Isolation, Characterization, Complete Structural Assignment, and Anticancer Activities of the Methoxylated Flavonoids from <i>Rhamnus disperma</i> Roots
Different chromatographic methods including reversed-phase HPLC led to the isolation and purification of three <i>O</i>-methylated flavonoids; 5,4’-dihydroxy-3,6,7-tri-<i>O</i>-methyl flavone (penduletin) (<b>1</b>), 5,3’-dihydroxy-3,6,7,4’,5’-penta-<i>O<...
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| Format: | Article |
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MDPI AG
2021-09-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/26/19/5827 |
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| author | Hamdoon A. Mohammed Mohammed F. Abd El-Wahab Usama Shaheen Abd El-Salam I. Mohammed Ashraf N. Abdalla Ehab A. Ragab |
| author_facet | Hamdoon A. Mohammed Mohammed F. Abd El-Wahab Usama Shaheen Abd El-Salam I. Mohammed Ashraf N. Abdalla Ehab A. Ragab |
| author_sort | Hamdoon A. Mohammed |
| collection | DOAJ |
| description | Different chromatographic methods including reversed-phase HPLC led to the isolation and purification of three <i>O</i>-methylated flavonoids; 5,4’-dihydroxy-3,6,7-tri-<i>O</i>-methyl flavone (penduletin) (<b>1</b>), 5,3’-dihydroxy-3,6,7,4’,5’-penta-<i>O</i>-methyl flavone (<b>2</b>), and 5-hydroxy-3,6,7,3’,4’,5’-hexa-<i>O</i>-methyl flavone (<b>3</b>) from <i>Rhamnus disperma</i> roots. Additionlly, four flavonoid glycosides; kampferol 7-<i>O</i>-<i>α</i>-L-rhamnopyranoside (<b>4</b>), isorhamnetin-3-<i>O</i>-<i>β</i>-D-glucopyranoside (<b>5</b>), quercetin 7-<i>O</i>-<i>α</i>-L-rhamnopyranoside (<b>6</b>), and kampferol 3, 7-di-<i>O</i>-<i>α</i>-L-rhamnopyranoside (<b>7</b>) along with benzyl-<i>O</i>-<i>β</i>-D-glucopyranoside (<b>8</b>) were successfully isolated. Complete structure characterization of these compounds was assigned based on NMR spectroscopic data, MS analyses, and comparison with the literature. The <i>O</i>-methyl protons and carbons of the three <i>O</i>-methylated flavonoids (<b>1</b>–<b>3</b>) were unambiguously assigned based on 2D NMR data. The occurrence of compounds <b>1</b>, <b>4</b>, <b>5</b>, and <b>8</b> in <i>Rhamnus disperma</i> is was reported here for the first time. Compound <b>3</b> was acetylated at 5-OH position to give 5-<i>O</i>-acetyl-3,6,7,3’,4’,5’-hexa-<i>O</i>-methyl flavone (<b>9</b>). Compound <b>1</b> exhibited the highest cytotoxic activity against MCF 7, A2780, and HT29 cancer cell lines with IC<sub>50</sub> values at 2.17 µM, 0.53 µM, and 2.16 µM, respectively, and was 2–9 folds more selective against tested cancer cell lines compared to the normal human fetal lung fibroblasts (MRC5). It also doubled MCF 7 apoptotic populations and caused G<sub>1</sub> cell cycle arrest. The acetylated compound <b>9</b> exhibited cytotoxic activity against MCF 7 and HT29 cancer cell lines with IC<sub>50</sub> values at 2.19 µM and 3.18 µM, respectively, and was 6–8 folds more cytotoxic to tested cancer cell lines compared to the MRC5 cells. |
| first_indexed | 2024-03-10T06:54:39Z |
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| institution | Directory Open Access Journal |
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| language | English |
| last_indexed | 2024-03-10T06:54:39Z |
| publishDate | 2021-09-01 |
| publisher | MDPI AG |
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| series | Molecules |
| spelling | doaj.art-0e1097ab6b6b426683773a022d2401522023-11-22T16:33:15ZengMDPI AGMolecules1420-30492021-09-012619582710.3390/molecules26195827Isolation, Characterization, Complete Structural Assignment, and Anticancer Activities of the Methoxylated Flavonoids from <i>Rhamnus disperma</i> RootsHamdoon A. Mohammed0Mohammed F. Abd El-Wahab1Usama Shaheen2Abd El-Salam I. Mohammed3Ashraf N. Abdalla4Ehab A. Ragab5Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, Qassim University, Buraydah 51452, Saudi ArabiaDepartment of Pharmacognosy, Faculty of Pharmacy, Al-Azhar University, Cairo 11371, EgyptDepartment of Pharmacognosy, Faculty of Pharmacy, Al-Azhar University, Cairo 11371, EgyptDepartment of Pharmacognosy, Faculty of Pharmacy, Al-Azhar University, Cairo 11371, EgyptDepartment of Pharmacology and Toxicology, Faculty of Pharmacy, Umm Al-Qura University, Makkah 21955, Saudi ArabiaDepartment of Pharmacognosy, Faculty of Pharmacy, Al-Azhar University, Cairo 11371, EgyptDifferent chromatographic methods including reversed-phase HPLC led to the isolation and purification of three <i>O</i>-methylated flavonoids; 5,4’-dihydroxy-3,6,7-tri-<i>O</i>-methyl flavone (penduletin) (<b>1</b>), 5,3’-dihydroxy-3,6,7,4’,5’-penta-<i>O</i>-methyl flavone (<b>2</b>), and 5-hydroxy-3,6,7,3’,4’,5’-hexa-<i>O</i>-methyl flavone (<b>3</b>) from <i>Rhamnus disperma</i> roots. Additionlly, four flavonoid glycosides; kampferol 7-<i>O</i>-<i>α</i>-L-rhamnopyranoside (<b>4</b>), isorhamnetin-3-<i>O</i>-<i>β</i>-D-glucopyranoside (<b>5</b>), quercetin 7-<i>O</i>-<i>α</i>-L-rhamnopyranoside (<b>6</b>), and kampferol 3, 7-di-<i>O</i>-<i>α</i>-L-rhamnopyranoside (<b>7</b>) along with benzyl-<i>O</i>-<i>β</i>-D-glucopyranoside (<b>8</b>) were successfully isolated. Complete structure characterization of these compounds was assigned based on NMR spectroscopic data, MS analyses, and comparison with the literature. The <i>O</i>-methyl protons and carbons of the three <i>O</i>-methylated flavonoids (<b>1</b>–<b>3</b>) were unambiguously assigned based on 2D NMR data. The occurrence of compounds <b>1</b>, <b>4</b>, <b>5</b>, and <b>8</b> in <i>Rhamnus disperma</i> is was reported here for the first time. Compound <b>3</b> was acetylated at 5-OH position to give 5-<i>O</i>-acetyl-3,6,7,3’,4’,5’-hexa-<i>O</i>-methyl flavone (<b>9</b>). Compound <b>1</b> exhibited the highest cytotoxic activity against MCF 7, A2780, and HT29 cancer cell lines with IC<sub>50</sub> values at 2.17 µM, 0.53 µM, and 2.16 µM, respectively, and was 2–9 folds more selective against tested cancer cell lines compared to the normal human fetal lung fibroblasts (MRC5). It also doubled MCF 7 apoptotic populations and caused G<sub>1</sub> cell cycle arrest. The acetylated compound <b>9</b> exhibited cytotoxic activity against MCF 7 and HT29 cancer cell lines with IC<sub>50</sub> values at 2.19 µM and 3.18 µM, respectively, and was 6–8 folds more cytotoxic to tested cancer cell lines compared to the MRC5 cells.https://www.mdpi.com/1420-3049/26/19/5827<i>Rhamnus disperma</i>flavonoidsmethoxylated flavonoidscytotoxicityapoptosiscell cycle |
| spellingShingle | Hamdoon A. Mohammed Mohammed F. Abd El-Wahab Usama Shaheen Abd El-Salam I. Mohammed Ashraf N. Abdalla Ehab A. Ragab Isolation, Characterization, Complete Structural Assignment, and Anticancer Activities of the Methoxylated Flavonoids from <i>Rhamnus disperma</i> Roots Molecules <i>Rhamnus disperma</i> flavonoids methoxylated flavonoids cytotoxicity apoptosis cell cycle |
| title | Isolation, Characterization, Complete Structural Assignment, and Anticancer Activities of the Methoxylated Flavonoids from <i>Rhamnus disperma</i> Roots |
| title_full | Isolation, Characterization, Complete Structural Assignment, and Anticancer Activities of the Methoxylated Flavonoids from <i>Rhamnus disperma</i> Roots |
| title_fullStr | Isolation, Characterization, Complete Structural Assignment, and Anticancer Activities of the Methoxylated Flavonoids from <i>Rhamnus disperma</i> Roots |
| title_full_unstemmed | Isolation, Characterization, Complete Structural Assignment, and Anticancer Activities of the Methoxylated Flavonoids from <i>Rhamnus disperma</i> Roots |
| title_short | Isolation, Characterization, Complete Structural Assignment, and Anticancer Activities of the Methoxylated Flavonoids from <i>Rhamnus disperma</i> Roots |
| title_sort | isolation characterization complete structural assignment and anticancer activities of the methoxylated flavonoids from i rhamnus disperma i roots |
| topic | <i>Rhamnus disperma</i> flavonoids methoxylated flavonoids cytotoxicity apoptosis cell cycle |
| url | https://www.mdpi.com/1420-3049/26/19/5827 |
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