Structural Characterisation of Metabolites from Pholiota spumosa BasidiomycetesReport as inadecuate

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Croatica Chemica Acta, Vol.77 No.4 November 2004. -

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.

Pholiota spumosa; Strophariaceae; fungi; terpenes; cinnamic acid amides; X-ray crystal structure

Author: Marco Clericuzio - ; Dipartimento di Chimica Generale ed Organica Applicata, Università di Torino, Via P. Giuria 7, 10125 Torino



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