from sitosterol with high yield by a Rhodococcus species. J Ferment Technol 63: 559-561.
12. Johnson WS, Vredenburgh WA, Pike JE (1960) Steroid total synthesis- hydrochrysene approach. Part XII: an alternative route to testosterone, the synthesis of testosterone and of dl-13-isotestosterone. J Am Chem Soc 82: 3409-3415.
13. Kieslich K (1985) Microbial side-chain degradation of sterols. J Basic Microbiol 25: 461-474.
14. Kim KK, Lee KC, Klenk H-P, Oh HM, Lee JS (2009) Gordonia kroppenstedtii sp. nov., a phenol-degrading actinomycete isolated from a polluted stream. Int J Syst Evol Microbiol 59: 1992-1996.
15. Lee CY, Chen CD, Liu WH (1993) Production of androsta-1, 4-diene-3, 17-dione from cholesterol using two-step microbial transformation. Appl Microbiol Biotechnol 38: 447-452.
16. Lin Y, Song X, Fu J, Lin J, Qu Y (2009) Microbial transformation of phytosterol in corn flour and soybean flour to 4-androstene-3 17-dione by Fusarium moniliforme. Bioresour Technol 100: 1864-1867.
17. Linos A, Berekaa MM, Steinbüchel A, Kim KK, Sproer C, Kroppenstedt RM (2002) Gordonia westfalica sp. nov., a novel rubber-degrading actinomycete. Int J Syst Evol Microbiol 52: 1133-1139.
18. Liu YC, Ge FL, Chen GY, Li W, Ma PM, Zhang GX, Zeng LH (2010) Gordonia neofelifaecis sp. nov., a cholesterol side-chain cleaving actinomycete isolated from the faeces of Neofelis nebulosa. Int J Syst Evol Microbiol (in press).
19. Malaviya N, Gomes J (2008) Androstenedione production by biotransformation of phytosterols. Bioresour Technol 99: 6725-6737.
20. Minami I, Takahashi K, Shimizu I, Kimura T, Tsuji J (1986) New synthetic methods for α, β-unsaturated ketones, aldehydes, ester and lactones by the palladium- catalyzed reactions of silyl enol ethers, ketene silyl acetals, and enol acetates with allyl carbonates. Tetrahedron 42: 2971-2977.
21. Nagasawa M, Bae M, Tamura G, Arima K (1969) Microbial transformation of sterols part II. Cleavage of sterol side chains by microorganisms. Agric Biol Chem 33: 1644-1650.
22. Owen RW, Mason AN, Bilton RF (1983) The degradation of cholesterol by Pseudomonas sp. NCIB 10590 under aerobic conditions. J Lipid Res 24: 1500-1511.
23. Wang ZL, Zhao F, Chen D, Li D (2006) Biotransformation of phytosterol to produce androstadienedione by resting cells of Mycobacterium in cloud point system. Process Biochem 41: 557-561.
24. Wilds AL, Djerassi C (1946) The preparation and partial aromatization of 1, 4-cholestadienone-3 by dienone-phenol rearrangement. J Am Chem Soc 68: 1712-1715.
25. Yamakawa K, Satoh T, Ohba N, Sakaguchi R (1979) Angular hydroxylation of polycyclic ketones using benzeneseleninic anhydride. Chem Lett 763-764.
26. Ye DP, Lei J, Li W, Ge F (2008) Purification and characterization of extracellular cholesterol oxidase from Enterobacter sp. World J Microbiol Biotechnol 24: 2227-2233.
27. Yuan Z, Han L, Su H, Shi D, Sun J, LI S, Shi J (2008) The chemical constituents from red alga Gymnogongrus flabelliformis Harv. Chin J Oceanol Limnol 26: 190-192.