Structure Elucidation and Absolute Configuration Determination of Nortriterpenoids from Picramnia glazioviana

Autor(es)

Gimenes, Leila ^{[1, 2]} ; Luna-Dulcey, Liany ^[3] ; Batista, Jr., Joao M. ^[4] ; dos Santos, Jr., Fernando M. ^[5] ; Popolin, Cecilia P. ^[3] ; Cominetti, Marcia R. ^[3] ; Fernandes, Joao B. ^[1] ; Staerk, Dan ^[2]

Afiliação do(s) autor(es)

^[1] Fed Univ Sao Carlos UFSCar, Dept Chem, BR-13565905 Sao Carlos, SP - Brazil

^[2] Univ Copenhagen, Fac Hlth & Med Sci, Dept Drug Design & Pharmacol, DK-2100 Copenhagen - Denmark

^[3] Univ Fed Sao Carlos, Dept Gerontol, BR-13565905 Sao Carlos, SP - Brazil

^[4] Univ Fed Sao Paulo, Inst Sci & Technol, BR-12231280 Sao Jose Dos Campos, SP - Brazil

^[5] Fluminense Fed Univ UFF, Chem Inst, Dept Organ Chem, Niteroi, RJ - Brazil

• Tipo de documento: Artigo Científico
• Fonte: Journal of Natural Products; v. 83, n. 6, p. 1859-1875, JUN 26 2020.
• Citações Web of Science: 1

Resumo

In this study, HPLC-PDA-HRMS-SPE-NMR data were used for initial analysis of the CH2Cl2 fraction of an EtOH extract of the leaves of Picramnia glazioviana. The HRMS, UV, and NMR data obtained from the HPLC-PDA-HRMS-SPE-NMR analysis were used to direct semipreparative HPLC isolation toward nortriterpenoids, which resulted in the isolation of 18 new and highly oxygenated nortriterpenoids (1-3, 5-10, 12-19, and 21), named picravianes C-T. Their structures were determined on the basis of analysis of UV, HRMS, and 2D NMR spectroscopic data, including determination of the relative configuration on the basis of coupling pattern analysis and nuclear Overhauser effect correlations. The absolute configurations of compounds 7, 9, 10, 14, 15, 17, 18, 19, and 21 were assigned using electronic circular dichroism data, and the cytotoxicity of compounds 6, 10, 14, 16, 17, 18, 19, and 21 was evaluated against MDA-MB-231 triple-negative breast cancer, SKBR-3 Her2-overexpressing breast cancer, and A549 lung cancer cells lines. The isolated compounds contain a hitherto undescribed modification of the terminal backbone and/or E-ring, and a possible biosynthetic pathway for their formation is proposed. (AU)

• Processo FAPESP: 12/25299-6 - Estudos integrados para o controle de formigas cortadeiras
• Beneficiário: João Batista Fernandes
• Modalidade de apoio: Auxílio à Pesquisa - Temático
• Processo FAPESP: 13/20458-1 - Controle de formigas-cortadeiras através do estudo fitoquímico biomonitorado de Picramnia glazioviana e Picramnia bahiensis- Busca de substâncias inseticidas, fungicidas e desenvolvimento de processos de nanoencapsulamento.
• Beneficiário: Leila Gimenes
• Modalidade de apoio: Bolsas no Brasil - Doutorado
• Processo FAPESP: 16/18024-1 - Estudo de Picramnia usando a plataforma tecnológica hifenada HPLC-HRMS-SPE-NMR/bioensaio de alta resolução
• Beneficiário: Leila Gimenes
• Modalidade de apoio: Bolsas no Exterior - Estágio de Pesquisa - Doutorado