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

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, a...

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Bibliographic Details
Published in:Phytochemistry (Oxford) 2013-06, Vol.90, p.128-134
Main Authors: Nord, Christina L, Menkis, Audrius, Vasaitis, Rimvydas, Broberg, Anders
Format: Article
Language:English
Subjects:
Basidiomycetes
Coniophora puteana
Phlebiopsis gigantea
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Summary: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 10 mu M, 500 mu M and 100 mu M, respectively. None of the other substances tested gave rise to any growth inhibition.
ISSN:0031-9422