Cytotoxic prenylated indole alkaloid produced by the endophytic fungus Aspergillus terreus P63
Autor(a) principal: | |
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Data de Publicação: | 2019 |
Outros Autores: | , , , , , , , , , , , , , , , , , , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Repositório Institucional da UNESP |
Texto Completo: | http://dx.doi.org/10.1016/j.phytol.2019.06.003 http://hdl.handle.net/11449/185935 |
Resumo: | Prenyl indole alkaloids constitute a diverse class of natural products with complex chemical structures and potent biological activities. Investigation of the growth medium EtOAc extract produced by the endophytic fungus Aspergillus terreus P63 collected from roots of the grass Axonopus leptostachyus, yielded the prenylated indole alkaloid, giluterrin, bearing an unprecedented carbon skeleton. The structure of giluterrin was established by analysis of spectroscopic data and HRMS. The absolute configuration of giluterrin was determined by combination of electronic and vibrational circular dichroism analyses. Giluterrin presented antiproliferative profile for prostate (PC-3) and kidney (786-0) cancer cell lines. |
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Repositório Institucional da UNESP |
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2946 |
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Cytotoxic prenylated indole alkaloid produced by the endophytic fungus Aspergillus terreus P63Prenylated indole alkaloidFungal alkaloidEndophytic fungusAspergillus terreusPrenyl indole alkaloids constitute a diverse class of natural products with complex chemical structures and potent biological activities. Investigation of the growth medium EtOAc extract produced by the endophytic fungus Aspergillus terreus P63 collected from roots of the grass Axonopus leptostachyus, yielded the prenylated indole alkaloid, giluterrin, bearing an unprecedented carbon skeleton. The structure of giluterrin was established by analysis of spectroscopic data and HRMS. The absolute configuration of giluterrin was determined by combination of electronic and vibrational circular dichroism analyses. Giluterrin presented antiproliferative profile for prostate (PC-3) and kidney (786-0) cancer cell lines.Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)National Institute of Science and Technology (INCT BioNat), BrazilNational Institute of Science and Technology (INCT Areas Umidas), BrazilFundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)Centre for Scientific Computing (NCC/GridUNESP) of Sao Paulo State University (UNESP)Univ Sao Paulo, Inst Quim Sao Carlos, CP 780, BR-13560970 Sao Carlos, SP, BrazilUniv Fed Mato Grosso, Dept Quim, Inst Ciencias Exatas & Terra, BR-78060900 Cuiaba, MT, BrazilUniv Fed Mato Grosso, Dept Biol, Inst Ciencias Exatas & Nat, Campus Rondonopolis, BR-78735901 Rondonopolis, MT, BrazilInst Fed Mato Grosso, BR-78721520 Rondonopolis, MT, BrazilUniv Fed Mato Grosso do Sul, Inst Quim, BR-79070900 Campo Grande, MS, BrazilUniv Fed Mato Grosso, Inst Biociencias, BR-78060900 Cuiaba, MT, BrazilUniv Estadual Paulista, Inst Quim, Nuleo Bioensaios Biossintese & Ecofisiol Prod Nat, Dept Quim Organ, BR-14800900 Araraquara, SP, BrazilUniv Fed Mato Grosso, Dept Enfermagem, Campus Rondonopolis, BR-78735901 Rondonopolis, MT, BrazilUniv Fed Sao Carlos, Dept Quim, BR-13565905 Sao Carlos, SP, BrazilUniv Estadual Campinas, Inst Biol, Dept Biol Func & Estrutural, BR-13083865 Campinas, SP, BrazilUniv Sao Francisco, Lab Pesquisa Biol Celular & Mol Tumores & Compost, BR-12916900 Braganca Paulista, SP, BrazilUniv Fed Sao Paulo, Inst Ciencia & Tecnol, BR-12231280 Sao Jose Dos Campos, SP, BrazilUniv Estadual Paulista, Inst Quim, Nuleo Bioensaios Biossintese & Ecofisiol Prod Nat, Dept Quim Organ, BR-14800900 Araraquara, SP, BrazilNational Institute of Science and Technology (INCT BioNat), Brazil: 465637/2014-0National Institute of Science and Technology (INCT Areas Umidas), Brazil: 421733/2017-9FAPESP: 2013/50228-8FAPESP: 2014/25222-9Elsevier B.V.Universidade de São Paulo (USP)Universidade Federal de Mato Grosso do Sul (UFMS)Inst Fed Mato GrossoUniversidade Estadual Paulista (Unesp)Universidade Federal de São Carlos (UFSCar)Universidade Estadual de Campinas (UNICAMP)Univ Sao FranciscoUniversidade Federal de São Paulo (UNIFESP)Gubiani, Juliana R.Oliveira, Michele C. S.Neponuceno, Ricardo A. R.Camargo, Maria J.Garcez, Walmir S.Biz, Andressa R.Soares, Marcos A.Araujo, Angela R. [UNESP]Bolzani, Vanderlan da S. [UNESP]Lisboa, Helen C. F.Sousa Jr, Paulo T. deVasconcelos, Leonardo G. deRibeiro, Tereza A. N.Oliveira, Juliana M. deBanzato, Thais P.Lima, Carolina A.Longato, Giovanna B.Batista Jr, Joao M.Berlinck, Roberto G. S.Teles, Helder L.2019-10-04T12:39:55Z2019-10-04T12:39:55Z2019-08-01info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/article162-167http://dx.doi.org/10.1016/j.phytol.2019.06.003Phytochemistry Letters. Amsterdam: Elsevier, v. 32, p. 162-167, 2019.1874-3900http://hdl.handle.net/11449/18593510.1016/j.phytol.2019.06.003WOS:000476725000031Web of Sciencereponame:Repositório Institucional da UNESPinstname:Universidade Estadual Paulista (UNESP)instacron:UNESPengPhytochemistry Lettersinfo:eu-repo/semantics/openAccess2021-10-23T12:23:55Zoai:repositorio.unesp.br:11449/185935Repositório InstitucionalPUBhttp://repositorio.unesp.br/oai/requestopendoar:29462024-08-05T21:05:19.389361Repositório Institucional da UNESP - Universidade Estadual Paulista (UNESP)false |
dc.title.none.fl_str_mv |
Cytotoxic prenylated indole alkaloid produced by the endophytic fungus Aspergillus terreus P63 |
title |
Cytotoxic prenylated indole alkaloid produced by the endophytic fungus Aspergillus terreus P63 |
spellingShingle |
Cytotoxic prenylated indole alkaloid produced by the endophytic fungus Aspergillus terreus P63 Gubiani, Juliana R. Prenylated indole alkaloid Fungal alkaloid Endophytic fungus Aspergillus terreus |
title_short |
Cytotoxic prenylated indole alkaloid produced by the endophytic fungus Aspergillus terreus P63 |
title_full |
Cytotoxic prenylated indole alkaloid produced by the endophytic fungus Aspergillus terreus P63 |
title_fullStr |
Cytotoxic prenylated indole alkaloid produced by the endophytic fungus Aspergillus terreus P63 |
title_full_unstemmed |
Cytotoxic prenylated indole alkaloid produced by the endophytic fungus Aspergillus terreus P63 |
title_sort |
Cytotoxic prenylated indole alkaloid produced by the endophytic fungus Aspergillus terreus P63 |
author |
Gubiani, Juliana R. |
author_facet |
Gubiani, Juliana R. Oliveira, Michele C. S. Neponuceno, Ricardo A. R. Camargo, Maria J. Garcez, Walmir S. Biz, Andressa R. Soares, Marcos A. Araujo, Angela R. [UNESP] Bolzani, Vanderlan da S. [UNESP] Lisboa, Helen C. F. Sousa Jr, Paulo T. de Vasconcelos, Leonardo G. de Ribeiro, Tereza A. N. Oliveira, Juliana M. de Banzato, Thais P. Lima, Carolina A. Longato, Giovanna B. Batista Jr, Joao M. Berlinck, Roberto G. S. Teles, Helder L. |
author_role |
author |
author2 |
Oliveira, Michele C. S. Neponuceno, Ricardo A. R. Camargo, Maria J. Garcez, Walmir S. Biz, Andressa R. Soares, Marcos A. Araujo, Angela R. [UNESP] Bolzani, Vanderlan da S. [UNESP] Lisboa, Helen C. F. Sousa Jr, Paulo T. de Vasconcelos, Leonardo G. de Ribeiro, Tereza A. N. Oliveira, Juliana M. de Banzato, Thais P. Lima, Carolina A. Longato, Giovanna B. Batista Jr, Joao M. Berlinck, Roberto G. S. Teles, Helder L. |
author2_role |
author author author author author author author author author author author author author author author author author author author |
dc.contributor.none.fl_str_mv |
Universidade de São Paulo (USP) Universidade Federal de Mato Grosso do Sul (UFMS) Inst Fed Mato Grosso Universidade Estadual Paulista (Unesp) Universidade Federal de São Carlos (UFSCar) Universidade Estadual de Campinas (UNICAMP) Univ Sao Francisco Universidade Federal de São Paulo (UNIFESP) |
dc.contributor.author.fl_str_mv |
Gubiani, Juliana R. Oliveira, Michele C. S. Neponuceno, Ricardo A. R. Camargo, Maria J. Garcez, Walmir S. Biz, Andressa R. Soares, Marcos A. Araujo, Angela R. [UNESP] Bolzani, Vanderlan da S. [UNESP] Lisboa, Helen C. F. Sousa Jr, Paulo T. de Vasconcelos, Leonardo G. de Ribeiro, Tereza A. N. Oliveira, Juliana M. de Banzato, Thais P. Lima, Carolina A. Longato, Giovanna B. Batista Jr, Joao M. Berlinck, Roberto G. S. Teles, Helder L. |
dc.subject.por.fl_str_mv |
Prenylated indole alkaloid Fungal alkaloid Endophytic fungus Aspergillus terreus |
topic |
Prenylated indole alkaloid Fungal alkaloid Endophytic fungus Aspergillus terreus |
description |
Prenyl indole alkaloids constitute a diverse class of natural products with complex chemical structures and potent biological activities. Investigation of the growth medium EtOAc extract produced by the endophytic fungus Aspergillus terreus P63 collected from roots of the grass Axonopus leptostachyus, yielded the prenylated indole alkaloid, giluterrin, bearing an unprecedented carbon skeleton. The structure of giluterrin was established by analysis of spectroscopic data and HRMS. The absolute configuration of giluterrin was determined by combination of electronic and vibrational circular dichroism analyses. Giluterrin presented antiproliferative profile for prostate (PC-3) and kidney (786-0) cancer cell lines. |
publishDate |
2019 |
dc.date.none.fl_str_mv |
2019-10-04T12:39:55Z 2019-10-04T12:39:55Z 2019-08-01 |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/article |
format |
article |
status_str |
publishedVersion |
dc.identifier.uri.fl_str_mv |
http://dx.doi.org/10.1016/j.phytol.2019.06.003 Phytochemistry Letters. Amsterdam: Elsevier, v. 32, p. 162-167, 2019. 1874-3900 http://hdl.handle.net/11449/185935 10.1016/j.phytol.2019.06.003 WOS:000476725000031 |
url |
http://dx.doi.org/10.1016/j.phytol.2019.06.003 http://hdl.handle.net/11449/185935 |
identifier_str_mv |
Phytochemistry Letters. Amsterdam: Elsevier, v. 32, p. 162-167, 2019. 1874-3900 10.1016/j.phytol.2019.06.003 WOS:000476725000031 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
Phytochemistry Letters |
dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
eu_rights_str_mv |
openAccess |
dc.format.none.fl_str_mv |
162-167 |
dc.publisher.none.fl_str_mv |
Elsevier B.V. |
publisher.none.fl_str_mv |
Elsevier B.V. |
dc.source.none.fl_str_mv |
Web of Science reponame:Repositório Institucional da UNESP instname:Universidade Estadual Paulista (UNESP) instacron:UNESP |
instname_str |
Universidade Estadual Paulista (UNESP) |
instacron_str |
UNESP |
institution |
UNESP |
reponame_str |
Repositório Institucional da UNESP |
collection |
Repositório Institucional da UNESP |
repository.name.fl_str_mv |
Repositório Institucional da UNESP - Universidade Estadual Paulista (UNESP) |
repository.mail.fl_str_mv |
|
_version_ |
1808129282526937088 |