Spirostanol Saponins from Flowers of <i>Allium Porrum</i> and Related Compounds Indicating Cytotoxic Activity and Affecting Nitric Oxide Production Inhibitory Effect in Peritoneal Macrophages
Saponins, a diverse group of natural compounds, offer an interesting pool of derivatives with biomedical application. In this study, three structurally related spirostanol saponins were isolated and identified from the leek flowers of <i>Allium porrum</i> L. (garden leek). Two of them we...
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MDPI AG
2021-10-01
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| Series: | Molecules |
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| author | Juraj Harmatha Miloš Buděšínský Zdeněk Zídek Eva Kmoníčková |
| author_facet | Juraj Harmatha Miloš Buděšínský Zdeněk Zídek Eva Kmoníčková |
| author_sort | Juraj Harmatha |
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| description | Saponins, a diverse group of natural compounds, offer an interesting pool of derivatives with biomedical application. In this study, three structurally related spirostanol saponins were isolated and identified from the leek flowers of <i>Allium porrum</i> L. (garden leek). Two of them were identical with the already known leek plant constituents: aginoside (1) and 6-deoxyaginoside (2). The third one was identified as new component of <i>A. porrum</i>; however, it was found identical with yayoisaponin A (3) obtained earlier from a mutant of elephant garlic <i>Allium ampeloprasun</i> L. It is a derivative of the aginoside (1) with additional glucose in its glycosidic chain, identified by MS and NMR analysis as (2α, 3β, 6β, 25<i>R</i>)-2,6-dihydroxyspirostan-3-yl β-D-glucopyranosyl-(1 → 3)-β-D-glucopranosyl-(1 → 2)-[β-D-xylopyranosyl-(1 → 3)]-β-D-glucopyranosyl]-(1 → 4)-β-D-galactopyranoside, previously reported also under the name alliporin. The leek native saponins were tested together with other known and structurally related saponins (tomatonin and digitonin) and with their related aglycones (agigenin and diosgenin) for in vitro cytotoxicity and for effects on NO production in mouse peritoneal cells. The highest inhibitory effects were exhibited by 6-deoxyaginoside. The obtained toxicity data, however, closely correlated with the suppression of NO production. Therefore, an unambiguous linking of obtained bioactivities of saponins with their expected immunobiological properties remained uncertain. |
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| last_indexed | 2024-03-10T05:55:38Z |
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| spelling | doaj.art-2d9f670eda3840e58c74abb17dc88a202023-11-22T21:22:45ZengMDPI AGMolecules1420-30492021-10-012621653310.3390/molecules26216533Spirostanol Saponins from Flowers of <i>Allium Porrum</i> and Related Compounds Indicating Cytotoxic Activity and Affecting Nitric Oxide Production Inhibitory Effect in Peritoneal MacrophagesJuraj Harmatha0Miloš Buděšínský1Zdeněk Zídek2Eva Kmoníčková3Institute of Organic Chemistry and Biochemistry, Czech Academy of Sciences, 166 10 Prague, Czech RepublicInstitute of Organic Chemistry and Biochemistry, Czech Academy of Sciences, 166 10 Prague, Czech RepublicInstitute of Experimental Medicine, Czech Academy of Sciences, 142 20 Prague, Czech RepublicInstitute of Experimental Medicine, Czech Academy of Sciences, 142 20 Prague, Czech RepublicSaponins, a diverse group of natural compounds, offer an interesting pool of derivatives with biomedical application. In this study, three structurally related spirostanol saponins were isolated and identified from the leek flowers of <i>Allium porrum</i> L. (garden leek). Two of them were identical with the already known leek plant constituents: aginoside (1) and 6-deoxyaginoside (2). The third one was identified as new component of <i>A. porrum</i>; however, it was found identical with yayoisaponin A (3) obtained earlier from a mutant of elephant garlic <i>Allium ampeloprasun</i> L. It is a derivative of the aginoside (1) with additional glucose in its glycosidic chain, identified by MS and NMR analysis as (2α, 3β, 6β, 25<i>R</i>)-2,6-dihydroxyspirostan-3-yl β-D-glucopyranosyl-(1 → 3)-β-D-glucopranosyl-(1 → 2)-[β-D-xylopyranosyl-(1 → 3)]-β-D-glucopyranosyl]-(1 → 4)-β-D-galactopyranoside, previously reported also under the name alliporin. The leek native saponins were tested together with other known and structurally related saponins (tomatonin and digitonin) and with their related aglycones (agigenin and diosgenin) for in vitro cytotoxicity and for effects on NO production in mouse peritoneal cells. The highest inhibitory effects were exhibited by 6-deoxyaginoside. The obtained toxicity data, however, closely correlated with the suppression of NO production. Therefore, an unambiguous linking of obtained bioactivities of saponins with their expected immunobiological properties remained uncertain.https://www.mdpi.com/1420-3049/26/21/6533<i>Allium porrum</i>leek flowerssteroid saponinsaginosidealliporincytotoxicity |
| spellingShingle | Juraj Harmatha Miloš Buděšínský Zdeněk Zídek Eva Kmoníčková Spirostanol Saponins from Flowers of <i>Allium Porrum</i> and Related Compounds Indicating Cytotoxic Activity and Affecting Nitric Oxide Production Inhibitory Effect in Peritoneal Macrophages Molecules <i>Allium porrum</i> leek flowers steroid saponins aginoside alliporin cytotoxicity |
| title | Spirostanol Saponins from Flowers of <i>Allium Porrum</i> and Related Compounds Indicating Cytotoxic Activity and Affecting Nitric Oxide Production Inhibitory Effect in Peritoneal Macrophages |
| title_full | Spirostanol Saponins from Flowers of <i>Allium Porrum</i> and Related Compounds Indicating Cytotoxic Activity and Affecting Nitric Oxide Production Inhibitory Effect in Peritoneal Macrophages |
| title_fullStr | Spirostanol Saponins from Flowers of <i>Allium Porrum</i> and Related Compounds Indicating Cytotoxic Activity and Affecting Nitric Oxide Production Inhibitory Effect in Peritoneal Macrophages |
| title_full_unstemmed | Spirostanol Saponins from Flowers of <i>Allium Porrum</i> and Related Compounds Indicating Cytotoxic Activity and Affecting Nitric Oxide Production Inhibitory Effect in Peritoneal Macrophages |
| title_short | Spirostanol Saponins from Flowers of <i>Allium Porrum</i> and Related Compounds Indicating Cytotoxic Activity and Affecting Nitric Oxide Production Inhibitory Effect in Peritoneal Macrophages |
| title_sort | spirostanol saponins from flowers of i allium porrum i and related compounds indicating cytotoxic activity and affecting nitric oxide production inhibitory effect in peritoneal macrophages |
| topic | <i>Allium porrum</i> leek flowers steroid saponins aginoside alliporin cytotoxicity |
| url | https://www.mdpi.com/1420-3049/26/21/6533 |
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