Cytotoxic prenylated indole alkaloid produced by the endophytic fungus Aspergillus terreus P63

Detalhes bibliográficos
Autor(a) principal: Gubiani, Juliana R.
Data de Publicação: 2019
Outros Autores: 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.
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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spelling 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
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