A new ursane-type triterpene oxoglucopyranoside from Crossopteryx febrifuga
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Modjinan Kayangar
Abstract
A new saponin, 3-O-β-d-3-oxo-glucopyranosyl-ursa-12,20(30)-diene-27,28-dioic acid (1), was isolated from the methanol extract of stem bark of Crossopteryx febrifuga together with the known 3β-d-glucopyranosyl-ursa-12,20(30)-diene-27,28-dioic acid (2), shanzhiside methyl ester (3), shanzhiside (4), β-sitosterol (5), β-sitosterol-3-O-β-d-glucopyranoside (6), ursa-12,20(30)-diene-27,28-dioic acid (7), hederagenin (8), and oleanolic acid (9). The structures were established by comprehensive interpretation of their spectral data 1D- (1H and 13C), 2D-NMR (1H-1H COSY, HMQC, HMBC), spectroscopic, and electrospray ionisation time-of-flight mass spectrometry analysis. The isolated compounds and extracts were screened for their antibacterial properties. Although the EtOAc and n-BuOH extracts exhibited considerable antibacterial activity against Pseudomonas aeruginosa with minimum inhibitory concentration (MIC) value of 32 μg/mL, compounds 2 and 8 showed moderate activity against Enterococcus faecalis with MIC values of 256 and 128 μg/mL, respectively. The new compound (1) exhibited a moderate antibacterial activity against Staphylococcus aureus with an MIC value of 512 μg/mL.
Acknowledgements
The authors are grateful to the Alexander von Humboldt Foundation (AvH), Bonn, Germany, for the financial support of this work. We thank the Rhineland Palatinate Center of Natural Products Research (Mainz) for funding part of the analytical chemistry involved.
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Supplementary Material
The online version of this article offers supplementary material (https://doi.org/10.1515/znc-2019-0113).
©2019 Walter de Gruyter GmbH, Berlin/Boston
Articles in the same Issue
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Articles in the same Issue
- Frontmatter
- Research Articles
- Secondary metabolites from Penicillium sp. 8PKH isolated from deteriorated rice straws
- A new ursane-type triterpene oxoglucopyranoside from Crossopteryx febrifuga
- Fisetin effects on cell proliferation and apoptosis in glioma cells
- Cytotoxic and anti-inflammatory resorcinol and alkylbenzoquinone derivatives from the leaves of Ardisia sieboldii
- Isolation and characterization of antiplasmodial constituents from the marine sponge Coscinoderma sp.
- The Hordeum bulbosum 25S-18S rDNA region: comparison with Hordeum vulgare and other Triticeae
- Hepatoprotective activity of a purified methanol extract and saponins from the roots of Chenopodium bonus-henricus L.
