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Applied Microbiology and Biotechnology

, Volume 67, Issue 4, pp 477–483 | Cite as

Bioconversion of (+)-valencene in submerged cultures of the ascomycete Chaetomium globosum

  • Rüdiger Kaspera
  • Ulrich Krings
  • Tsevegsuren Nanzad
  • Ralf G. BergerEmail author
Biotechnological Products and Process Engineering

Abstract

Submerged cultures of the ascomycete Chaetomium globosum oxidised the exogenous sesquiterpene (+)-valencene to nootkatone via the stereoselective generation of α-nootkatol. Inhibition experiments suggested that the first introduction of oxygen, the rate-limiting step of the bioconversion, may have been catalysed by a cytochrome-P450-monooxygenase. However, nootkatone was not the final metabolite: further flavour-active and inactive, non-volatile oxidation products were identified. (+)-Valencene and the flavour-active mono-oxyfunctionalised transformation products, α-nootkatol, nootkatone, and valencene-11,12-epoxide accumulated preferably inside the fungal cells. Di- and poly-oxygenated products, such as nootkatone-11,12-epoxide, were found solely in the culture medium, indicating an active transport of these metabolites into the extracellular compartment during (+)-valencene detoxification. These metabolic properties may have contributed to the high tolerance of the fungus towards the exogenous hydrocarbon.

Keywords

Valencene Epoxide Transformation Product Rhodococcus Erythropolis Allylic Oxidation 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Notes

Acknowledgements

This project was supported by the Federal Ministry of Education and Research (BMBF 0330062) and is part of the joint initiative project ‘Biologisch aktive Naturstoffe—Chemische Diversität’ at the University of Hannover. We thank E. Hofer of the Department of Organic Chemistry from the University of Hannover for his help in NMR analyses

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Copyright information

© Springer-Verlag 2004

Authors and Affiliations

  • Rüdiger Kaspera
    • 1
  • Ulrich Krings
    • 1
  • Tsevegsuren Nanzad
    • 2
  • Ralf G. Berger
    • 1
    Email author
  1. 1.Zentrum für Angewandte Chemie der Universität HannoverInstitut für LebensmittelchemieHannoverGermany
  2. 2.Department of Organic and Food ChemistryNational University of MongoliaUlaanbaatarMongolia

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