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Enantiomeric Lignans and Neolignans from Phyllanthus glaucus: Enantioseparation and Their Absolute Configurations

Eight pairs of enantiomeric neolignans, norlignans, and sesquineolignans (1a/1b–8a/8b), together with five known neolignans (9a/9b and 10–12), have been isolated from 70% acetone extract of the whole plants of Phyllanthus glaucus Wall. (Euphorbiaceae). The racemic or partial racemic mixtures were su...

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Autores principales: Wu, Zhaodi, Lai, Yongji, Zhou, Lei, Wu, Ye, Zhu, Hucheng, Hu, Zhengxi, Yang, Jing, Zhang, Jinwen, Wang, Jianping, Luo, Zengwei, Xue, Yongbo, Zhang, Yonghui
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group 2016
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4850383/
https://www.ncbi.nlm.nih.gov/pubmed/27126373
http://dx.doi.org/10.1038/srep24809
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author Wu, Zhaodi
Lai, Yongji
Zhou, Lei
Wu, Ye
Zhu, Hucheng
Hu, Zhengxi
Yang, Jing
Zhang, Jinwen
Wang, Jianping
Luo, Zengwei
Xue, Yongbo
Zhang, Yonghui
author_facet Wu, Zhaodi
Lai, Yongji
Zhou, Lei
Wu, Ye
Zhu, Hucheng
Hu, Zhengxi
Yang, Jing
Zhang, Jinwen
Wang, Jianping
Luo, Zengwei
Xue, Yongbo
Zhang, Yonghui
author_sort Wu, Zhaodi
collection PubMed
description Eight pairs of enantiomeric neolignans, norlignans, and sesquineolignans (1a/1b–8a/8b), together with five known neolignans (9a/9b and 10–12), have been isolated from 70% acetone extract of the whole plants of Phyllanthus glaucus Wall. (Euphorbiaceae). The racemic or partial racemic mixtures were successfully separated by chiral HPLC using different types of chiral columns with various mobile phases. Their structures were elucidated on the basis of extensive spectroscopic data. The absolute configurations of 2a/2b were determined by computational analysis of their electronic circular dichroism (ECD) spectrum, and the absolute configurations of other isolates were ascertained by comparing their experimental ECD spectra and optical rotation values with those of structure-relevant compounds reported in literatures. Compounds 4a/4b featured unique sesquineolignan skeletons with a novel 7-4′-epoxy-8′-8′′/7′-2′′ scaffold, consisting of an aryltetrahydronaphthalene and a dihydrobenzofuran moiety. The planar structures of compounds 2, 3, 7, and 8 were documented previously; however, their absolute configurations were established for the first time in this study. The antioxidant activities of 1a/1b–8a/8b were evaluated using DPPH free radical scavenging assay, and the results demonstrated that compounds 1b and 3b showed potent DPPH radical scavenging activities with IC(50) values of 5.987 ± 1.212 and 9.641 ± 0.865 μg/mL, respectively.
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spelling pubmed-48503832016-05-05 Enantiomeric Lignans and Neolignans from Phyllanthus glaucus: Enantioseparation and Their Absolute Configurations Wu, Zhaodi Lai, Yongji Zhou, Lei Wu, Ye Zhu, Hucheng Hu, Zhengxi Yang, Jing Zhang, Jinwen Wang, Jianping Luo, Zengwei Xue, Yongbo Zhang, Yonghui Sci Rep Article Eight pairs of enantiomeric neolignans, norlignans, and sesquineolignans (1a/1b–8a/8b), together with five known neolignans (9a/9b and 10–12), have been isolated from 70% acetone extract of the whole plants of Phyllanthus glaucus Wall. (Euphorbiaceae). The racemic or partial racemic mixtures were successfully separated by chiral HPLC using different types of chiral columns with various mobile phases. Their structures were elucidated on the basis of extensive spectroscopic data. The absolute configurations of 2a/2b were determined by computational analysis of their electronic circular dichroism (ECD) spectrum, and the absolute configurations of other isolates were ascertained by comparing their experimental ECD spectra and optical rotation values with those of structure-relevant compounds reported in literatures. Compounds 4a/4b featured unique sesquineolignan skeletons with a novel 7-4′-epoxy-8′-8′′/7′-2′′ scaffold, consisting of an aryltetrahydronaphthalene and a dihydrobenzofuran moiety. The planar structures of compounds 2, 3, 7, and 8 were documented previously; however, their absolute configurations were established for the first time in this study. The antioxidant activities of 1a/1b–8a/8b were evaluated using DPPH free radical scavenging assay, and the results demonstrated that compounds 1b and 3b showed potent DPPH radical scavenging activities with IC(50) values of 5.987 ± 1.212 and 9.641 ± 0.865 μg/mL, respectively. Nature Publishing Group 2016-04-29 /pmc/articles/PMC4850383/ /pubmed/27126373 http://dx.doi.org/10.1038/srep24809 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
Wu, Zhaodi
Lai, Yongji
Zhou, Lei
Wu, Ye
Zhu, Hucheng
Hu, Zhengxi
Yang, Jing
Zhang, Jinwen
Wang, Jianping
Luo, Zengwei
Xue, Yongbo
Zhang, Yonghui
Enantiomeric Lignans and Neolignans from Phyllanthus glaucus: Enantioseparation and Their Absolute Configurations
title Enantiomeric Lignans and Neolignans from Phyllanthus glaucus: Enantioseparation and Their Absolute Configurations
title_full Enantiomeric Lignans and Neolignans from Phyllanthus glaucus: Enantioseparation and Their Absolute Configurations
title_fullStr Enantiomeric Lignans and Neolignans from Phyllanthus glaucus: Enantioseparation and Their Absolute Configurations
title_full_unstemmed Enantiomeric Lignans and Neolignans from Phyllanthus glaucus: Enantioseparation and Their Absolute Configurations
title_short Enantiomeric Lignans and Neolignans from Phyllanthus glaucus: Enantioseparation and Their Absolute Configurations
title_sort enantiomeric lignans and neolignans from phyllanthus glaucus: enantioseparation and their absolute configurations
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4850383/
https://www.ncbi.nlm.nih.gov/pubmed/27126373
http://dx.doi.org/10.1038/srep24809
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