title: (±)-Melicolones A and B, rearranged prenylated acetophenone stereoisomers with an unusual 9-oxatricyclo[3.2.1.1(3,8)]nonane core from the leaves of Melicope ptelefolia.
abstract: Melicolones A (1) and B (2), a pair of rearranged prenylated acetophenone epimers with an unusual 9-oxatricyclo[3.2.1.1(3,8)]nonane core, were isolated from the leaves of Melicope ptelefolia. Further chiral high-performance liquid chromatography resolution gave enantiomers (+)- and (-)-1, as well as (+)- and (-)-2, respectively. The structures and absolute configurations of the pure enantiomers were determined by extensive spectroscopic data and single crystal X-ray diffraction. All the isolated enantiomers exhibited potent cell protecting activities against high glucose-induced oxidative stress in human vein endothelial cells.
authors.affiliation: State Key Laboratory of Natural Medicines, Department of Natural Medicinal Chemistry, China Pharmaceutical University , 24 Tong Jia Xiang, Nanjing 210009, People's Republic of China.
authors.forename: Jin-Fang
authors.initials: JF
authors.lastname: Xu
authors.forename: Hui-Jun
authors.initials: HJ
authors.lastname: Zhao
authors.forename: Xiao-Bing
authors.initials: XB
authors.lastname: Wang
authors.forename: Zhong-Rui
authors.initials: ZR
authors.lastname: Li
authors.forename: Jun
authors.initials: J
authors.lastname: Luo
authors.forename: Ming-Hua
authors.initials: MH
authors.lastname: Yang
authors.forename: Lei
authors.initials: L
authors.lastname: Yang
authors.forename: Wen-Ying
authors.initials: WY
authors.lastname: Yu
authors.forename: He-Quan
authors.initials: HQ
authors.lastname: Yao
authors.forename: Jian-Guang
authors.initials: JG
authors.lastname: Luo
authors.forename: Ling-Yi
authors.initials: LY
authors.lastname: Kong
mesh_terms: D000098:Acetophenones / Q000737:chemistry* / Q000302:isolation & purification* / Q000494:pharmacology; D000473:Alkanes; D002851:Chromatography, High Pressure Liquid; D018360:Crystallography, X-Ray; D042783:Endothelial Cells / Q000187:drug effects; D006575:Heterocyclic Compounds, 3-Ring; D006801:Humans; D008968:Molecular Conformation; D015394:Molecular Structure; D018515:Plant Leaves / Q000737:chemistry; D054876:Prenylation; D027821:Rutaceae / Q000737:chemistry*; D013237:Stereoisomerism; D014961:X-Ray Diffraction
chemical_list: D000098:Acetophenones; D000473:Alkanes; D006575:Heterocyclic Compounds, 3-Ring; C000595756:melicolone A; C017573:nonane