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Characterization of 3-aminospirostane alkaloids from roots of Solanum paniculatum L. with hepatoprotective activity

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Autor(es):
Gazolla, Matheus Coutinho [1] ; Mauriz Marques, Lucas Maciel [1] ; Gama e Silva, Mariana [2] ; Moura Fontes Araujo, Maria Tais [2] ; Mendes, Rosemairy Luciane [2] ; Guedes da Silva Almeida, Jackson Roberto [2] ; Vessecchi, Ricardo [3] ; Lopes, Norberto Peporine [1]
Número total de Autores: 8
Afiliação do(s) autor(es):
[1] Univ Sao Paulo, Fac Ciencias Farmaceut Ribeirao Preto, Dept Ciencias BioMol, Nucleo Pesquisa Prod Nat & Sintet, BR-14040903 Ribeirao Preto, SP - Brazil
[2] Univ Fed Vale Sao Francisco, Nucleo Estudos & Pesquisa Plantas Med, BR-56304205 Petrolina, PE - Brazil
[3] Univ Sao Paulo, Fac Filosofia Ciencias & Letras Ribeirao Preto, Dept Quim, BR-14040901 Ribeirao Preto, SP - Brazil
Número total de Afiliações: 3
Tipo de documento: Artigo Científico
Fonte: RAPID COMMUNICATIONS IN MASS SPECTROMETRY; FEB 2020.
Citações Web of Science: 0
Resumo

Rationale Solanum paniculatum L., popularly known as jurubeba, has traditionally been used in Brazilian folk medicine for liver diseases. However, there is a lack of knowledge about the chemical characterization of 3-aminospirostane alkaloids, an important class related to pharmacological activities. This work aimed to characterize the alkaloids using liquid chromatography with tandem mass spectrometry (LC/MS/MS) supported by molecular networking and theoretical calculations as well as to evaluate the contribution to hepatoprotective activity. Methods S. paniculatum roots were collected and macerated with MeOH/H2O (8:2) obtaining the crude extract (SP-CE). From this, partition using EtOAc with pH variation yielded the alkaloidic fraction (SP-AF). Both were evaluated in an acute liver injury model (100 and 200 mg/kg), after intraperitoneal administration of carbon tetrachloride (CCl4) in mice. AST (aspartate transaminase) and ALT (alanine transaminase) serum levels were investigated, as well as the histopathological characteristics. The SP-CE and SP-AF were analyzed by LC/MS/MS, using quadrupole/time-of-flight and ion-trap systems. The alkaloids annotated by the GNPS molecular network had their structures defined using gas-phase ionization and fragmentation reaction supported by theoretical calculations. Results The SP-CE and SP-AF decreased the ALT serum levels compared with the negative control. The group treated with the SP-CE (at the highest dose) demonstrated a significant decrease of ALT. Hepatic cell degeneration decrease was observed mainly at the highest dose of the treatment. Detailed electrospray ionization MS/MS data allowed us to identify alkaloids not previously reported, to propose their gas-phase reactions and to redefine the initial open ring fragmentation mechanism of the steroidal alkaloids with the jurubidine moiety. Conclusions The results allowed us to identify seven steroidal alkaloids from jurubeba and redefine the initial mechanism of fragmentation. A significant hepatoprotective effect was also demonstrated, corroborating its traditional use. (AU)

Processo FAPESP: 14/50265-3 - Metabolismo e distribuição de xenobióticos naturais e sintéticos: da compreensão dos processos reacionais à geração de imagens teciduais
Beneficiário:Norberto Peporine Lopes
Linha de fomento: Auxílio à Pesquisa - Programa BIOTA - Temático
Processo FAPESP: 17/19330-1 - Metabolismo in vitro dos alcalóides esteroidais de Solanum paniculatum l. (Solanaceae)
Beneficiário:Matheus Coutinho Gazolla
Linha de fomento: Bolsas no Brasil - Mestrado
Processo FAPESP: 14/23604-1 - Química computacional: uma ferramenta para estudos envolvendo espectrometria de massas, reatividade e mecanismos de reação/fragmentação de compostos orgânicos
Beneficiário:Ricardo Vessecchi Lourenço
Linha de fomento: Auxílio à Pesquisa - Regular