Journal
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
Volume 8, Issue -, Pages 763-775Publisher
BEILSTEIN-INSTITUT
DOI: 10.3762/bjoc.8.87
Keywords
Acanthophyllum gypsophiloides; adjuvant; hemolysis; NMR; saponin; structure
Categories
Funding
- Ministry of Education and Science of the Russian Federation [16.512.11.2089]
- Siberian branch of RAS [93]
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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 alpha-L-Arap-(1 -> 3)-[alpha-D-Galp-(1 -> 2)]-beta-D-GlcpA and pentasaccharide beta-D-Xylp-(1 -> 3)-beta-D-Xylp-(1 -> 3)-alpha-L-Rhap-(1 -> 2)-[beta-D-Quip-(1 -> 4)]-beta-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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