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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...

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Autores principales: 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
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
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.
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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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