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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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
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author Han, Bing
Zhang, Xu
Feng, Zi-Ming
Jiang, Jian-Shuang
Li, Li
Yang, Ya-Nan
Zhang, Pei-Cheng
author_facet Han, Bing
Zhang, Xu
Feng, Zi-Ming
Jiang, Jian-Shuang
Li, Li
Yang, Ya-Nan
Zhang, Pei-Cheng
author_sort Han, Bing
collection PubMed
description 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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spelling pubmed-49620782016-08-08 Ligubenzocycloheptanone A, a Novel Tricyclic Butenolide with a 6/7/5 Skeleton from Ligusticum chuanxiong Han, Bing Zhang, Xu Feng, Zi-Ming Jiang, Jian-Shuang Li, Li Yang, Ya-Nan Zhang, Pei-Cheng Sci Rep Article 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. Nature Publishing Group 2016-07-27 /pmc/articles/PMC4962078/ /pubmed/27461841 http://dx.doi.org/10.1038/srep28783 Text en Copyright © 2016, Macmillan Publishers Limited http://creativecommons.org/licenses/by/4.0/ This work is licensed under a Creative Commons Attribution 4.0 International License. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in the credit line; if the material is not included under the Creative Commons license, users will need to obtain permission from the license holder to reproduce the material. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/
spellingShingle Article
Han, Bing
Zhang, Xu
Feng, Zi-Ming
Jiang, Jian-Shuang
Li, Li
Yang, Ya-Nan
Zhang, Pei-Cheng
Ligubenzocycloheptanone A, a Novel Tricyclic Butenolide with a 6/7/5 Skeleton from Ligusticum chuanxiong
title Ligubenzocycloheptanone A, a Novel Tricyclic Butenolide with a 6/7/5 Skeleton from Ligusticum chuanxiong
title_full Ligubenzocycloheptanone A, a Novel Tricyclic Butenolide with a 6/7/5 Skeleton from Ligusticum chuanxiong
title_fullStr Ligubenzocycloheptanone A, a Novel Tricyclic Butenolide with a 6/7/5 Skeleton from Ligusticum chuanxiong
title_full_unstemmed Ligubenzocycloheptanone A, a Novel Tricyclic Butenolide with a 6/7/5 Skeleton from Ligusticum chuanxiong
title_short Ligubenzocycloheptanone A, a Novel Tricyclic Butenolide with a 6/7/5 Skeleton from Ligusticum chuanxiong
title_sort ligubenzocycloheptanone a, a novel tricyclic butenolide with a 6/7/5 skeleton from ligusticum chuanxiong
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4962078/
https://www.ncbi.nlm.nih.gov/pubmed/27461841
http://dx.doi.org/10.1038/srep28783
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