Pipecolisporin, a Novel Cyclic Peptide with Antimalarial and Antitrypanosome Activities from a Wheat Endophytic <em>Nigrospora oryzae</em>
A novel cyclic antimalarial and antitrypanosome hexapeptide, pipecolisporin (<b>1</b>), was isolated from cultures of <i>Nigrospora oryzae</i> CF-298113, a fungal endophyte isolated from roots of <i>Triticum</i> sp. collected in a traditional agricultural land of...
| Main Authors: | , , , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2021-03-01
|
| Series: | Pharmaceuticals |
| Subjects: | |
| Online Access: | https://www.mdpi.com/1424-8247/14/3/268 |
| _version_ | 1797541191501217792 |
|---|---|
| author | Ignacio Fernández-Pastor Victor González-Menéndez Frederick Annang Clara Toro Thomas A. Mackenzie Cristina Bosch-Navarrete Olga Genilloud Fernando Reyes |
| author_facet | Ignacio Fernández-Pastor Victor González-Menéndez Frederick Annang Clara Toro Thomas A. Mackenzie Cristina Bosch-Navarrete Olga Genilloud Fernando Reyes |
| author_sort | Ignacio Fernández-Pastor |
| collection | DOAJ |
| description | A novel cyclic antimalarial and antitrypanosome hexapeptide, pipecolisporin (<b>1</b>), was isolated from cultures of <i>Nigrospora oryzae</i> CF-298113, a fungal endophyte isolated from roots of <i>Triticum</i> sp. collected in a traditional agricultural land of Montefrío, Granada, Spain. The structure of this compound, including its absolute configuration, was elucidated by HRMS, 1-D and 2-D NMR spectroscopy, and Marfey’s analysis. This metabolite displayed interesting activity against <i>Plasmodium falciparum</i> and <i>Trypanosoma cruzi</i>, with IC<sub>50</sub> values in the micromolar range, and no significant cytotoxicity against the human cancer cell lines A549, A2058, MCF7, MIA PaCa-2, and HepG2. |
| first_indexed | 2024-03-10T13:12:42Z |
| format | Article |
| id | doaj.art-897cfac6364e4723b639884aefc694ab |
| institution | Directory Open Access Journal |
| issn | 1424-8247 |
| language | English |
| last_indexed | 2024-03-10T13:12:42Z |
| publishDate | 2021-03-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Pharmaceuticals |
| spelling | doaj.art-897cfac6364e4723b639884aefc694ab2023-11-21T10:40:00ZengMDPI AGPharmaceuticals1424-82472021-03-0114326810.3390/ph14030268Pipecolisporin, a Novel Cyclic Peptide with Antimalarial and Antitrypanosome Activities from a Wheat Endophytic <em>Nigrospora oryzae</em>Ignacio Fernández-Pastor0Victor González-Menéndez1Frederick Annang2Clara Toro3Thomas A. Mackenzie4Cristina Bosch-Navarrete5Olga Genilloud6Fernando Reyes7Fundación MEDINA, Centro de Excelencia en Investigación de Medicamentos Innovadores de Andalucía, Parque Tecnológico de Ciencias de la Salud, Avda. del Conocimiento 34, 18016 Granada, SpainFundación MEDINA, Centro de Excelencia en Investigación de Medicamentos Innovadores de Andalucía, Parque Tecnológico de Ciencias de la Salud, Avda. del Conocimiento 34, 18016 Granada, SpainFundación MEDINA, Centro de Excelencia en Investigación de Medicamentos Innovadores de Andalucía, Parque Tecnológico de Ciencias de la Salud, Avda. del Conocimiento 34, 18016 Granada, SpainFundación MEDINA, Centro de Excelencia en Investigación de Medicamentos Innovadores de Andalucía, Parque Tecnológico de Ciencias de la Salud, Avda. del Conocimiento 34, 18016 Granada, SpainFundación MEDINA, Centro de Excelencia en Investigación de Medicamentos Innovadores de Andalucía, Parque Tecnológico de Ciencias de la Salud, Avda. del Conocimiento 34, 18016 Granada, SpainInstituto de Parasitología y Biomedicina “López-Neyra”, Consejo Superior de Investigaciones Científicas (CSIC) Avda. del Conocimiento 17, Armilla, 18016 Granada, SpainFundación MEDINA, Centro de Excelencia en Investigación de Medicamentos Innovadores de Andalucía, Parque Tecnológico de Ciencias de la Salud, Avda. del Conocimiento 34, 18016 Granada, SpainFundación MEDINA, Centro de Excelencia en Investigación de Medicamentos Innovadores de Andalucía, Parque Tecnológico de Ciencias de la Salud, Avda. del Conocimiento 34, 18016 Granada, SpainA novel cyclic antimalarial and antitrypanosome hexapeptide, pipecolisporin (<b>1</b>), was isolated from cultures of <i>Nigrospora oryzae</i> CF-298113, a fungal endophyte isolated from roots of <i>Triticum</i> sp. collected in a traditional agricultural land of Montefrío, Granada, Spain. The structure of this compound, including its absolute configuration, was elucidated by HRMS, 1-D and 2-D NMR spectroscopy, and Marfey’s analysis. This metabolite displayed interesting activity against <i>Plasmodium falciparum</i> and <i>Trypanosoma cruzi</i>, with IC<sub>50</sub> values in the micromolar range, and no significant cytotoxicity against the human cancer cell lines A549, A2058, MCF7, MIA PaCa-2, and HepG2.https://www.mdpi.com/1424-8247/14/3/268pipecolisporin<i>Nigrospora oryzae</i>fungal endophytestructural elucidationMarfey’s analysisantiparasitic activity |
| spellingShingle | Ignacio Fernández-Pastor Victor González-Menéndez Frederick Annang Clara Toro Thomas A. Mackenzie Cristina Bosch-Navarrete Olga Genilloud Fernando Reyes Pipecolisporin, a Novel Cyclic Peptide with Antimalarial and Antitrypanosome Activities from a Wheat Endophytic <em>Nigrospora oryzae</em> Pharmaceuticals pipecolisporin <i>Nigrospora oryzae</i> fungal endophyte structural elucidation Marfey’s analysis antiparasitic activity |
| title | Pipecolisporin, a Novel Cyclic Peptide with Antimalarial and Antitrypanosome Activities from a Wheat Endophytic <em>Nigrospora oryzae</em> |
| title_full | Pipecolisporin, a Novel Cyclic Peptide with Antimalarial and Antitrypanosome Activities from a Wheat Endophytic <em>Nigrospora oryzae</em> |
| title_fullStr | Pipecolisporin, a Novel Cyclic Peptide with Antimalarial and Antitrypanosome Activities from a Wheat Endophytic <em>Nigrospora oryzae</em> |
| title_full_unstemmed | Pipecolisporin, a Novel Cyclic Peptide with Antimalarial and Antitrypanosome Activities from a Wheat Endophytic <em>Nigrospora oryzae</em> |
| title_short | Pipecolisporin, a Novel Cyclic Peptide with Antimalarial and Antitrypanosome Activities from a Wheat Endophytic <em>Nigrospora oryzae</em> |
| title_sort | pipecolisporin a novel cyclic peptide with antimalarial and antitrypanosome activities from a wheat endophytic em nigrospora oryzae em |
| topic | pipecolisporin <i>Nigrospora oryzae</i> fungal endophyte structural elucidation Marfey’s analysis antiparasitic activity |
| url | https://www.mdpi.com/1424-8247/14/3/268 |
| work_keys_str_mv | AT ignaciofernandezpastor pipecolisporinanovelcyclicpeptidewithantimalarialandantitrypanosomeactivitiesfromawheatendophyticemnigrosporaoryzaeem AT victorgonzalezmenendez pipecolisporinanovelcyclicpeptidewithantimalarialandantitrypanosomeactivitiesfromawheatendophyticemnigrosporaoryzaeem AT frederickannang pipecolisporinanovelcyclicpeptidewithantimalarialandantitrypanosomeactivitiesfromawheatendophyticemnigrosporaoryzaeem AT claratoro pipecolisporinanovelcyclicpeptidewithantimalarialandantitrypanosomeactivitiesfromawheatendophyticemnigrosporaoryzaeem AT thomasamackenzie pipecolisporinanovelcyclicpeptidewithantimalarialandantitrypanosomeactivitiesfromawheatendophyticemnigrosporaoryzaeem AT cristinaboschnavarrete pipecolisporinanovelcyclicpeptidewithantimalarialandantitrypanosomeactivitiesfromawheatendophyticemnigrosporaoryzaeem AT olgagenilloud pipecolisporinanovelcyclicpeptidewithantimalarialandantitrypanosomeactivitiesfromawheatendophyticemnigrosporaoryzaeem AT fernandoreyes pipecolisporinanovelcyclicpeptidewithantimalarialandantitrypanosomeactivitiesfromawheatendophyticemnigrosporaoryzaeem |