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Triterpenoid saponins from the roots of<i>Acanthophyllum gypsophiloides</i>Regel

Е. А. ХатунцеваLaboratory of Glycoconjugate Chemistry, N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky prospect 47, 119991 Moscow, Russian FederationV.M. Men'shovN.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences,Alexander S. ShashkovLaboratory of NMR spectroscopy, N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky prospect 47, 119991 Moscow, Russian Federation,Yury E. TsvetkovLaboratory of Glycoconjugate Chemistry, N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky prospect 47, 119991 Moscow, Russian Federation,R. N. StepanenkoInstitute of Immunology, Ministry of Health and Social Development of Russian Federation, Kashirskoe Chausse, 24/2, 115478 Moscow, Russian Federation,Raymonda Ya VlasenkoInstitute of Immunology, Ministry of Health and Social Development of Russian Federation, Kashirskoe Chausse, 24/2, 115478 Moscow, Russian Federation,Elvira E. ShultsLaboratory 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 Federation,Genrikh A. TolstikovLaboratory 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 Federation,Т. Г. ТолстиковаLaboratory 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 Federation,Dmitry S. BaevLaboratory 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 Federation,Vasiliy A KaledinInstitute of Cytology and Genetics Siberian Branch of the Russian Academy of Sciences, 10 prospect Acad. Lavrent'eva, 630090 Novosibirsk, Russian Federation,Nelli A PopovaInstitute of Cytology and Genetics Siberian Branch of the Russian Academy of Sciences, 10 prospect Acad. Lavrent'eva, 630090 Novosibirsk, Russian Federation,В. П. НиколинInstitute of Cytology and Genetics Siberian Branch of the Russian Academy of Sciences, 10 prospect Acad. Lavrent'eva, 630090 Novosibirsk, Russian Federation,Pavel P. LaktionovInstitute of Chemical Biology and Fundamental Medicine, Siberian Branch of the Russian Academy of Sciences, 8 prospect Acad. Lavrent'eva, 630090 Novosibirsk, Russian Federation andAnna V. CherepanovaInstitute of Chemical Biology and Fundamental Medicine, Siberian Branch of the Russian Academy of Sciences, 8 prospect Acad. Lavrent'eva, 630090 Novosibirsk, Russian Federation andT. V. KulakovskayaG. K. Skryabin Institute of Biochemistry and Physiology of Microorganisms, Russian Academy of Sciences, 142290 Pushchino, Moscow region, Russian FederationEkaterina KulakovskayaLaboratory of Glycoconjugate Chemistry, N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky prospect 47, 119991 Moscow, Russian Federation,Nikolay E. NifantievG. K. Skryabin Institute of Biochemistry and Physiology of Microorganisms, Russian Academy of Sciences, 142290 Pushchino, Moscow region, Russian Federation
2012en
ABI

Аннотация

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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