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...
| Main Authors: | , , , , , , , , , , , , , , , , , |
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| Format: | Article |
| Language: | English |
| Published: |
Beilstein-Institut
2012-05-01
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| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.8.87 |
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| author | Elena A. Khatuntseva Vladimir M. Men’shov Alexander S. Shashkov Yury E. Tsvetkov Rodion N. Stepanenko Raymonda Ya. Vlasenko Elvira E. Shults Genrikh A. Tolstikov Tatjana G. Tolstikova Dimitri S. Baev Vasiliy A. Kaledin Nelli A. Popova Valeriy P. Nikolin Pavel P. Laktionov Anna V. Cherepanova Tatiana V. Kulakovskaya Ekaterina V. Kulakovskaya Nikolay E. Nifantiev |
| author_facet | Elena A. Khatuntseva Vladimir M. Men’shov Alexander S. Shashkov Yury E. Tsvetkov Rodion N. Stepanenko Raymonda Ya. Vlasenko Elvira E. Shults Genrikh A. Tolstikov Tatjana G. Tolstikova Dimitri S. Baev Vasiliy A. Kaledin Nelli A. Popova Valeriy P. Nikolin Pavel P. Laktionov Anna V. Cherepanova Tatiana V. Kulakovskaya Ekaterina V. Kulakovskaya Nikolay E. Nifantiev |
| author_sort | Elena A. Khatuntseva |
| collection | DOAJ |
| 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. |
| first_indexed | 2024-12-16T16:48:14Z |
| format | Article |
| id | doaj.art-f1def3b89a094092865bf971756cd8e7 |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-16T16:48:14Z |
| publishDate | 2012-05-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-f1def3b89a094092865bf971756cd8e72022-12-21T22:24:08ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972012-05-018176377510.3762/bjoc.8.871860-5397-8-87Triterpenoid saponins from the roots of Acanthophyllum gypsophiloides RegelElena A. Khatuntseva0Vladimir M. Men’shov1Alexander S. Shashkov2Yury E. Tsvetkov3Rodion N. Stepanenko4Raymonda Ya. Vlasenko5Elvira E. Shults6Genrikh A. Tolstikov7Tatjana G. Tolstikova8Dimitri S. Baev9Vasiliy A. Kaledin10Nelli A. Popova11Valeriy P. Nikolin12Pavel P. Laktionov13Anna V. Cherepanova14Tatiana V. Kulakovskaya15Ekaterina V. Kulakovskaya16Nikolay E. Nifantiev17Laboratory of Glycoconjugate Chemistry, N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky prospect 47, 119991 Moscow, Russian FederationLaboratory of Glycoconjugate Chemistry, N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky prospect 47, 119991 Moscow, Russian FederationLaboratory of NMR spectroscopy, N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky prospect 47, 119991 Moscow, Russian FederationLaboratory of Glycoconjugate Chemistry, N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky prospect 47, 119991 Moscow, Russian FederationInstitute of Immunology, Ministry of Health and Social Development of Russian Federation, Kashirskoe Chausseе, 24/2, 115478 Moscow, Russian FederationInstitute of Immunology, Ministry of Health and Social Development of Russian Federation, Kashirskoe Chausseе, 24/2, 115478 Moscow, Russian FederationLaboratory of Pharmacological Researches N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, prospect Acad. Lavrent’eva, 9, 630090 Novosibirsk, Russian FederationLaboratory of Pharmacological Researches N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, prospect Acad. Lavrent’eva, 9, 630090 Novosibirsk, Russian FederationLaboratory of Pharmacological Researches N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, prospect Acad. Lavrent’eva, 9, 630090 Novosibirsk, Russian FederationLaboratory of Pharmacological Researches N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, prospect Acad. Lavrent’eva, 9, 630090 Novosibirsk, Russian FederationInstitute of Cytology and Genetics Siberian Branch of the Russian Academy of Sciences, 10 prospect Acad. Lavrent’eva, 630090 Novosibirsk, Russian FederationInstitute of Cytology and Genetics Siberian Branch of the Russian Academy of Sciences, 10 prospect Acad. Lavrent’eva, 630090 Novosibirsk, Russian FederationInstitute of Cytology and Genetics Siberian Branch of the Russian Academy of Sciences, 10 prospect Acad. Lavrent’eva, 630090 Novosibirsk, Russian FederationInstitute of Chemical Biology and Fundamental Medicine, Siberian Branch of the Russian Academy of Sciences, 8 prospect Acad. Lavrent’eva, 630090 Novosibirsk, Russian FederationInstitute of Chemical Biology and Fundamental Medicine, Siberian Branch of the Russian Academy of Sciences, 8 prospect Acad. Lavrent’eva, 630090 Novosibirsk, Russian FederationG. K. Skryabin Institute of Biochemistry and Physiology of Microorganisms, Russian Academy of Sciences, 142290 Pushchino, Moscow region, Russian FederationG. K. Skryabin Institute of Biochemistry and Physiology of Microorganisms, Russian Academy of Sciences, 142290 Pushchino, Moscow region, Russian FederationLaboratory of Glycoconjugate Chemistry, N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky prospect 47, 119991 Moscow, Russian FederationTwo 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.https://doi.org/10.3762/bjoc.8.87Acanthophyllum gypsophiloidesadjuvanthemolysisNMRsaponinstructure |
| spellingShingle | Elena A. Khatuntseva Vladimir M. Men’shov Alexander S. Shashkov Yury E. Tsvetkov Rodion N. Stepanenko Raymonda Ya. Vlasenko Elvira E. Shults Genrikh A. Tolstikov Tatjana G. Tolstikova Dimitri S. Baev Vasiliy A. Kaledin Nelli A. Popova Valeriy P. Nikolin Pavel P. Laktionov Anna V. Cherepanova Tatiana V. Kulakovskaya Ekaterina V. Kulakovskaya Nikolay E. Nifantiev Triterpenoid saponins from the roots of Acanthophyllum gypsophiloides Regel Beilstein Journal of Organic Chemistry Acanthophyllum gypsophiloides adjuvant hemolysis NMR saponin structure |
| 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 | Acanthophyllum gypsophiloides adjuvant hemolysis NMR saponin structure |
| url | https://doi.org/10.3762/bjoc.8.87 |
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