Triterpenoid saponins from the roots of Acanthophyllum gypsophiloides Regel

Triterpenoid saponins from the roots of Acanthophyllum gypsophiloides Regel Full article

Journal

Beilstein Journal of Organic Chemistry
ISSN: 1860-5397

Output data

Year: 2012, Volume: 8, Pages: 763-775 Pages count : 13 DOI: 10.3762/bjoc.8.87

Tags

Acanthophyllum gypsophiloides; adjuvant; hemolysis; NMR; saponin; structure

Authors

Khatuntseva Elena A. ¹ , Men'shov Vladimir M. ¹ , Shashkov Alexander S. ² , Tsvetkov Yury E. ¹ , Stepanenko Rodion N. ³ , Vlasenko Raymonda Ya ³ , Shults Elvira E. ⁴ , Tolstikov Genrikh A. ⁴ , Tolstikova Tatjana G. ⁴ , Baev Dimitri S. ⁴ , Kaledin Vasiliy A. ⁵ , Popova Nelli A. ⁵ , Nikolin Valeriy P. ⁵ , Laktionov Pavel P. ⁶ , Cherepanova Anna V. ⁶ , Kulakovskaya Tatiana V. ⁷ , Kulakovskaya Ekaterina V. ⁷ , Nifantiev Nikolay E. ¹

Affiliations

1	(Данные Web of science) Russian Acad Sci, Lab Glycoconjugate Chem, ND Zelinsky Inst Organ Chem, Moscow 119991, Russia
2	(Данные Web of science) Russian Acad Sci, Lab NMR, ND Zelinsky Inst Organ Chem, Moscow 119991, Russia
3	(Данные Web of science) Minist Hlth & Social Dev Russian Federat, Inst Immunol, Moscow 115478, Russia
4	(Данные Web of science) Russian Acad Sci, Lab Pharmacol Res, NN Vorozhtsov Novosibirsk Inst Organ Chem, Siberian Branch, Novosibirsk 630090, Russia
5	(Данные Web of science) Russian Acad Sci, Inst Cytol & Genet, Siberian Branch, Novosibirsk 630090, Russia
6	(Данные Web of science) Russian Acad Sci, Inst Chem Biol & Fundamental Med, Siberian Branch, Novosibirsk 630090, Russia
7	(Данные Web of science) Russian Acad Sci, GK Skryabin Inst Biochem & Physiol Microorganisms, Pushchino 142290, Moscow Region, Russia

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.

Khatuntseva E.A. , Men'shov V.M. , Shashkov A.S. , Tsvetkov Y.E. , Stepanenko R.N. , Vlasenko R.Y. , Shults E.E. , Tolstikov G.A. , Tolstikova T.G. , Baev D.S. , Kaledin V.A. , Popova N.A. , Nikolin V.P. , Laktionov P.P. , Cherepanova A.V. , Kulakovskaya T.V. , Kulakovskaya E.V. , Nifantiev N.E.
Triterpenoid saponins from the roots of Acanthophyllum gypsophiloides Regel

Beilstein Journal of Organic Chemistry. 2012. V.8. P.763-775. DOI: 10.3762/bjoc.8.87 WOS Scopus РИНЦ

Full text from publisher

Published online:

May 23, 2012

Web of science	WOS:000304347100001
Scopus	2-s2.0-84861543329
Elibrary	17987045
OpenAlex	W2017706819