Lanostane-Type Saponins from <i>Vitaliana primuliflora</i>
The phytochemistry of the genera <i>Androsace</i>, <i>Cortusa</i>, <i>Soldanella</i>, and <i>Vitaliana</i>, belonging to the Primulaceae family is not well studied so far. Hence, in this paper, we present the results of UHPLC-MS/MS analysis of several...
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MDPI AG
2019-04-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/24/8/1606 |
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| author | Maciej Włodarczyk Antoni Szumny Michał Gleńsk |
| author_facet | Maciej Włodarczyk Antoni Szumny Michał Gleńsk |
| author_sort | Maciej Włodarczyk |
| collection | DOAJ |
| description | The phytochemistry of the genera <i>Androsace</i>, <i>Cortusa</i>, <i>Soldanella</i>, and <i>Vitaliana</i>, belonging to the Primulaceae family is not well studied so far. Hence, in this paper, we present the results of UHPLC-MS/MS analysis of several primrose family members as well as isolation and structure determination of two new saponins from <i>Vitaliana primuliflora</i> subsp. <i>praetutiana</i>. These two <i>nor</i>-triterpenoid saponins were characterized as (23<i>S</i>)-17α,23-epoxy-29-hydroxy-3β-[(<i>O</i>-β-<span style="font-variant: small-caps;">d</span>-glucopyranosyl-(1→2)-<i>O</i>-α-<span style="font-variant: small-caps;">l</span>-rhamnopyranosyl-(1→2)-<i>O</i>-β-<span style="font-variant: small-caps;">d</span>-glucopyranosyl-(1→2)-<i>O</i>-α-<span style="font-variant: small-caps;">l</span>-arabinopyranosyl-(1→6)-β-<span style="font-variant: small-caps;">d</span>-glucopyranosyl)oxy]-27-<i>nor</i>-lanost-8-en-25-one and (23<i>S</i>)-17α,23-epoxy-29-hydroxy-3β-[(<i>O</i>-α-<span style="font-variant: small-caps;">l</span>-rhamnopyranosyl-(1→2)-<i>O</i>-β-<span style="font-variant: small-caps;">d</span>-glucopyranosyl-(1→2)-<i>O</i>-α-<span style="font-variant: small-caps;">l</span>-arabinopyranosyl-(1→6)-β-<span style="font-variant: small-caps;">d</span>-glucopyranosyl)oxy]-27-<i>nor</i>-lanost-8-en-25-one, respectively. Their structures were determined by high resolution mass spectrometry (HRMS), tandem mass spectrometry (MS/MS), one- and two-dimensional nuclear magnetic resonance spectroscopy (1D-, and 2D-NMR) analyses. So far, the 27-<i>nor</i>-lanostane monodesmosides were rarely found in dicotyledon plants. Therefore their presence in <i>Vitaliana</i> and also in <i>Androsace</i> species belonging to the <i>Aretia</i> section is unique and reported here for the first time. Additionally, eleven other saponins were determined by HRMS and MS/MS spectra. The isolated lanostane saponins can be considered as chemotaxonomic markers of the family Primulaceae. |
| first_indexed | 2024-12-19T18:10:20Z |
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| last_indexed | 2024-12-19T18:10:20Z |
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| series | Molecules |
| spelling | doaj.art-3b1ab6ede65c48ee9cb51aa4b72493002022-12-21T20:11:19ZengMDPI AGMolecules1420-30492019-04-01248160610.3390/molecules24081606molecules24081606Lanostane-Type Saponins from <i>Vitaliana primuliflora</i>Maciej Włodarczyk0Antoni Szumny1Michał Gleńsk2Department of Pharmacognosy and Herbal Medicines, Faculty of Pharmacy with Division of Laboratory Diagnostics, Wroclaw Medical University, Borowska 211a, 50-556 Wroclaw, PolandDepartment of Chemistry, Faculty of Food Science, Wrocław University of Environmental and Life Sciences, Norwida 25, 50-375 Wroclaw, PolandDepartment of Pharmacognosy and Herbal Medicines, Faculty of Pharmacy with Division of Laboratory Diagnostics, Wroclaw Medical University, Borowska 211a, 50-556 Wroclaw, PolandThe phytochemistry of the genera <i>Androsace</i>, <i>Cortusa</i>, <i>Soldanella</i>, and <i>Vitaliana</i>, belonging to the Primulaceae family is not well studied so far. Hence, in this paper, we present the results of UHPLC-MS/MS analysis of several primrose family members as well as isolation and structure determination of two new saponins from <i>Vitaliana primuliflora</i> subsp. <i>praetutiana</i>. These two <i>nor</i>-triterpenoid saponins were characterized as (23<i>S</i>)-17α,23-epoxy-29-hydroxy-3β-[(<i>O</i>-β-<span style="font-variant: small-caps;">d</span>-glucopyranosyl-(1→2)-<i>O</i>-α-<span style="font-variant: small-caps;">l</span>-rhamnopyranosyl-(1→2)-<i>O</i>-β-<span style="font-variant: small-caps;">d</span>-glucopyranosyl-(1→2)-<i>O</i>-α-<span style="font-variant: small-caps;">l</span>-arabinopyranosyl-(1→6)-β-<span style="font-variant: small-caps;">d</span>-glucopyranosyl)oxy]-27-<i>nor</i>-lanost-8-en-25-one and (23<i>S</i>)-17α,23-epoxy-29-hydroxy-3β-[(<i>O</i>-α-<span style="font-variant: small-caps;">l</span>-rhamnopyranosyl-(1→2)-<i>O</i>-β-<span style="font-variant: small-caps;">d</span>-glucopyranosyl-(1→2)-<i>O</i>-α-<span style="font-variant: small-caps;">l</span>-arabinopyranosyl-(1→6)-β-<span style="font-variant: small-caps;">d</span>-glucopyranosyl)oxy]-27-<i>nor</i>-lanost-8-en-25-one, respectively. Their structures were determined by high resolution mass spectrometry (HRMS), tandem mass spectrometry (MS/MS), one- and two-dimensional nuclear magnetic resonance spectroscopy (1D-, and 2D-NMR) analyses. So far, the 27-<i>nor</i>-lanostane monodesmosides were rarely found in dicotyledon plants. Therefore their presence in <i>Vitaliana</i> and also in <i>Androsace</i> species belonging to the <i>Aretia</i> section is unique and reported here for the first time. Additionally, eleven other saponins were determined by HRMS and MS/MS spectra. The isolated lanostane saponins can be considered as chemotaxonomic markers of the family Primulaceae.https://www.mdpi.com/1420-3049/24/8/1606<i>Androsace</i><i>Douglasia</i><i>Primula</i><i>Vitaliana</i>Primulaceaeprimrosetriterpenoid saponinsteroid saponinslanostaneUHPLC screening |
| spellingShingle | Maciej Włodarczyk Antoni Szumny Michał Gleńsk Lanostane-Type Saponins from <i>Vitaliana primuliflora</i> Molecules <i>Androsace</i> <i>Douglasia</i> <i>Primula</i> <i>Vitaliana</i> Primulaceae primrose triterpenoid saponin steroid saponins lanostane UHPLC screening |
| title | Lanostane-Type Saponins from <i>Vitaliana primuliflora</i> |
| title_full | Lanostane-Type Saponins from <i>Vitaliana primuliflora</i> |
| title_fullStr | Lanostane-Type Saponins from <i>Vitaliana primuliflora</i> |
| title_full_unstemmed | Lanostane-Type Saponins from <i>Vitaliana primuliflora</i> |
| title_short | Lanostane-Type Saponins from <i>Vitaliana primuliflora</i> |
| title_sort | lanostane type saponins from i vitaliana primuliflora i |
| topic | <i>Androsace</i> <i>Douglasia</i> <i>Primula</i> <i>Vitaliana</i> Primulaceae primrose triterpenoid saponin steroid saponins lanostane UHPLC screening |
| url | https://www.mdpi.com/1420-3049/24/8/1606 |
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