Diketopiperazines and arylethylamides produced by Schizophyllum commune, an endophytic fungus in Alchornea glandulosa

Chemical investigation of the crude PDB extract obtained from the endophytic fungus Schizophyllum commune afforded the pure substances, cyclo(L-Pro-L-Val) (1), uracil (2), cyclo(Pro-Tyr) (3), p-hydroxybenzoic acid (4) and a mixture of Rel.cyclo(Pro-Phe) (5) and Rel.cyclo(Pro-Ile) (6). When cultured...

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Bibliographic Details
Main Authors: Carolina Rabal Biasetto, Andressa Somensi, Fernanda Sales Figueiro, Luiz Alberto Beraldo de Moraes, Geraldo Humberto Silva, Maria Claudia Marx Young, Vanderlan da Silva Bolzani, Angela Regina Araújo
Format: Article
Language:English
Published: Universidade Estadual Paulista 2019-07-01
Series:Eclética Química
Online Access:https://revista.iq.unesp.br/ojs/index.php/ecletica/article/view/977
Description
Summary:Chemical investigation of the crude PDB extract obtained from the endophytic fungus Schizophyllum commune afforded the pure substances, cyclo(L-Pro-L-Val) (1), uracil (2), cyclo(Pro-Tyr) (3), p-hydroxybenzoic acid (4) and a mixture of Rel.cyclo(Pro-Phe) (5) and Rel.cyclo(Pro-Ile) (6). When cultured in corn, the extract of this fungus yielded N-(2-phenylethyl) acetamide (7) and N-(4-hydroxyphenylethyl) acetamide (8). The structures of all compounds were determined based on the analyses of their MS, 1D and 2D-NMR spectroscopic data. Analysis of the crude extracts obtained from small-scale cultures (in PBD, YM, Nutrient, Czapek, Malt Extract, Corn and Rice) and a large-scale culture (in PDB) by mass spectrometry showed the presence of diketopiperazines 1, 3, 5 and 6. The crude extracts showed promising antioxidant, antifungal and acetylcholinesterase (AChE) inhibitory activities. The metabolites 7 and 8 showed antifungal and AChE inhibitory activities in vitro. This is the first report of the identification and isolation of diketopiperazines, arylethylamides, p-hydroxybenzoic acid in endophytic fungus of the Schizophyllum genus.
ISSN:1678-4618