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.
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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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Kaspera, R., Krings, U., Nanzad, T. et al. Bioconversion of (+)-valencene in submerged cultures of the ascomycete Chaetomium globosum. Appl Microbiol Biotechnol 67, 477–483 (2005). https://doi.org/10.1007/s00253-004-1794-0
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DOI: https://doi.org/10.1007/s00253-004-1794-0