Fragmentation study of clerodane diterpenes from Casearia species by tandem mass spectrometry (quadrupole time-of-flight and ion trap)

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Autor(es): dc.contributorUniversidade de São Paulo (USP)-
Autor(es): dc.contributorUniversidade Federal de Uberlândia (UFU)-
Autor(es): dc.contributorUniversidade Estadual Paulista (Unesp)-
Autor(es): dc.contributorYork Univ-
Autor(es): dc.contributorImperial Coll London-
Autor(es): dc.contributorUniv Fed Piaui-
Autor(es): dc.creatorDanuello, Amanda-
Autor(es): dc.creatorCastro, Rogerio Cardoso de [UNESP]-
Autor(es): dc.creatorPilon, Alan Cesar [UNESP]-
Autor(es): dc.creatorPires Bueno, Paula Carolina-
Autor(es): dc.creatorPivatto, Marcos-
Autor(es): dc.creatorVieira Junior, Gerardo Magela-
Autor(es): dc.creatorCarvalho, Flavio Alexandre [UNESP]-
Autor(es): dc.creatorOda, Fernando Bombarda [UNESP]-
Autor(es): dc.creatorPerez, Consuelo Javiera-
Autor(es): dc.creatorLopes, Norberto Peporine-
Autor(es): dc.creatorDos Santos, Andre Gonzaga [UNESP]-
Autor(es): dc.creatorIfa, Demian Rocha-
Autor(es): dc.creatorCavalheiro, Alberto Jose [UNESP]-
Data de aceite: dc.date.accessioned2022-02-22T00:20:09Z-
Data de disponibilização: dc.date.available2022-02-22T00:20:09Z-
Data de envio: dc.date.issued2020-12-10-
Data de envio: dc.date.issued2020-12-10-
Data de envio: dc.date.issued2020-05-20-
Fonte completa do material: dc.identifierhttp://dx.doi.org/10.1002/rcm.8781-
Fonte completa do material: dc.identifierhttp://hdl.handle.net/11449/197782-
Fonte: dc.identifier.urihttp://educapes.capes.gov.br/handle/11449/197782-
Descrição: dc.descriptionRationale Clerodane-type diterpenes from Casearia species show important pharmacological activites such as antitumor, antimicrobial and anti-inflamatory. There are several mass spectrometry (MS)-based methods for identification of diterpenes; however, there is still a lack of MS procedures capable of providing characteristic fragmentation pathways for a rapid and unambiguous elucidation of casearin-like compounds. Methods Casearin-like compounds were investigated by electrospray ionization tandem mass spectrometry (ESI-MS/MS). The fragmentation studies were carried out by tandem mass spectrometry in space (quadrupole time-of-flight (QTOF)) using different collision energies and also by tandem mass spectrometry in time (QIT) by selective isolation of product ions. Results Casearin-like compounds presented a predominance of sodium- and potassium-cationized precursor ions. Both QIT and QTOF techniques provided sequential neutral losses of esters related to the R-1 to R-5 substituents linked to the nucleus of the clerodane diterpenes. The fragmentation pathway is initiated with a cleavage of the ester moieties R-2 followed by the elimination of the ester groups R-3, both losing neutral carboxylic acids. Using QIT, it was also possible to observe the cleavage of the ester groups R-1 or R-5 by MS4 experiments. Conclusions Through a rational analysis of the fragmentation mechanisms of Casearia diterpenes it was possible to suggest an annotation strategy based on the sequential cleavages of the ester groups related to the R-2, R-3 and R-5 substituents. These results will assist studies of the dereplication and metabolomics involving casearin-like compounds present in complex extracts of Casearia species.-
Descrição: dc.descriptionConselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)-
Descrição: dc.descriptionCoordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES)-
Descrição: dc.descriptionFundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)-
Descrição: dc.descriptionUniv Sao Paulo, Ribeirao Preto Sch Pharmaceut Sci, Ribeirao Preto, SP, Brazil-
Descrição: dc.descriptionUniv Fed Uberlandia, Inst Chem, Uberlandia, MG, Brazil-
Descrição: dc.descriptionSao Paulo State Univ, Sch Pharmaceut Sci, Lab Pharmacognosy, Araraquara, SP, Brazil-
Descrição: dc.descriptionYork Univ, Dept Chem, Ctr Res Mass Spectrometry, Toronto, ON, Canada-
Descrição: dc.descriptionSao Paulo State Univ, Inst Chem, Araraquara, SP, Brazil-
Descrição: dc.descriptionImperial Coll London, Dept Life Sci, Silwood Pk Campus, Ascot, Berks, England-
Descrição: dc.descriptionUniv Fed Piaui, Chem Dept, Teresina, Piaui, Brazil-
Descrição: dc.descriptionSao Paulo State Univ, Sch Pharmaceut Sci, Lab Pharmacognosy, Araraquara, SP, Brazil-
Descrição: dc.descriptionSao Paulo State Univ, Inst Chem, Araraquara, SP, Brazil-
Descrição: dc.descriptionCNPq: 207745/2014-5-
Descrição: dc.descriptionCNPq: INCT 465637/2014-0-
Descrição: dc.descriptionCAPES: 001-
Descrição: dc.descriptionFAPESP: 2011/21440-3-
Descrição: dc.descriptionFAPESP: 2012/23775-5-
Descrição: dc.descriptionFAPESP: 2013/07600-3-
Descrição: dc.descriptionFAPESP: 2014/50926-0-
Descrição: dc.descriptionFAPESP: 2016/13292-8-
Descrição: dc.descriptionFAPESP: 2017/19702-6-
Formato: dc.format7-
Idioma: dc.languageen-
Publicador: dc.publisherWiley-Blackwell-
Relação: dc.relationRapid Communications In Mass Spectrometry-
???dc.source???: dc.sourceWeb of Science-
Título: dc.titleFragmentation study of clerodane diterpenes from Casearia species by tandem mass spectrometry (quadrupole time-of-flight and ion trap)-
Tipo de arquivo: dc.typelivro digital-
Aparece nas coleções:Repositório Institucional - Unesp

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