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Formation of hydroxylated steroid lactones from dehydroepiandrosterone by Spicaria fumoso-rosea F-881

  • To the 50th Anniversary of the Skryabin Institute of Biochemistry and Physiology of Microorganisms, Russian Academy of Sciences
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Abstract

The transformation of dehydroepiandrosterone by Spicaria fumoso-rosea VKM F-881 produced 7α- and 7β-hydroxy-dehydroepiandrosterone, 3β,7α-dihydroxy-17a-oxa-D-homo-androst-5-en-17-one, and 3β,7β-dihydroxy-17a-oxa-D-homo-androst-5-en-17-one. The yield of the main product—3β,7β-dihydroxy-17a-oxa-D-homo-androst-5-en-17-one—was 49.5–72 mol % at substrate loadings of 5–20 g/L. Lactone formation proceeded through 7α- and 7β-hydroxy derivatives of dehydroepiandrosterone. The structure of the products was determined by mass spectrometry, 1H-NMR spectroscopy, and 13C-NMR spectroscopy. The proposed microbiological method for producing steroid lactones opens prospects for the synthesis of novel steroid compounds.

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Authors and Affiliations

  1. Skryabin Institute of Biochemistry and Physiology of Microorganisms, Russian Academy of Sciences, Pushchino, Moscow oblast, 142290, Russia

    T. G. Lobastova, S. M. Khomutov & M. V. Donova

Authors
  1. T. G. Lobastova
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  2. S. M. Khomutov
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  3. M. V. Donova
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Correspondence to T. G. Lobastova.

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Original Russian Text © T.G. Lobastova, S.M. Khomutov, M.V. Donova, 2015, published in Prikladnaya Biokhimiya i Mikrobiologiya, 2015, Vol. 51, No. 2, pp. 174–182.

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Lobastova, T.G., Khomutov, S.M. & Donova, M.V. Formation of hydroxylated steroid lactones from dehydroepiandrosterone by Spicaria fumoso-rosea F-881. Appl Biochem Microbiol 51, 180–187 (2015). https://doi.org/10.1134/S000368381502012X

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  • DOI: https://doi.org/10.1134/S000368381502012X

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