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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...

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Autores principales: 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
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2012
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.
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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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