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Triterpenoid saponins from the roots of Acanthophyllum gypsophiloides Regel
Two new triterpenoid saponins 1 and 2 were isolated from the methanol extract of the roots of Acanthophyllum gypsophiloides Regel. These saponins have quillaic acid or gypsogenin moieties as an aglycon, and both bear similar sets of two oligosaccharide chains, which are 3-O-linked to the triterpenoi...
Autores principales: | , , , , , , , , , , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Beilstein-Institut
2012
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3388865/ https://www.ncbi.nlm.nih.gov/pubmed/23015825 http://dx.doi.org/10.3762/bjoc.8.87 |
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author | Khatuntseva, Elena A Men’shov, Vladimir M Shashkov, Alexander S Tsvetkov, Yury E Stepanenko, Rodion N Vlasenko, Raymonda Ya Shults, Elvira E Tolstikov, Genrikh A Tolstikova, Tatjana G Baev, Dimitri S Kaledin, Vasiliy A Popova, Nelli A Nikolin, Valeriy P Laktionov, Pavel P Cherepanova, Anna V Kulakovskaya, Tatiana V Kulakovskaya, Ekaterina V Nifantiev, Nikolay E |
author_facet | Khatuntseva, Elena A Men’shov, Vladimir M Shashkov, Alexander S Tsvetkov, Yury E Stepanenko, Rodion N Vlasenko, Raymonda Ya Shults, Elvira E Tolstikov, Genrikh A Tolstikova, Tatjana G Baev, Dimitri S Kaledin, Vasiliy A Popova, Nelli A Nikolin, Valeriy P Laktionov, Pavel P Cherepanova, Anna V Kulakovskaya, Tatiana V Kulakovskaya, Ekaterina V Nifantiev, Nikolay E |
author_sort | Khatuntseva, Elena A |
collection | PubMed |
description | Two new triterpenoid saponins 1 and 2 were isolated from the methanol extract of the roots of Acanthophyllum gypsophiloides Regel. These saponins have quillaic acid or gypsogenin moieties as an aglycon, and both bear similar sets of two oligosaccharide chains, which are 3-O-linked to the triterpenoid part trisaccharide α-L-Arap-(1→3)-[α-D-Galp-(1→2)]-β-D-GlcpA and pentasaccharide β-D-Xylp-(1→3)-β-D-Xylp-(1→3)-α-L-Rhap-(1→2)-[β-D-Quip-(1→4)]-β-D-Fucp connected through an ester linkage to C-28. The structures of the obtained saponins were elucidated by a combination of mass spectrometry and 2D NMR spectroscopy. A study of acute toxicity, hemolytic, anti-inflammatory, immunoadjuvant and antifungal activity was carried out. Both saponins 1 and 2 were shown to exhibit immunoadjuvant properties within the vaccine composition with keyhole limpet hemocyanin-based immunogen. The availability of saponins 1 and 2 as individual pure compounds from the extract of the roots of A. gypsophiloides makes it a prospective source of immunoactive agents. |
format | Online Article Text |
id | pubmed-3388865 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2012 |
publisher | Beilstein-Institut |
record_format | MEDLINE/PubMed |
spelling | pubmed-33888652012-09-26 Triterpenoid saponins from the roots of Acanthophyllum gypsophiloides Regel Khatuntseva, Elena A Men’shov, Vladimir M Shashkov, Alexander S Tsvetkov, Yury E Stepanenko, Rodion N Vlasenko, Raymonda Ya Shults, Elvira E Tolstikov, Genrikh A Tolstikova, Tatjana G Baev, Dimitri S Kaledin, Vasiliy A Popova, Nelli A Nikolin, Valeriy P Laktionov, Pavel P Cherepanova, Anna V Kulakovskaya, Tatiana V Kulakovskaya, Ekaterina V Nifantiev, Nikolay E Beilstein J Org Chem Full Research Paper Two new triterpenoid saponins 1 and 2 were isolated from the methanol extract of the roots of Acanthophyllum gypsophiloides Regel. These saponins have quillaic acid or gypsogenin moieties as an aglycon, and both bear similar sets of two oligosaccharide chains, which are 3-O-linked to the triterpenoid part trisaccharide α-L-Arap-(1→3)-[α-D-Galp-(1→2)]-β-D-GlcpA and pentasaccharide β-D-Xylp-(1→3)-β-D-Xylp-(1→3)-α-L-Rhap-(1→2)-[β-D-Quip-(1→4)]-β-D-Fucp connected through an ester linkage to C-28. The structures of the obtained saponins were elucidated by a combination of mass spectrometry and 2D NMR spectroscopy. A study of acute toxicity, hemolytic, anti-inflammatory, immunoadjuvant and antifungal activity was carried out. Both saponins 1 and 2 were shown to exhibit immunoadjuvant properties within the vaccine composition with keyhole limpet hemocyanin-based immunogen. The availability of saponins 1 and 2 as individual pure compounds from the extract of the roots of A. gypsophiloides makes it a prospective source of immunoactive agents. Beilstein-Institut 2012-05-23 /pmc/articles/PMC3388865/ /pubmed/23015825 http://dx.doi.org/10.3762/bjoc.8.87 Text en Copyright © 2012, Khatuntseva et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms) |
spellingShingle | Full Research Paper Khatuntseva, Elena A Men’shov, Vladimir M Shashkov, Alexander S Tsvetkov, Yury E Stepanenko, Rodion N Vlasenko, Raymonda Ya Shults, Elvira E Tolstikov, Genrikh A Tolstikova, Tatjana G Baev, Dimitri S Kaledin, Vasiliy A Popova, Nelli A Nikolin, Valeriy P Laktionov, Pavel P Cherepanova, Anna V Kulakovskaya, Tatiana V Kulakovskaya, Ekaterina V Nifantiev, Nikolay E Triterpenoid saponins from the roots of Acanthophyllum gypsophiloides Regel |
title | Triterpenoid saponins from the roots of Acanthophyllum gypsophiloides Regel |
title_full | Triterpenoid saponins from the roots of Acanthophyllum gypsophiloides Regel |
title_fullStr | Triterpenoid saponins from the roots of Acanthophyllum gypsophiloides Regel |
title_full_unstemmed | Triterpenoid saponins from the roots of Acanthophyllum gypsophiloides Regel |
title_short | Triterpenoid saponins from the roots of Acanthophyllum gypsophiloides Regel |
title_sort | triterpenoid saponins from the roots of acanthophyllum gypsophiloides regel |
topic | Full Research Paper |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3388865/ https://www.ncbi.nlm.nih.gov/pubmed/23015825 http://dx.doi.org/10.3762/bjoc.8.87 |
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