title: Diterpenoids from aerial parts of Flickingeria fimbriata and their nuclear factor-kappaB inhibitory activities.
abstract: Chemical investigation of the aerial parts of Flickingeria fimbriata (Bl.) Hawkes resulted in isolation of sixteen ent-pimarane diterpenoids, including five rare 16-nor-ent-pimarane diterpenoids, two 15,16-dinor-ent-pimarane diterpenoids and one ent-pimarane diterpenoid. Structures were mainly elucidated by extensive spectroscopic analysis, and their absolute configurations were unequivocally determined by the exciton chirality method, the modified Mosher's method, the CD experiments (including Snatzke's method) and chemical transformations, respectively. All the isolated compounds were screened for inhibitory effects on the nuclear factor-kappaB (NF-κB) in lipopolysaccharide (LPS) induced murine macrophage RAW264.7 cells, using a NF-κB-dependent luciferase reporter gene assay. Several of these compounds displayed comparable or even better activities than the positive control pyrrolidinedithiocarbamate (PDTC) (IC50=26.3 μM) with IC50 values in the range of 14.7-29.2 μM and structure-activity relationships are briefly proposed.
authors.affiliation: School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou, Guangdong 510006, China.
authors.forename: Hang
authors.initials: H
authors.lastname: Li
authors.affiliation: School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou, Guangdong 510006, China.
authors.forename: Jing-Jun
authors.initials: JJ
authors.lastname: Zhao
authors.affiliation: School of Environmental and Chemical Engineering, Nanchang University, Nanchang, Jiangxi 330031, China.
authors.forename: Jin-Long
authors.initials: JL
authors.lastname: Chen
authors.affiliation: School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou, Guangdong 510006, China; Guangdong Technology Research Center for Advanced Chinese Medicine, Guangzhou, Guangdong 510006, China.
authors.forename: Long-Ping
authors.initials: LP
authors.lastname: Zhu
authors.affiliation: School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou, Guangdong 510006, China; Guangdong Technology Research Center for Advanced Chinese Medicine, Guangzhou, Guangdong 510006, China.
authors.forename: Dong-Mei
authors.initials: DM
authors.lastname: Wang
authors.affiliation: School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou, Guangdong 510006, China; Guangdong Technology Research Center for Advanced Chinese Medicine, Guangzhou, Guangdong 510006, China.
authors.forename: Lin
authors.initials: L
authors.lastname: Jiang
authors.affiliation: School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou, Guangdong 510006, China; Guangdong Technology Research Center for Advanced Chinese Medicine, Guangzhou, Guangdong 510006, China. Electronic address: lssydp@mail.sysu.edu.cn.
authors.forename: De-Po
authors.initials: DP
authors.lastname: Yang
authors.affiliation: School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou, Guangdong 510006, China; Guangdong Technology Research Center for Advanced Chinese Medicine, Guangzhou, Guangdong 510006, China. Electronic address: zhaozhm2@mail.sysu.edu.cn.
authors.forename: Zhi-Min
authors.initials: ZM
authors.lastname: Zhao
mesh_terms: D000818:Animals; D002460:Cell Line / Q000187:drug effects; D002942:Circular Dichroism; D004224:Diterpenes / Q000737:chemistry* / Q000494:pharmacology*; D004353:Drug Evaluation, Preclinical / Q000379:methods; D020128:Inhibitory Concentration 50; D008070:Lipopolysaccharides / Q000494:pharmacology; D008264:Macrophages / Q000187:drug effects / Q000378:metabolism; D051379:Mice; D015394:Molecular Structure; D016328:NF-kappa B / Q000037:antagonists & inhibitors*; D029595:Orchidaceae / Q000737:chemistry*; D035261:Plant Components, Aerial / Q000737:chemistry; D013329:Structure-Activity Relationship
chemical_list: D004224:Diterpenes; D008070:Lipopolysaccharides; D016328:NF-kappa B
keywords: Absolute configuration; Flickingeria fimbriata; NF-κB; Norditerpenoids; Orchidaceae