title: Anti-inflammatory sesquiterpene lactones from the flower of Vernonia cinerea.
abstract: Bioassay-guided fractionation of the hexane extract from the flowers of Vernonia cinerea (Asteraceae) led to the isolation of a new sesquiterpene lactone, 8α-hydroxyhirsutinolide (2), and a new naturally occurring derivative, 8α-hydroxyl-1-O-methylhirsutinolide (3), along with seven known compounds (1 and 4-9). The structures of the new compounds were determined by 1D and 2D NMR experiments and by comparison with the structure of compound 1, whose relative stereochemistry was determined by X-ray analysis. The isolated compounds were evaluated for their cancer chemopreventive potential based on their ability to inhibit nitric oxide (NO) production and tumor necrosis factor alpha (TNF-α)-induced NF-κB activity. Compounds 1, 2, 4, 5, and 9 inhibited TNF-α-induced NF-κB activity with IC(50) values of 3.1, 1.9, 0.6, 5.2, and 1.6 μM, respectively; compounds 4 and 6-9 exhibited significant NO inhibitory activity with IC(50) values of 2.0, 1.5, 1.2, 2.7, and 2.4 μM, respectively.
authors: Department of Pharmaceutical Sciences, College of Pharmacy, University of Hawaii at Hilo, Hilo, HI 96720, United States.
authors: Ui Joung
authors: UJ
authors: Youn
authors: Eun-Jung
authors: EJ
authors: Park
authors: Tamara P
authors: TP
authors: Kondratyuk
authors: Charles J
authors: CJ
authors: Simmons
authors: Robert P
authors: RP
authors: Borris
authors: Patcharawan
authors: P
authors: Tanamatayarat
authors: Supakit
authors: S
authors: Wongwiwatthananukit
authors: Onoomar
authors: O
authors: Toyama
authors: Thanapat
authors: T
authors: Songsak
authors: John M
authors: JM
authors: Pezzuto
authors: Leng Chee
authors: LC
authors: Chang
mesh_terms: D000818:Animals; D000893:Anti-Inflammatory Agents / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D002460:Cell Line; D018360:Crystallography, X-Ray; D035264:Flowers / Q000737:chemistry; D006801:Humans; D007783:Lactones / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D009682:Magnetic Resonance Spectroscopy; D051379:Mice; D008958:Models, Molecular; D016328:NF-kappa B / Q000276:immunology; D009369:Neoplasms / Q000517:prevention & control; D009569:Nitric Oxide / Q000037:antagonists & inhibitors; D010936:Plant Extracts / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D012717:Sesquiterpenes / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D014409:Tumor Necrosis Factor-alpha / Q000276:immunology; D035741:Vernonia / Q000737:chemistry*
chemical_list: D000893:Anti-Inflammatory Agents; D007783:Lactones; D016328:NF-kappa B; D010936:Plant Extracts; D012717:Sesquiterpenes; D014409:Tumor Necrosis Factor-alpha; D009569:Nitric Oxide