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Soyauxinine, a New Indolopyridoquinazoline Alkaloid from the Stem Bark of Araliopsis soyauxii Engl. (Rutaceae)
The chemical investigation of the total alkaloid extract (TAE) of the stem bark of Araliopsis soyauxii (Rutaceae) afforded an unreported indolopyridoquinazoline (compound 1) along with nine previously known alkaloids 2–10. In addition, six semi-synthetic derivatives 3a–c, 4b, 5a and 6a were prepared...
Autores principales: | , , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2022
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8838469/ https://www.ncbi.nlm.nih.gov/pubmed/35164367 http://dx.doi.org/10.3390/molecules27031104 |
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author | Noulala, Cédric Guy Tchatchouang Ouete, Judith Laure Nantchouang Atangana, Albert Fouda Mbahbou, Gabin Thierry Bitchagno Fotso, Ghislain Wabo Stammler, Hans-Georg Lenta, Bruno Ndjakou Happi, Emmanuel Ngeufa Sewald, Norbert Ngadjui, Bonaventure Tchaleu |
author_facet | Noulala, Cédric Guy Tchatchouang Ouete, Judith Laure Nantchouang Atangana, Albert Fouda Mbahbou, Gabin Thierry Bitchagno Fotso, Ghislain Wabo Stammler, Hans-Georg Lenta, Bruno Ndjakou Happi, Emmanuel Ngeufa Sewald, Norbert Ngadjui, Bonaventure Tchaleu |
author_sort | Noulala, Cédric Guy Tchatchouang |
collection | PubMed |
description | The chemical investigation of the total alkaloid extract (TAE) of the stem bark of Araliopsis soyauxii (Rutaceae) afforded an unreported indolopyridoquinazoline (compound 1) along with nine previously known alkaloids 2–10. In addition, six semi-synthetic derivatives 3a–c, 4b, 5a and 6a were prepared by allylation and acetonidation of soyauxinium nitrate (5), edulinine (3), ribalinine (4) and arborinine (6). 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 N-allylindolopyridoquinazoline 5a 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 2–4 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 (5). The TAE, fractions, compounds 1–7 and 9, and semi-synthetic derivatives 3a–c, 4b, 5a and 6a 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 9, which showed moderate activity against the tested cancer cell lines. |
format | Online Article Text |
id | pubmed-8838469 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-88384692022-02-13 Soyauxinine, a New Indolopyridoquinazoline Alkaloid from the Stem Bark of Araliopsis soyauxii Engl. (Rutaceae) Noulala, Cédric Guy Tchatchouang Ouete, Judith Laure Nantchouang Atangana, Albert Fouda Mbahbou, Gabin Thierry Bitchagno Fotso, Ghislain Wabo Stammler, Hans-Georg Lenta, Bruno Ndjakou Happi, Emmanuel Ngeufa Sewald, Norbert Ngadjui, Bonaventure Tchaleu Molecules Article The chemical investigation of the total alkaloid extract (TAE) of the stem bark of Araliopsis soyauxii (Rutaceae) afforded an unreported indolopyridoquinazoline (compound 1) along with nine previously known alkaloids 2–10. In addition, six semi-synthetic derivatives 3a–c, 4b, 5a and 6a were prepared by allylation and acetonidation of soyauxinium nitrate (5), edulinine (3), ribalinine (4) and arborinine (6). 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 N-allylindolopyridoquinazoline 5a 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 2–4 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 (5). The TAE, fractions, compounds 1–7 and 9, and semi-synthetic derivatives 3a–c, 4b, 5a and 6a 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 9, which showed moderate activity against the tested cancer cell lines. MDPI 2022-02-07 /pmc/articles/PMC8838469/ /pubmed/35164367 http://dx.doi.org/10.3390/molecules27031104 Text en © 2022 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Article Noulala, Cédric Guy Tchatchouang Ouete, Judith Laure Nantchouang Atangana, Albert Fouda Mbahbou, Gabin Thierry Bitchagno Fotso, Ghislain Wabo Stammler, Hans-Georg Lenta, Bruno Ndjakou Happi, Emmanuel Ngeufa Sewald, Norbert Ngadjui, Bonaventure Tchaleu Soyauxinine, a New Indolopyridoquinazoline Alkaloid from the Stem Bark of Araliopsis soyauxii Engl. (Rutaceae) |
title | Soyauxinine, a New Indolopyridoquinazoline Alkaloid from the Stem Bark of Araliopsis soyauxii Engl. (Rutaceae) |
title_full | Soyauxinine, a New Indolopyridoquinazoline Alkaloid from the Stem Bark of Araliopsis soyauxii Engl. (Rutaceae) |
title_fullStr | Soyauxinine, a New Indolopyridoquinazoline Alkaloid from the Stem Bark of Araliopsis soyauxii Engl. (Rutaceae) |
title_full_unstemmed | Soyauxinine, a New Indolopyridoquinazoline Alkaloid from the Stem Bark of Araliopsis soyauxii Engl. (Rutaceae) |
title_short | Soyauxinine, a New Indolopyridoquinazoline Alkaloid from the Stem Bark of Araliopsis soyauxii Engl. (Rutaceae) |
title_sort | soyauxinine, a new indolopyridoquinazoline alkaloid from the stem bark of araliopsis soyauxii engl. (rutaceae) |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8838469/ https://www.ncbi.nlm.nih.gov/pubmed/35164367 http://dx.doi.org/10.3390/molecules27031104 |
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