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Structure elucidation and absolute configuration determination of nortriterpenoids from Picramnia glazioviana

Publikation: Bidrag til tidsskriftTidsskriftartikelForskningfagfællebedømt

  • Leila Gimenes
  • Liany Luna-Dulcey
  • Joao Marcos Batista Junior
  • Fernando Martins dos Santos Junior
  • Cecilia P. Popolin
  • Marcia Regina Cominetti
  • Joao Bastita Fernandes
  • Stærk, Dan
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 towards nortriterpenoids, which resulted in 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 (ECD) 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.
OriginalsprogEngelsk
TidsskriftJournal of Natural Products
Vol/bind83
Sider (fra-til)1859-1876
ISSN0163-3864
DOI
StatusUdgivet - 2020

ID: 241226201