Diterpenoids with Potent Anti-Psoriasis Activity from Euphorbia helioscopia L.
Abstract
:1. Introduction
2. Results
2.1. Structure Elucidation
2.2. Biological Activity Results
3. Discussion
4. Materials and Methods
4.1. General Experimental Procedures
4.2. Plant Material
4.3. Extraction and Isolation
4.4. Spectroscopic Data
4.5. Biological Activity Assays
4.5.1. Immunosuppressive Activities Assay
4.5.2. Cell Viability Assays of Lymphocytes
4.5.3. Antiproliferative Activity against HaCaT Cells
4.5.4. EdU Assay
4.5.5. Cytokine Analysis by ELISA of Induced T Cells
4.5.6. Immunofluorescence Protocol (Cell Climbing Slides)
4.5.7. Statistics and Reproducibility
4.5.8. Ethic Statement
4.6. Molecular Docking Studies
5. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
References
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No. | 1 | 2 | ||
---|---|---|---|---|
δC | δH | δC | δH | |
1 | 39.0 | 2.79, d (19.7) | 39.5 | 3.21, d (20.3) |
2.32, d (19.7) | 2.68, d (20.3) | |||
2 | 178.7 | 178.6 | ||
3 | 187.5 | 186.9 | ||
4 | 45.5. C | 45.5 | ||
5 | 48.3 | 2.54, d (12.4) | 48.1 | 2.84, d (12.0) |
6 | 19.5 | 1.61, m | 23.3 | 2.03, m |
1.03, overlapped | 1.53, overlapped | |||
7 | 31.2 | 2.32, overlapped | 36.1 | 2.55, d (13.8) |
0.98, overlapped | 2.34, m, overlapped | |||
8 | 47.7 | 151.1 | ||
9 | 45.9 | 2.69 (m, overlap) | 45.9 | 3.32, d (7.2) |
10 | 41.3 | 43.6 | ||
11 | 28.1 | 1.82, m | 28.0 | 2.38, m |
1.56, m | 1.59, m | |||
12 | 38.6 | 2.74, m, overlapped | 75.6 | 4.86 dd (13.0, 5.7) |
13 | 44.7 | 2.31, m, overlapped | 155.6 | |
14 | 217.2 | 114.5 | 6.30, s | |
15 | 42.9 | 2.27, m, overlapped | 116.9 | |
1.76, m, overlapped | ||||
16 | 147.0 | 175.1 | ||
17 | 107.3 | 4.88, s | 8.3 | 1.83, s |
4.67, s | ||||
18 | 29.5 | 1.21, s | 29.5 | 1.23, s |
19 | 21.7 | 1.12, s | 21.3 | 1.20, s |
20 | 17.4 | 0.78, s | 21.0 | 1.01, s |
No. | 3 | 4 | 5 | 6 | 7 |
---|---|---|---|---|---|
1 | 2.57, dd (12.5, 5.2) 2.12, overlapped | 2.20, overlapped 1.53, dd (13.4, 11.1) | 2.51, dd (14.0, 6.1) 1.95, t (14.0) | 2.54, dd (13.6, 6.0) 1.99, d (13.6) | 2.13, dd (14.5, 8.2) 1.51, dd (14.5, 8.6) |
2 | 2.15, m | 2.75, m | 2.06, m | 2.06, m | 2.43, m |
3 | 5.65, t-like (4.0) | 5.20, dd (8.5, 5.7) | 5.41, t-like (4.5) | 5.45, t-like (4.4) | 5.17, dd (6.8, 3.6) |
4 | 3.61, dd (9.4, 4.0) | 3.28, dd (9.8, 8.5) | 3.26, dd (10.4, 4.5) | 3.25, dd (9.9, 4.4) | 3.16, dd (8.8, 3.6) |
5 | 6.82, dd (9.3, 1.1) | 6.77, brs (9.8, 1.3) | 5.55, d (10.4) | 5.69, d (9.9) | 5.60, dd (8.8, 1.7) |
7 | 9.36, s | 9.32, s | 4.16, t (7.5) | 5.03, dd (8.1, 1.7) | 4.39, dd (10.8, 4.5) |
8 | 2.06, s | 2.16, s | 3.01, dd (14.5, 1.7) 2.44, dd (14.5, 6.9) | 2.77, dd (13.6, 2.2) 2.86, dd (13.6, 8.4) | 2.95, dd (15.4, 10.5) 2.69, dd (15.5, 4.6) |
11 | 5.38, d (15.6) | 5.58, d (15.9) | 5.15, d (15.4) | 5.16, d (15.4) | 5.43, d (16.1) |
12 | 5.27, dd (15.6, 8.8) | 5.64, dd (15.9, 8.6) | 5.25, dd (15.4, 8.8) | 5.25, dd (15.4, 8.7) | 5.15, dd (16.1, 9.0) |
13 | 2.20, m | 2.68, m | 2.36, m | 2.37, m | 2.95, m |
14 | 5.82, d (9.5) | 4.94, d (3.1) | 5.90, d (9.7) | 5.93, d (9.9) | 5.14, d (1.7) |
16 | 0.96, d (7.0) | 1.22, d (6.9) | 0.92, d (6.6) | 0.92, d (6.4) | 1.08, d (5.9) |
17 | 1.94, d (1.1) | 1.68, d (1.4) | 1.72, d (0.8) | 1.81, br. s | 1.81, d (1.5) |
18 | 1.15, s | 1.29, s | 1.20, s | 1.12, s | 1.09, s |
19 | 1.16, s | 1.29, s | 1.10, s | 1.14, s | 1.21, s |
20 | 0.98, d (6.9) | 0.99, d (6.9) | 0.95, d (6.7) | 0.97, d (6.7) | 0.93, d (7.2) |
3′, 7′ | 7.99, dd (7.5, 1.3) | 7.93, dd (7.5, 1.3) | 7.95, dd (7.5, 1.3) | 7.97, d (7.5,1.3) | 7.94, dd (7.5, 1.2) |
4′, 6′ | 7.46, t (7.5) | 7.39, t (7.5) | 7.42, t (7.5) | 7.43, t (7.5) | 7.44, t (7.5) |
5′ | 7.60, t (7.5) | 7.52, t (7.5) | 7.54, t (7.5) | 7.55, t (7.5) | 7.56, t (7.5) |
OAc-14 | 2.17, s | 1.90, s | 2.16, s | 2.14, s | 2.16, s |
OAc-15 | 2.05, s | 2.14, s | 2.20, s | ||
OAc-7 | 1.31, s |
No. | 3 | 4 | 5 | 6 | 7 |
---|---|---|---|---|---|
1 | 46.8 | 45.0 | 46.7 | 46.8 | 48.3 |
2 | 39.4 | 38.7 | 38.8 | 38.6 | 36.4 |
3 | 80.7 | 82.7 | 80.9 | 80.8 | 85.8 |
4 | 47.9 | 51.3 | 46.2 | 46.3 | 43.5 |
5 | 147.3 | 149.6 | 120.1 | 123 | 120.6 |
6 | 141.1 | 140.7 | 136.1 | 133.7 | 140.6 |
7 | 194.7 | 195 | 73.2 | 73.8 | 71.9 |
8 | 25.5 | 25.3 | 38.8 | 39.2 | 45.5 |
9 | 211.2 | 212.8 | 212.2 | 206.7 | 210.0 |
10 | 50.1 | 50.2 | 50.8 | 51.0 | 49.2 |
11 | 135.2 | 135.7 | 130.3 | 132.4 | 130.1 |
12 | 132.1 | 130.1 | 132.6 | 130.7 | 134.5 |
13 | 40.1 | 39.6 | 40.9 | 41.4 | 37.1 |
14 | 74.7 | 81.2 | 75.8 | 75.8 | 78.2 |
15 | 90.4 | 84.3 | 90.2 | 90.4 | 83.6 |
16 | 14.0 | 18.5 | 13.9 | 13.8 | 19.2 |
17 | 10.5 | 9.5 | 16.2 | 17.1 | 18.9 |
18 | 24.3 | 23.9 | 24.6 | 25.0 | 25.7 |
19 | 24 | 24.9 | 19.6 | 20.2 | 21.2 |
20 | 17.9 | 19.1 | 21.1 | 20.9 | 22.7 |
1′ | 165.9 | 166 | 166.1 | 165.4 | 166.3 |
2′ | 129.8 | 133.2 | 130.5 | 130.3 | 133.4 |
3′, 7′ | 129.6 | 129.6 | 129.6 | 129.6 | 129.5 |
4′, 6′ | 128.7 | 128.5 | 128.5 | 128.6 | 128.8 |
5′ | 133.5 | 131.7 | 133 | 133.1 | 133.5 |
OAc-14 | 169.3 | 170.6 | 169.8 | 170.0 | 170.7 |
22.3 | 20.8 | 22.3 | 21.1 | 24.8 | |
OAc-15 | 169.5 | 170.0 | 169.5 | ||
21.2 | 20.9 | 22.4 | |||
OAc-7 | 170.2 | ||||
20.2 |
1H NMR Data | Configurations | Suitable Type |
---|---|---|
H-3, t-like, J = 3.0–5.0 Hz | 16α-CH3 | A, B |
H-3, dd, J ≈ 8.0, 3.0–5.0 Hz | 16β-CH3 | A, B |
H-14, d, J = 1.0–4.0 Hz | CH3-20/OR-14 same orientation | A |
H-14, d, J = 1.0–4.0 Hz | CH3-20/OR-14 same orientation | B |
H-14, d, J > 8.0 Hz | CH3-20/OR-14 different orientation | A, B |
δH-11 > δH-12 | 20β-CH3 | A, B |
δH-11 < δH-12 | 20α-CH3 | A, B |
13C NMR Data | Configurations | Suitable Type |
---|---|---|
When OBz-3, δC-16 < 15 | 16α-CH3 | A, B |
When OBz-3, δC-16 > 15 | 16β-CH3 | A, B |
When OAc-14, δC-4 < 45 | 14β-OAc | A |
When OAc-14, δC-4 > 45 | 14α-OAc or 14β-OAc | A |
When OAc-14, δC-20 > 22 | CH3-20/OR-14 same orientation | A |
when OAc-14, δC-20 > 18.5 | CH3-20/OR-14 same orientation | B |
When OAc-15, δC-13 < 40 | 20β-CH3 | A, B |
Compound | Inhibition Rate (%) | Compound | Inhibition Rate (%) | ||
---|---|---|---|---|---|
T Cells | B Cells | T Cells | B Cells | ||
1 | 23.7 ± 4.9 | <10 | 13 | 15.0 ± 2.7 | 27.2 ± 4.5 |
2 | 23.7 ± 6.8 | <10 | 14 | 46.5 ± 8.3 | 28.2 ± 4.8 |
3 | 34.5 ± 5.4 | 20.0 ± 9.5 | 15 | 25.4 ± 3.5 | 17.1 ± 7.3 |
4 | 23.8 ± 4.5 | 26.6 ± 9.7 | 16 | 44.4 ± 8.6 | 26.6 ± 5.4 |
5 | 58.2 ± 1.4 | 64.9 ± 4.6 | 17 | 35.6 ± 1.1 | <10 |
6 | 34.8 ± 7.4 | <10 | 18 | 37.5 ± 5.6 | 33.5 ± 2.8 |
7 | 83.8 ± 2.5 | 92.4 ± 9.6 | 19 | 42.5 ± 7.5 | 48.3 ± 8.8 |
8 | 49.8 ± 6.9 | 43.1 ± 8.8 | 20 | 48.5 ± 7.1 | 46.6 ± 1.7 |
9 | 32.2 ± 2.9 | 27.1 ± 2.4 | 21 | 49.8 ± 7.8 | 48.2 ± 6.4 |
10 | 48.4 ± 3.2 | 48.7 ± 5.7 | 22 | <10 | <10 |
11 | 46.0 ± 3.2 | 17.6 ± 2.4 | 23 | 33.0 ± 8.9 | <10 |
12 | 34.0 ± 3.3 | 14.2 ± 4.6 | Dex | 46.7 ± 4.3 | 79.3 ± 7.7 |
Compound | IC50 (μM) | |
---|---|---|
T Cells | B Cells | |
5 | 17.6 ± 2.7 | 10.3 ± 1.3 |
7 | 6.7 ± 1.8 | 11.4 ± 1.5 |
Dex | 1.6 ± 0.3 | 0.8 ± 0.05 |
Compound | IC50 (μM) | Compound | IC50 (μM) |
---|---|---|---|
7 | 31.0 ± 3.7 | 16 | 25.9 ± 2.4 |
8 | 26.0 ± 2.2 | 17 | 31.5 ± 3.3 |
9 | 19.7 ± 2.0 | 18 | 29.8 ± 2.9 |
10 | 31.3 ± 1.7 | 21 | 28.5 ± 3.0 |
12 | 23.7 ± 2.5 | 22 | 29.6 ± 2.3 |
13 | 6.9 ± 0.8 | 23 | 30.4 ± 3.0 |
15 | 23.4 ± 1.6 | MTX | 18.1 ± 2.1 |
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Zhao, Z.-Z.; Liang, X.-B.; He, H.-J.; Xue, G.-M.; Sun, Y.-J.; Chen, H.; Zhao, Y.-S.; Bian, L.-N.; Feng, W.-S.; Zheng, X.-K. Diterpenoids with Potent Anti-Psoriasis Activity from Euphorbia helioscopia L. Molecules 2024, 29, 4104. https://doi.org/10.3390/molecules29174104
Zhao Z-Z, Liang X-B, He H-J, Xue G-M, Sun Y-J, Chen H, Zhao Y-S, Bian L-N, Feng W-S, Zheng X-K. Diterpenoids with Potent Anti-Psoriasis Activity from Euphorbia helioscopia L. Molecules. 2024; 29(17):4104. https://doi.org/10.3390/molecules29174104
Chicago/Turabian StyleZhao, Zhen-Zhu, Xu-Bo Liang, Hong-Juan He, Gui-Min Xue, Yan-Jun Sun, Hui Chen, Yin-Sheng Zhao, Li-Na Bian, Wei-Sheng Feng, and Xiao-Ke Zheng. 2024. "Diterpenoids with Potent Anti-Psoriasis Activity from Euphorbia helioscopia L." Molecules 29, no. 17: 4104. https://doi.org/10.3390/molecules29174104