Triterpenoid saponins from the roots of two Gypsophila species (original) (raw)

New Triterpenoidal Saponins from Gypsophila repens

Six new triterpene glycosides, repensosides A–F (1–6, resp.), were isolated from the roots of Gypsophila repens L. Their structures, established by extensive 1D- and 2D-NMRspectroscopi c experiments as well as MS analyses, were found to be based on gypsogenic acid (or gypsogenin) as aglycone, with three to nine branched or unbranched sugar moieties.

Triterpenoid Saponins from the Roots of Gypsophila paniculata

Chinese Journal of Natural Medicines, 2010

Eleven triterpenoid saponins were isolated from the roots of Gypsophila trichotoma Wender. (G. trichotoma Wender. var. trichotoma) (Caryophyllaceae), together with one known compound. The structures were established on the basis of extensive NMR analysis (1 H, 13 C NMR, COSY, TOCSY, ROESY, HSQC, and HMBC), completed by analysis of HR-ESI-MS and ESI-MS n. The saponins have the commonly found gypsogenin as the aglycone substituted at C-3 with trisaccharide and at C-28 with oligosaccharide through a fucose residue, as saponins isolated from Gypsophila perfoliata L. originated from China. The oligosaccharide attached to C-28 is substituted with acetyl and (or) sulfate groups. The cytotoxicity of the saponin extract from G. trichotoma was evaluated against a rat alveolar macrophage-like cell line NR8383 and human leukemia cell lines U937 and BV-173. The synergistic effect of the aminoacyl saponins, previously isolated from G. trichotoma, was tested for its ability to enhance the cytotoxicity of the targeted toxin in HER14 cells.

Acylated triterpenoid saponins from roots of Gypsophila trichotoma

Planta Medica, 2012

Eleven triterpenoid saponins were isolated from the roots of Gypsophila trichotoma Wender. (G. trichotoma Wender. var. trichotoma) (Caryophyllaceae), together with one known compound. The structures were established on the basis of extensive NMR analysis ( 1 H, 13 C NMR, COSY, TOCSY, ROESY, HSQC, and HMBC), completed by analysis of HR-ESI-MS and ESI-MS n . The saponins have the commonly found gypsogenin as the aglycone substituted at C-3 with trisaccharide and at C-28 with oligosaccharide through a fucose residue, as saponins isolated from Gypsophila perfoliata L. originated from China. The oligosaccharide attached to C-28 is substituted with acetyl and (or) sulfate groups.

Triterpenoid saponins from the roots of Gypsophila trichotoma Wender

Phytochemistry, 2013

Eleven triterpenoid saponins were isolated from the roots of Gypsophila trichotoma Wender. (G. trichotoma Wender. var. trichotoma) (Caryophyllaceae), together with one known compound. The structures were established on the basis of extensive NMR analysis ( 1 H, 13 C NMR, COSY, TOCSY, ROESY, HSQC, and HMBC), completed by analysis of HR-ESI-MS and ESI-MS n . The saponins have the commonly found gypsogenin as the aglycone substituted at C-3 with trisaccharide and at C-28 with oligosaccharide through a fucose residue, as saponins isolated from Gypsophila perfoliata L. originated from China. The oligosaccharide attached to C-28 is substituted with acetyl and (or) sulfate groups.

3-O-Sulfo-triterpenoid Saponins from Gypsophila trichotoma Wend

Zeitschrift für Naturforschung B, 2009

Three new sulfated oleanane-type saponins were isolated from the roots of Gypsophila trichotoma Wend. (Caryophyllaceae). Their structures were established as 3-O-sulfoechinocystic acid 28-β -glucopyranosyl ester (1), 3-O-sulfooleanolic acid 28-β -glucopyranosyl ester (2) and 3-Osulfoquillaic acid 28-β -glucopyranosyl ester (3) on the basis of chemical and spectral evidences.

ChemInform Abstract: 3-O-Sulfo-triterpenoid Saponins (I) from Gypsophila trichotoma Wend

ChemInform, 2009

Three new sulfated oleanane-type saponins were isolated from the roots of Gypsophila trichotoma Wend. (Caryophyllaceae). Their structures were established as 3-O-sulfoechinocystic acid 28-β -glucopyranosyl ester (1), 3-O-sulfooleanolic acid 28-β -glucopyranosyl ester (2) and 3-Osulfoquillaic acid 28-β -glucopyranosyl ester (3) on the basis of chemical and spectral evidences.

New triterpenoid saponins from the roots of Saponaria officinalis

Natural product communications, 2013

Three new triterpenoid saponins (1-3), along with nine known saponins, were isolated from the roots of Saponaria officinalis L. Two of them: vaccaroside D (4) and dianchinenoside B (5) are known, but not previously reported for S. officinalis, and seven others: saponarioside C (6), D (7), F (8), G (9), I (10), K (11), and L (12) have been previously isolated from this plant. The structures of the new saponins were established as 3-O-beta-D-xylopyranosyl-16alpha-hydroxygypsogenic acid-28-O-[beta-D-glucopyranosyl-(1 -->6)-beta-D-glucopyranoside (1), 3-O-beta-D-xylopyranosyl-16alpha-hydroxygypsogenic acid-28-O-[beta-D-glucopyranosyl-(1-->3)]-[alpha-D-galactopyranosyl-(1-->6)-alpha-D-galactopyranosyl-(1-->6)-beta-D-glucopyranosyl-(1-->6)]-beta-D-glucopyranoside (2) and 3-O-beta-D-xylopyranosyl-gypsogenic acid-28-O-[beta-D-glucopyranosyl-(1-->3)]-[6-O-(3-hydroxy-3-methylglutaryl)-beta-D-glucopyranosyl-(1-->6)]-beta-D-glucopyranoside (3). Their structures were elucida...

Triterpenoid saponins from the roots of Acanthophyllum gypsophiloides Regel

Beilstein Journal of Organic Chemistry, 2012

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 pentasac-Beilstein J. Org. Chem. 2012, 8, 763-775. 764 charide 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.

Triterpenoid saponins from the roots of Zygophyllum species

Phytochemistry, 1997

Two new triterpenoid saponins, 3-O-[P-D-2-O-sulphonylglucopyranosyl]-quinovic acid-28-O-[P-Dglucopyranosyl] ester (zygophyloside G), 3-O-[a-L-arabinopyranosyl-( 1 -+ 2)-P-D-quinovopyranosyl]-quinovic acid-28-0-[/3-D-glucopyranosyl] ester (zygophyloside H), and seven known saponins have been isolated. The structures were established primarily on the basis of NMR spectroscopy. The assignment of all NMR signals was performed by means of 'H-'H COSY-45, NOESY, TOCSY, 13C APT, HMQC and HMBC experiments. The determination of the glycosylation sites was possible by the HMBC experiments. Copyright 0 1997 Elsevier Science Ltd

Complete1H- and13C NMR assignments of saponins from roots ofGypsophila trichotoma Wend

Magnetic Resonance in Chemistry, 2006

The assignments of 1 H and 13 C NMR spectra of two new aminoacyl triterpene saponins from roots of Gypsophila trichotoma Wend. are reported. In addition to 1D NMR methods, 2D NMR techniques (COSY, TOCSY, ROESY, HSQC, HMBC, and HSQC-TOCSY) were used for the assignments. The structures were completed by analysis of HR