Protoilludane sesquiterpenes from the wood decomposing fungus Granulobasidium vellereum (Ellis & Cragin) Julich

Abstract

The secondary metabolites of the saprotrophic wood-decay basidiomycete fungus Granulobasidium vellereum were studied. Six sesquiterpenes were obtained; 2-hydroxycoprinolone (1), 8-deoxy-4a-hydroxytsugicoline (2), 8-deoxydihydrotsugicoline (3), which were previously not described, radulone A and B, and coprinolone ketodiol. Additionally, base-treatment of 1 yielded the diagnostic degradation products la and 1b, whereas radulone A was found to form 4 under mild acidic conditions. The structures were determined by NMR, MS, CD and polarimetry, along with biosynthetic considerations. Radulone A fully inhibited the spore germination of the potentially competing fungi Phlebiopsis gigantea, Coniophora puteana and Heterobasidion occidentale at 10 mu M, 500 mu M and 100 mu M, respectively. None of the other substances tested gave rise to any growth inhibition. (C) 2013 Elsevier Ltd. All rights reserved.

Keywords

Cyphellaceae; Granulobasidium vellereum; Structural elucidation; Sesquiterpenes; Protoilludane

Published in

Phytochemistry
2013, volume: 90, pages: 128-134
Publisher: PERGAMON-ELSEVIER SCIENCE LTD

SLU Authors

• Nord, Christina

  • Department of Molecular Sciences, Swedish University of Agricultural Sciences
    

• Menkis, Audrius

  • Department of Forest Mycology and Plant Pathology, Swedish University of Agricultural Sciences
    

• Vasaitis, Rimvydas

  • Department of Forest Mycology and Plant Pathology, Swedish University of Agricultural Sciences
    

• Broberg, Anders

  • Department of Molecular Sciences, Swedish University of Agricultural Sciences
    

UKÄ Subject classification

Organic Chemistry
Microbiology

Publication identifier

• DOI: https://doi.org/10.1016/j.phytochem.2013.02.015

Permanent link to this page (URI)

https://res.slu.se/id/publ/56007