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Structural Characterisation of Metabolites from Pholiota spumosa (Basidiomycetes)

Marco Clericuzio ; Dipartimento di Chimica Generale ed Organica Applicata, Università di Torino, Via P. Giuria 7, 10125 Torino, Italy
Marisa Piovano ; Departamento de Quimica, Universidad Tecnica Federico Santa Maria, Casilla 110-V, Valparaiso, Chile
Maria C. Chamy ; Departamento de Quimica, Universidad Tecnica Federico Santa Maria, Casilla 110-V, Valparaiso, Chile
Juan A. Garbarino ; Departamento de Quimica, Universidad Tecnica Federico Santa Maria, Casilla 110-V, Valparaiso, Chile
Marco Milanesio ; Dipartimento di Scienze e Tecnologie Avanzate, Università del Piemonte Orientale, Corso Borsalino 54, 15100, Alessandria, Italy
Davide Viterbo ; Dipartimento di Scienze e Tecnologie Avanzate, Università del Piemonte Orientale, Corso Borsalino 54, 15100, Alessandria, Italy
Giovanni Vidari ; Dipartimento di Chimica Organica, Università di Pavia, Via Taramelli 10, 27100 Pavia, Italy
Paola Vita Finzi ; Dipartimento di Chimica Organica, Università di Pavia, Via Taramelli 10, 27100 Pavia, Italy

Sažetak

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.

Ključne riječi

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

Hrčak ID:

102987

URI

https://hrcak.srce.hr/102987

Datum izdavanja:

30.11.2004.

Posjeta: 1.770 *