2. Academic Validation
  3. (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

(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

  • Phytochemistry. 2018 May;149:140-145. doi: 10.1016/j.phytochem.2018.02.012.
Lin Chen 1,  Gui-Hua Tang 1,  Fu-Liang Guo 1,  Wei Li 1,  Jun-Sheng Zhang 1,  Bo Liu 2,  Sheng Yin 3
Affiliations

Affiliations

  • 1 School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou 510006, China.
  • 2 The Second Clinical Medical College, Guangzhou University of Chinese Medicine, Guangzhou 510006, China. Electronic address: doctliu@263.net.
  • 3 School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou 510006, China. Electronic address: yinsh2@mail.sysu.edu.cn.
PMID: 29501013 DOI: 10.1016/j.phytochem.2018.02.012
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 μM.

Keywords

Axial chirality; Bicoumarin; Coriaria nepalensis (Coriariaceae); PDE4 inhibition.

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