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Three pairs of alkaloid enantiomers from the root of Isatis indigotica
Three pairs of enantiomerically pure alkaloids with diverse structure features, named isatindigoticoic acid A and epiisatindigoticoic acid A [(−)-1 and (+)-1], phaitanthrin A and epiphaitanthrin A [(−)-2 and (+)-2], and isatindopyrromizol A and epiisatindopyrromizol A [(−)-3 and (+)-3], respectively...
Autores principales: | , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Elsevier
2016
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4788710/ https://www.ncbi.nlm.nih.gov/pubmed/27006898 http://dx.doi.org/10.1016/j.apsb.2016.01.003 |
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author | Liu, Yufeng Wang, Xiaoliang Chen, Minghua Lin, Sheng Li, Li Shi, Jiangong |
author_facet | Liu, Yufeng Wang, Xiaoliang Chen, Minghua Lin, Sheng Li, Li Shi, Jiangong |
author_sort | Liu, Yufeng |
collection | PubMed |
description | Three pairs of enantiomerically pure alkaloids with diverse structure features, named isatindigoticoic acid A and epiisatindigoticoic acid A [(−)-1 and (+)-1], phaitanthrin A and epiphaitanthrin A [(−)-2 and (+)-2], and isatindopyrromizol A and epiisatindopyrromizol A [(−)-3 and (+)-3], respectively, were isolated from an aqueous extract of the roots of Isatis indigotica. Racemic and scalemic mixtures of these enantiomers were separated by HPLC on a chiral semi-preparative column. Their structures including absolute configurations were determined by extensive spectroscopic analysis in conjunction with the calculation of electronic circular dichroism (ECD) spectra. The enantiomer pairs possess parent structures of 2-oxo-1,2,3,4-tetrahydroquinoline-4-carboxylic acid, indolo[2,1-b]quinazolinone, and 3-thioxohexahydro-1H-pyrrolo[1,2-c]imidazol-1-one, respectively. Except for phaitanthrin A [(−)-2] which the configuration was previously undetermined, these compounds are new enantiomeric natural products. |
format | Online Article Text |
id | pubmed-4788710 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2016 |
publisher | Elsevier |
record_format | MEDLINE/PubMed |
spelling | pubmed-47887102016-03-22 Three pairs of alkaloid enantiomers from the root of Isatis indigotica Liu, Yufeng Wang, Xiaoliang Chen, Minghua Lin, Sheng Li, Li Shi, Jiangong Acta Pharm Sin B Original Article Three pairs of enantiomerically pure alkaloids with diverse structure features, named isatindigoticoic acid A and epiisatindigoticoic acid A [(−)-1 and (+)-1], phaitanthrin A and epiphaitanthrin A [(−)-2 and (+)-2], and isatindopyrromizol A and epiisatindopyrromizol A [(−)-3 and (+)-3], respectively, were isolated from an aqueous extract of the roots of Isatis indigotica. Racemic and scalemic mixtures of these enantiomers were separated by HPLC on a chiral semi-preparative column. Their structures including absolute configurations were determined by extensive spectroscopic analysis in conjunction with the calculation of electronic circular dichroism (ECD) spectra. The enantiomer pairs possess parent structures of 2-oxo-1,2,3,4-tetrahydroquinoline-4-carboxylic acid, indolo[2,1-b]quinazolinone, and 3-thioxohexahydro-1H-pyrrolo[1,2-c]imidazol-1-one, respectively. Except for phaitanthrin A [(−)-2] which the configuration was previously undetermined, these compounds are new enantiomeric natural products. Elsevier 2016-03 2016-02-11 /pmc/articles/PMC4788710/ /pubmed/27006898 http://dx.doi.org/10.1016/j.apsb.2016.01.003 Text en © 2016 Chinese Pharmaceutical Association and Institute of Materia Medica, Chinese Academy of Medical Sciences. Production and hosting by Elsevier B.V. http://creativecommons.org/licenses/by-nc-nd/4.0/ This is an open access article under the CC BY-NC-ND license (http://creativecommons.org/licenses/by-nc-nd/4.0/). |
spellingShingle | Original Article Liu, Yufeng Wang, Xiaoliang Chen, Minghua Lin, Sheng Li, Li Shi, Jiangong Three pairs of alkaloid enantiomers from the root of Isatis indigotica |
title | Three pairs of alkaloid enantiomers from the root of Isatis indigotica |
title_full | Three pairs of alkaloid enantiomers from the root of Isatis indigotica |
title_fullStr | Three pairs of alkaloid enantiomers from the root of Isatis indigotica |
title_full_unstemmed | Three pairs of alkaloid enantiomers from the root of Isatis indigotica |
title_short | Three pairs of alkaloid enantiomers from the root of Isatis indigotica |
title_sort | three pairs of alkaloid enantiomers from the root of isatis indigotica |
topic | Original Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4788710/ https://www.ncbi.nlm.nih.gov/pubmed/27006898 http://dx.doi.org/10.1016/j.apsb.2016.01.003 |
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