Copper and Manganese Cations Alter Secondary Metabolism in the Fungus Penicillium brasilianum
The fungus Penicillium brasilianum LaBioMMi 136 was isolated as an endophyte from Melia azedarach and has shown to be a prominent producer of great diversity of secondary metabolites, although it does not express some biosynthetic routes to other natural compounds found in Penicillium genera. The present study aimed at the diversification of P. brasilianum secondary metabolism by varying the chemical composition used for its growth. Medium composition supplemented with CuSO4 and MnSO4 locked verruculogen biosynthesis and addressed proline to the production of a series of cyclodepsipeptides identified as JBIR 113, JBIR 114 and JBIR 115, never described for this species so far. The induced cyclodepsipeptide JBIR 113 was isolated by the use of combined chromatographic procedures and identified by spectroscopic methods. The unique structure with three neighboring cyclic amino acids proline and twice pipecolinic acid is rare as natural products and has been described for the first time in terrestrial organism. Verruculogen and JBIR 113 exhibited weak antiparasitary activity against Leishmania amazonensis.
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Sociedade Brasileira de Química
2016
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oai:scielo:S0103-505320160008014442016-08-19Copper and Manganese Cations Alter Secondary Metabolism in the Fungus Penicillium brasilianumFill,Taícia PachecoPallini,Heloisa FassinaAmaral,Luciana da SilvaSilva,José Vinicius daBidóia,Danielle LazarinPeron,FrancieliGarcia,Francielle PelegrinNakamura,Celso VataruRodrigues-Filho,Edson cyclodepsipeptide verruculogen Penicillium brasilianum JBIR 113 The fungus Penicillium brasilianum LaBioMMi 136 was isolated as an endophyte from Melia azedarach and has shown to be a prominent producer of great diversity of secondary metabolites, although it does not express some biosynthetic routes to other natural compounds found in Penicillium genera. The present study aimed at the diversification of P. brasilianum secondary metabolism by varying the chemical composition used for its growth. Medium composition supplemented with CuSO4 and MnSO4 locked verruculogen biosynthesis and addressed proline to the production of a series of cyclodepsipeptides identified as JBIR 113, JBIR 114 and JBIR 115, never described for this species so far. The induced cyclodepsipeptide JBIR 113 was isolated by the use of combined chromatographic procedures and identified by spectroscopic methods. The unique structure with three neighboring cyclic amino acids proline and twice pipecolinic acid is rare as natural products and has been described for the first time in terrestrial organism. Verruculogen and JBIR 113 exhibited weak antiparasitary activity against Leishmania amazonensis.info:eu-repo/semantics/openAccessSociedade Brasileira de QuímicaJournal of the Brazilian Chemical Society v.27 n.8 20162016-08-01info:eu-repo/semantics/articletext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532016000801444en10.5935/0103-5053.20160163 |
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| author |
Fill,Taícia Pacheco Pallini,Heloisa Fassina Amaral,Luciana da Silva Silva,José Vinicius da Bidóia,Danielle Lazarin Peron,Francieli Garcia,Francielle Pelegrin Nakamura,Celso Vataru Rodrigues-Filho,Edson |
| spellingShingle |
Fill,Taícia Pacheco Pallini,Heloisa Fassina Amaral,Luciana da Silva Silva,José Vinicius da Bidóia,Danielle Lazarin Peron,Francieli Garcia,Francielle Pelegrin Nakamura,Celso Vataru Rodrigues-Filho,Edson Copper and Manganese Cations Alter Secondary Metabolism in the Fungus Penicillium brasilianum |
| author_facet |
Fill,Taícia Pacheco Pallini,Heloisa Fassina Amaral,Luciana da Silva Silva,José Vinicius da Bidóia,Danielle Lazarin Peron,Francieli Garcia,Francielle Pelegrin Nakamura,Celso Vataru Rodrigues-Filho,Edson |
| author_sort |
Fill,Taícia Pacheco |
| title |
Copper and Manganese Cations Alter Secondary Metabolism in the Fungus Penicillium brasilianum |
| title_short |
Copper and Manganese Cations Alter Secondary Metabolism in the Fungus Penicillium brasilianum |
| title_full |
Copper and Manganese Cations Alter Secondary Metabolism in the Fungus Penicillium brasilianum |
| title_fullStr |
Copper and Manganese Cations Alter Secondary Metabolism in the Fungus Penicillium brasilianum |
| title_full_unstemmed |
Copper and Manganese Cations Alter Secondary Metabolism in the Fungus Penicillium brasilianum |
| title_sort |
copper and manganese cations alter secondary metabolism in the fungus penicillium brasilianum |
| description |
The fungus Penicillium brasilianum LaBioMMi 136 was isolated as an endophyte from Melia azedarach and has shown to be a prominent producer of great diversity of secondary metabolites, although it does not express some biosynthetic routes to other natural compounds found in Penicillium genera. The present study aimed at the diversification of P. brasilianum secondary metabolism by varying the chemical composition used for its growth. Medium composition supplemented with CuSO4 and MnSO4 locked verruculogen biosynthesis and addressed proline to the production of a series of cyclodepsipeptides identified as JBIR 113, JBIR 114 and JBIR 115, never described for this species so far. The induced cyclodepsipeptide JBIR 113 was isolated by the use of combined chromatographic procedures and identified by spectroscopic methods. The unique structure with three neighboring cyclic amino acids proline and twice pipecolinic acid is rare as natural products and has been described for the first time in terrestrial organism. Verruculogen and JBIR 113 exhibited weak antiparasitary activity against Leishmania amazonensis. |
| publisher |
Sociedade Brasileira de Química |
| publishDate |
2016 |
| url |
http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532016000801444 |
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| _version_ |
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