Synthesis of Novel Stilbene–Coumarin Derivatives and Antifungal Screening of Monotes kerstingii-Specialized Metabolites Against Fusarium oxysporum
Abstract
:1. Introduction
2. Results and Discussion
2.1. Antifungal Activity of Crude Extract, Fractions, and Specialized metabolites from Monotes kerstingii against Fo32931 and Fo4287
2.2. Alkylation of Compound 1: Semisynthesis of Allylated, Propargylated, Prenylated, and Benzylated Derivatives 1a–e
2.2.1. Characterization of Compounds 1a–e
2.2.2. Antifungal Activity of Semi-Synthetic Derivatives against Fo32931 and Fo4287
3. Materials and Methods
3.1. General Methods
3.2. Plant Material
3.3. Extraction of M. kerstingii Stem Barks and Isolation of Specialized Metabolites
3.4. Alkylation of Compound 1
3.5. Antifungal Bioassay
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Acknowledgments
Conflicts of Interest
References
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Type | Code | Fo32931 MIC (µg/mL) | Fo4287 MIC (µg/mL) |
---|---|---|---|
Extract | MKS | 841 | 679 |
Fractions | MKSHEX | >1000 | 331 |
MKSEA | >1000 | 171 | |
MKSBUT | 448 | 23 | |
Hemisynthetic | 1a | 477 | >1000 |
1b | 281 | 658 | |
1c | 103 | >1000 | |
1d | 708 | >1000 | |
1e | 341 | 621 | |
Natural | 1 | 116 | 96 |
2 | 337 | 286 | |
3 | 327 | 330 | |
4 | 553 | 273 | |
5 | 98 | 180 | |
6 | 116 | 361 | |
7 | 408 | 915 | |
8 | 174 | 457 | |
9 | 473 | >1000 | |
10 | >1000 | >1000 | |
11 | 523 | >1000 | |
Pop | Nystatin | 50 | 50 |
N° | Compound 1a δH (m, J in Hz) | Compound 1b δH (m, J in Hz) | Compound 1c δH (m, J in Hz) | Compound 1d δH (m, J in Hz) | Compound 1e δH (m, J in Hz) |
---|---|---|---|---|---|
3 | 5.49 (1H, s) | 5.52 (1H, s) | 5.49 (1H, s) | 5.51 (1H, s) | 5.62 (1H, s) |
4 | - | - | - | - | - |
5 | - | - | - | - | - |
6 | 6.87 (1H, d, 2.6) | 6.89 (1H, d, 2.4) | 6.87 (1H, d, 2.6) | 6.89 (1H, d, 2.6) | 6.99 (1H, d, 2.5) |
7 | - | - | - | - | - |
8 | 6.66 (1H, d, 2.5) | 6.68 (1H, d, 2.6) | 6.65 (1H, d, 2.6) | 6.67 (1H, d, 2.6) | 6.79 (1H, d, 2.5) |
9 | - | - | - | - | - |
10 | - | - | - | - | - |
1′ | 7.68 (1H, d, 16.0) | 7.71 (1H, d, 16.0) | 7.67 (1H, d, 15.9) | 7.69 (1H, d, 16.0) | 7.80 (1H, d, 15.9) |
2′ | 6.70 (1H, d, 16.0) | 6.73 (1H, d, 16.0) | 6.71 (1H, d, 15.9) | 6.73 (1H, d, 16.0) | 6.81 (1H, d, 15.9) |
1″ | - | - | - | - | - |
2″, 6″ | 7.35 (2H, d, 8.7) | 7.39 (2H, d, 8.6) | 7.35 (2H, d, 8.7) | 7.35 (2H, d, 8.8) | 7.47 (2H, d, 8.7) |
4″ | - | - | - | - | - |
3″, 5″ | 6.86 (2H, d, 8.7) | 6.93 (2H, d, 8.8) | 6.85 (2H, d, 8.7) | 6.92 (2H, d, 8.8) | 6.99 (2H, d, 8.7) |
1‴ | 4.50 (2H, d, 2.6) | 4.66 (2H, d, 2.4) | 4.46 (2H, d, 6.7) | 5.04 (2H, s) | 5.09 (2H, s) |
2‴ | 5.99 (1H, m) | 5.43 (1H, t, 2.7) | |||
3‴ | 5.36 (1H, dd, 17.3; 1.5) 5.24 (1H, d, 11.8) | 2.48 (1H, d, 2.4) | |||
4‴ | 1.73 (3H, s) | ||||
5‴ | 1.68 (3H, s) | ||||
2⁗, 6⁗ | 7.25–7.40 m | 7.35 (2H, d, 8.5) | |||
3⁗, 5⁗ | 7.55 (2H, d, 8.5) | ||||
4⁗ | - | ||||
4-OMe | 3.88 (3H, s) | 3.92 (3H, s) | 3.87 (3H, s) | 3.90 (3H, s) | 3.99 (3H, s) |
7-OMe | 3.80 (3H, s) | 3.89 (3H, s) | 3.80 (3H, s) | 3.82 (3H, s) | 3.92 (3H, s) |
N° | Compound 1a δC (m) | Compound 1b δc (m) | Compound 1c δc (m) | Compound 1d δc (m) | Compound 1e δc (m) |
---|---|---|---|---|---|
2 | 162.1 (s) | 162.1 (s) | 162.1 (s) | 162.0 (s) | 162.1 (s) |
3 | 88.2 (d) | 88.2 (d) | 88.2 (d) | 88.0 (d) | 88.2 (d) |
4 | 169.2 (s) | 169.2 (s) | 169.3 (s) | 169.2 (s) | 169.2 (s) |
5 | 131.0 (s) | 131.0 (s) | 130.0 (s) | 130.2 (s) | 130.5 (s) |
6 | 111.7 (d) | 111.9 (d) | 111.7 (d) | 111.6 (d) | 111.8 (d) |
7 | 162.9 (s) | 162.9 (s) | 162.9 (s) | 162.8 (s) | 162.9 (s) |
8 | 100.0 (d) | 100.1 (d) | 100.0 (d) | 100.0 (d) | 100.1 (d) |
9 | 156.4 (s) | 156.4 (s) | 156.4 (s) | 156.4 (s) | 156.5 (s) |
10 | 106.7 (s) | 106.7 (s) | 106.7 (s) | 106.6 (s) | 106.7 (s) |
1′ | 126.7 (d) | 127.2 (d) | 126.5 (d) | 126.7 (d) | 127.0 (d) |
2′ | 131.4 (d) | 131.2 (d) | 131.4 (d) | 131.3 (d) | 131.3 (d) |
1″ | 138.8 (s) | 138.8 (s) | 138.9 (s) | 138.9 (s) | 138.9 (s) |
2″, 6″ | 127.9 (d) | 115.2 (d) | 127.9 (d) | 127.9 (d) | 128.0 (d) |
4″ | 157.5 (s) | 157.5 (s) | 158.9 (s) | 158.7 (s) | 158.5 |
3″, 5″ | 115.1 (d) | 127.9 (d) | 115.0 (d) | 115.1 (d) | 115.2 (d) |
1‴ | 68.9 (t) | 55.9 (t) | 64.9 (t) | 70.0 (t) | 69.3 |
2‴ | 133.1 (d) | 78.4 (s) | 119.5 (d) | ||
3‴ | 117.4 (t) | 75.7 (d) | 138.4 (s) | ||
4‴ | 25.9 (q) | ||||
5‴ | 18.2 (q) | ||||
1⁗ | 136.7 (s) | 135.9 | |||
2⁗ | 128.6 (d) | 129.0 | |||
3⁗ | 127.9 (d) | 131.8 | |||
4⁗ | 128.0 (d) | 129.0 | |||
5⁗ | 127.9 (d) | 131.8 | |||
6⁗ | 128.6 (d) | 122.0 | |||
4-OMe | 56.3 (q) | 56.4 (q) | 56.3 (q) | 56.4 (q) | 56.4 |
7-OMe | 55.7 (q) | 55.7 (q) | 55.7 (q) | 55.7 (q) | 55.7 |
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Fotso, G.W.; Ngameni, B.; Storr, T.E.; Ngadjui, B.T.; Mafu, S.; Stephenson, G.R. Synthesis of Novel Stilbene–Coumarin Derivatives and Antifungal Screening of Monotes kerstingii-Specialized Metabolites Against Fusarium oxysporum. Antibiotics 2020, 9, 537. https://doi.org/10.3390/antibiotics9090537
Fotso GW, Ngameni B, Storr TE, Ngadjui BT, Mafu S, Stephenson GR. Synthesis of Novel Stilbene–Coumarin Derivatives and Antifungal Screening of Monotes kerstingii-Specialized Metabolites Against Fusarium oxysporum. Antibiotics. 2020; 9(9):537. https://doi.org/10.3390/antibiotics9090537
Chicago/Turabian StyleFotso, Ghislain Wabo, Bathelemy Ngameni, Thomas E. Storr, Bonaventure Tchaleu Ngadjui, Sibongile Mafu, and G. Richard Stephenson. 2020. "Synthesis of Novel Stilbene–Coumarin Derivatives and Antifungal Screening of Monotes kerstingii-Specialized Metabolites Against Fusarium oxysporum" Antibiotics 9, no. 9: 537. https://doi.org/10.3390/antibiotics9090537