Antifungal Activity of New Diterpenoid Alkaloids Isolated by Different Chromatographic Methods from Delphinium peregrinum L. var. eriocarpum Boiss
Abstract
:1. Introduction
2. Results and Discussion
2.1. Chemistry
2.2. Biology
Antifungal Activity
3. Materials and Methods
3.1. Chemistry
3.2. Biology
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Data Availability Statement
Conflicts of Interest
Sample Availability
References
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Position | Delcarpum 1 CDCl3 | Peregrine 2 CDCl3 | Delphitisine 3 CDCl3 | Hydrodavisine 4 MeOD | ||||
---|---|---|---|---|---|---|---|---|
HMQC δH | HMQC δH | HMQC δH | HMQC δH | |||||
δC | (mult., J = Hz) | δC | (mult., J = Hz) | δC | (mult., J = Hz) | δC | (mult., J = Hz) | |
1 | 82.3 | 3.22 m | 84.1 | 3.11 - | 73.3 | 2.67 s | 72.9 | 3.10 s |
2 | 24.6 | 1.87 m | 25.9 | 2.01 - | 25.1 | 1.79 m | 31.5 | 1.38 m |
2.15 - | 2.08 - | 1.94 m | ||||||
3 | 28.8 | 1.25 m | 36.5 | 1.25 - | 28.1 | 1.29 m | 25.9 | 1.84 m |
1.57 - | 1.90 m | |||||||
4 | 32.8 | - | 33.9 | - | 35.7 | - | 35.4 | - |
5 | 54 | 1.50 s | 55.7 | 1.48 s | 54.1 | 1.99 m | 54 | 2.21 m |
6 | 71.4 | 5.29 d (7.53) | 72.8 | 5.25 d (7.28) | 64.2 | 4.23 m | 63.6 | 4.20 s |
7 | 35.2 | 3.17 - | 41.7 | 2.75 d (7.29) | 26 | 1.29 m | 25.9 | 1.84 m |
1.79 m | ||||||||
8 | 80.8 | - | 78.5 | - | 44.1 | - | 36.3 | - |
9 | 40.6 | 3.35 - | 44 | 3.05 - | 31.8 | 2.26 d (2.29) | 33.1 | 2.25 m |
10 | 44.3 | 2.15 - | 45.6 | 2.01 - | 53.4 | - | 54.2 | - |
11 | 47.6 | - | 47.6 | - | 31.3 | 1.10 m | 30.9 | 1.70 m |
1.79 m | ||||||||
12 | 28.2 | 1.97 - | 28 | 1.88 m | 39.8 | 2.07 m | 42.3 | 2.11 m |
2.50 dd (3.17, 12.6) | 2.25 dd (5.31) | |||||||
13 | 36.4 | 2.32 t (5.54) | 37.9 | 2.35 t (5.67) | 25.4 | 1.79 m | 26.6 | 1.38 m |
1.94 m | 1.84 m | |||||||
14 | 75.1 | 4.67 t (4.71) | 74.8 | 4.02 q (10.59) | 41.1 | 2.07 m | 41.4 | 2.11 m |
15 | 74.1 | 4.18 d (6.91) | 32.5 | 2.08 - | 69.4 | 4.05 s | 69.5 | 3.99 s |
16 | 91.4 | 3.11 - | 81.9 | 3.39 - | 154.1 | - | 154.2 | - |
17 | 62.8 | 3.22 - | 64.3 | 3.16 d (2.07) | 107.6 | 4.99 d (7.60) | 108.1 | 5.01 d (7.21) |
18 | 25.2 | 0.85 s | 25.3 | 0.85 s | 26.7 | 1.08 s | 26.6 | 1.16 s |
19 | 56.8 | 2.08 d (5.78) | 56. 9 | 60.1 | 2.50 d (12.45) | 59.4 | 2. 86 q (12.29) | |
2.86 d (11.93) | 2.69 d (12.44) | |||||||
20 | 48.5 | 2.63 m | 48.7 | 2.47 m | 64.4 | 3.56 m | 66.3 | 3.93 s |
2.72 m | ||||||||
21 | 11.9 | 1.14 t (6.99) | 13.1 | 1.07 t (7.12) | 30.4 | 1.79 m | - | - |
2.07 m | ||||||||
1′ | 55 | 3.32 s | 55. 6 | 3.28 s | - | - | - | - |
6′ | 170.3 | - | 170.7 | - | - | - | - | |
6′′ | 20.6 | 1.97 - | 21.2 | 2.08 - | - | - | - | - |
8′ | 48.6 | 3.17 - | 47.7 | 3.11 - | - | - | - | - |
14′ | 170 | - | - | - | - | - | - | - |
14′′ | 20.2 | 1.97 - | - | - | - | - | - | - |
16′ | 56.2 | 3.45 s | 55.9 | 3.39 - | - | - | - | - |
Alkaloid Derivative | Dermatophytes (Five Isolates Tested for Each Species) | |||||
---|---|---|---|---|---|---|
Epidermophyton floccosum | Microsporum canis | Trichophyton rubrum | ||||
MIC | MFC | MIC | MFC | MIC | MFC | |
Delcarpum (1) | 265 | 512 | 64 | 128–265 | 32–64 | 256 |
Peregrine (2) | 128–256 | >512 | 32–64 | 128 | 32 | 128 |
Delphitisine (3) | 512 | >512 | 128–265 | 512 | 64–128 | 512 |
Hydrodavisine (4) | 512 | >512 | 128 | 512 | 64–128 | 512 |
Mixture of the four alkaloids | 64 | 128 | 32 | 128–258 | 16 | 64 |
Fluconazole | 32–64 | 64 | 16 | 32–64 | 32 | 64 |
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Alhilal, M.; Sulaiman, Y.A.M.; Alhilal, S.; Gomha, S.M.; Ouf, S.A. Antifungal Activity of New Diterpenoid Alkaloids Isolated by Different Chromatographic Methods from Delphinium peregrinum L. var. eriocarpum Boiss. Molecules 2021, 26, 1375. https://doi.org/10.3390/molecules26051375
Alhilal M, Sulaiman YAM, Alhilal S, Gomha SM, Ouf SA. Antifungal Activity of New Diterpenoid Alkaloids Isolated by Different Chromatographic Methods from Delphinium peregrinum L. var. eriocarpum Boiss. Molecules. 2021; 26(5):1375. https://doi.org/10.3390/molecules26051375
Chicago/Turabian StyleAlhilal, Mohammad, Yaser A. M. Sulaiman, Suzan Alhilal, Sobhi M. Gomha, and Salama A. Ouf. 2021. "Antifungal Activity of New Diterpenoid Alkaloids Isolated by Different Chromatographic Methods from Delphinium peregrinum L. var. eriocarpum Boiss" Molecules 26, no. 5: 1375. https://doi.org/10.3390/molecules26051375