2. Academic Validation
  3. Lignans from Schisandra sphenathera Rehd. et Wils. and semisynthetic schisantherin A analogues: absolute configuration, and their estrogenic and anti-proliferative activity

Lignans from Schisandra sphenathera Rehd. et Wils. and semisynthetic schisantherin A analogues: absolute configuration, and their estrogenic and anti-proliferative activity

  • Eur J Med Chem. 2013 Jan:59:265-73. doi: 10.1016/j.ejmech.2012.11.003.
Han-Wei Liu 1,  Xiu-Zhu Yu,  Daniele Padula,  Gennaro Pescitelli,  Zhi-Wei Lin,  Fei Wang,  Kai Ding,  Ming Lei,  Jin-Ming Gao
Affiliations

Affiliation

  • 1 Shaanxi Engineering Center of Bioresource Chemistry & Sustainable Utilization, College of Sciences, Northwest A&F University, 3 Taicheng, Yangling, 712100 Shaanxi, China.
PMID: 23237974 DOI: 10.1016/j.ejmech.2012.11.003
Abstract

A new dibenzocyclooctene-type lignan, named schisandrin A1 (1), together with nine known Lignans (2-10), was isolated from the stems of Schisandra sphenathera. The structure of schisandrin A1, which contains a spirocyclic epoxy unit, was established by means of spectroscopic methods. The absolute configurations of schisandrin A1 (1) and schisantherin A (2) were determined by electronic circular dichroism (CD) and TDDFT calculations, with 2 further confirmed by X-ray crystallographic data. Ten new schisantherin A derivatives (11-20) and 6,7-secoschisantherol A (2b) were synthesized. In addition, natural Lignans and semisynthetic schisantherin A derivatives showed the antiproliferative activity on four human Cancer cell lines and Id1 (an inhibitor of DNA binding protein) and estrogenic potency. Compounds 5, 7, and 8 exhibited very potent estrogenic activity.

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