title: Two dimeric lignans with an unusual α,β-unsaturated ketone motif from Zanthoxylum podocarpum and their inhibitory effects on nitric oxide production.
abstract: Two new dimeric lignans, zanthpodocarpins A (1) and B (2), and five known lignans, eudesmin (3), (1R,2R,5R,6S)-2-(3,4-dimethoxyphenyl)-6-(3,4-dihydroxyphenyl)-3,7-dioxabicyclo[3.3.0]octane (4), dimethoxysamin (5), rel-(1R,5R,6S)-6-(4-hydroxy-3-methoxyphenyl)-3,7-dioxabicyclo[3.3.0]octan-2-one (6), and magnone A (7), were isolated from the barks of Zanthoxylum podocarpum. Their structures were identified by using spectroscopic methods. Compounds 1 and 2 are rare dilignans bearing an unusual α,β-unsaturated ketone group from a natural source. Bioassay showed that compounds 1 and 2 could inhibit nitric oxide (NO) production in LPS stimulated RAW 264.7 cells with IC(50) values of 5.31 μM and 12.15 μM, respectively.
authors.affiliation: State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650204, PR China.
authors.forename: Xiao-Jiang
authors.initials: XJ
authors.lastname: Zhou
authors.forename: Xiao-Liang
authors.initials: XL
authors.lastname: Chen
authors.forename: Xue-Song
authors.initials: XS
authors.lastname: Li
authors.forename: Jia
authors.initials: J
authors.lastname: Su
authors.forename: Jiang-Bo
authors.initials: JB
authors.lastname: He
authors.forename: Yue-Hu
authors.initials: YH
authors.lastname: Wang
authors.forename: Yan
authors.initials: Y
authors.lastname: Li
authors.forename: Yong-Xian
authors.initials: YX
authors.lastname: Cheng
mesh_terms: D000818:Animals; D045744:Cell Line, Tumor; D019281:Dimerization; D007659:Ketones / Q000737:chemistry*; D017705:Lignans / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D051379:Mice; D008968:Molecular Conformation; D009569:Nitric Oxide / Q000378:metabolism*; D024301:Plant Bark / Q000737:chemistry; D032106:Zanthoxylum / Q000737:chemistry*
chemical_list: D007659:Ketones; D017705:Lignans; C557266:zanthpodocarpin A; C557267:zanthpodocarpin B; D009569:Nitric Oxide