FRAGMENTATION OF DEPROTONATED PLUMERAN INDOLE ALKALOIDS BY ELECTROSPRAY IONIZATION TANDEM MASS SPECTROMETRY
The fragmentation of four deprotonated plumeran indole alkaloids (PIAs), namely aspidospermidine (1), demethoxypalosine (2), aspidocarpine (3), and aspidolimine (4), previously isolated from Aspidosperma spruceanum has been investigated by electrospray ionization tandem mass spectrometry (ESI-MS/MS)...
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Sociedade Brasileira de Química
2025-06-01
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| Series: | Química Nova |
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| Online Access: | http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0100-40422025000600302&lng=en&tlng=en |
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| author | Yan R. Robles Ricardo Vessecchi Ivo J. C. Vieira Raimundo Braz-Filho Antonio E. M. Crotti |
| author_facet | Yan R. Robles Ricardo Vessecchi Ivo J. C. Vieira Raimundo Braz-Filho Antonio E. M. Crotti |
| author_sort | Yan R. Robles |
| collection | DOAJ |
| description | The fragmentation of four deprotonated plumeran indole alkaloids (PIAs), namely aspidospermidine (1), demethoxypalosine (2), aspidocarpine (3), and aspidolimine (4), previously isolated from Aspidosperma spruceanum has been investigated by electrospray ionization tandem mass spectrometry (ESI-MS/MS) in the negative ion mode. The fragmentation pathways have been established on the basis of accurate mass data. Our results demonstrated that the main product ions of deprotonated 1-4 result from remote hydrogen rearrangements. The most abundant product ion in the product ion spectrum of 2, 3, and 4 was the result of a ketene loss (methylketene for 2 and 3, and a ketene for 4) directly from the precursor ion. The product ion of m/z 183 was diagnostic for compound 2, whereas the radical loss of •CH3 occurred only for 3 and 4, which display an aromatic methoxyl group in their structures. These results indicated that ESI(-)-MS/MS could be also used for the identification of PIAs 1-4 in crude extracts using LC-ESI-MS/MS, especially when the extracts are more complex. |
| format | Article |
| id | doaj-art-7f2ea6e7bfc94451a2a8126263c67dfa |
| institution | OA Journals |
| issn | 1678-7064 |
| language | English |
| publishDate | 2025-06-01 |
| publisher | Sociedade Brasileira de Química |
| record_format | Article |
| series | Química Nova |
| spelling | doaj-art-7f2ea6e7bfc94451a2a8126263c67dfa2025-08-20T02:24:25ZengSociedade Brasileira de QuímicaQuímica Nova1678-70642025-06-0148610.21577/0100-4042.20250138FRAGMENTATION OF DEPROTONATED PLUMERAN INDOLE ALKALOIDS BY ELECTROSPRAY IONIZATION TANDEM MASS SPECTROMETRYYan R. RoblesRicardo VessecchiIvo J. C. Vieirahttps://orcid.org/0000-0002-2724-0106Raimundo Braz-FilhoAntonio E. M. Crottihttps://orcid.org/0000-0002-1730-1729The fragmentation of four deprotonated plumeran indole alkaloids (PIAs), namely aspidospermidine (1), demethoxypalosine (2), aspidocarpine (3), and aspidolimine (4), previously isolated from Aspidosperma spruceanum has been investigated by electrospray ionization tandem mass spectrometry (ESI-MS/MS) in the negative ion mode. The fragmentation pathways have been established on the basis of accurate mass data. Our results demonstrated that the main product ions of deprotonated 1-4 result from remote hydrogen rearrangements. The most abundant product ion in the product ion spectrum of 2, 3, and 4 was the result of a ketene loss (methylketene for 2 and 3, and a ketene for 4) directly from the precursor ion. The product ion of m/z 183 was diagnostic for compound 2, whereas the radical loss of •CH3 occurred only for 3 and 4, which display an aromatic methoxyl group in their structures. These results indicated that ESI(-)-MS/MS could be also used for the identification of PIAs 1-4 in crude extracts using LC-ESI-MS/MS, especially when the extracts are more complex.http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0100-40422025000600302&lng=en&tlng=endeprotonated moleculegas-phase fragmentation reactionsindole alkaloidsnegative ion electrospray |
| spellingShingle | Yan R. Robles Ricardo Vessecchi Ivo J. C. Vieira Raimundo Braz-Filho Antonio E. M. Crotti FRAGMENTATION OF DEPROTONATED PLUMERAN INDOLE ALKALOIDS BY ELECTROSPRAY IONIZATION TANDEM MASS SPECTROMETRY Química Nova deprotonated molecule gas-phase fragmentation reactions indole alkaloids negative ion electrospray |
| title | FRAGMENTATION OF DEPROTONATED PLUMERAN INDOLE ALKALOIDS BY ELECTROSPRAY IONIZATION TANDEM MASS SPECTROMETRY |
| title_full | FRAGMENTATION OF DEPROTONATED PLUMERAN INDOLE ALKALOIDS BY ELECTROSPRAY IONIZATION TANDEM MASS SPECTROMETRY |
| title_fullStr | FRAGMENTATION OF DEPROTONATED PLUMERAN INDOLE ALKALOIDS BY ELECTROSPRAY IONIZATION TANDEM MASS SPECTROMETRY |
| title_full_unstemmed | FRAGMENTATION OF DEPROTONATED PLUMERAN INDOLE ALKALOIDS BY ELECTROSPRAY IONIZATION TANDEM MASS SPECTROMETRY |
| title_short | FRAGMENTATION OF DEPROTONATED PLUMERAN INDOLE ALKALOIDS BY ELECTROSPRAY IONIZATION TANDEM MASS SPECTROMETRY |
| title_sort | fragmentation of deprotonated plumeran indole alkaloids by electrospray ionization tandem mass spectrometry |
| topic | deprotonated molecule gas-phase fragmentation reactions indole alkaloids negative ion electrospray |
| url | http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0100-40422025000600302&lng=en&tlng=en |
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