Soyauxinine, a New Indolopyridoquinazoline Alkaloid from the Stem Bark of Araliopsis soyauxii Engl. (Rutaceae)

Noulala CGT, Ouete JLN, Atangana AF, Mbahbou GTB, Fotso GW, Stammler H-G, Lenta BN, Happi EN, Sewald N, Ngadjui BT (2022)
Molecules 27(3): 1104.

Zeitschriftenaufsatz | Veröffentlicht | Englisch
 
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Autor*in
Noulala, Cédric Guy Tchatchouang; Ouete, Judith Laure Nantchouang; Atangana, Albert Fouda; Mbahbou, Gabin Thierry Bitchagno; Fotso, Ghislain Wabo; Stammler, Hans-GeorgUniBi; Lenta, Bruno Ndjakou; Happi, Emmanuel Ngeufa; Sewald, NorbertUniBi ; Ngadjui, Bonaventure Tchaleu
Abstract / Bemerkung
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.
Stichworte
Araliopsis soyauxii; Rutaceae; alkaloids; soyauxinine; cytotoxic activity
Erscheinungsjahr
2022
Zeitschriftentitel
Molecules
Band
27
Ausgabe
3
Art.-Nr.
1104
eISSN
1420-3049
Finanzierungs-Informationen
Open-Access-Publikationskosten wurden durch die Universität Bielefeld gefördert.
Page URI
https://pub.uni-bielefeld.de/record/2961182

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Noulala CGT, Ouete JLN, Atangana AF, et al. Soyauxinine, a New Indolopyridoquinazoline Alkaloid from the Stem Bark of Araliopsis soyauxii Engl. (Rutaceae). Molecules. 2022;27(3): 1104.
Noulala, C. G. T., Ouete, J. L. N., Atangana, A. F., Mbahbou, G. T. B., Fotso, G. W., Stammler, H. - G., Lenta, B. N., et al. (2022). Soyauxinine, a New Indolopyridoquinazoline Alkaloid from the Stem Bark of Araliopsis soyauxii Engl. (Rutaceae). Molecules, 27(3), 1104. https://doi.org/10.3390/molecules27031104
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, and Ngadjui, Bonaventure Tchaleu. 2022. “Soyauxinine, a New Indolopyridoquinazoline Alkaloid from the Stem Bark of Araliopsis soyauxii Engl. (Rutaceae)”. Molecules 27 (3): 1104.
Noulala, C. G. T., Ouete, J. L. N., Atangana, A. F., Mbahbou, G. T. B., Fotso, G. W., Stammler, H. - G., Lenta, B. N., Happi, E. N., Sewald, N., and Ngadjui, B. T. (2022). Soyauxinine, a New Indolopyridoquinazoline Alkaloid from the Stem Bark of Araliopsis soyauxii Engl. (Rutaceae). Molecules 27:1104.
Noulala, C.G.T., et al., 2022. Soyauxinine, a New Indolopyridoquinazoline Alkaloid from the Stem Bark of Araliopsis soyauxii Engl. (Rutaceae). Molecules, 27(3): 1104.
C.G.T. Noulala, et al., “Soyauxinine, a New Indolopyridoquinazoline Alkaloid from the Stem Bark of Araliopsis soyauxii Engl. (Rutaceae)”, Molecules, vol. 27, 2022, : 1104.
Noulala, C.G.T., Ouete, J.L.N., Atangana, A.F., Mbahbou, G.T.B., Fotso, G.W., Stammler, H.-G., Lenta, B.N., Happi, E.N., Sewald, N., Ngadjui, B.T.: Soyauxinine, a New Indolopyridoquinazoline Alkaloid from the Stem Bark of Araliopsis soyauxii Engl. (Rutaceae). Molecules. 27, : 1104 (2022).
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, and Ngadjui, Bonaventure Tchaleu. “Soyauxinine, a New Indolopyridoquinazoline Alkaloid from the Stem Bark of Araliopsis soyauxii Engl. (Rutaceae)”. Molecules 27.3 (2022): 1104.
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