title: Two new morphinane alkaloids from Sinomenium acutum.
abstract: Two new morphinane alkaloids, 1-hydroxy-10-oxo-sinomenine (1) and 4,5-epoxy-14-hydroxy sinomenine N-oxide (2), have been isolated from the stems of Sinomenium acutum. Their structures were established by various spectral analyses, especially 2D NMR experiments. The structure of 2 was confirmed by single crystal X-ray diffraction. The absolute configurations of 1 and 2 were deduced by comparison of CD spectra with the known alkaloid sinomenine (3). Compound 1 was tested for DPPH inhibition and gave IC(50) of 27.9 μM. Compound 2 was tested for neuroprotective effect and showed significant activity against β-amyloid(25-35)-induced oxidative injury (*P < 0.05) at 10 μM in PC-12 cells.
authors.affiliation: Key Laboratory of Phytochemistry of Shaanxi Province, Baoji University of Arts and Sciences, Baoji, China. xlwang6811@hotmail.com
authors.forename: Xiao-Ling
authors.initials: XL
authors.lastname: Wang
authors.forename: Bing-Rui
authors.initials: BR
authors.lastname: Liu
authors.forename: Jun-Ru
authors.initials: JR
authors.lastname: Wang
authors.forename: Chien-Kuang
authors.initials: CK
authors.lastname: Chen
authors.forename: Guo-Wei
authors.initials: GW
authors.lastname: Qin
authors.forename: Shoei-Sheng
authors.initials: SS
authors.lastname: Lee
mesh_terms: D000470:Alkaloids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D000818:Animals; D001713:Biphenyl Compounds / Q000493:pharmacokinetics; D003497:Cyclic N-Oxides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D004365:Drugs, Chinese Herbal / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D015394:Molecular Structure; D009019:Morphinans / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D018696:Neuroprotective Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D019906:Nuclear Magnetic Resonance, Biomolecular; D016716:PC12 Cells; D010851:Picrates / Q000493:pharmacokinetics; D018547:Plant Stems / Q000737:chemistry; D051381:Rats; D032841:Sinomenium / Q000737:chemistry; D014961:X-Ray Diffraction
chemical_list: C560688:1-hydroxy-10-oxo-sinomenine; C560689:4,5-epoxy-14-hydroxy sinomenine N-oxide; D000470:Alkaloids; D001713:Biphenyl Compounds; D003497:Cyclic N-Oxides; D004365:Drugs, Chinese Herbal; D009019:Morphinans; D018696:Neuroprotective Agents; D010851:Picrates; C009271:sinomenine; C004931:1,1-diphenyl-2-picrylhydrazyl