title: Bioactive constituents of Clausena lansium and a method for discrimination of aldose enantiomers.
abstract: Glycosides, clausenosides A and B, and carbazole alkaloids, clausenaline A, claulamine A, and claulamine B, together with 50 known compounds, were isolated from the stems of Clausena lansium. Their structures were determined by means of spectroscopic methods, including that of CD and 1D/2D NMR analysis. Claulamine A has a 1-oxygenated carbazole skeleton with a rare 2,3-lactone ring, and claulamine B represents an hitherto unknown acetal carbazole alkaloid. Thirty-one of the isolated known compounds were evaluated in various assays for anti-inflammatory activity. Among them, imperatorin, isoheraclenin, and osthol exhibited selective and potent inhibition of formyl-l-methionyl-l-leucyl-l-phenylalanine/cytochalasin B (fMLP/CB)-induced superoxide anion generation, and lansiumarin C also decreased nitric oxide (NO) and tumor necrosis factor-α (TNF-α) production in lipopolysaccharide (LPS)-induced macrophages. In addition, a modified HPLC method of pre-column derivatization was developed that is more practical for simultaneous analysis of aldose enantiomers as compared to the literature method. The absolute configurations of the sugar moieties in clausenosides A and B were determined with this modified method.
authors: Department of Chemistry, National Cheng Kung University, Tainan, Taiwan.
authors: De-Yang
authors: DY
authors: Shen
authors: Chih-Hua
authors: CH
authors: Chao
authors: Hsiu-Hui
authors: HH
authors: Chan
authors: Guan-Jhong
authors: GJ
authors: Huang
authors: Tsong-Long
authors: TL
authors: Hwang
authors: Chin-Yu
authors: CY
authors: Lai
authors: Kuo-Hsiung
authors: KH
authors: Lee
authors: Tran Dinh
authors: TD
authors: Thang
authors: Tian-Shung
authors: TS
authors: Wu
mesh_terms: D000818:Animals; D000893:Anti-Inflammatory Agents / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D000970:Antineoplastic Agents / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D045744:Cell Line, Tumor; D054700:Clausena / Q000737:chemistry*; D004365:Drugs, Chinese Herbal / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D006801:Humans; D020128:Inhibitory Concentration 50; D051379:Mice; D009005:Monosaccharides / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D009504:Neutrophils / Q000187:drug effects / Q000378:metabolism; D018547:Plant Stems / Q000737:chemistry; D013057:Spectrum Analysis; D013237:Stereoisomerism; D013481:Superoxides / Q000378:metabolism
chemical_list: D000893:Anti-Inflammatory Agents; D000970:Antineoplastic Agents; D004365:Drugs, Chinese Herbal; D009005:Monosaccharides; D013481:Superoxides