title: D-ring-opened phragmalin-type limonoids from Chukrasia tabularis var. velutina.
abstract: Five new D-ring-opened phragmalin-type limonoids, tabulalins A-E (1-5, resp.), were isolated from the stem bark of Chukrasia tabularis var. velutina. In the structures of these new isolates, the D-ring (C(16)/C(17) δ-lactone ring) of phragmalins was cleaved, and rare C(16)/C(30) δ-lactone ring in 1-3 or C(16)/C(8) γ-lactone ring in 4 and 5 were formed. The structures of these new compounds were elucidated based on extensive 1D- and 2D-spectroscopic analyses (HSQC, HMBC, and ROESY) and HR-ESI-MS. The major compounds, 2, 3, and 5, were evaluated for their inhibitory activities against lipopolysaccharide (LPS)-induced nitric oxide (NO) production in a macrophage (RAW264.7) cell line with IC(50) values of 15.3±0.6, 13.0±0.5, and 17.1±0.7 μM, respectively.
authors.affiliation: School of Traditional Chinese Medicine, China Pharmaceutical University, Nanjing, P R. China.
authors.forename: Jun
authors.initials: J
authors.lastname: Luo
authors.forename: Yi
authors.initials: Y
authors.lastname: Li
authors.forename: Jun-Song
authors.initials: JS
authors.lastname: Wang
authors.forename: Ling-Yi
authors.initials: LY
authors.lastname: Kong
mesh_terms: D000818:Animals; D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology / Q000633:toxicity; D002460:Cell Line; D002470:Cell Survival / Q000187:drug effects; D004365:Drugs, Chinese Herbal / Q000737:chemistry* / Q000302:isolation & purification*; D007783:Lactones / Q000737:chemistry / Q000302:isolation & purification; D036701:Limonins / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology / Q000633:toxicity; D008264:Macrophages / Q000187:drug effects / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D029582:Meliaceae / Q000737:chemistry*; D051379:Mice; D008958:Models, Molecular; D015394:Molecular Structure; D009569:Nitric Oxide / Q000096:biosynthesis; D024301:Plant Bark / Q000737:chemistry; D018547:Plant Stems / Q000737:chemistry; D021241:Spectrometry, Mass, Electrospray Ionization
chemical_list: D000894:Anti-Inflammatory Agents, Non-Steroidal; D004365:Drugs, Chinese Herbal; D007783:Lactones; D036701:Limonins; D009569:Nitric Oxide