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Picraviane A and B: Nortriterpenes with limonoid-like skeletons containing a heptanolide E-ring system from Picramnia glazioviana

Gimenes, Leila, Batista Junior, Joao Marcos, Martins dos Santos Junior, Fernando, da Silva Souza, Matheus, Luna-Dulcey, Liany, Ellena, Javier Esteves, Cominetti, Marcia Regina, Fatima das Graças Fernandes da Silva, Maria, Vieira, Paulo Cezar, Fernandes, Joao Batista, Staerk, Dan
Phytochemistry 2019 v.163 pp. 38-45
Picramnia, X-ray diffraction, breast neoplasms, cell lines, circular dichroism spectroscopy, cytotoxicity, mass spectrometry, neoplasm cells, nuclear magnetic resonance spectroscopy, spectral analysis
Two highly oxygenated nortriterpenes, picraviane A and B, were isolated from the ethanolic extract of Picramnia glazioviana Engl. The structures were determined by analysis of HRMS and 2D NMR spectroscopic data. Single-crystal X-ray diffraction data was also obtained for picraviane B. The absolute configuration of both compounds were assigned by comparison of experimental and calculated vibrational and electronic circular dichroism spectroscopy, respectively. Picraviane A showed a moderate cytotoxic activity against the triple negative MDA-MB-231 breast cancer cell line. These compounds represent an undescribed class of natural products with limonoid-like skeletons containing a heptanolide as the E-ring.