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Communications chemistry
Apr 24, 2023;6 (1): 79.

Isolation, (bio)synthetic studies and evaluation of antimicrobial properties of drimenol-type sesquiterpenes of Termitomyces fungi.

Nina B Kreuzenbeck, Seema Dhiman, D��vid Roman, Immo Burkhardt, Benjamin H Conlon, Janis Fricke, Huijuan Guo, Janis Blume, Helmar G��rls, Michael Poulsen, Jeroen S Dickschat, Tobias G K��llner, Hans-Dieter Arndt, Christine Beemelmanns
Author Information
  1. Nina B Kreuzenbeck: Chemical Biology of Microbe-Host Interactions, Leibniz Institute for Natural Product Research and Infection Biology - Hans Kn��ll-Institute (HKI), Beutenbergstra��e 11a, 07745, Jena, Germany.
  2. Seema Dhiman: Institute for Organic and Macromolecular Chemistry, Friedrich-Schiller-University Jena, Humboldtstr. 10, 07743, Jena, Germany.
  3. D��vid Roman: Chemical Biology of Microbe-Host Interactions, Leibniz Institute for Natural Product Research and Infection Biology - Hans Kn��ll-Institute (HKI), Beutenbergstra��e 11a, 07745, Jena, Germany. ORCID
  4. Immo Burkhardt: Kekul��-Institute of Organic Chemistry and Biochemistry, University of Bonn, Gerhard-Domagk-Stra��e 1, 53121, Bonn, Germany.
  5. Benjamin H Conlon: Section for Ecology and Evolution, Department of Biology, University of Copenhagen, Universitetsparken 15 2100, Copenhagen, Denmark.
  6. Janis Fricke: Chemical Biology of Microbe-Host Interactions, Leibniz Institute for Natural Product Research and Infection Biology - Hans Kn��ll-Institute (HKI), Beutenbergstra��e 11a, 07745, Jena, Germany.
  7. Huijuan Guo: Chemical Biology of Microbe-Host Interactions, Leibniz Institute for Natural Product Research and Infection Biology - Hans Kn��ll-Institute (HKI), Beutenbergstra��e 11a, 07745, Jena, Germany. ORCID
  8. Janis Blume: Institute for Organic and Macromolecular Chemistry, Friedrich-Schiller-University Jena, Humboldtstr. 10, 07743, Jena, Germany.
  9. Helmar G��rls: Institute for Inorganic and Analytical Chemistry, Friedrich-Schiller University, Humboldtstrasse 8, 07743, Jena, Germany.
  10. Michael Poulsen: Section for Ecology and Evolution, Department of Biology, University of Copenhagen, Universitetsparken 15 2100, Copenhagen, Denmark. ORCID
  11. Jeroen S Dickschat: Kekul��-Institute of Organic Chemistry and Biochemistry, University of Bonn, Gerhard-Domagk-Stra��e 1, 53121, Bonn, Germany. ORCID
  12. Tobias G K��llner: Department of Natural Product Biosynthesis, Max Planck Institute for Chemical Ecology, Hans-Kn��ll-Stra��e 8, 07745, Jena, Germany.
  13. Hans-Dieter Arndt: Institute for Organic and Macromolecular Chemistry, Friedrich-Schiller-University Jena, Humboldtstr. 10, 07743, Jena, Germany.
  14. Christine Beemelmanns: Chemical Biology of Microbe-Host Interactions, Leibniz Institute for Natural Product Research and Infection Biology - Hans Kn��ll-Institute (HKI), Beutenbergstra��e 11a, 07745, Jena, Germany. Christine.Beemelmanns@helmholtz-hips.de. ORCID
PMID: 37095327 DOI: 10.1038/s42004-023-00871-z

Abstract

Macrotermitinae termites have farmed fungi in the genus Termitomyces as a food source for millions of years. However, the biochemical mechanisms orchestrating this mutualistic relationship are largely unknown. To deduce fungal signals and ecological patterns that relate to the stability of this symbiosis, we explored the volatile organic compound (VOC) repertoire of Termitomyces from Macrotermes natalensis colonies. Results show that mushrooms emit a VOC pattern that differs from mycelium grown in fungal gardens and laboratory cultures. The abundance of sesquiterpenoids from mushrooms allowed targeted isolation of five drimane sesquiterpenes from plate cultivations. The total synthesis of one of these, drimenol, and related drimanes assisted in structural and comparative analysis of volatile organic compounds (VOCs) and antimicrobial activity testing. Enzyme candidates putatively involved in terpene biosynthesis were heterologously expressed and while these were not involved in the biosynthesis of the complete drimane skeleton, they catalyzed the formation of two structurally related monocyclic sesquiterpenes named nectrianolins.

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Grants

  1. 796194/EC | EC Seventh Framework Programm | FP7 People: Marie-Curie Actions (FP7-PEOPLE - Specific Programme "People" Implementing the Seventh Framework Programme of the European Community for Research, Technological Development and Demonstration Activities (2007 to 2013))
  2. 771349/EC | EU Framework Programme for Research and Innovation H2020 | H2020 Priority Excellent Science | H2020 European Research Council (H2020 Excellent Science - European Research Council)
  3. Project-ID 239748522/Deutsche Forschungsgemeinschaft (German Research Foundation)
  4. INST 275/442-1 FUGG/Deutsche Forschungsgemeinschaft (German Research Foundation)
  5. Project-ID 239748522/Deutsche Forschungsgemeinschaft (German Research Foundation)
Journal Article
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Word Cloud

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