Systematic UPLC-ESI-MS/MS study on the occurrence of staurosporine and derivatives in associated marine microorganisms from Eudistoma vannamei

Former bioactivity-guided analysis of the marine invertebrate Eudistoma vannamei led to the isolation of staurosporine derivatives, which revealed strong cytotoxic activity against several human cancer cell lines. The occurrence of such alkaloids in E. vannamei may be correlated to the presence of associated biota, such as Streptomyces bacteria. In agreement to this hypothesis, marine microorganisms associated with E. vannamei were recovered and cultured, leading to a total of 84 isolated bacterial strains. Gas phase fragmentation reactions of staurosporine and derivatives were systematically studied and the analyzed results further supported by computational chemistry studies. The resulting fragment patterns were used to search for the presence of different derivatives in extracts of isolated microorganisms, thereby using LC-MS/MS analysis in MRM mode. These results evidenced that one isolated Streptomyces sp. was able to generate staurosporine, while none of the hydroxy-7-oxo derivatives were detected. Finally, significant cytotoxic activity against human cancer lines was observed for one of the extracts.

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Main Authors: Andréo,Márcio A., Jimenez,Paula C., Siebra,Josy B. C. N., Costa-Lotufo,Leticia V., Vessecchi,Ricardo, Niehues,Michael, Lopes,João L. C., Lopes,Norberto P.
Format: Digital revista
Language:English
Published: Sociedade Brasileira de Química 2012
Online Access:http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532012000200021
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spelling oai:scielo:S0103-505320120002000212016-12-08Systematic UPLC-ESI-MS/MS study on the occurrence of staurosporine and derivatives in associated marine microorganisms from Eudistoma vannameiAndréo,Márcio A.Jimenez,Paula C.Siebra,Josy B. C. N.Costa-Lotufo,Leticia V.Vessecchi,RicardoNiehues,MichaelLopes,João L. C.Lopes,Norberto P. Eudistoma vannamei Streptomyces staurosporine LC-MS/MS ascidian Former bioactivity-guided analysis of the marine invertebrate Eudistoma vannamei led to the isolation of staurosporine derivatives, which revealed strong cytotoxic activity against several human cancer cell lines. The occurrence of such alkaloids in E. vannamei may be correlated to the presence of associated biota, such as Streptomyces bacteria. In agreement to this hypothesis, marine microorganisms associated with E. vannamei were recovered and cultured, leading to a total of 84 isolated bacterial strains. Gas phase fragmentation reactions of staurosporine and derivatives were systematically studied and the analyzed results further supported by computational chemistry studies. The resulting fragment patterns were used to search for the presence of different derivatives in extracts of isolated microorganisms, thereby using LC-MS/MS analysis in MRM mode. These results evidenced that one isolated Streptomyces sp. was able to generate staurosporine, while none of the hydroxy-7-oxo derivatives were detected. Finally, significant cytotoxic activity against human cancer lines was observed for one of the extracts.info:eu-repo/semantics/openAccessSociedade Brasileira de QuímicaJournal of the Brazilian Chemical Society v.23 n.2 20122012-02-01info:eu-repo/semantics/articletext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532012000200021en10.1590/S0103-50532012000200021
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libraryname SciELO
language English
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author Andréo,Márcio A.
Jimenez,Paula C.
Siebra,Josy B. C. N.
Costa-Lotufo,Leticia V.
Vessecchi,Ricardo
Niehues,Michael
Lopes,João L. C.
Lopes,Norberto P.
spellingShingle Andréo,Márcio A.
Jimenez,Paula C.
Siebra,Josy B. C. N.
Costa-Lotufo,Leticia V.
Vessecchi,Ricardo
Niehues,Michael
Lopes,João L. C.
Lopes,Norberto P.
Systematic UPLC-ESI-MS/MS study on the occurrence of staurosporine and derivatives in associated marine microorganisms from Eudistoma vannamei
author_facet Andréo,Márcio A.
Jimenez,Paula C.
Siebra,Josy B. C. N.
Costa-Lotufo,Leticia V.
Vessecchi,Ricardo
Niehues,Michael
Lopes,João L. C.
Lopes,Norberto P.
author_sort Andréo,Márcio A.
title Systematic UPLC-ESI-MS/MS study on the occurrence of staurosporine and derivatives in associated marine microorganisms from Eudistoma vannamei
title_short Systematic UPLC-ESI-MS/MS study on the occurrence of staurosporine and derivatives in associated marine microorganisms from Eudistoma vannamei
title_full Systematic UPLC-ESI-MS/MS study on the occurrence of staurosporine and derivatives in associated marine microorganisms from Eudistoma vannamei
title_fullStr Systematic UPLC-ESI-MS/MS study on the occurrence of staurosporine and derivatives in associated marine microorganisms from Eudistoma vannamei
title_full_unstemmed Systematic UPLC-ESI-MS/MS study on the occurrence of staurosporine and derivatives in associated marine microorganisms from Eudistoma vannamei
title_sort systematic uplc-esi-ms/ms study on the occurrence of staurosporine and derivatives in associated marine microorganisms from eudistoma vannamei
description Former bioactivity-guided analysis of the marine invertebrate Eudistoma vannamei led to the isolation of staurosporine derivatives, which revealed strong cytotoxic activity against several human cancer cell lines. The occurrence of such alkaloids in E. vannamei may be correlated to the presence of associated biota, such as Streptomyces bacteria. In agreement to this hypothesis, marine microorganisms associated with E. vannamei were recovered and cultured, leading to a total of 84 isolated bacterial strains. Gas phase fragmentation reactions of staurosporine and derivatives were systematically studied and the analyzed results further supported by computational chemistry studies. The resulting fragment patterns were used to search for the presence of different derivatives in extracts of isolated microorganisms, thereby using LC-MS/MS analysis in MRM mode. These results evidenced that one isolated Streptomyces sp. was able to generate staurosporine, while none of the hydroxy-7-oxo derivatives were detected. Finally, significant cytotoxic activity against human cancer lines was observed for one of the extracts.
publisher Sociedade Brasileira de Química
publishDate 2012
url http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532012000200021
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