title: 3, 4-seco-labdane diterpenoids from the leaves of Callicarpa nudiflora and their inhibitory effects on nitric oxide production.
abstract: As a part of our ongoing search for bioactive compounds from the leaves of Callicarpa nudiflora that inhibit nitric oxide (NO) production, the 90% EtOH fraction eluted by macroporous resin adsorption was found to show significant inhibitory activity against the production of NO in RAW 264.7 stimulated by lipopolysaccharide (LPS). Bioactivity-guided isolation of the fraction yielded three new bioactive diterpenoids, named ent-3, 4-seco-14-carbonyl-15, 16-epoxy-4(18), 8(17), 13(14)-labdatrien-3-oic acid (1), syn-3, 4-seco-12R-hydroxy-15, 16-epoxy-4(18), 8(17), 13(16), 14(15)-labdatetraen-3-oic acid (2) and syn-3, 4-seco-12S-hydroxy-15, 16-epoxy-4(18), 8(17), 13(16), 14(15)-labdatetraen-3-oic acid (3). Their structures and configurations were elucidated by comprehensive spectroscopic analysis. All the three compounds exhibited potent inhibitory activity on NO production in LPS-activated RAW 264.7 macrophage cells.
authors.affiliation: School of Traditional Chinese Medicine, Shenyang Pharmaceutical University, Shenyang 110016, China.
authors.forename: Lei
authors.initials: L
authors.lastname: Zhang
authors.forename: Lin
authors.initials: L
authors.lastname: Dong
authors.forename: Jian
authors.initials: J
authors.lastname: Huang
authors.forename: Mingsheng
authors.initials: M
authors.lastname: Liu
authors.forename: Guoyu
authors.initials: G
authors.lastname: Li
authors.forename: Cui
authors.initials: C
authors.lastname: Zhang
authors.forename: Ke
authors.initials: K
authors.lastname: Zhang
authors.forename: Jinhui
authors.initials: J
authors.lastname: Wang
mesh_terms: D000893:Anti-Inflammatory Agents / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D032408:Callicarpa / Q000737:chemistry*; D004224:Diterpenes / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D008070:Lipopolysaccharides; D008264:Macrophages / Q000187:drug effects / Q000378:metabolism; D015394:Molecular Structure; D009569:Nitric Oxide / Q000096:biosynthesis*; D010936:Plant Extracts / Q000737:chemistry / Q000494:pharmacology*; D018515:Plant Leaves / Q000737:chemistry
chemical_list: D000893:Anti-Inflammatory Agents; D004224:Diterpenes; D008070:Lipopolysaccharides; D010936:Plant Extracts; C586592:ent-3,4-seco-14-carbonyl-15,16-epoxy-4(18), 8(17),13(14)-labdatrien-3-oic acid; C586593:syn-3,4-seco-12R-hydroxy-15,16-epoxy-4(18),8(17),13(16),14(15)-labdatetraen-3-oic acid; D009569:Nitric Oxide
keywords: 3, 4-seco-Labdane diterpenoids; Callicarpa nudiflora; Nitric oxide; RAW 264.7