Euphosantianane E–G: Three New Premyrsinane Type Diterpenoids from Euphorbia sanctae-catharinae with Contribution to Chemotaxonomy
Abstract
:1. Introduction
2. Results and Discussion
2.1. Structure Elucidation of the Isolated Compounds
2.2. Study of Chemosystematic Significance
3. Conclusions
4. Materials and Methods
4.1. General Experimental Procedures
4.2. Plant Material
4.3. Extraction and Isolation
4.4. Spectroscopic Data of Euphosantianane E–G (1–3)
4.5. Statistical Analysis
Supplementary Materials
Author Contributions
Funding
Acknowledgments
Conflicts of Interest
References
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Sample Availability: Samples of the compounds 1–7 are available or not from the authors. |
No. | Euphosantianane E (1) | Euphosantianane F (2) | Euphosantianane G (3) | |||||
---|---|---|---|---|---|---|---|---|
δH | δC | δH | δC | δH | δC | |||
1α | 3.15 dd (8.05, 13.86) | 42.8, t | 2.64 dd (10.85, 14.64) | 41.1, t | 3.16 dd (8.10, 13.62) | 42.8, t | ||
1β | 1.64 t (13.26) | 1.60 m | 1.61 m | |||||
2 | 2.26 qd (1.56, 7.56) | 35.1, d | 2.31 m | 33.8, d | 2.25 m | 34.0, d | ||
3 | 5.35 br t (3.48) | 78.2, d | 5.46 br dd (3.06, 6.12) | 78.7, d | 5.20 s | 78.6, d | ||
4 | 2.37 dd (3.78, 11.5) | 50.1, d | 3.01 dd (3.30, 10.50) | 50.4, d | 2.37 brd (11.6) | 50.4, d | ||
5 | 6.42 d (11.46) | 70.5, d | 5.79 d (8.80) | 68.5, d | 6.23 d (11.52) | 69.0, d | ||
6 | ----- | 47.8, s | ----- | 48.2, s | ----- | 47.7, s | ||
7 | 4.77 d (6.72) | 70.6, d | 4.90 d (6.54) | 68.8, d | 4.68 d (6.54) | 70.7, d | ||
8α | 3.50 br d (6.54) | 22.1, t | 2.34 d (7.44) | 23.2, t | 2.32 d (7.14) | 22.4, d | ||
8β | 1.84 t (16.92) | 1.72 t (13.92) | 1.88 br d (17.40) | |||||
9 | 0.73 m | 18.9, d | 0.75 m | 19.4, d | 0.79 m | 19.0, d | ||
10 | ----- | 18.4, s | ----- | 19.1, s | ----- | 18.4, s | ||
11 | 0.73 m | 23.8, d | 0.75 m | 23.3, d | 0.79 m | 23.9, d | ||
12 | 3.48 s | 37.4, d | 3.47 br d (6.11) | 36.0, d | 3.45 br d (3.42) | 35.0, d | ||
13 | ----- | 85.7, s | ----- | 79.8, s | ----- | 85.5, s | ||
14 | ----- | 204.1, s | ----- | 210.2, s | ----- | 204.2, s | ||
15 | ----- | 84.2, s | ----- | 83.6, s | ----- | 84.1, s | ||
16 | 1.04 s | 13.9, q | 0.92 d (5.01) | 15.2, q | 0.77 d (5.04) | 14.2, q | ||
17α | 4.35 d (11.70) | 62.8, t | 4.55 d (12.18) | 62.6, t | 4.49 d (11.82) | 64.4, t | ||
17β | 4.67 d (11.70) | 5.28 d (12.30) | 5.86 d (11.94) | |||||
18 | 0.94 s | 29.5, q | 1.07 s | 28.8, q | 1.05 s | 29.6, q | ||
19 | 1.04 s | 14.9, q | 0.94 s | 15.3, q | 0.92 s | 14.9, q | ||
20 | 1.57 s | 25.0, q | 1.57 s | 23.0, q | 1.72 s | 24.6, q | ||
3-O-Prop | 3-O-Prop | 3-O-iBut | ||||||
CO | ----- | 173.5, s | CO | ----- | 172.9 | CO | ----- | 175.1, s |
2` | 2.26 qd (7.62) | 27.5, t | 2` | 2.32 q (7.14) | 27.6, t | 2` | 2.15 m | 27.6, d |
3` | 0.98 t (7.5) | 8.8, q | 3` | 1.15 t (6.66) | 8.8, q | 3` | 1.05 d (7.02) | 8.9, q |
5-O-3-hydroxy-Bz | 5-O-Prop | 4` | 1.05 d (7.02) | 8.9, q | ||||
CO | ----- | 168.9, s | CO | ----- | 170.1, s | 5-O-Ac | ||
2`` | ----- | 129.6, s | 2`` | 2.36 q (7.14) | 27.6, t | CO | ----- | 170.1, s |
3`` | 7.39 d (1.56) | 111.9, d | 3`` | 0.95 t (7.56) | 8.8, q | 2`` | 2.00 s | 21.3 |
4`` | ----- | 161.9, s | 7-O-Ac | 7-O-Ac | ||||
5`` | 6.92 (8.40) | 117.9, d | CO | ----- | 175.1, s | CO | ----- | 170.8, s |
6`` | 6.80 t (9.18) | 136.1, d | 2``` | 1.94 s | 21.5, q | 2``` | 2.10 s | 21.4 |
7`` | 7.58 dd (1.68, 7.98) | 119.2, d | 17-O-Nic | 17-O-Nic | ||||
7-O-Ac | CO | ----- | 164.9, s | CO | ----- | 165.7, s | ||
CO | ----- | 170.8, s | 2```` | ----- | 129.7, s | 2```` | ----- | 129.7, s |
2``` | 2.11 s | 21.4, q | 3```` | 9.22 s | 128.4, d | 3```` | 9.15 s | 128.3, d |
13-O-Ac | 8.30 d (7.44) | 137.4, d | 4```` | 8.21 d (7.50) | 137.1, d | |||
CO | ----- | 170.8, s | 7.37 m | 123.9, d | 5```` | 7.48 m | 123.9, d | |
2```` | 2.11 s | 21.4, q | 7.67 d (7.74) | 153.7, d | 6```` | 7.68 d (7.44) | 150.4, d | |
17-O-Ac | 4```` | |||||||
CO | ----- | 170.0, s | 5```` | |||||
2````` | 2.12 s | 20.8, q | 6```` |
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Elshamy, A.I.; Mohamed, T.A.; Al-Rowaily, S.L.; Abd-ElGawad, A.M.; Dar, B.A.; Shahat, A.A.; Hegazy, M.-E.F. Euphosantianane E–G: Three New Premyrsinane Type Diterpenoids from Euphorbia sanctae-catharinae with Contribution to Chemotaxonomy. Molecules 2019, 24, 2412. https://doi.org/10.3390/molecules24132412
Elshamy AI, Mohamed TA, Al-Rowaily SL, Abd-ElGawad AM, Dar BA, Shahat AA, Hegazy M-EF. Euphosantianane E–G: Three New Premyrsinane Type Diterpenoids from Euphorbia sanctae-catharinae with Contribution to Chemotaxonomy. Molecules. 2019; 24(13):2412. https://doi.org/10.3390/molecules24132412
Chicago/Turabian StyleElshamy, Abdelsamed I., Tarik A. Mohamed, Saud L. Al-Rowaily, Ahmed M. Abd-ElGawad, Basharat A. Dar, Abdelaaty A. Shahat, and Mohamed-Elamir F. Hegazy. 2019. "Euphosantianane E–G: Three New Premyrsinane Type Diterpenoids from Euphorbia sanctae-catharinae with Contribution to Chemotaxonomy" Molecules 24, no. 13: 2412. https://doi.org/10.3390/molecules24132412