TY - JOUR
T1 - Protoilludane sesquiterpenes from the wood decomposing fungus Granulobasidium vellereum (Ellis & Cragin) Julich
AU - Nord, Christina
AU - Menkis, Audrius
AU - Vasaitis, Rimvydas
AU - Broberg, Anders
PY - 2013
Y1 - 2013
N2 - 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.
AB - 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.
KW - Cyphellaceae
KW - Granulobasidium vellereum
KW - Structural elucidation
KW - Sesquiterpenes
KW - Protoilludane
KW - Cyphellaceae
KW - Granulobasidium vellereum
KW - Structural elucidation
KW - Sesquiterpenes
KW - Protoilludane
UR - https://res.slu.se/id/publ/56007
U2 - 10.1016/j.phytochem.2013.02.015
DO - 10.1016/j.phytochem.2013.02.015
M3 - Journal article
C2 - 23517685
SN - 0031-9422
VL - 90
SP - 128
EP - 134
JO - Phytochemistry
JF - Phytochemistry
ER -