Spirostanol Sapogenins and Saponins from <i>Convallaria majalis</i> L. Structural Characterization by 2D NMR, Theoretical GIAO DFT Calculations and Molecular Modeling
Two new spirostanol sapogenins (5β-spirost-25(27)-en-1β,2β,3β,5β-tetrol <b>3</b> and its 25,27-dihydro derivative, (25S)-spirostan-1β,2β,3β,5β-tetrol <b>4</b>) and four new saponins were isolated from the roots and rhizomes of <i>Convallaria majalis</i> L. togethe...
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MDPI AG
2021-05-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/26/10/2999 |
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| author | Karolina Dąbrowska-Balcerzak Jadwiga Nartowska Iwona Wawer Paweł Siudem Katarzyna Paradowska |
| author_facet | Karolina Dąbrowska-Balcerzak Jadwiga Nartowska Iwona Wawer Paweł Siudem Katarzyna Paradowska |
| author_sort | Karolina Dąbrowska-Balcerzak |
| collection | DOAJ |
| description | Two new spirostanol sapogenins (5β-spirost-25(27)-en-1β,2β,3β,5β-tetrol <b>3</b> and its 25,27-dihydro derivative, (25S)-spirostan-1β,2β,3β,5β-tetrol <b>4</b>) and four new saponins were isolated from the roots and rhizomes of <i>Convallaria majalis</i> L. together with known sapogenins (isolated from <i>Liliaceae</i>): 5β-spirost-25(27)-en-1β,3β-diol <b>1</b>, (25S)-spirostan-1β,3β-diol <b>2</b>, 5β-spirost-25(27)-en-1β,3β,4β,5β-tetrol <b>5</b>, (25S)-spirostan-1β,3β,4β,5β-tetrol <b>6</b>, 5β-spirost-25(27)-en-1β,2β,3β,4β,5β-pentol <b>7</b> and (25S)-spirostan-1β,2β,3β,4β,5β-pentol <b>8</b>. New steroidal saponins were found to be pentahydroxy 5-<i>O</i>-glycosides; 5β-spirost-25(27)-en-1β,2β,3β,4β,5β-pentol 5-<i>O</i>-β-galactopyranoside <b>9</b>, 5β-spirost-25(27)-en-1β,2β,3β,4β,5β-pentol 5-<i>O</i>-β-arabinonoside <b>11</b>, 5β-(25S)-spirostan-1β,2β,3β,4β,5β-pentol 5-<i>O</i>-galactoside <b>10</b> and 5β-(25S)-spirostan-1β,2β,3β,4β,5β-pentol 5-<i>O</i>-arabinoside <b>12</b> were isolated for the first time. The structures of those compounds were determined by NMR spectroscopy, including 2D COSY, HMBC, HSQC, NOESY, ROESY experiments, theoretical calculations of shielding constants by GIAO DFT, and mass spectrometry (FAB/LSI HR MS). An attempt was made to test biological activity, particularly as potential chemotherapeutic agents, using in silico methods. A set of 12 compounds was docked to the PDB structures of HER2 receptor and tubulin. The results indicated that diols have a higher affinity to the analyzed targets than tetrols and pentols. Two compounds (25S)-spirosten-1β,3β-diol <b>1</b> and 5β-spirost-25(27)-en-1β,2β,3β,4β,5β-pentol 5-<i>O</i>-galactoside <b>9</b> were selected for further evaluation of biological activity. |
| first_indexed | 2024-03-10T11:17:58Z |
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| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T11:17:58Z |
| publishDate | 2021-05-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-44a9619d898744bc9d88addee402a8312023-11-21T20:16:32ZengMDPI AGMolecules1420-30492021-05-012610299910.3390/molecules26102999Spirostanol Sapogenins and Saponins from <i>Convallaria majalis</i> L. Structural Characterization by 2D NMR, Theoretical GIAO DFT Calculations and Molecular ModelingKarolina Dąbrowska-Balcerzak0Jadwiga Nartowska1Iwona Wawer2Paweł Siudem3Katarzyna Paradowska4Department of Physical Chemistry, Faculty of Pharmacy, Medical University of Warsaw, Banacha 1, 02-097 Warsaw, PolandDepartment of Pharmacognosy, Faculty of Pharmacy, Medical University of Warsaw, Banacha 1, 02-097 Warsaw, PolandDepartment of Physical Chemistry, Faculty of Pharmacy, Medical University of Warsaw, Banacha 1, 02-097 Warsaw, PolandDepartment of Physical Chemistry, Faculty of Pharmacy, Medical University of Warsaw, Banacha 1, 02-097 Warsaw, PolandDepartment of Physical Chemistry, Faculty of Pharmacy, Medical University of Warsaw, Banacha 1, 02-097 Warsaw, PolandTwo new spirostanol sapogenins (5β-spirost-25(27)-en-1β,2β,3β,5β-tetrol <b>3</b> and its 25,27-dihydro derivative, (25S)-spirostan-1β,2β,3β,5β-tetrol <b>4</b>) and four new saponins were isolated from the roots and rhizomes of <i>Convallaria majalis</i> L. together with known sapogenins (isolated from <i>Liliaceae</i>): 5β-spirost-25(27)-en-1β,3β-diol <b>1</b>, (25S)-spirostan-1β,3β-diol <b>2</b>, 5β-spirost-25(27)-en-1β,3β,4β,5β-tetrol <b>5</b>, (25S)-spirostan-1β,3β,4β,5β-tetrol <b>6</b>, 5β-spirost-25(27)-en-1β,2β,3β,4β,5β-pentol <b>7</b> and (25S)-spirostan-1β,2β,3β,4β,5β-pentol <b>8</b>. New steroidal saponins were found to be pentahydroxy 5-<i>O</i>-glycosides; 5β-spirost-25(27)-en-1β,2β,3β,4β,5β-pentol 5-<i>O</i>-β-galactopyranoside <b>9</b>, 5β-spirost-25(27)-en-1β,2β,3β,4β,5β-pentol 5-<i>O</i>-β-arabinonoside <b>11</b>, 5β-(25S)-spirostan-1β,2β,3β,4β,5β-pentol 5-<i>O</i>-galactoside <b>10</b> and 5β-(25S)-spirostan-1β,2β,3β,4β,5β-pentol 5-<i>O</i>-arabinoside <b>12</b> were isolated for the first time. The structures of those compounds were determined by NMR spectroscopy, including 2D COSY, HMBC, HSQC, NOESY, ROESY experiments, theoretical calculations of shielding constants by GIAO DFT, and mass spectrometry (FAB/LSI HR MS). An attempt was made to test biological activity, particularly as potential chemotherapeutic agents, using in silico methods. A set of 12 compounds was docked to the PDB structures of HER2 receptor and tubulin. The results indicated that diols have a higher affinity to the analyzed targets than tetrols and pentols. Two compounds (25S)-spirosten-1β,3β-diol <b>1</b> and 5β-spirost-25(27)-en-1β,2β,3β,4β,5β-pentol 5-<i>O</i>-galactoside <b>9</b> were selected for further evaluation of biological activity.https://www.mdpi.com/1420-3049/26/10/2999<i>Convallaria majalis</i><i>Liliaceae</i>steroidal sapogeninsspirostanol sapogeninsNMRGIAO DFT |
| spellingShingle | Karolina Dąbrowska-Balcerzak Jadwiga Nartowska Iwona Wawer Paweł Siudem Katarzyna Paradowska Spirostanol Sapogenins and Saponins from <i>Convallaria majalis</i> L. Structural Characterization by 2D NMR, Theoretical GIAO DFT Calculations and Molecular Modeling Molecules <i>Convallaria majalis</i> <i>Liliaceae</i> steroidal sapogenins spirostanol sapogenins NMR GIAO DFT |
| title | Spirostanol Sapogenins and Saponins from <i>Convallaria majalis</i> L. Structural Characterization by 2D NMR, Theoretical GIAO DFT Calculations and Molecular Modeling |
| title_full | Spirostanol Sapogenins and Saponins from <i>Convallaria majalis</i> L. Structural Characterization by 2D NMR, Theoretical GIAO DFT Calculations and Molecular Modeling |
| title_fullStr | Spirostanol Sapogenins and Saponins from <i>Convallaria majalis</i> L. Structural Characterization by 2D NMR, Theoretical GIAO DFT Calculations and Molecular Modeling |
| title_full_unstemmed | Spirostanol Sapogenins and Saponins from <i>Convallaria majalis</i> L. Structural Characterization by 2D NMR, Theoretical GIAO DFT Calculations and Molecular Modeling |
| title_short | Spirostanol Sapogenins and Saponins from <i>Convallaria majalis</i> L. Structural Characterization by 2D NMR, Theoretical GIAO DFT Calculations and Molecular Modeling |
| title_sort | spirostanol sapogenins and saponins from i convallaria majalis i l structural characterization by 2d nmr theoretical giao dft calculations and molecular modeling |
| topic | <i>Convallaria majalis</i> <i>Liliaceae</i> steroidal sapogenins spirostanol sapogenins NMR GIAO DFT |
| url | https://www.mdpi.com/1420-3049/26/10/2999 |
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