Diketopiperazines and arylethylamides produced by Schizophyllum commune, an endophytic fungus in Alchornea glandulosa
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| Format: | Artículo científico |
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Universidade Estadual Paulista Júlio de Mesquita Filho
2019
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| author | Carolina Rabal Biasetto |
| author_facet | Carolina Rabal Biasetto |
| contents | Diketopiperazines and arylethylamides produced by Schizophyllum commune, an endophytic fungus in Alchornea glandulosa 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 Química arylethylamides Endophytic fungi diketopiperazines Alchornea glandulosa Schizophyllum commune 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. 2019 artículo científico 0100-4670 https://www.redalyc.org/articulo.oa?id=42959945003 https://www.redalyc.org/journal/429/42959945003/ https://www.redalyc.org/journal/429/42959945003/html/ https://www.redalyc.org/journal/429/42959945003/42959945003.epub https://www.redalyc.org/journal/429/42959945003/movil https://doi.org/10.26850/1678-4618eqj.v44.3.2019.p36-42 en http://www.redalyc.org/revista.oa?id=429 Eclética Química application/pdf Universidade Estadual Paulista Júlio de Mesquita Filho Eclética Química (Brasil) Num.3 Vol.44 |
| format | Artículo científico |
| id | redalyc_42959945003 |
| institution | Redalyc |
| language | en |
| publishDate | 2019 |
| publisher | Universidade Estadual Paulista Júlio de Mesquita Filho |
| spellingShingle | Diketopiperazines and arylethylamides produced by Schizophyllum commune, an endophytic fungus in Alchornea glandulosa Carolina Rabal Biasetto Química arylethylamides Endophytic fungi diketopiperazines Alchornea glandulosa Schizophyllum commune Diketopiperazines and arylethylamides produced by Schizophyllum commune, an endophytic fungus in Alchornea glandulosa 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 Química arylethylamides Endophytic fungi diketopiperazines Alchornea glandulosa Schizophyllum commune 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. 2019 artículo científico 0100-4670 https://www.redalyc.org/articulo.oa?id=42959945003 https://www.redalyc.org/journal/429/42959945003/ https://www.redalyc.org/journal/429/42959945003/html/ https://www.redalyc.org/journal/429/42959945003/42959945003.epub https://www.redalyc.org/journal/429/42959945003/movil https://doi.org/10.26850/1678-4618eqj.v44.3.2019.p36-42 en http://www.redalyc.org/revista.oa?id=429 Eclética Química application/pdf Universidade Estadual Paulista Júlio de Mesquita Filho Eclética Química (Brasil) Num.3 Vol.44 |
| title | Diketopiperazines and arylethylamides produced by Schizophyllum commune, an endophytic fungus in Alchornea glandulosa |
| topic | Química arylethylamides Endophytic fungi diketopiperazines Alchornea glandulosa Schizophyllum commune |
| url | https://www.redalyc.org/articulo.oa?id=42959945003 https://www.redalyc.org/journal/429/42959945003/ https://www.redalyc.org/journal/429/42959945003/html/ https://www.redalyc.org/journal/429/42959945003/42959945003.epub https://www.redalyc.org/journal/429/42959945003/movil https://doi.org/10.26850/1678-4618eqj.v44.3.2019.p36-42 |