Isolation, Characterization and In Silico Studies of Secondary Metabolites from the Whole Plant of <i>Polygala inexpectata</i> Peşmen & Erik
<i>Polygala</i> species are frequently used worldwide in the treatment of various diseases, such as inflammatory and autoimmune disorders as well as metabolic and neurodegenerative diseases, due to the large number of secondary metabolites they contain. The present study was performed on...
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MDPI AG
2022-01-01
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| author | Ayşe Ünlü Kerem Teralı Zübeyde Uğurlu Aydın Ali A. Dönmez Hasan Soliman Yusufoğlu İhsan Çalış |
| author_facet | Ayşe Ünlü Kerem Teralı Zübeyde Uğurlu Aydın Ali A. Dönmez Hasan Soliman Yusufoğlu İhsan Çalış |
| author_sort | Ayşe Ünlü |
| collection | DOAJ |
| description | <i>Polygala</i> species are frequently used worldwide in the treatment of various diseases, such as inflammatory and autoimmune disorders as well as metabolic and neurodegenerative diseases, due to the large number of secondary metabolites they contain. The present study was performed on <i>Polygala inexpectata</i>, which is a narrow endemic species for the flora of Turkey, and resulted in the isolation of nine known compounds, 6,3′-disinapoyl-sucrose (<b>1</b>), 6-<i>O</i>-sinapoyl,3′-<i>O</i>-trimethoxy-cinnamoyl-sucrose (tenuifoliside C) (<b>2</b>), 3′-<i>O</i>-(<i>O</i>-methyl-feruloyl)-sucrose (<b>3</b>), 3′-<i>O</i>-(sinapoyl)-sucrose (<b>4</b>), 3′-<i>O</i>-trimethoxy-cinnamoyl-sucrose (glomeratose) (<b>5</b>), 3′-<i>O</i>-feruloyl-sucrose (sibiricose A5) (<b>6</b>), sinapyl alcohol 4-<i>O</i>-glucoside (syringin or eleutheroside B) (<b>7</b>), liriodendrin (<b>8</b>), and 7,4′-di-<i>O</i>-methylquercetin-3-<i>O</i>-β-rutinoside (ombuin 3-<i>O</i>-rutinoside or ombuoside) (<b>9</b>). The structures of the compounds were determined by the spectroscopic methods including 1D-NMR (<sup>1</sup>H NMR, <sup>13</sup>C NMR, DEPT-135), 2D-NMR (COSY, NOESY, HSQC, HMBC), and HRMS. The isolated compounds were shown in an in silico setting to be accommodated well within the inhibitor-binding pockets of myeloperoxidase and inducible nitric oxide synthase and anchored mainly through hydrogen-bonding interactions and π-effects. It is therefore plausible to suggest that the previously established anti-inflammatory properties of some <i>Polygala</i>-derived phytochemicals may be due, in part, to the modulation of pro-inflammatory enzyme activities. |
| first_indexed | 2024-03-09T23:30:10Z |
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| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-09T23:30:10Z |
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| spelling | doaj.art-5ff73e52b8e1483e9dae0af13ec5d1802023-11-23T17:10:49ZengMDPI AGMolecules1420-30492022-01-0127368410.3390/molecules27030684Isolation, Characterization and In Silico Studies of Secondary Metabolites from the Whole Plant of <i>Polygala inexpectata</i> Peşmen & ErikAyşe Ünlü0Kerem Teralı1Zübeyde Uğurlu Aydın2Ali A. Dönmez3Hasan Soliman Yusufoğlu4İhsan Çalış5Department of Biology, Faculty of Science, Hacettepe University, Ankara 06800, TurkeyDepartment of Medical Biochemistry, Faculty of Medicine, Girne American University, Kyrenia 99428, CyprusDepartment of Biology, Faculty of Science, Hacettepe University, Ankara 06800, TurkeyDepartment of Biology, Faculty of Science, Hacettepe University, Ankara 06800, TurkeyDepartment of Pharmacognosy & Pharmaceutical Chemistry, College of Dentistry & Pharmacy, Buraydah Private Colleges, Buraydah 51418, Saudi ArabiaDepartment of Pharmacognosy, Faculty of Pharmacy, Near East University, Nicosia 99138, Cyprus<i>Polygala</i> species are frequently used worldwide in the treatment of various diseases, such as inflammatory and autoimmune disorders as well as metabolic and neurodegenerative diseases, due to the large number of secondary metabolites they contain. The present study was performed on <i>Polygala inexpectata</i>, which is a narrow endemic species for the flora of Turkey, and resulted in the isolation of nine known compounds, 6,3′-disinapoyl-sucrose (<b>1</b>), 6-<i>O</i>-sinapoyl,3′-<i>O</i>-trimethoxy-cinnamoyl-sucrose (tenuifoliside C) (<b>2</b>), 3′-<i>O</i>-(<i>O</i>-methyl-feruloyl)-sucrose (<b>3</b>), 3′-<i>O</i>-(sinapoyl)-sucrose (<b>4</b>), 3′-<i>O</i>-trimethoxy-cinnamoyl-sucrose (glomeratose) (<b>5</b>), 3′-<i>O</i>-feruloyl-sucrose (sibiricose A5) (<b>6</b>), sinapyl alcohol 4-<i>O</i>-glucoside (syringin or eleutheroside B) (<b>7</b>), liriodendrin (<b>8</b>), and 7,4′-di-<i>O</i>-methylquercetin-3-<i>O</i>-β-rutinoside (ombuin 3-<i>O</i>-rutinoside or ombuoside) (<b>9</b>). The structures of the compounds were determined by the spectroscopic methods including 1D-NMR (<sup>1</sup>H NMR, <sup>13</sup>C NMR, DEPT-135), 2D-NMR (COSY, NOESY, HSQC, HMBC), and HRMS. The isolated compounds were shown in an in silico setting to be accommodated well within the inhibitor-binding pockets of myeloperoxidase and inducible nitric oxide synthase and anchored mainly through hydrogen-bonding interactions and π-effects. It is therefore plausible to suggest that the previously established anti-inflammatory properties of some <i>Polygala</i>-derived phytochemicals may be due, in part, to the modulation of pro-inflammatory enzyme activities.https://www.mdpi.com/1420-3049/27/3/684liriodendrinmolecular dockingombuosidesucrose esterssyringin |
| spellingShingle | Ayşe Ünlü Kerem Teralı Zübeyde Uğurlu Aydın Ali A. Dönmez Hasan Soliman Yusufoğlu İhsan Çalış Isolation, Characterization and In Silico Studies of Secondary Metabolites from the Whole Plant of <i>Polygala inexpectata</i> Peşmen & Erik Molecules liriodendrin molecular docking ombuoside sucrose esters syringin |
| title | Isolation, Characterization and In Silico Studies of Secondary Metabolites from the Whole Plant of <i>Polygala inexpectata</i> Peşmen & Erik |
| title_full | Isolation, Characterization and In Silico Studies of Secondary Metabolites from the Whole Plant of <i>Polygala inexpectata</i> Peşmen & Erik |
| title_fullStr | Isolation, Characterization and In Silico Studies of Secondary Metabolites from the Whole Plant of <i>Polygala inexpectata</i> Peşmen & Erik |
| title_full_unstemmed | Isolation, Characterization and In Silico Studies of Secondary Metabolites from the Whole Plant of <i>Polygala inexpectata</i> Peşmen & Erik |
| title_short | Isolation, Characterization and In Silico Studies of Secondary Metabolites from the Whole Plant of <i>Polygala inexpectata</i> Peşmen & Erik |
| title_sort | isolation characterization and in silico studies of secondary metabolites from the whole plant of i polygala inexpectata i pesmen erik |
| topic | liriodendrin molecular docking ombuoside sucrose esters syringin |
| url | https://www.mdpi.com/1420-3049/27/3/684 |
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