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(Reference retrieved automatically from Web of Science through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

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

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Danuello, Amanda [1, 2] ; de Castro, Rogerio Cardoso [3, 4] ; Pilon, Alan Cesar [5, 6, 2] ; Pires Bueno, Paula Carolina [2] ; Pivatto, Marcos [1] ; Vieira Junior, Gerardo Magela [7] ; Carvalho, Flavio Alexandre [3] ; Oda, Fernando Bombarda [3] ; Perez, Consuelo Javiera [4] ; Lopes, Norberto Peporine [2] ; Dos Santos, Andre Gonzaga [3] ; Ifa, Demian Rocha [4] ; Cavalheiro, Alberto Jose [5]
Total Authors: 13
[1] Univ Fed Uberlandia, Inst Chem, Uberlandia, MG - Brazil
[2] Univ Sao Paulo, Ribeirao Preto Sch Pharmaceut Sci, Ribeirao Preto, SP - Brazil
[3] Sao Paulo State Univ, Sch Pharmaceut Sci, Lab Pharmacognosy, Araraquara, SP - Brazil
[4] York Univ, Dept Chem, Ctr Res Mass Spectrometry, Toronto, ON - Canada
[5] Sao Paulo State Univ, Inst Chem, Araraquara, SP - Brazil
[6] Imperial Coll London, Dept Life Sci, Silwood Pk Campus, Ascot, Berks - England
[7] Univ Fed Piaui, Chem Dept, Teresina, Piaui - Brazil
Total Affiliations: 7
Document type: Journal article
Web of Science Citations: 3

Rationale 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. (AU)

FAPESP's process: 11/21440-3 - Infra-specific chemical variability and dynamics of phenolic and diterpenic secondary metabolites in Casearia sylvestris Sw (Salicaceae) from different Brazilian ecosystems: metabolomics and proteomics correlation
Grantee:Paula Carolina Pires Bueno
Support Opportunities: Scholarships in Brazil - Doctorate
FAPESP's process: 16/13292-8 - Analysis of nitrogen content in antropic influenced areas in Amazon and Atlantic Forest using a metabolomic tools
Grantee:Alan Cesar Pilon
Support Opportunities: Scholarships in Brazil - Post-Doctoral
FAPESP's process: 17/19702-6 - Integrated omics approaches for the evaluation of the micromolecular phenotypic dynamics of Glycine max (soja) genetically modified for water stress tolerance
Grantee:Paula Carolina Pires Bueno
Support Opportunities: Scholarships in Brazil - Post-Doctoral
FAPESP's process: 13/07600-3 - CIBFar - Center for Innovation in Biodiversity and Drug Discovery
Grantee:Glaucius Oliva
Support Opportunities: Research Grants - Research, Innovation and Dissemination Centers - RIDC
FAPESP's process: 14/50926-0 - INCT 2014: biodiversity and natural products
Grantee:Vanderlan da Silva Bolzani
Support Opportunities: BIOTA-FAPESP Program - Thematic Grants