Soyauxinine, a New Indolopyridoquinazoline Alkaloid from the Stem Bark of <i>Araliopsis soyauxii</i> Engl. (Rutaceae)
The chemical investigation of the total alkaloid extract (TAE) of the stem bark of <i>Araliopsis soyauxii</i> (Rutaceae) afforded an unreported indolopyridoquinazoline (compound <b>1</b>) along with nine previously known alkaloids <b>2</b>–<b>10</b>. I...
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MDPI AG
2022-02-01
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| author | Cédric Guy Tchatchouang Noulala Judith Laure Nantchouang Ouete Albert Fouda Atangana Gabin Thierry Bitchagno Mbahbou Ghislain Wabo Fotso Hans-Georg Stammler Bruno Ndjakou Lenta Emmanuel Ngeufa Happi Norbert Sewald Bonaventure Tchaleu Ngadjui |
| author_facet | Cédric Guy Tchatchouang Noulala Judith Laure Nantchouang Ouete Albert Fouda Atangana Gabin Thierry Bitchagno Mbahbou Ghislain Wabo Fotso Hans-Georg Stammler Bruno Ndjakou Lenta Emmanuel Ngeufa Happi Norbert Sewald Bonaventure Tchaleu Ngadjui |
| author_sort | Cédric Guy Tchatchouang Noulala |
| collection | DOAJ |
| description | The chemical investigation of the total alkaloid extract (TAE) of the stem bark of <i>Araliopsis soyauxii</i> (Rutaceae) afforded an unreported indolopyridoquinazoline (compound <b>1</b>) along with nine previously known alkaloids <b>2</b>–<b>10</b>. In addition, six semi-synthetic derivatives <b>3a</b>–<b>c</b>, <b>4b</b>, <b>5a</b> and <b>6a</b> were prepared by allylation and acetonidation of soyauxinium nitrate (<b>5</b>), edulinine (<b>3</b>), ribalinine (<b>4</b>) and arborinine (<b>6</b>). The structures and spectroscopic data of five of them are reported herein for the first time. The suggested mechanism for the formation of the new <i>N</i>-allylindolopyridoquinazoline <b>5a</b> is presented. The structures of natural and derived compounds were determined employing extensive NMR and MS techniques. The absolute configuration of stereogenic centers in compounds <b>2</b>–<b>4</b> were determined using NOESY technique and confirmed by the single-crystal X-ray diffraction (SC-XRD) technique. The use of SC-XRD further enabled us to carry out a structural revision of soyauxinium chloride recently isolated from the same plant to soyauxinium nitrate (<b>5</b>). The TAE, fractions, compounds <b>1</b>–<b>7</b> and <b>9</b>, and semi-synthetic derivatives <b>3a</b>–<b>c</b>, <b>4b</b>, <b>5a</b> and <b>6a</b> were evaluated for their cytotoxic activity towards the cervix carcinoma cell line KB-3-1. No significant activity was recorded for most of the compounds except for <b>9</b>, which showed moderate activity against the tested cancer cell lines. |
| first_indexed | 2024-03-09T23:26:25Z |
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| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-09T23:26:25Z |
| publishDate | 2022-02-01 |
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| series | Molecules |
| spelling | doaj.art-763edef067934a72b3ad72e12a27ed7c2023-11-23T17:17:38ZengMDPI AGMolecules1420-30492022-02-01273110410.3390/molecules27031104Soyauxinine, a New Indolopyridoquinazoline Alkaloid from the Stem Bark of <i>Araliopsis soyauxii</i> Engl. (Rutaceae)Cédric Guy Tchatchouang Noulala0Judith Laure Nantchouang Ouete1Albert Fouda Atangana2Gabin Thierry Bitchagno Mbahbou3Ghislain Wabo Fotso4Hans-Georg Stammler5Bruno Ndjakou Lenta6Emmanuel Ngeufa Happi7Norbert Sewald8Bonaventure Tchaleu Ngadjui9Department of Organic Chemistry, Faculty of Science, University of Yaoundé 1, Yaoundé P.O. Box 812, CameroonDepartment of Organic Chemistry, Faculty of Science, University of Yaoundé 1, Yaoundé P.O. Box 812, CameroonDepartment of Chemistry, Faculty of Science, University of Maroua, Maroua P.O. Box 55, CameroonOrganic and Bioorganic Chemistry, Department of Chemistry, Bielefeld University, 33501 Bielefeld, GermanyDepartment of Organic Chemistry, Faculty of Science, University of Yaoundé 1, Yaoundé P.O. Box 812, CameroonDepartment of Chemistry, Inorganic and Structural Chemistry, Bielefeld University, 33501 Bielefeld, GermanyDepartment of Chemistry, Higher Teacher Training College, University of Yaoundé 1 1, Yaoundé P.O. Box 47, CameroonDepartment of Chemistry, Faculty of Science, University of Douala, Douala P.O. Box 24157, CameroonOrganic and Bioorganic Chemistry, Department of Chemistry, Bielefeld University, 33501 Bielefeld, GermanyDepartment of Organic Chemistry, Faculty of Science, University of Yaoundé 1, Yaoundé P.O. Box 812, CameroonThe chemical investigation of the total alkaloid extract (TAE) of the stem bark of <i>Araliopsis soyauxii</i> (Rutaceae) afforded an unreported indolopyridoquinazoline (compound <b>1</b>) along with nine previously known alkaloids <b>2</b>–<b>10</b>. In addition, six semi-synthetic derivatives <b>3a</b>–<b>c</b>, <b>4b</b>, <b>5a</b> and <b>6a</b> were prepared by allylation and acetonidation of soyauxinium nitrate (<b>5</b>), edulinine (<b>3</b>), ribalinine (<b>4</b>) and arborinine (<b>6</b>). The structures and spectroscopic data of five of them are reported herein for the first time. The suggested mechanism for the formation of the new <i>N</i>-allylindolopyridoquinazoline <b>5a</b> is presented. The structures of natural and derived compounds were determined employing extensive NMR and MS techniques. The absolute configuration of stereogenic centers in compounds <b>2</b>–<b>4</b> were determined using NOESY technique and confirmed by the single-crystal X-ray diffraction (SC-XRD) technique. The use of SC-XRD further enabled us to carry out a structural revision of soyauxinium chloride recently isolated from the same plant to soyauxinium nitrate (<b>5</b>). The TAE, fractions, compounds <b>1</b>–<b>7</b> and <b>9</b>, and semi-synthetic derivatives <b>3a</b>–<b>c</b>, <b>4b</b>, <b>5a</b> and <b>6a</b> were evaluated for their cytotoxic activity towards the cervix carcinoma cell line KB-3-1. No significant activity was recorded for most of the compounds except for <b>9</b>, which showed moderate activity against the tested cancer cell lines.https://www.mdpi.com/1420-3049/27/3/1104<i>Araliopsis soyauxii</i>Rutaceaealkaloidssoyauxininecytotoxic activity |
| spellingShingle | Cédric Guy Tchatchouang Noulala Judith Laure Nantchouang Ouete Albert Fouda Atangana Gabin Thierry Bitchagno Mbahbou Ghislain Wabo Fotso Hans-Georg Stammler Bruno Ndjakou Lenta Emmanuel Ngeufa Happi Norbert Sewald Bonaventure Tchaleu Ngadjui Soyauxinine, a New Indolopyridoquinazoline Alkaloid from the Stem Bark of <i>Araliopsis soyauxii</i> Engl. (Rutaceae) Molecules <i>Araliopsis soyauxii</i> Rutaceae alkaloids soyauxinine cytotoxic activity |
| title | Soyauxinine, a New Indolopyridoquinazoline Alkaloid from the Stem Bark of <i>Araliopsis soyauxii</i> Engl. (Rutaceae) |
| title_full | Soyauxinine, a New Indolopyridoquinazoline Alkaloid from the Stem Bark of <i>Araliopsis soyauxii</i> Engl. (Rutaceae) |
| title_fullStr | Soyauxinine, a New Indolopyridoquinazoline Alkaloid from the Stem Bark of <i>Araliopsis soyauxii</i> Engl. (Rutaceae) |
| title_full_unstemmed | Soyauxinine, a New Indolopyridoquinazoline Alkaloid from the Stem Bark of <i>Araliopsis soyauxii</i> Engl. (Rutaceae) |
| title_short | Soyauxinine, a New Indolopyridoquinazoline Alkaloid from the Stem Bark of <i>Araliopsis soyauxii</i> Engl. (Rutaceae) |
| title_sort | soyauxinine a new indolopyridoquinazoline alkaloid from the stem bark of i araliopsis soyauxii i engl rutaceae |
| topic | <i>Araliopsis soyauxii</i> Rutaceae alkaloids soyauxinine cytotoxic activity |
| url | https://www.mdpi.com/1420-3049/27/3/1104 |
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