title: Bioactive quassinoids from the seeds of Brucea javanica.
abstract: Six new quassinoids (1-6) and eight known compounds of this type (7-14) were isolated from the seeds of Brucea javanica. Their structures were elucidated by analysis of their spectroscopic data and from chemical evidence. Compounds 1-5 were found to be unusual quassinoids with a 2,3-seco A ring. The configurations at C-4 in 4 and 5 were determined by a difference circular dichroism method. In in vitro bioassays, 8 and 10 showed inhibitory activities for nitric oxide production in LPS-activated macrophages, with IC(50) values of 1.9 and 5.0 μM, respectively, while compounds 6, 8-11, 13, and 14 exhibited cytotoxicity against five human tumor cell lines (HCT-8, HepG2, BGC-823, A549, and SKVO3), having IC(50) values in the range 0.12-9.3 μM.
authors.affiliation: State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, NO.1 Xian Nong Tan Street, Beijing 100050, People's Republic of China.
authors.forename: Jun-Hong
authors.initials: JH
authors.lastname: Liu
authors.forename: Nan
authors.initials: N
authors.lastname: Zhao
authors.forename: Gui-Jie
authors.initials: GJ
authors.lastname: Zhang
authors.forename: Shi-Shan
authors.initials: SS
authors.lastname: Yu
authors.forename: Li-Jun
authors.initials: LJ
authors.lastname: Wu
authors.forename: Jing
authors.initials: J
authors.lastname: Qu
authors.forename: Shuang-Gang
authors.initials: SG
authors.lastname: Ma
authors.forename: Xiao-Guang
authors.initials: XG
authors.lastname: Chen
authors.forename: Tian-Qi
authors.initials: TQ
authors.lastname: Zhang
authors.forename: Jian
authors.initials: J
authors.lastname: Bai
authors.forename: Hui
authors.initials: H
authors.lastname: Chen
authors.forename: Zhen-Feng
authors.initials: ZF
authors.lastname: Fang
authors.forename: Fen
authors.initials: F
authors.lastname: Zhao
authors.forename: Wei-Bin
authors.initials: WB
authors.lastname: Tang
mesh_terms: D000818:Animals; D032269:Brucea / Q000737:chemistry*; D006801:Humans; D020128:Inhibitory Concentration 50; D008070:Lipopolysaccharides / Q000494:pharmacology; D008264:Macrophages / Q000187:drug effects; D051379:Mice; D015394:Molecular Structure; D009569:Nitric Oxide / Q000096:biosynthesis; D019906:Nuclear Magnetic Resonance, Biomolecular; D036702:Quassins / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D012639:Seeds / Q000737:chemistry
chemical_list: D008070:Lipopolysaccharides; D036702:Quassins; D009569:Nitric Oxide