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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| Format: | Article |
| Language: | English |
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Universidade Estadual Paulista
2019-07-01
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| Series: | Eclética Química |
| Online Access: | https://revista.iq.unesp.br/ojs/index.php/ecletica/article/view/977 |
| _version_ | 1818995683142664192 |
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| author | 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 |
| author_facet | 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 |
| author_sort | Carolina Rabal Biasetto |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-12-20T21:17:44Z |
| format | Article |
| id | doaj.art-c98fc9aa8eec49b6816ece80e92b3e5c |
| institution | Directory Open Access Journal |
| issn | 1678-4618 |
| language | English |
| last_indexed | 2024-12-20T21:17:44Z |
| publishDate | 2019-07-01 |
| publisher | Universidade Estadual Paulista |
| record_format | Article |
| series | Eclética Química |
| spelling | doaj.art-c98fc9aa8eec49b6816ece80e92b3e5c2022-12-21T19:26:22ZengUniversidade Estadual PaulistaEclética Química1678-46182019-07-01443364210.26850/1678-4618eqj.v44.3.2019.p36-42977Diketopiperazines and arylethylamides produced by Schizophyllum commune, an endophytic fungus in Alchornea glandulosaCarolina Rabal Biasetto0Andressa Somensi1Fernanda Sales Figueiro2Luiz Alberto Beraldo de Moraes3Geraldo Humberto Silva4Maria Claudia Marx Young5Vanderlan da Silva Bolzani6Angela Regina Araújo7São Paulo State University (Unesp), Institute of Chemistry, 55 Prof. Francisco Degni Av., Araraquara, São Paulo, BrazilSão Paulo State University (Unesp), Institute of Chemistry, 55 Prof. Francisco Degni Av., Araraquara, São Paulo, BrazilUniversity of São Paulo (USP), Faculty of Philosophy, Sciences and Letters, 3900 Bandeirantes Av., Ribeirão Preto, São Paulo, BrazilUniversity of São Paulo (USP), Faculty of Philosophy, Sciences and Letters, 3900 Bandeirantes Av., Ribeirão Preto, São Paulo, BrazilFederal University of Viçosa (UFV), Institute of Science Exact and Technological, Peter Henry Rolfs Av., Viçosa, Minas Gerais, BrazilSão Paulo Institute of Botany, Nucleus of Research in Physiology and Biochemistry, 3687 Miguel Stéfano Av., São Paulo, São Paulo, BrazilSão Paulo State University (Unesp), Institute of Chemistry, 55 Prof. Francisco Degni Av., Araraquara, São Paulo, BrazilSão Paulo State University (Unesp), Institute of Chemistry, 55 Prof. Francisco Degni Av., Araraquara, São Paulo, BrazilChemical 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.https://revista.iq.unesp.br/ojs/index.php/ecletica/article/view/977 |
| spellingShingle | 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 Diketopiperazines and arylethylamides produced by Schizophyllum commune, an endophytic fungus in Alchornea glandulosa Eclética Química |
| title | Diketopiperazines and arylethylamides produced by Schizophyllum commune, an endophytic fungus in Alchornea glandulosa |
| title_full | Diketopiperazines and arylethylamides produced by Schizophyllum commune, an endophytic fungus in Alchornea glandulosa |
| title_fullStr | Diketopiperazines and arylethylamides produced by Schizophyllum commune, an endophytic fungus in Alchornea glandulosa |
| title_full_unstemmed | Diketopiperazines and arylethylamides produced by Schizophyllum commune, an endophytic fungus in Alchornea glandulosa |
| title_short | Diketopiperazines and arylethylamides produced by Schizophyllum commune, an endophytic fungus in Alchornea glandulosa |
| title_sort | diketopiperazines and arylethylamides produced by schizophyllum commune an endophytic fungus in alchornea glandulosa |
| url | https://revista.iq.unesp.br/ojs/index.php/ecletica/article/view/977 |
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