The First Phytochemical Investigation of Artemisia divaricate: Sesquiterpenes and Their Anti-Inflammatory Activity
Abstract
:1. Introduction
2. Results and Discussion
2.1. Structural Elucidation
2.2. Anti-Inflammatory Activity Assay
3. Materials and Methods
3.1. General Experimental Procedures
3.2. Plant Material
3.3. Extraction and Isolation
3.4. Computational Section
3.5. Cell Culture
3.6. Cell Viability
3.7. Measurement of Nitric Oxide (NO) Production
3.8. Statistical Analysis
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
Sample Availability
References
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No. | 1 | 2 | 3 | 4 | 5 | 6 | 7 | 8 | 9 |
---|---|---|---|---|---|---|---|---|---|
1 | 75.6 | 73.3 | 78.5 | 41.2 | 40.9 | 67.7 | 76.2 | 76.2 | 37.3 |
2 | 32.8 | 32.3 | 31.8 | 24.8 | 24.8 | 29.8 | 27.8 | 27.8 | 23.7 |
3 | 122.1 | 120.1 | 34.9 | 123.4 | 132.3 | 22.7 | 38.0 | 38.0 | 77.7 |
4 | 134.5 | 134.7 | 144.6 | 127.2 | 127.3 | 150.0 | 74.0 | 73.7 | 144.5 |
5 | 52.0 | 45.3 | 54.8 | 45.4 | 45.3 | 74.6 | 138.0 | 138.0 | 41.9 |
6 | 71.3 | 71.5 | 68.5 | 77.4 | 76.7 | 31.2 | 130.9 | 130.9 | 81.8 |
7 | 57.2 | 57.6 | 54.8 | 55.8 | 58.8 | 42.2 | 52.0 | 52.0 | 49.7 |
8 | 70.0 | 70.3 | 69.6 | 132.5 | 125.0 | 28.7 | 31.6 | 31.6 | 73.9 |
9 | 40.2 | 39.3 | 41.9 | 147.1 | 145.1 | 128.4 | 30.5 | 30.5 | 77.1 |
10 | 38.9 | 38.7 | 41.1 | 73.0 | 72.9 | 136.0 | 150.3 | 151.4 | 69.8 |
11 | 138.6 | 138.6 | 138.5 | 139.6 | 42.2 | 147.1 | 148.0 | 148.0 | 138.7 |
12 | 167.0 | 166.9 | 166.9 | 170.6 | 178.1 | 23.5 | 21.5 | 21.5 | 168.8 |
13 | 128.9 | 128.8 | 128.2 | 121.1 | 12.6 | 110.5 | 109.3 | 109.3 | 120.6 |
14 | 24.2 | 24.8 | 12.4 | 23.3 | 23.3 | 16.5 | 110.6 | 110.5 | 20.6 |
15 | 11.5 | 14.3 | 109.1 | 17.8 | 17.8 | 113.0 | 29.3 | 29.3 | 118.2 |
OAc | 170.3 21.2 | 170.5 21.2 | 170.3 21.2 | 173.0 20.6 | |||||
1′ | 61.2 | 61.3 | 61.1 | ||||||
2′ | 14.3 | 17.6 | 14.3 |
No | 1 | 2 | 3 | 4 | 5 |
---|---|---|---|---|---|
1 | 3.61 (dd, 10.1, 7.1) | 3.40–3.36 (m) | 3.47 (dd, 11.6, 4.7) | 1.72 (2H, m) | 1.74–1.68 (2H, m) |
2 | 2.36–2.45 (m) | 2.46 (overlapped) | 1.88 (m) | 2.27 (m) | 2.25 (m) |
1.90 (overlapped) | 2.02 (ddd, 10.5, 4.5, 2.2) | 1.58 (overlapped) | 2.17 (m) | 2.17–2.11 (m) | |
3 | 5.34 (dd, 4.2, 2.3) | 5.30 (dd, 4.5, 2.2) | 2.36 (ddd, 13.6, 6.4, 3.7) 2.09 (ddd, 14.9, 13.6, 5.3) | 5.18 (dd, 8.2, 8.1) | 5.10 (dd, 11.1, 2.1) |
5 | 1.97 (overlapped) | 2.26 (d, 10.9) | 1.83 (d, 10.4) | 2.77 (dd, 12.2, 2.9) 2.61 (dd, 12.2, 12.2) | 2.73 (dd, 12.1, 2.9) 2.49 (dd, 12.1, 9.9) |
6 | 4.03 (dd, 11.4, 10.4) | 4.07 (dd, 10.9, 10.5) | 4.23 (dd, 10.4, 10.4) | 3.97 (ddd, 12.2, 9.8, 2.9) | 3.99 (ddd, 12.1, 9.9, 2.9) |
7 | 2.50 (dd, 11.7, 10.4) | 2.50 (dd, 11.4, 10.5) | 2.62 (dd, 11.3, 10.4) | 3.57 (dd, 9.8, 8.8) | 2.62 (dd, 12.1, 9.5) |
8 | 5.41 (ddd, 11.7, 11.1, 4.8) | 5.43 (ddd, 11.8, 11.4, 5.2) | 5.33 (ddd, 11.3, 11.2, 4.6) | 5.15 (dd, 16.1, 8.8) | 5.16 (dd, 16.0, 9.5) |
9 | 2.32 (dd, 12.2, 4.8) 1.19 (dd, 12.2, 11.1) | 1.88 (dd, 12.2, 11.8) 1.65 (dd, 12.2, 5.2) | 2.34–2.31 (m) 1.29 (dd, 11.2, 4.9) | 5.71 (d, 16.1) | 5.60 (d, 16.0) |
11 | 2.43 (dq, 12.1, 6.9) | ||||
12 | |||||
13 | 6.35 (s) 5.73 (s) | 6.34 (d, 1.2) 5.72 (d, 1.2) | 6.33 (d, 1.1) 5.71 (d, 1.1) | 6.17 (d, 3.3) 5.46 (d, 3.3) | 1.19 (3H, d, 6.9) |
14 | 0.94 (3H. s) | 0.94 (3H, s) | 0.88 (3H, s) | 1.39 (3H, s) | 1.37 (3H, s) |
15 | 1.86 (3H, s) | 1.91 (3H, br s) | 5.03 (d, 1.6) 4.76 (d, 1.6) | 1.50 (3H, overlapped) | 1.60 (3H, s) |
OAc | 1.95 (3H, s) | 1.95 (3H, s) | 1.95 (3H, s) | ||
1′ | 4.25 (2H, q, 7.1) | 4.24 (2H, q, 7.1) | 4.25 (2H, q, 7.1) | ||
2′ | 1.33 (3H, t, 7.1) | 1.32 (3H, t, 7.1) | 1.32 (3H, t, 7.1) |
No. | 6 | 7 | 8 | 9 |
---|---|---|---|---|
1 | 4.91 (dd, 11.5, 5.3) | 4.10 (dd, 7.9, 3.3) | 4.11 (dd, 7.8, 3.2) | 1.73–1.67 (m) 1.66 (ddd, 10.8, 5.3, 2.9) |
2 | 2.16 (m) | 1.91 (m) | 1.91 (dd, 7.5, 3.2) | 2.06 (2H, m) |
1.81–1.75 (m) | 1.78 (overlapped) | 1.80–1.76 (m) | ||
3 | 2.09 (m) 1.90 (ddd, 17.3, 13.6, 4.0) | 1.69 (overlapped) 1.59 (ddd, 12.0, 7.7, 3.8) | 1.60 (m) 1.57 (m) | 4.47 (dd, 4.8, 2.3) |
5 | 4.10 (dd, 11.0, 3.1) | 5.51 (d, 16.0) | 5.51 (d, 16, 0) | 2.97 (br s) 2.51 (dd, 12.8, 10.8) |
6 | 2.04 (ddd, 14.3, 11.0, 3.3) 1.74 (m) | 5.10 (dd, 16.0, 10.1) | 5.11 (dd, 16.0, 10.1) | 4.16 (ddd, 10.8, 9.2, 1.7) |
7 | 2.26 (m) | 2.59 (ddd, 11.8, 10.1, 5.0) | 2.60 (ddd, 11.3, 10.1, 5.0) | 3.59 (dd, 9.2, 8.9) |
8 | 2.66 (ddd, 12.8, 12.6, 11.8) 1.83 (overlap) | 1.96 (m) 1.80 (m) | 2.00–1.93 (m) 1.84–1.80 (m) | 5.32 (dd, 8.9, 2.2) |
9 | 5.25 (d, 11.8) | 2.38–2.28 (m) 1.70 (overlapped) | 2.34 (m) 1.70 (overlapped) | 3.00 (d, 2.2) |
11 | ||||
12 | 1.85 (3H, s) | 1.72 (3H, s) | 1.73 (3H, s) | |
13 | 4.89 (s) 4.64 (s) | 4.72 (2H, s) | 4.73 (2H, s) | 6.18 (d, 3.2) 5.40 (d, 3.2) |
14 | 1.71 (3H, s) | 5.16 (s) 4.99 (s) | 5.00 (d, 1.9) 5.17 (d, 1.9) | 1.23 (3H, s) |
15 | 5.17 (s) 5.01 (s) | 1.30 (3H, s) | 1.31 (3H, s) | 5.39 (d, 2.0) 5.16 (d, 2.0) |
OAc | 2.21 (3H, s) |
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Yan, S.; Ke, C.; Feng, Z.; Tang, C.; Ye, Y. The First Phytochemical Investigation of Artemisia divaricate: Sesquiterpenes and Their Anti-Inflammatory Activity. Molecules 2023, 28, 4254. https://doi.org/10.3390/molecules28104254
Yan S, Ke C, Feng Z, Tang C, Ye Y. The First Phytochemical Investigation of Artemisia divaricate: Sesquiterpenes and Their Anti-Inflammatory Activity. Molecules. 2023; 28(10):4254. https://doi.org/10.3390/molecules28104254
Chicago/Turabian StyleYan, Siqi, Changqiang Ke, Zheling Feng, Chunping Tang, and Yang Ye. 2023. "The First Phytochemical Investigation of Artemisia divaricate: Sesquiterpenes and Their Anti-Inflammatory Activity" Molecules 28, no. 10: 4254. https://doi.org/10.3390/molecules28104254