title: Lignans from Schisandra sphenathera Rehd. et Wils. and semisynthetic schisantherin A analogues: absolute configuration, and their estrogenic and anti-proliferative activity.
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.
authors.affiliation: Shaanxi Engineering Center of Bioresource Chemistry & Sustainable Utilization, College of Sciences, Northwest A&F University, 3 Taicheng, Yangling, 712100 Shaanxi, China.
authors.forename: Han-Wei
authors.initials: HW
authors.lastname: Liu
authors.forename: Xiu-Zhu
authors.initials: XZ
authors.lastname: Yu
authors.forename: Daniele
authors.initials: D
authors.lastname: Padula
authors.forename: Gennaro
authors.initials: G
authors.lastname: Pescitelli
authors.forename: Zhi-Wei
authors.initials: ZW
authors.lastname: Lin
authors.forename: Fei
authors.initials: F
authors.lastname: Wang
authors.forename: Kai
authors.initials: K
authors.lastname: Ding
authors.forename: Ming
authors.initials: M
authors.lastname: Lei
authors.forename: Jin-Ming
authors.initials: JM
authors.lastname: Gao
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D002942:Circular Dichroism; D018360:Crystallography, X-Ray; D004305:Dose-Response Relationship, Drug; D004967:Estrogens / Q000737:chemistry / Q000494:pharmacology; D006801:Humans; D017705:Lignans / Q000737:chemistry* / Q000494:pharmacology*; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D011789:Quantum Theory; D032141:Schisandra / Q000737:chemistry*
chemical_list: D000970:Antineoplastic Agents; D004967:Estrogens; D017705:Lignans