Abstract
Aspidosperma pyrifolium Mart., Apocynaceae, is a species popularly known with the popular Brazilian names of “pereiro” and “pau-pereiro.” It is a native tree from the Caatinga biome, and the flowers frequently attract bees. The species is known for the presence of plumeran indole alkaloids. In this study, the alkaloidal fraction of A. pyrifolium flowers resulted in the characterization of eighteen plumeran indolic alkaloids via ultra-performance liquid chromatography coupled with diode array and quadrupole time-of-flight mass spectrometry. Four of these alkaloids were isolated, and their structures were established by different spectroscopic methods. The novel indole alkaloid N-formyl-15-methoxy-aspidofractinin, in addition to the known alkaloids pyrifoline, aspidospermine, and 15-methoxy-aspidospermine, was identified from the analyzed plant.
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References
Agra MF, Freitas PF, Barbosa-Filho JM (2007) Synopsis of the plants known as medicinal and poisonous in northeast of Brazil. Rev Bras Farmacogn 17:114–140. https://doi.org/10.1590/S0102-695X2007000100021
Aguiar GP, Wakabayashi KALF, Luz G, Oliveira VB, Mathias L, Vieira IJC, Braz-Filho R, Crotti AEM (2010) Fragmentation of plumeran indole alkaloids from Aspidosperma spruceanum by electrospray ionization tandem mass spectrometry. Rapid Commun Mass Spectrom 24:295–308. https://doi.org/10.1002/rcm.4389
Craveiro AA, Matos FJA, Serur LM (1983) Alkaloids of Aspidosperma pyrifolium. Phytochemistry 22:1526–1528. https://doi.org/10.1016/S0031-9422(00)84061-3
Araujo-Jr JX, Antheaume C, Trindade RCP, Schmitt M, Bourguignon JJ, Sant’ana AEG (2007) Isolation and characterisation of the monoterpenoid indole alkaloids of Aspidosperm pyrifolium. Phytochem Rev 6:183–188. https://doi.org/10.1007/s11101-006-9044-y
Li LM, Li GY, Fang DM, Wu ZJ, Zhang GL (2015) Analysis of monoterpenoid indole alkaloids using electrospray ionization tandem mass spectrometry. Chem Nat Compd 51:116–120. https://doi.org/10.1007/s10600-015-1215-x
Mitaine AC, Mesbah K, Richard B, Petermann C, Arrazola S, Moretti C, Zèches-Hanrot M, Le Men-Olivier L (1996) Alkaloids from Aspidosperma species from Bolivia. Planta Med 62:458–461. https://doi.org/10.1055/s-2006-957939
Nogueira PCN, Araújo RM, Viana GSB, de Araújo DP, Filho RB, Silveira ER (2014) Plumeran alkaloids and glycosides from the seeds of Aspidosperma pyrifolium Mart. J Braz Chem Soc 25:2108–2120. https://doi.org/10.5935/0103-5053.20140204
Oliveira GP, Silva TMG, Camara CA, Santana ALBD, Moreira MSA, Silva TMS (2017) Isolation and structure of flavonoids from Amburana cearensis resin and identification of human DNA topoisomerase. Phytochem Lett 22:61–70. https://doi.org/10.1016/j.phytol.2017.09.006
Funding
This work was financially supported by grants from Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq grant no. 425493/2018-0 and 301935/2018-1), Fundação de Amparo à Ciência e Tecnologia de Pernambuco (FACEPE-PRONEM APQ-0741106/2014), and Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES).
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SPC and TMSS performed experiments and wrote the manuscript, SPC, TMSS, ALBM, TMGS, and CAC interpreted data and prepared and provided the key materials. All the authors have read the final manuscript and approved the submission.
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Cabrera, S.P., da Silva, T.M.G., Monteiro, A.L.B. et al. Plumeran Indole Alkaloids From Aspidosperma pyrifolium Flowers. Rev. Bras. Farmacogn. 30, 346–349 (2020). https://doi.org/10.1007/s43450-020-00048-y
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DOI: https://doi.org/10.1007/s43450-020-00048-y