Integrative Approach Based on Leaf Spray Mass Spectrometry, HPLC-DAD-MS/MS, and NMR for Comprehensive Characterization of Isoquinoline-Derived Alkaloids in Leaves of Onychopetalum amazonicum R. E. Fr.

Autor(es)

de Lima, Bruna R. ^[1] ; da Silva, Felipe M. A. ^{[1, 2]} ; Soares, Elzalina R. ^[1] ; de Almeida, Richardson A. ^[1] ; da Silva-Filho, Francinaldo A. ^[1] ; Benison, Andersson ^[3] ; Costa, V, Emmanoel ; Koolen, Hector H. F. ^[4] ; de Souza, Afonso D. L. ^{[1, 5]} ; Pinheiro, Maria Lucia B. ^{[1, 5]}

Afiliação do(s) autor(es)

^[1] Univ Fed Amazonas UFAM, Cent Analit Ctr Apoio Multidisciplinar CAM, BR-69077000 Manaus, Amazonas - Brazil

^[2] Univ Fed Amazonas UFAM, Dept Quim, BR-69077000 Manaus, Amazonas - Brazil

^[3] Univ Fed Parana UFPR, Lab RMN, BR-81531990 Curitiba, Parana - Brazil

^[4] Univ Estado Amazonas, Grp Pesquisa Metabolom & Espectrometria Massas, BR-69050010 Manaus, Amazonas - Brazil

^[5] Costa, Emmanoel, V, Univ Fed Amazonas UFAM, Dept Quim, BR-69077000 Manaus, Amazonas - Brazil

• Tipo de documento: Artigo Científico
• Fonte: Journal of the Brazilian Chemical Society; v. 31, n. 1, p. 79-89, JAN 2020.
• Citações Web of Science: 1

Resumo

Onychopetalum is an Amazonian botanical genus close-related with Bocageopsis and Unonopsis, whose species are used in traditional medicine. Although these genera are widely investigated from the phytochemical viewpoint, the knowledge about Onychopetalum remains almost unexplored. In order to perform a comprehensive characterization of isoquinoline-derived alkaloids from Onychopetalum amazonicum, an integrative approach based on the alkaloid profile analysis by leaf spray mass spectrometry (LS-MS), followed by a robust dereplication through high-performance liquid chromatography coupled with diode array detector and atmospheric pressure chemical ionization tandem mass spectrometry, (HPLC-DAD-APCI-MS/MS) and nuclear magnetic resonance (NMR) analysis was adopted. LS-MS allowed the tentative identification of reticuline, norjuziphine, nornuciferine, O-methylisopiline, nuciferine, N-methyl-O-methylisopiline, anonaine, and N-methylanonaine. HPLC-DAD-MS/MS analysis supported the tentative identification of N-methylasimilobine, asimilobine, norushinsunine, N-methylisopiline, isopiline, liriodenine, and lysicamine. Moreover, the integration of MS and NMR data allowed the additional identification of stepholidine and isocorypalmine. The applied integrative approach proposed herein enabled a comprehensive analysis of the alkaloid content from the O. amazonicum, showing to be a useful strategy for the dereplication of isoquinoline-derived alkaloids. (AU)

• Processo FAPESP: 14/50244-6 - UHPLC acoplado a espectrômetro de massa do tipo híbrido com analisador quadrupolar e time of flight
• Beneficiário: Quezia Bezerra Cass
• Modalidade de apoio: Auxílio à Pesquisa - Programa Equipamentos Multiusuários