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

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Published: Jul 21, 2019
DOI: https://doi.org/10.26850/1678-4618eqj.v44.3.2019.p36-42

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Angela Regina Araujo
São Paulo State University (Unesp), Institute of Chemistry, 55 Prof. Francisco Degni Av., Araraquara, São Paulo, Brazil
http://orcid.org/0000-0001-7616-9652
Carolina Rabal Biasetto
São Paulo State University (Unesp), Institute of Chemistry, 55 Prof. Francisco Degni Av., Araraquara, São Paulo, Brazil
http://orcid.org/0000-0003-3751-8922
Andressa Somensi
São Paulo State University (Unesp), Institute of Chemistry, 55 Prof. Francisco Degni Av., Araraquara, São Paulo, Brazil
http://orcid.org/0000-0001-6968-6205
Fernanda Sales Figueiro
University of São Paulo (USP), Faculty of Philosophy, Sciences and Letters, 3900 Bandeirantes Av., Ribeirão Preto, São Paulo, Brazil
http://orcid.org/0000-0002-1749-177X
Luiz Alberto Beraldo de Moraes
University of São Paulo (USP), Faculty of Philosophy, Sciences and Letters, 3900 Bandeirantes Av., Ribeirão Preto, São Paulo, Brazil
http://orcid.org/0000-0002-0853-1944
Geraldo Humberto Silva
Federal University of Viçosa (UFV), Institute of Science Exact and Technological, Peter Henry Rolfs Av., Viçosa, Minas Gerais, Brazil
http://orcid.org/0000-0001-7928-8980
Maria Claudia Marx Young
São Paulo Institute of Botany, Nucleus of Research in Physiology and Biochemistry, 3687 Miguel Stéfano Av., São Paulo, São Paulo, Brazil
http://orcid.org/0000-0002-2860-6659
Vanderlan da da Silva Bolzani
São Paulo State University (Unesp), Institute of Chemistry, 55 Prof. Francisco Degni Av., Araraquara, São Paulo, Brazil
http://orcid.org/0000-0001-7019-5825

Abstract

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.

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Araujo, A. R., Biasetto, C. R., Somensi, A., Figueiro, F. S., de Moraes, L. A. B., Silva, G. H., Young, M. C. M., & Bolzani, V. da da S. (2019). Diketopiperazines and arylethylamides produced by Schizophyllum commune, an endophytic fungus in Alchornea glandulosa. Eclética Química, 44(3), 36–42. https://doi.org/10.26850/1678-4618eqj.v44.3.2019.p36-42
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Vol. 44 No. 3 (2019): Eclética Química Journal
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Original articles

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