Coumarinolignoid and Indole Alkaloids from the Roots of the Hybrid Plant <i>Citrus × paradisi</i> Macfad (Rutaceae)
A phytochemical investigation of the roots of <i>Citrus × paradisi</i> Macfad. (Rutaceae) led to the isolation of two new compounds, namely 1-formyl-5-hydroxy-<i>N</i>-methylindolin-1-ium (<b>1</b>) and decyloxycleomiscosin D (<b>2</b>), along with ten...
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MDPI AG
2023-01-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/28/3/1078 |
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| author | Fanny-Aimée Essombe Malolo Ariane Dolly Kenmogne Kouam Judith Caroline Ngo Nyobe Lidwine Ngah Marcel Frese Jean Claude Ndom Moses K. Langat Bruno Ndjakou Lenta Dulcie A. Mulholland Norbert Sewald Jean Duplex Wansi |
| author_facet | Fanny-Aimée Essombe Malolo Ariane Dolly Kenmogne Kouam Judith Caroline Ngo Nyobe Lidwine Ngah Marcel Frese Jean Claude Ndom Moses K. Langat Bruno Ndjakou Lenta Dulcie A. Mulholland Norbert Sewald Jean Duplex Wansi |
| author_sort | Fanny-Aimée Essombe Malolo |
| collection | DOAJ |
| description | A phytochemical investigation of the roots of <i>Citrus × paradisi</i> Macfad. (Rutaceae) led to the isolation of two new compounds, namely 1-formyl-5-hydroxy-<i>N</i>-methylindolin-1-ium (<b>1</b>) and decyloxycleomiscosin D (<b>2</b>), along with ten known compounds: 1,1-dimethylpyrrolidin-1-ium-2-carboxylate (<b>3</b>), furan-2,3-diol (<b>4</b>), 5-methoxyseselin (<b>5</b>), umbelliferone (<b>6</b>), scopoletin (<b>7</b>), citracridone I (<b>8</b>), citracridone II (<b>9</b>), citracridone III (<b>10</b>), limonin (<b>11</b>) and lupeol (<b>12</b>). The structures were determined through the comprehensive spectroscopic analysis of 1D and 2D NMR and EI- and ESI-MS, as well as a comparison with the published data. Notably, compounds <b>3</b> and <b>4</b> from the genus <i>Citrus</i> are reported here for the first time. In addition, the MeOH extract of the roots and compounds <b>1</b>–<b>7</b> were screened against the human adenocarcinoma alveolar basal epithelial cell line A549 and the Caucasian prostate adenocarcinoma cell line PC3 using the MTT assay. While the extract showed significant activity, with IC<sub>50</sub> values of 35.2 and 38.1 µg/mL, respectively, compounds <b>1</b>–<b>7</b> showed weak activity, with IC<sub>50</sub> values of 99.2 to 250.2 µM and 99.5 to 192.7 µM, respectively. |
| first_indexed | 2024-03-11T09:33:17Z |
| format | Article |
| id | doaj.art-53ee43f2d5094e148e94f574ea3fc3f9 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-11T09:33:17Z |
| publishDate | 2023-01-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-53ee43f2d5094e148e94f574ea3fc3f92023-11-16T17:27:20ZengMDPI AGMolecules1420-30492023-01-01283107810.3390/molecules28031078Coumarinolignoid and Indole Alkaloids from the Roots of the Hybrid Plant <i>Citrus × paradisi</i> Macfad (Rutaceae)Fanny-Aimée Essombe Malolo0Ariane Dolly Kenmogne Kouam1Judith Caroline Ngo Nyobe2Lidwine Ngah3Marcel Frese4Jean Claude Ndom5Moses K. Langat6Bruno Ndjakou Lenta7Dulcie A. Mulholland8Norbert Sewald9Jean Duplex Wansi10Department of Chemistry, Faculty of Sciences, University of Douala, Douala P.O. Box 24157, CameroonDepartment of Chemistry, Faculty of Sciences, University of Douala, Douala P.O. Box 24157, CameroonDepartment of Pharmaceutical Sciences, Faculty of Medicine and Pharmaceutical Sciences, University of Douala, Douala P.O. Box 2701, CameroonDepartment of Pharmaceutical Sciences, Faculty of Medicine and Pharmaceutical Sciences, University of Douala, Douala P.O. Box 2701, CameroonOrganic and Bioorganic Chemistry, Department of Chemistry, Bielefeld University, 33501 Bielefeld, GermanyDepartment of Chemistry, Faculty of Sciences, University of Douala, Douala P.O. Box 24157, CameroonRoyal Botanic Gardens, Kew, Richmond TW9 3AE, UKOrganic and Bioorganic Chemistry, Department of Chemistry, Bielefeld University, 33501 Bielefeld, GermanyNatural Products Research Group, Department of Chemistry, Faculty of Engineering and Physical Sciences, University of Surrey, Guildford GU2 7XH, UKOrganic and Bioorganic Chemistry, Department of Chemistry, Bielefeld University, 33501 Bielefeld, GermanyDepartment of Chemistry, Faculty of Sciences, University of Douala, Douala P.O. Box 24157, CameroonA phytochemical investigation of the roots of <i>Citrus × paradisi</i> Macfad. (Rutaceae) led to the isolation of two new compounds, namely 1-formyl-5-hydroxy-<i>N</i>-methylindolin-1-ium (<b>1</b>) and decyloxycleomiscosin D (<b>2</b>), along with ten known compounds: 1,1-dimethylpyrrolidin-1-ium-2-carboxylate (<b>3</b>), furan-2,3-diol (<b>4</b>), 5-methoxyseselin (<b>5</b>), umbelliferone (<b>6</b>), scopoletin (<b>7</b>), citracridone I (<b>8</b>), citracridone II (<b>9</b>), citracridone III (<b>10</b>), limonin (<b>11</b>) and lupeol (<b>12</b>). The structures were determined through the comprehensive spectroscopic analysis of 1D and 2D NMR and EI- and ESI-MS, as well as a comparison with the published data. Notably, compounds <b>3</b> and <b>4</b> from the genus <i>Citrus</i> are reported here for the first time. In addition, the MeOH extract of the roots and compounds <b>1</b>–<b>7</b> were screened against the human adenocarcinoma alveolar basal epithelial cell line A549 and the Caucasian prostate adenocarcinoma cell line PC3 using the MTT assay. While the extract showed significant activity, with IC<sub>50</sub> values of 35.2 and 38.1 µg/mL, respectively, compounds <b>1</b>–<b>7</b> showed weak activity, with IC<sub>50</sub> values of 99.2 to 250.2 µM and 99.5 to 192.7 µM, respectively.https://www.mdpi.com/1420-3049/28/3/1078<i>Citrus × paradisi</i>coumarinolignoidindole alkaloidschemotaxonomycytotoxicity |
| spellingShingle | Fanny-Aimée Essombe Malolo Ariane Dolly Kenmogne Kouam Judith Caroline Ngo Nyobe Lidwine Ngah Marcel Frese Jean Claude Ndom Moses K. Langat Bruno Ndjakou Lenta Dulcie A. Mulholland Norbert Sewald Jean Duplex Wansi Coumarinolignoid and Indole Alkaloids from the Roots of the Hybrid Plant <i>Citrus × paradisi</i> Macfad (Rutaceae) Molecules <i>Citrus × paradisi</i> coumarinolignoid indole alkaloids chemotaxonomy cytotoxicity |
| title | Coumarinolignoid and Indole Alkaloids from the Roots of the Hybrid Plant <i>Citrus × paradisi</i> Macfad (Rutaceae) |
| title_full | Coumarinolignoid and Indole Alkaloids from the Roots of the Hybrid Plant <i>Citrus × paradisi</i> Macfad (Rutaceae) |
| title_fullStr | Coumarinolignoid and Indole Alkaloids from the Roots of the Hybrid Plant <i>Citrus × paradisi</i> Macfad (Rutaceae) |
| title_full_unstemmed | Coumarinolignoid and Indole Alkaloids from the Roots of the Hybrid Plant <i>Citrus × paradisi</i> Macfad (Rutaceae) |
| title_short | Coumarinolignoid and Indole Alkaloids from the Roots of the Hybrid Plant <i>Citrus × paradisi</i> Macfad (Rutaceae) |
| title_sort | coumarinolignoid and indole alkaloids from the roots of the hybrid plant i citrus paradisi i macfad rutaceae |
| topic | <i>Citrus × paradisi</i> coumarinolignoid indole alkaloids chemotaxonomy cytotoxicity |
| url | https://www.mdpi.com/1420-3049/28/3/1078 |
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