title: Anti-inflammatory coumarin and benzocoumarin derivatives from Murraya alata.
abstract: Two new rare 8-methylbenzo[h]coumarins, muralatins A and B (1, 2), nine new C-8-substituted coumarins, muralatins C-K (3-11), and 22 known analogues (12-33) were isolated from the leaves of Murraya alata. The absolute configurations of compounds 5, 11, 23, 24, 27, 30, and 33 were assigned via comparison of their specific rotations, by Mosher's method, and by single-crystal X-ray diffraction and electronic circular dichroism (ECD) data of the in situ formed transition metal complexes. A putative biosynthesis pathway to 1 and 2 is proposed, and the chemical synthesis of 1 was accomplished through electrocyclization of 5,7-dimethoxy-8-[(Z)-3-methylbut-1,3-dienyl)]coumarin (12). Compounds 1, 2, 8, 12, and 31 showed inhibition of nitric oxide production in lipopolysaccharide-induced RAW 264.7 macrophages with IC50 values of 6.0-14.5 μM.
authors.affiliation: State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University , Beijing 100191, People's Republic of China.
authors.forename: Hai-Ning
authors.initials: HN
authors.lastname: Lv
authors.forename: Shu
authors.initials: S
authors.lastname: Wang
authors.forename: Ke-Wu
authors.initials: KW
authors.lastname: Zeng
authors.forename: Jun
authors.initials: J
authors.lastname: Li
authors.forename: Xiao-Yu
authors.initials: XY
authors.lastname: Guo
authors.forename: Daneel
authors.initials: D
authors.lastname: Ferreira
authors.forename: Jordan K
authors.initials: JK
authors.lastname: Zjawiony
authors.forename: Peng-Fei
authors.initials: PF
authors.lastname: Tu
authors.forename: Yong
authors.initials: Y
authors.lastname: Jiang
mesh_terms: D000818:Animals; D000893:Anti-Inflammatory Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D002942:Circular Dichroism; D003374:Coumarins / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D004365:Drugs, Chinese Herbal / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D008070:Lipopolysaccharides / Q000494:pharmacology; D008264:Macrophages / Q000187:drug effects; D051379:Mice; D015394:Molecular Structure; D032101:Murraya / Q000737:chemistry*; D009569:Nitric Oxide / Q000096:biosynthesis; D018515:Plant Leaves / Q000737:chemistry
chemical_list: D000893:Anti-Inflammatory Agents; D003374:Coumarins; D004365:Drugs, Chinese Herbal; D008070:Lipopolysaccharides; C000600239:muralatin A; C000600240:muralatin B; D009569:Nitric Oxide