TY - JOUR
T1 - Structural characterisation of metabolites from Pholiota spumosa (Basidiomycetes)
AU - Clericuzio, Marco
AU - Piovano, Marisa
AU - Chamy, Maria C.
AU - Garbarino, Juan A.
AU - Milanesio, Marco
AU - Viterbo, Davide
AU - Vidari, Giovanni
AU - Finzi, Paola Vita
PY - 2004/11
Y1 - 2004/11
N2 - Three compounds of different biosynthetic origin were isolated from the fruiting bodies of the gilled mushroom Pholiota spumosa (Basidiomycetes, Strophariaceae). Fasciculol E, a lanostane triterpenoid conjugated to a depsipeptide unit, was isolated for the first time from genus Pholiota. In addition, the first isolation of putrescine-1,4-dicinnamamide as a natural compound is reported: its structure was established by single crystal X-ray diffraction, and by spectroscopic methods. Crystallographic analysis indicated the presence of a co-crystallised related dicinnamamide, namely the new compound (E)-2,3-dehydroputrescine-1,4-dicinnamamide, whose occurrence was confirmed by LC-MS analysis. An interesting evolutionary issue arises, following the observation that the cinnamamides produced by Pholiota spumosa bear an unsubstituted benzene ring, contrarily to those found in plants, which have always phenolic functionalities, and as such perform a variety of biological roles.
AB - Three compounds of different biosynthetic origin were isolated from the fruiting bodies of the gilled mushroom Pholiota spumosa (Basidiomycetes, Strophariaceae). Fasciculol E, a lanostane triterpenoid conjugated to a depsipeptide unit, was isolated for the first time from genus Pholiota. In addition, the first isolation of putrescine-1,4-dicinnamamide as a natural compound is reported: its structure was established by single crystal X-ray diffraction, and by spectroscopic methods. Crystallographic analysis indicated the presence of a co-crystallised related dicinnamamide, namely the new compound (E)-2,3-dehydroputrescine-1,4-dicinnamamide, whose occurrence was confirmed by LC-MS analysis. An interesting evolutionary issue arises, following the observation that the cinnamamides produced by Pholiota spumosa bear an unsubstituted benzene ring, contrarily to those found in plants, which have always phenolic functionalities, and as such perform a variety of biological roles.
KW - Cinnamic acid amides
KW - Fungi
KW - Pholiota spumosa
KW - Strophariaceae
KW - Terpenes
KW - X-ray crystal structure
UR - http://www.scopus.com/inward/record.url?scp=10644265939&partnerID=8YFLogxK
M3 - Article
SN - 0011-1643
VL - 77
SP - 605
EP - 611
JO - Croatica Chemica Acta
JF - Croatica Chemica Acta
IS - 4
ER -