(P)/(M)-corinepalensin A, a pair of axially chiral prenylated bicoumarin enantiomers with a rare C-5C-5′ linkage from the twigs of Coriaria nepalensis. (May 2018)

• Record Type: Journal Article
• Authors: Chen, Lin; Tang, Gui-Hua; Guo, Fu-Liang; Li, Wei; Zhang, Jun-Sheng; Liu, Bo; Yin, Sheng
• Is Part Of: Phytochemistry. Volume 149(2018)
• Page Start: 140
• Page End: 145
• Publication Date: 2018-05
• Subjects: Coriaria nepalensis (Coriariaceae) -- Bicoumarin -- Axial chirality -- PDE4 inhibition; Botanical chemistry -- Periodicals; Biochemistry -- Periodicals; Botany -- Periodicals; Chimie végétale -- Périodiques; 572.2
• DOI: 10.1016/j.phytochem.2018.02.012
• Languages: English
• ISSNs: 0031-9422

Abstract

Abstract: A pair of undescribed bicoumarin enantiomers, ( P )/( M )-corinepalensin A, two undescribed prenylated coumarins, corinepalensins B and C, along with ten known coumarins were isolated from the twigs of Coriaria nepalensis . ( P )/( M )-corinepalensin A feature a rare C-5C-5′ axially chiral linkage between two prenylated coumarin monomers. Their structures were determined by a combination of spectroscopic methods, single crystal X-ray diffraction, and ECD calculations. All isolates were evaluated for the inhibitory activity against phosphodiesterase-4 (PDE4), which is a drug target for the treatment of asthma and chronic obstructive pulmonary disease. Compounds ( P )-corinepalensin A, ( M )-corinepalensin A, corinepalensin B, norbraylin, braylin, and nepalin C exhibited significant inhibition with IC50 values ranging from 0.43 to 7.15 μ M. Graphical abstract: Image 1 Highlights: Four undescribed coumarins were isolated from Coriaria nepalensis. 1a and1b are a pair of axially chiral bicoumarin enantiomers with a rare linkage. 1a and1b exhibited significant inhibitory activity against PDE4D2.