Cytotoxic heterodimers of meroterpene phenol from the fruits of Psoralea corylifolia. (August 2020)

• Record Type: Journal Article
• Authors: Xu, Qing-Xia; Zhang, You-Bo; Liu, Xiao-Yan; Xu, Wei; Yang, Xiu-Wei
• Is Part Of: Phytochemistry. Volume 176(2020)
• Publication Date: 2020-08
• Subjects: Psoralea corylifolia -- Leguminosae -- Meroterpene phenol -- Heterodimer -- Spiroketal -- Cytotoxicity; Botanical chemistry -- Periodicals; Biochemistry -- Periodicals; Botany -- Periodicals; Chimie végétale -- Périodiques; 572.2
• DOI: 10.1016/j.phytochem.2020.112394
• Languages: English
• ISSNs: 0031-9422

Abstract

Abstract: Seventeen undescribed heterodimers of meroterpene phenol, psocorylins A–Q, were isolated from the fruits of Psoralea corylifolia . Their another monomeric unit derived from flavonone, chalcone, coumarin and isoflavone, respectively. Psocorylins A–E were rare natural spiroketals with the skeleton of 1, 4, 8-trioxaspiro[4.5]decane deriving from flavonone, and their plausible biosynthetic pathways were proposed. These structures were established by spectroscopic methods. Their absolute configurations were assigned via single-crystal X-ray diffraction, electronic circular dichroism (ECD) calculations and Rh2 (OCOCF3 )4 -induced ECD spectra. Psocorylins B–E, F, M and Q exhibited potent cytotoxic activities against different kinds of tumor cells with IC50 values less than 10 μ M. Graphical abstract: Image 1 Highlights: Seventeen undescribed heterodimers were isolated from Psoralea corylifolia. It was the first time that heterodimers were obtained from the plant. Natural spiroketals deriving from flavonone were reported for the first time. Absolute configurations were elucidated by crystal diffraction and ECD calculation. Some compounds exhibited potent cytotoxic activity against tumor cells.