Euphosantianane A–D: Antiproliferative Premyrsinane Diterpenoids from the Endemic Egyptian Plant Euphorbia Sanctae-Catharinae
Abstract
:1. Introduction
2. Results and Discussion
3. Experimental Section
3.1. General Experimental Procedures
3.2. Plant Material
3.3. Extraction and Isolation
3.4. Biological Activity
3.4.1. Cell Culture
3.4.2. Cell Proliferation Assay
3.4.3. Anti-Proliferation Quantitative Analysis
3.5. Computational Calculations
Supplementary Materials
Author Contributions
Funding
Acknowledgments
Conflicts of Interest
References
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Sample Availability: Samples of the compounds 1–13 are not available from the authors. |
No. | 1 | 2 | 3 | 4 | ||||
---|---|---|---|---|---|---|---|---|
dH (J in Hz) | δC | dH (J in Hz) | δC | dH (J in Hz) | δC | dH (J in Hz) | δC | |
1α | 3.12 dd (8.4, 13.8) | 42.9 | 3.14 dd (8.4, 13.8) | 42.9 | 3.15 dd (7.2, 13.8) | 42.9 | 3.14 dd (7.8, 13.2) | 42.9 |
1β | 1.59 dd (12.6, 13.2) | 1.60 dd (13.2) | 1.61 dd (13.8, 13.2) | 1.61 dd | ||||
2 | 1.80 m | 37.5 | 1.86 m | 37.5 | 1.87 m | 37.3 | 1.79 m | 37.5 |
3 | 5.24 dd (3.6, 6.0) | 78.4 | 5.23 t | 78.4 | 5.36 t (3.6) | 78.3 | 5.21 t | 77.3 |
4 | 2.32 m | 50.4 | 2.32 m | 50.5 | 2.34 m | 50.4 | 2.36 dd (3.0) | 50.6 |
5 | 6.18 d (11.4) | 68.8 | 6.21 d (12.0) | 69.1 | 6.46 d (11.4) | 69.9 | 6.23 d (12.0) | 69 |
6 | ---- | 47.4 | ---- | 47.8 | ---- | 48.2 | ---- | 47.7 |
7 | 4.48 d (6.6) | 70.7 | 4.72 d (6.6) | 71 | 4.97 d (6.6) | 70.7 | 4.85 d (12.6) | 70.8 |
8α | 2.09 m | 23.9 | 2.14 m | 21.4 | 2.05 m | 22.2 | 2.09 m | 23.9 |
8β | 1.80 brd (17.0) | 23.9 | 1.77 brd (17.0) | 21.4 | 1.87 brd (17.0) | 22.2 | 1.90 d (13.2) | 23.9 |
9 | 0.72 m | 18.9 | 0.77 m | 18.4 | 0.72 m | 19.1 | 0.62 m | 19 |
10 | ---- | 18.2 | ---- | 18.3 | ---- | 18.4 | ---- | 18.3 |
11 | 0.72 m | 21.4 | 0.77 m | 18.5 | 0.72 m | 21.5 | 0.62 m | 21.3 |
12 | 3.37 d (6) | 34.8 | 3.46 d (5.4) | 33.9 | 3.55 d (6.6) | 35.3 | 3.46 d (3.6) | 35 |
13 | ---- | 86.0 | ---- | 85.9 | ---- | 85.9 | ---- | 85.8 |
14 | ---- | 204.5 | ---- | 204.5 | ---- | 204.4 | ---- | 204.3 |
15-OH | 4.44 s | 84.1 | 4.44 s | 84.1 | 4.45 s | 84.2 | 4.48 s | 84.1 |
16 | 0.87 d (6.0) | 14.1 | 0.86 d (1.8) | 14.2 | 0.86 d (6.0) | 14 | 0.87 d (14.4) | 14.7 |
17α | 4.39 d (12.0) | 63.6 | 4.81 d (12.0) | 64 | 4.58 d (11.4) | 63.4 | 4.67 (d, J = 11.4 Hz) | 64.5 |
17β | 4.31 d (12.0) | 4.46 d (12.0) | 4.91 d (10.8) | 4.46 brd (11.4) | ||||
18 | 1.04 s | 29.5 | 1.05 s | 29.5 | 1.06 s | 29.5 | 1.05 s | 29.5 |
19 | 0.90 s | 14.9 | 0.94 s | 14.9 | 0.95 s | 15 | 0.93 s | 14.9 |
20 | 1.68 s | 24.6 | 1.73 s | 24.6 | 1.66 s | 25 | 1.71 s | 25.8 |
Compound | IC50 on Caco-2 (µM) a | IC50 on A549 (µM) a |
---|---|---|
1 | 75.8 (0.950) | >100 |
2 | 40.5 (0.989) | 48.5 (0.927) |
3 | 31.0 (0.999) | 21.5 (0.924) |
4 | 33.2 (0.993) | 32.8 (0.988) |
5 | 43.5 (0.999) | 50.1 (0.9960) |
6 | 33.3 (0.984) | 33.1 (0.983) |
7 | 40.3 (0.979) | 60.3 (0.937) |
8 | 26.1 (0.979) | 31.3 (0.971) |
9 | 29.4 (0.972) | 3.3 (0.996) |
10 | 43.9 (0.975) | >100 |
11 | 50.2 (0.993) | >100 |
12 | 44.7 (0.961) | >100 |
13 | 79.4 (0.843) | >100 |
Doxorubicin HCl | 0.7 (0.999) | 0.4 (0.987) |
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Hegazy, M.-E.F.; Hamed, A.R.; Ibrahim, M.A.A.; Talat, Z.; Reda, E.H.; Abdel-Azim, N.S.; Hammouda, F.M.; Nakamura, S.; Matsuda, H.; Haggag, E.G.; et al. Euphosantianane A–D: Antiproliferative Premyrsinane Diterpenoids from the Endemic Egyptian Plant Euphorbia Sanctae-Catharinae. Molecules 2018, 23, 2221. https://doi.org/10.3390/molecules23092221
Hegazy M-EF, Hamed AR, Ibrahim MAA, Talat Z, Reda EH, Abdel-Azim NS, Hammouda FM, Nakamura S, Matsuda H, Haggag EG, et al. Euphosantianane A–D: Antiproliferative Premyrsinane Diterpenoids from the Endemic Egyptian Plant Euphorbia Sanctae-Catharinae. Molecules. 2018; 23(9):2221. https://doi.org/10.3390/molecules23092221
Chicago/Turabian StyleHegazy, Mohamed-Elamir F., Ahmed R. Hamed, Mahmoud A. A. Ibrahim, Zienab Talat, Eman H. Reda, Nahla S. Abdel-Azim, Faiza M. Hammouda, Seikou Nakamura, Hisashi Matsuda, Eman G. Haggag, and et al. 2018. "Euphosantianane A–D: Antiproliferative Premyrsinane Diterpenoids from the Endemic Egyptian Plant Euphorbia Sanctae-Catharinae" Molecules 23, no. 9: 2221. https://doi.org/10.3390/molecules23092221