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

Christina L Nord; Audrius Menkis; Rimvydas Vasaitis; Anders Broberg

doi:10.1016/j.phytochem.2013.02.015

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

Phytochemistry. 2013 Jun:90:128-34. doi: 10.1016/j.phytochem.2013.02.015. Epub 2013 Mar 19.

Authors

Christina L Nord¹, Audrius Menkis, Rimvydas Vasaitis, Anders Broberg

Affiliation

¹ Department of Chemistry, Uppsala BioCenter, Swedish University of Agricultural Sciences, P.O. Box 7015, SE-75007 Uppsala, Sweden.

PMID: 23517685
DOI: 10.1016/j.phytochem.2013.02.015

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 1a 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 10μM, 500μM and 100μM, respectively. None of the other substances tested gave rise to any growth inhibition.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Fungi / chemistry*
Molecular Conformation
Polycyclic Sesquiterpenes
Sesquiterpenes / chemistry
Sesquiterpenes / isolation & purification*

Substances

Polycyclic Sesquiterpenes
Sesquiterpenes
protoilludane