Ligubenzocycloheptanone A, a Novel Tricyclic Butenolide with a 6/7/5 Skeleton from Ligusticum chuanxiong

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 experime...

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Detalles Bibliográficos
Autores principales: Han, Bing, Zhang, Xu, Feng, Zi-Ming, Jiang, Jian-Shuang, Li, Li, Yang, Ya-Nan, Zhang, Pei-Cheng
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group 2016
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4962078/
https://www.ncbi.nlm.nih.gov/pubmed/27461841
http://dx.doi.org/10.1038/srep28783
Descripción
Sumario: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 IC(50) value of 2.3 μM.

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