Skip to main content
SpringerLink
Log in

Microbial conversion of sterols

1. Selection of mutants for production of 20-carboxy-pregna-1,4-dien-3-one (BNC)

  • Published:
European journal of applied microbiology and biotechnology Aims and scope Submit manuscript

Abstract

By preselection of microorganisms which preferentially attack the side chain of cholesterol we have been able to isolate a mutant of Corynebacterium spec. Chol 73 which forms 20-carboxy-pregna-1,4-dien-3-one (BNC) from cholesterol in nearly quantitative yields. The structure of this compound has been established by means of13C NMR-,1H NMR and CD spectroscopy.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  • Arima K, Nagasava M, Bae M, Tamura G (1969) Microbial transformation of sterols. Agric Biol Chem 33:1636–1443, 1644–1650

    Google Scholar 

  • Arima K, Beppu T, Nakamatsu W (1977) Microbial production of 3-oxobisnorchola-1,4-dienoic acid. Japan Kokai 7776484; CA 87:182618j

  • Arima K, Nakamatsu W, Beppu T (1978) Microbial production of 3-oxobisnorchola-1,4-dien-22-oic acid. Agric Biol Chem 42:411–416

    Google Scholar 

  • Atrat P, Hiller E, Hörhold C, Buchar MI, Arubasara AY, Koschtschejenko KA (1980) Steroidtransformation mit immobilisierten Mikroorganismen. II Abbau der Seitenkette von Cholesterol mit immobilisierten Zellen vonNocardia erythropolis. Z Allg Mikrobiol 20:159–166

    PubMed  Google Scholar 

  • Böhme KH, Hörhold C (1980) Mikrobieller Seitenkettenabbau von strukturmodifizierten Sterolen. Z Allg Mikrobiol 20:85–93

    PubMed  Google Scholar 

  • Brown RL, Peterson GE (1966) Cholesterol oxidation by soilActinomycetes. J Gen Microbiol 45:441–450

    Google Scholar 

  • Breitmaier E, Voelter W (1978) “13C NMR Spectroscopy”. Verlag Chemie, Weinheim, 2. Auflage

    Google Scholar 

  • Fried J, Thoma RW, Klingsberg A (1953) Oxidation of steroids by microorganisms III. Side-chain degradation, ring D-cleavage and dehydrogenation in ring A. J Am Chem Soc 75:5764–5765

    Article  Google Scholar 

  • Hanson JR, Siverns M (1975)13C NMR spectra of some steroid unsaturated ketones. J Chem Soc Perkin Trans I:1956–1958

    Article  Google Scholar 

  • Henkel KGaA (1979) Verfahren zum selektiven Seitenkettenabbau von Steroidverbindungen und zur Herstellung hierzu geeigneter Mikroorganismen-Defektmutanten sowie neue Mikroorganismen-Stämme Eur Pat Appl 4913; CA 92:106618b

  • Henkel KGaA (1980) Verfahren zum selektiven Seitenkettenabbau von Steroidverbindungen und zur Herstellung hierzu geeigneter Mikroorganismen-Defektmutanten sowie neue Mikroorganismen-Stämme (II). Eur Pat Appl 15308; CA 93:236940c

  • Jaffé HH, Orchin M (1962) Theory and application of UV spectroscopy, John Wiley, New York

    Google Scholar 

  • Jung G, Koenig WA, Voelter W, Gupta D, Breitmaier G, Bierich JR (1973) 1,4-Androsta-diene-3,17-dione found in the urine of a boy. Steroids 22(2):293–306

    Article  PubMed  Google Scholar 

  • Kieslich K (1980a) Industrial aspects of biotechnological production of steroids. Biotechnol Letters 2:211–217

    Article  Google Scholar 

  • Kieslich K (1980b) “Steroid conversions” in Economic Micobiology, Vol 5, Rose AH (ed). Academic Press, London New York Toronto Sydney San Francisco, pp 370–413

    Google Scholar 

  • Marshek WJ, Kraychy S, Muir RD (1972) Microbial degradation of sterols. Appl Microbiol 23:72–77

    PubMed  Google Scholar 

  • Mason SF (1963) Optical rotatory power. Quart Rev 17:20–66

    Article  Google Scholar 

  • Martin CKA (1977) Microbial cleavage of sterol side chains. Adv Appl Microbiol 22:29–58

    PubMed  Google Scholar 

  • Martin CKA, Wagner F (1976) Microbial transformation of β-sitosterol byNocardia sp M 29. Eur J Appl Microbiol Biotechnol 2:243–255

    Google Scholar 

  • Mitsubishi Chemical Industries Co. Ltd. (1979) Steroidal alcohols by cultivatingMycobacterium. Eur Pat Appl 1622; CA 92:4699g

  • Mogil'nitskii GM, Andreev LV, Koshcheenko KA (1974) Enzymatic destruction of steroids in the process of 11α-and 11β-hydroxylation of the 21-acetate of the Reichstein substance “S” by the fungus Tieghemella orchidis. Mikrobiologiya 44:351–356

    Google Scholar 

  • Nagasava M, Watanabe N, Hashiba H, Tamura G, Arima K (1970) Microbial transformation of sterols. Agric Biol Chem 34:798–800, 801–804, 838–844

    Google Scholar 

  • Neff G, Eder U, Seeger A, Wiechert R (1980) Aufbau von Pregnan-Seitenketten. Chem Ber 113:1184–1188

    Google Scholar 

  • Nominé G (1980) La place des bioconversions dans l'accès industriel aux steroides. Bull Soc Chim France II:18–23

    Google Scholar 

  • Schatz A, Savard K, Pintner IF (1949) The ability of soil microorganisms to decompose steroids. J Bacteriol 58:117–125

    Google Scholar 

  • Schering AG (1979) Verfahren zur Herstellung von 21-Hydroxy-20-methyl-pregnan-Derivaten. Eur Pat Appl 2535; CA 91:173386n

  • Schoemer U, Martin CKA (1980) Microbial transformation of sterols. Biotechnol Bioeng 80: (Suppl I Ferment Sci Technol Future): 11–25

    Google Scholar 

  • Schoemer U, Wagner F (1980) Production of steroid-ring-b-seco acid from β-sitosterol and influence of surfactants on sterol uptake inNocardia sp. M29-40. Eur J Appl Microbiol Biotechnol 10:99–106

    Article  Google Scholar 

  • Schubert K, Böhme KH, Hörhold C (1978) Verfahren zur Herstellung von 20-Carboxy-pregna-1,4-dien-3-one. East-G. patent 132271; CA 91:106618b

  • Sih CJ, Wang KC, Tai HH (1967a) Mechanism of steroid oxidation by microorganisms XIII. C22 acid intermediates in the degradation of the cholesterol side chain. Biochem 7:796–807

    Google Scholar 

  • Sih CJ, Tai HH, Tsong YY (1967b) The mechanism of microbial conversion of cholesterol into 17-keto steroids. J Am Chem Soc 89:1957–1958

    Article  PubMed  Google Scholar 

  • Stadtman TC, Cherkes A, Anfinsen CB (1954) Studies on the microbial degradation of cholesterol. J Biol Chem 206:511–235

    PubMed  Google Scholar 

  • Turfitt GE (1944) Microbial agencies in the degradation of sterols. J Bacteriol 47:487–494, 54:557–562

    Google Scholar 

  • VanRheenen V, Shephard KP (1979) New synthesis of corticosteroids from 17-keto steroids: application and sterochemical study of the unsaturated sulfoxide-sulfonate rearrangement. J Org Chem 44:1582–1584

    Article  Google Scholar 

  • Whitmarsh JM (1964) Intermediates of microbiological metabolism of cholesterol. Biochem J 90:23p-24p

    Google Scholar 

  • Wovcha MG, Antosz FJ, Knight JC, Kominek LA, Pyke, TR (1978) Bioconversion of sitosterol to useful steroidal intermediates by mutants ofMycobacterium fortuitum. Biochim Biophys Acta 531:308–321

    PubMed  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Henkel KGaA, D-4000, Düsseldorf

    F. F. Hill, J. Schindler, R. Schmid & R. Wagner

  2. Abteilung für Organische und Physikalische Biochemie, Physiologisch-Chemisches Institut der Universität Tübingen, D-7400, Tübingen, Federal Republic of Germany

    W. Voelter

Authors
  1. F. F. Hill
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. J. Schindler
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. R. Schmid
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. R. Wagner
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. W. Voelter
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Dedicated to Dr. Bruno Werdelmann

Rights and permissions

Reprints and permissions

About this article

Cite this article

Hill, F.F., Schindler, J., Schmid, R. et al. Microbial conversion of sterols. European J. Appl. Microbiol. Biotechnol. 15, 25–32 (1982). https://doi.org/10.1007/BF01875396

Download citation

  • Received:

  • Revised:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF01875396

Keywords

Search

Navigation