title: Ligubenzocycloheptanone A, a Novel Tricyclic Butenolide with a 6/7/5 Skeleton from Ligusticum chuanxiong.
abstract: Ligubenzocycloheptanone A (1), a novel tricyclic butenolide with a 6/7/5-membered ring skeleton, was isolated from the rhizome of Ligusticum chuanxiong. Its unusual structure was determined using UV, IR, HRESIMS, 1D and 2D NMR data, X-ray diffraction crystallography and by the comparison of experimental and calculated electronic circular dichroism (ECD) spectra. 1 possessed a benzocycloheptanone core featuring butyrolactone, which is rarely observed in nature. A possible biosynthetic pathway was proposed. Ligubenzocycloheptanone A showed strong radical scavenging activity with an IC50 value of 2.3 μM.
authors.affiliation: State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, P. R. China.
authors.forename: Bing
authors.initials: B
authors.lastname: Han
authors.affiliation: State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, P. R. China.
authors.forename: Xu
authors.initials: X
authors.lastname: Zhang
authors.affiliation: State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, P. R. China.
authors.forename: Zi-Ming
authors.initials: ZM
authors.lastname: Feng
authors.affiliation: State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, P. R. China.
authors.forename: Jian-Shuang
authors.initials: JS
authors.lastname: Jiang
authors.affiliation: State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, P. R. China.
authors.forename: Li
authors.initials: L
authors.lastname: Li
authors.affiliation: State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, P. R. China.
authors.forename: Ya-Nan
authors.initials: YN
authors.lastname: Yang
authors.affiliation: State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, P. R. China.
authors.forename: Pei-Cheng
authors.initials: PC
authors.lastname: Zhang
mesh_terms: D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D002942:Circular Dichroism; D003461:Crystallography; D016166:Free Radical Scavengers / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D030004:Ligusticum / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D018629:Spectrometry, Mass, Secondary Ion; D013055:Spectrophotometry, Infrared; D013056:Spectrophotometry, Ultraviolet; D014961:X-Ray Diffraction
chemical_list: D016166:Free Radical Scavengers; C004511:butenolide; D015107:4-Butyrolactone