Insights into the Metabolomic Capacity of Podaxis and Isolation of Podaxisterols A-D, Ergosterol Derivatives Carrying Nitrosyl Cyanide-Derived Modifications
Publikation: Bidrag til tidsskrift › Tidsskriftartikel › Forskning › fagfællebedømt
Cultures of a termite-associated and a free-living member of the fungal genus Podaxis, revived from spores maintained in century-old herbarium collections, were analyzed for their insecticidal and antimicrobial effects. Their secondary metabolomes were explored to uncover possible adaptive mechanisms of termite association, and dereplication of LC-HRMS/MS data sets led to the isolation of podaxisterols A-D (1-4), modified ergosterol derivatives that result from a Diels-Alder reaction with endogenous nitrosyl cyanide. Chemical structures were determined based on HRMS/MS and NMR analyses as well as X-ray crystallography. The putative origin of the endogenous fungal nitrosyl cyanide and ergosterol derivatives is discussed based on results obtained from stable isotope experiments and in silico analysis. Our "omics"-driven analysis of this underexplored yet worldwide distributed fungal genus builds a foundation for studies on a potential metabolic adaptations to diverse lifestyles.
Originalsprog | Engelsk |
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Tidsskrift | Journal of Natural Products |
Vol/bind | 85 |
Udgave nummer | 9 |
Sider (fra-til) | 2159-2167 |
ISSN | 0163-3864 |
DOI | |
Status | Udgivet - 2022 |
Bibliografisk note
Funding Information:
We are grateful for financial support from the German Research Foundation (BE 4799/3-1, BE 4799/4-1 within the FOR 5170/1) and the Collaborative Research Center 1127 ChemBioSys (project number 09161509, projects A6 and B07). We acknowledge funding by the Independent Research Fund Denmark (DFF-7014-00178) to M.P. and the Max Planck Society to D.G.V. We wish to thank Ms. Heike Heinecke (Hans Knöll Institute, Jena) for measurement of NMR spectra, Mr. Janis Fricke for assistance with fungal genome analysis, and Ms. Christiane Weigel and Dr. Hans-Martin Dahse for initial bioactivity studies.
Publisher Copyright:
© 2022 American Chemical Society and American Society of Pharmacognosy.
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