Soyauxinine, a New Indolopyridoquinazoline Alkaloid from the Stem Bark of Araliopsis soyauxii Engl. (Rutaceae)
Abstract
:1. Introduction
2. Results and Discussion
2.1. Structural Identification of Compounds
2.2. SC-XRD Analyses
2.3. Semi-Synthesis of Allylated and Acetonitaded Derivatives of Some Naturally Isolated Alkaloids
2.4. Cytotoxic Activity of the Extract, Fractions, and Isolated Compounds
3. Materials and Methods
3.1. General Information
3.2. Plant Material
3.3. Extraction and Isolation
3.4. X-ray Diffraction Analyses
3.5. Cytotoxic Activity of the Extract, Fractions, Isolates, and Semi-Synthetic Derivatives
3.6. Preparation of the Semis-Ynthetic Derivatives
3.6.1. Allylation of Edulinine
3.6.2. Acetonidation of Edulinine
3.6.3. Allylation of Ribalinine
3.6.4. Allylation of Soyauxinium Nitrate
3.6.5. Allylation of Arborinine
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Acknowledgments
Conflicts of Interest
Sample Availability
References
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Position | 1 | ||
---|---|---|---|
δc | δH | HMBC | |
1 | 154.0 | ||
2 | 94.8 | 6.18(1H, d, J = 2.4) | 1, 3 |
3 | 165.4 | ||
4 | 102.2 | 6.11 (1H, dd; J = 9.0, 2.4) | 3, 5a |
5 | 135.5 | 7.45 (1H, d, J = 9.0) | 1, 3, 6 |
5a | 109.0 | ||
6 | 175.1 | ||
7 | 47.8 | 4.15 (2H, t, J = 6.4) | 6, 8a, 13 |
8 | 21.3 | 3.20 (2H, t, J = 6.4) | 8a, 13a |
8a | 122.3 | ||
9a | 125.0 | ||
9 | 120.7 | 7.63 (1H, d, J = 8.0) | 12, 12a |
10 | 120.7 | 7.16 (1H, t, J = 8.0) | 9a, 12 |
11 | 126.0 | 7.28 (1H, t, J = 8.0) | 9, 10, 12 |
12 | 113.0 | 7.14 (1H, t, J = 8.0) | 9, 9a, 10 |
12a | 138.4 | ||
13a | 126.4 | ||
13 | 162.1 | ||
1-NCH3 | 29.7 | 2.96 (3H, d, J = 5.0) | 1 |
1-NHCH3 | 7.80 (1H, q, J = 5.0) | 2 | |
3-OCH3 | 55.3 | 3.81(1H, s) | 3 |
NH | 9.69, brs | 8a, 12a |
IC50 (µM) | |
---|---|
Samples | KB-3-1 |
1 | ˃50 |
2 | Inactive |
3 | Inactive |
3a | Inactive |
3b | ˃500 |
3c | ˃500 |
4 | Inactive |
4b | Inactive |
5 | Inactive |
5a | Inactive |
6 | 50 |
6a | ˃500 |
7 | Inactive |
9 | 10 |
FTAE1 | Inactive |
FTAE2 | Inactive |
FTAE3 | Inactive |
TAE | Inactive |
Griseofulvin | 17–21 |
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Share and Cite
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 2022, 27, 1104. https://doi.org/10.3390/molecules27031104
Noulala CGT, Ouete JLN, Atangana AF, Mbahbou GTB, Fotso GW, Stammler H-G, Lenta BN, Happi EN, Sewald N, Ngadjui BT. Soyauxinine, a New Indolopyridoquinazoline Alkaloid from the Stem Bark of Araliopsis soyauxii Engl. (Rutaceae). Molecules. 2022; 27(3):1104. https://doi.org/10.3390/molecules27031104
Chicago/Turabian StyleNoulala, Cédric Guy Tchatchouang, 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, and Bonaventure Tchaleu Ngadjui. 2022. "Soyauxinine, a New Indolopyridoquinazoline Alkaloid from the Stem Bark of Araliopsis soyauxii Engl. (Rutaceae)" Molecules 27, no. 3: 1104. https://doi.org/10.3390/molecules27031104