A novel alkaloid isolated from Crotalaria paulina and identified by NMR and DFT calculations

Detalhes bibliográficos
Autor(a) principal: Oliveira, Ramon Prata
Data de Publicação: 2018
Outros Autores: Demuner, Antonio Jacinto, Alvarenga, Elson Santiago, Barbosa, Luiz Claudio Almeida, Silva, Thiago de Melo
Tipo de documento: Artigo
Idioma: eng
Título da fonte: LOCUS Repositório Institucional da UFV
Texto Completo: https://doi.org/10.1016/j.molstruc.2017.09.065
http://www.locus.ufv.br/handle/123456789/21954
Resumo: Pyrrolizidine alkaloids (PAs) are secondary metabolites found in Crotalaria genus and are known to have several biological activities. A novel macrocycle bislactone alkaloid, coined ethylcrotaline, was isolated and purified from the aerial parts of Crotalaria paulina. The novel macrocycle was identified with the aid of high resolution mass spectrometry and advanced nuclear magnetic resonance techniques. The relative stereochemistry of the alkaloid was defined by comparing the calculated quantum mechanical hydrogen and carbon chemical shifts of eight candidate structures with the experimental NMR data. The best fit between the eight candidate structures and the experimental NMR chemical shifts was defined by the DP4 statistical analyses and the Mean Absolute Error (MAE) calculations.
id UFV_b8cb08de9386832698cec93067c77e07
oai_identifier_str oai:locus.ufv.br:123456789/21954
network_acronym_str UFV
network_name_str LOCUS Repositório Institucional da UFV
repository_id_str 2145
spelling Oliveira, Ramon PrataDemuner, Antonio JacintoAlvarenga, Elson SantiagoBarbosa, Luiz Claudio AlmeidaSilva, Thiago de Melo2018-09-24T13:50:42Z2018-09-24T13:50:42Z2018-02-1500222860https://doi.org/10.1016/j.molstruc.2017.09.065http://www.locus.ufv.br/handle/123456789/21954Pyrrolizidine alkaloids (PAs) are secondary metabolites found in Crotalaria genus and are known to have several biological activities. A novel macrocycle bislactone alkaloid, coined ethylcrotaline, was isolated and purified from the aerial parts of Crotalaria paulina. The novel macrocycle was identified with the aid of high resolution mass spectrometry and advanced nuclear magnetic resonance techniques. The relative stereochemistry of the alkaloid was defined by comparing the calculated quantum mechanical hydrogen and carbon chemical shifts of eight candidate structures with the experimental NMR data. The best fit between the eight candidate structures and the experimental NMR chemical shifts was defined by the DP4 statistical analyses and the Mean Absolute Error (MAE) calculations.engJournal of Molecular Structurev. 1152, p. 337- 343, jan. 2018Elsevier B.V.info:eu-repo/semantics/openAccessMAEDP4MacrocycleEthylcrotalinePyrrolizidineBislactoneA novel alkaloid isolated from Crotalaria paulina and identified by NMR and DFT calculationsinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfreponame:LOCUS Repositório Institucional da UFVinstname:Universidade Federal de Viçosa (UFV)instacron:UFVORIGINALartigo.pdfartigo.pdftexto completoapplication/pdf409903https://locus.ufv.br//bitstream/123456789/21954/1/artigo.pdf54cc4feb815386668a956f64548b9769MD51LICENSElicense.txtlicense.txttext/plain; charset=utf-81748https://locus.ufv.br//bitstream/123456789/21954/2/license.txt8a4605be74aa9ea9d79846c1fba20a33MD52THUMBNAILartigo.pdf.jpgartigo.pdf.jpgIM Thumbnailimage/jpeg6478https://locus.ufv.br//bitstream/123456789/21954/3/artigo.pdf.jpg037e919686483b101e9172508117837dMD53123456789/219542018-09-24 23:00:41.234oai:locus.ufv.br:123456789/21954Tk9URTogUExBQ0UgWU9VUiBPV04gTElDRU5TRSBIRVJFClRoaXMgc2FtcGxlIGxpY2Vuc2UgaXMgcHJvdmlkZWQgZm9yIGluZm9ybWF0aW9uYWwgcHVycG9zZXMgb25seS4KCk5PTi1FWENMVVNJVkUgRElTVFJJQlVUSU9OIExJQ0VOU0UKCkJ5IHNpZ25pbmcgYW5kIHN1Ym1pdHRpbmcgdGhpcyBsaWNlbnNlLCB5b3UgKHRoZSBhdXRob3Iocykgb3IgY29weXJpZ2h0Cm93bmVyKSBncmFudHMgdG8gRFNwYWNlIFVuaXZlcnNpdHkgKERTVSkgdGhlIG5vbi1leGNsdXNpdmUgcmlnaHQgdG8gcmVwcm9kdWNlLAp0cmFuc2xhdGUgKGFzIGRlZmluZWQgYmVsb3cpLCBhbmQvb3IgZGlzdHJpYnV0ZSB5b3VyIHN1Ym1pc3Npb24gKGluY2x1ZGluZwp0aGUgYWJzdHJhY3QpIHdvcmxkd2lkZSBpbiBwcmludCBhbmQgZWxlY3Ryb25pYyBmb3JtYXQgYW5kIGluIGFueSBtZWRpdW0sCmluY2x1ZGluZyBidXQgbm90IGxpbWl0ZWQgdG8gYXVkaW8gb3IgdmlkZW8uCgpZb3UgYWdyZWUgdGhhdCBEU1UgbWF5LCB3aXRob3V0IGNoYW5naW5nIHRoZSBjb250ZW50LCB0cmFuc2xhdGUgdGhlCnN1Ym1pc3Npb24gdG8gYW55IG1lZGl1bSBvciBmb3JtYXQgZm9yIHRoZSBwdXJwb3NlIG9mIHByZXNlcnZhdGlvbi4KCllvdSBhbHNvIGFncmVlIHRoYXQgRFNVIG1heSBrZWVwIG1vcmUgdGhhbiBvbmUgY29weSBvZiB0aGlzIHN1Ym1pc3Npb24gZm9yCnB1cnBvc2VzIG9mIHNlY3VyaXR5LCBiYWNrLXVwIGFuZCBwcmVzZXJ2YXRpb24uCgpZb3UgcmVwcmVzZW50IHRoYXQgdGhlIHN1Ym1pc3Npb24gaXMgeW91ciBvcmlnaW5hbCB3b3JrLCBhbmQgdGhhdCB5b3UgaGF2ZQp0aGUgcmlnaHQgdG8gZ3JhbnQgdGhlIHJpZ2h0cyBjb250YWluZWQgaW4gdGhpcyBsaWNlbnNlLiBZb3UgYWxzbyByZXByZXNlbnQKdGhhdCB5b3VyIHN1Ym1pc3Npb24gZG9lcyBub3QsIHRvIHRoZSBiZXN0IG9mIHlvdXIga25vd2xlZGdlLCBpbmZyaW5nZSB1cG9uCmFueW9uZSdzIGNvcHlyaWdodC4KCklmIHRoZSBzdWJtaXNzaW9uIGNvbnRhaW5zIG1hdGVyaWFsIGZvciB3aGljaCB5b3UgZG8gbm90IGhvbGQgY29weXJpZ2h0LAp5b3UgcmVwcmVzZW50IHRoYXQgeW91IGhhdmUgb2J0YWluZWQgdGhlIHVucmVzdHJpY3RlZCBwZXJtaXNzaW9uIG9mIHRoZQpjb3B5cmlnaHQgb3duZXIgdG8gZ3JhbnQgRFNVIHRoZSByaWdodHMgcmVxdWlyZWQgYnkgdGhpcyBsaWNlbnNlLCBhbmQgdGhhdApzdWNoIHRoaXJkLXBhcnR5IG93bmVkIG1hdGVyaWFsIGlzIGNsZWFybHkgaWRlbnRpZmllZCBhbmQgYWNrbm93bGVkZ2VkCndpdGhpbiB0aGUgdGV4dCBvciBjb250ZW50IG9mIHRoZSBzdWJtaXNzaW9uLgoKSUYgVEhFIFNVQk1JU1NJT04gSVMgQkFTRUQgVVBPTiBXT1JLIFRIQVQgSEFTIEJFRU4gU1BPTlNPUkVEIE9SIFNVUFBPUlRFRApCWSBBTiBBR0VOQ1kgT1IgT1JHQU5JWkFUSU9OIE9USEVSIFRIQU4gRFNVLCBZT1UgUkVQUkVTRU5UIFRIQVQgWU9VIEhBVkUKRlVMRklMTEVEIEFOWSBSSUdIVCBPRiBSRVZJRVcgT1IgT1RIRVIgT0JMSUdBVElPTlMgUkVRVUlSRUQgQlkgU1VDSApDT05UUkFDVCBPUiBBR1JFRU1FTlQuCgpEU1Ugd2lsbCBjbGVhcmx5IGlkZW50aWZ5IHlvdXIgbmFtZShzKSBhcyB0aGUgYXV0aG9yKHMpIG9yIG93bmVyKHMpIG9mIHRoZQpzdWJtaXNzaW9uLCBhbmQgd2lsbCBub3QgbWFrZSBhbnkgYWx0ZXJhdGlvbiwgb3RoZXIgdGhhbiBhcyBhbGxvd2VkIGJ5IHRoaXMKbGljZW5zZSwgdG8geW91ciBzdWJtaXNzaW9uLgo=Repositório InstitucionalPUBhttps://www.locus.ufv.br/oai/requestfabiojreis@ufv.bropendoar:21452018-09-25T02:00:41LOCUS Repositório Institucional da UFV - Universidade Federal de Viçosa (UFV)false
dc.title.en.fl_str_mv A novel alkaloid isolated from Crotalaria paulina and identified by NMR and DFT calculations
title A novel alkaloid isolated from Crotalaria paulina and identified by NMR and DFT calculations
spellingShingle A novel alkaloid isolated from Crotalaria paulina and identified by NMR and DFT calculations
Oliveira, Ramon Prata
MAE
DP4
Macrocycle
Ethylcrotaline
Pyrrolizidine
Bislactone
title_short A novel alkaloid isolated from Crotalaria paulina and identified by NMR and DFT calculations
title_full A novel alkaloid isolated from Crotalaria paulina and identified by NMR and DFT calculations
title_fullStr A novel alkaloid isolated from Crotalaria paulina and identified by NMR and DFT calculations
title_full_unstemmed A novel alkaloid isolated from Crotalaria paulina and identified by NMR and DFT calculations
title_sort A novel alkaloid isolated from Crotalaria paulina and identified by NMR and DFT calculations
author Oliveira, Ramon Prata
author_facet Oliveira, Ramon Prata
Demuner, Antonio Jacinto
Alvarenga, Elson Santiago
Barbosa, Luiz Claudio Almeida
Silva, Thiago de Melo
author_role author
author2 Demuner, Antonio Jacinto
Alvarenga, Elson Santiago
Barbosa, Luiz Claudio Almeida
Silva, Thiago de Melo
author2_role author
author
author
author
dc.contributor.author.fl_str_mv Oliveira, Ramon Prata
Demuner, Antonio Jacinto
Alvarenga, Elson Santiago
Barbosa, Luiz Claudio Almeida
Silva, Thiago de Melo
dc.subject.pt-BR.fl_str_mv MAE
DP4
Macrocycle
Ethylcrotaline
Pyrrolizidine
Bislactone
topic MAE
DP4
Macrocycle
Ethylcrotaline
Pyrrolizidine
Bislactone
description Pyrrolizidine alkaloids (PAs) are secondary metabolites found in Crotalaria genus and are known to have several biological activities. A novel macrocycle bislactone alkaloid, coined ethylcrotaline, was isolated and purified from the aerial parts of Crotalaria paulina. The novel macrocycle was identified with the aid of high resolution mass spectrometry and advanced nuclear magnetic resonance techniques. The relative stereochemistry of the alkaloid was defined by comparing the calculated quantum mechanical hydrogen and carbon chemical shifts of eight candidate structures with the experimental NMR data. The best fit between the eight candidate structures and the experimental NMR chemical shifts was defined by the DP4 statistical analyses and the Mean Absolute Error (MAE) calculations.
publishDate 2018
dc.date.accessioned.fl_str_mv 2018-09-24T13:50:42Z
dc.date.available.fl_str_mv 2018-09-24T13:50:42Z
dc.date.issued.fl_str_mv 2018-02-15
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 https://doi.org/10.1016/j.molstruc.2017.09.065
http://www.locus.ufv.br/handle/123456789/21954
dc.identifier.issn.none.fl_str_mv 00222860
identifier_str_mv 00222860
url https://doi.org/10.1016/j.molstruc.2017.09.065
http://www.locus.ufv.br/handle/123456789/21954
dc.language.iso.fl_str_mv eng
language eng
dc.relation.ispartofseries.pt-BR.fl_str_mv v. 1152, p. 337- 343, jan. 2018
dc.rights.driver.fl_str_mv Elsevier B.V.
info:eu-repo/semantics/openAccess
rights_invalid_str_mv Elsevier B.V.
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv Journal of Molecular Structure
publisher.none.fl_str_mv Journal of Molecular Structure
dc.source.none.fl_str_mv reponame:LOCUS Repositório Institucional da UFV
instname:Universidade Federal de Viçosa (UFV)
instacron:UFV
instname_str Universidade Federal de Viçosa (UFV)
instacron_str UFV
institution UFV
reponame_str LOCUS Repositório Institucional da UFV
collection LOCUS Repositório Institucional da UFV
bitstream.url.fl_str_mv https://locus.ufv.br//bitstream/123456789/21954/1/artigo.pdf
https://locus.ufv.br//bitstream/123456789/21954/2/license.txt
https://locus.ufv.br//bitstream/123456789/21954/3/artigo.pdf.jpg
bitstream.checksum.fl_str_mv 54cc4feb815386668a956f64548b9769
8a4605be74aa9ea9d79846c1fba20a33
037e919686483b101e9172508117837d
bitstream.checksumAlgorithm.fl_str_mv MD5
MD5
MD5
repository.name.fl_str_mv LOCUS Repositório Institucional da UFV - Universidade Federal de Viçosa (UFV)
repository.mail.fl_str_mv fabiojreis@ufv.br
_version_ 1801212965987287040