Pubescenosides E–K, Seven New Triterpenoid Saponins from the Roots of Ilex pubescens and Their Anti-Inflammatory Activity
Abstract
:1. Introduction
2. Results
2.1. Characterization of the Compounds
2.2. Anti-Inflammatory Activity
3. Discussion
4. Materials and Methods
4.1. General Experimental Procedures
4.2. Plant Material
4.3. Extraction and Isolation
4.3.1. Pubescenoside E (1)
4.3.2. Pubescenoside F (2)
4.3.3. Pubescenoside G (3)
4.3.4. Pubescenoside H (4)
4.3.5. Pubescenoside I (5)
4.3.6. Pubescenoside J (6)
4.3.7. Pubescenoside K (7)
4.4. Acid Hydrolysis
4.5. Cell Culture and Western Blot
Supplementary Materials
Author Contributions
Acknowledgments
Conflicts of Interest
References
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Sample Availability: Samples of the compounds 1–10 are available from the authors. |
Position | 1 a | 2 b | 3 b | 4 b | 5 b | 6 b | 7 b |
---|---|---|---|---|---|---|---|
1 | 0.95 m; 1.77 m | 0.94 m;1.71 m | 0.95 m; 1.50 m | 0.91 m; 1.46 m | 0.97 m; 1.75 m | 0.98 m; 1.48 m | 0.90 m; 1.54 m |
2 | 1.68 m; 2.56 m | 1.75 m; 2.12 m | 1.88 m; 2.06 m | 1.86 m; 2.09 m | 1.96 m; 2.13 m | 1.89 m; 2.17 m | 1.93 m; 2.12 m |
3 | 3.30 dd (11.6, 3.7) | 3.28 dd (11.5, 4.1) | 3.28 dd (11.4, 3.6) | 3.27 dd (11.4, 4.1) | 3.27 dd (10.7, 3.1) | 3.40 dd (11.5, 3.8) | 3.29 dd (10.8, 2.5) |
5 | 0.83 m | 0.79 m | 0.80 m | 0.76 m | 0.76 m | 0.81 m | 0.80 m |
6 | 1.33 m; 1.54 m | 1.27 m; 1.52 m | 1.30 m; 1.49 m | 1.25 m; 1.44 m | 1.26 m; 1.47 m | 1.27 m; 1.46 m | 1.27 m; 1.45 m |
7 | 1.33 m | 1.26 m | 1.46 m | 1.31 m; 1.43 m | 1.16 m | 1.37 m; 1.46 m | 1.40 m; 1.54 m |
9 | 2.04 m | 1.98 m | 1.63 m | 1.61 m | - | 1.76 m | 1.78 m |
11 | 5.62 d (10.2) | 5.59 d (9.8) | 1.93 m | 1.87 m | 6.58 d (10.1) | 1.91 m; 1.98 m | 2.0 m; 2.06 m |
12 | 6.18 d (8.5) | 6.03 d (10.1) | 5.42 s | 5.45 s | 5.61 d (10.6) | 5.48 s | 5.57 s |
15 | 1.24 m; 1.92 m | 1.16 m; 1.90 m | 1.17 m; 2.33 m | 1.15 m; 2.32 m | 0.88 m; 1.93 m | 1.17 m; 2.35 m | 1.26 m; 2.44 m |
16 | 1.23 m; 2.15 m | 1.30 m; 2.13 m | 1.17 m; 1.26 m | 1.99 m; 2.16 m | 1.64 m; 2.15 m | 1.85 m; 1.99 m | 3.12 m |
18 | 5.88s | 5.72 s | 3.19 m | 3.28 m | 1.92 m | 3.99 s | 2.92 m |
19 | - | - | 1.25 m; 1.75 m | 1.40 m; 2.11 m | 2.30 m | 2.59 m | - |
20 | 2.53 m | 2.50 m | - | - | 1.44 m | - | 1.36 m |
21 | 1.33 m; 1.66 m | 1.32 m; 1.59 m | 1.08 m; 1.33 m | 1.24 m; 1.74 m | 1.50 m; 1.58 m | 1.28 m; 1.76 m | 2.04 m; 2.12 m |
22 | 1.99 m | 1.95 m | 1.75 m; 1.97 m | 1.73 m; 1.84 m | 1.28 m; 2.62 m | 1.76 m; 2.08 m | 1.79 m; 2.04 m |
23 | 1.34 s | 1.32 s | 1.33 s | 1.32 s | 1.27 s | 1.31 s | 1.42 s |
24 | 1.06 s | 1.03 s | 1.07 s | 1.08 s | 1.04 s | 0.99 s | 1.18 s |
25 | 0.82 s | 0.76 s | 0.82 s | 0.83 s | 0.81 s | 0.88 s | 0.89 s |
26 | 0.85 s | 0.82 s | 1.07 s | 1.09 s | 0.98 s | 1.09 s | 1.14 s |
27 | 1.06 s | 1.03 s | 1.24 s | 1.25 s | 0.99 s | 1.27 s | 1.73 s |
29 | 2.11 s | 2.13 s | 0.91 s | 3.56 m | 1.32 d (4.0) | 1.06 d (6.7) | 1.42 s |
30 | 1.08 d (8.7) | 1.03 d (7.1) | 0.87 s | 1.08 s | 0.76 d (5.9) | 5.04 c | 1.11 d (6.2) |
3-O- | Xyl | Xyl | Xyl | Xyl | Xyl | Xyl | 2-sulfo-Xyl |
1 | 4.92 d (5.2) | 4.89 d (6.7) | 4.88 d (6.6) | 4.88 d (6.6) | 4.84 d (6.1) | 4.85 d (7.4) | 4.97 d (6.6) |
2 | 4.42 e | 4.01 c | 4.29 d | 4.28 d | 4.22 d | 4.03 m | 5.05 m |
3 | 3.87 m | 3.87 m | 3.88 m | 3.86 m | 3.84 m | 4.17 m | 4.43 m |
4 | 4.08 c | 4.06 c | 4.08 c | 4.06 c | 4.02 c | 4.21 m | 4.21 m |
5 | 3.73 m; 4.28 d | 3.72 m; 4.28 d | 3.72 m; 4.28 d | 3.72 m; 4.27 d | 3.68 m; 4.25 d | 3.78 m; 4.38 m | 3.74 m; 4.21 m |
Intermediate | Glc | Glc | Glc | Glc | Glc | ||
1 | 5.79 d (5.8) | 5.80 d (7.3) | 5.81 d (7.8) | 5.82 d (7.2) | 5.71 d (6.8) | ||
2 | 4.24 d | 4.27 d | 4.24 d | 4.22 d | 4.22 d | ||
3 | 4.48 e | 4.44 e | 4.44 c | 4.41 e | 4.39 e | ||
4 | 4.07 c | 4.06 c | 4.04 c | 4.03 c | 3.83 m | ||
5 | 4.28 d | 4.27 d | 4.43 e | 4.29 d | 4.39 e | ||
6 | 4.27 d; 4.50 e | 4.28 d; 4.51 e | 4.28 d; 4.51 e | 4.27 d; 4.48 e | 4.21 d; 4.48 e | ||
Terminal | Rha | Rha | Rha | Rha | Rha | ||
1 | 6.39 br s | 6.38 br s | 6.39 br s | 6.40 br s | 6.30 br s | ||
2 | 4.71 m | 4.71 m | 4.75 m | 4.76 m | 4.69 s | ||
3 | 4.04 c | 4.05 c | 4.04 c | 4.04 c | 3.95 c | ||
4 | 4.33 d | 4.34 d | 4.34 e | 4.23 d | 4.29 d | ||
5 | 5.03 m | 5.04 m | 5.04 m | 5.04 m | 4.98 m | ||
6 | 1.81 f | 1.78 f | 1.79 d (6.0) | 1.8 d (6.0) | 1.75 d (5.5) | ||
28-O- | Glc | Glc | Glc | Glc | Glc | Glc | |
1 | 6.32 d (8.2) | 6.32 d (8.4) | 6.35 d (7.8) | 6.23 d (7.8) | 6.34 d (8.1) | 6.25 d (7.8) | |
2 | 4.48 e | 4.21 d | 4.33 e | 4.13 d | 4.23 m | 4.24 m | |
3 | 4.44 e | 4.29 d | 4.41 e | 4.39 e | 4.04 m | 4.33 c | |
4 | 4.29 d | 4.35 e | 4.35 e | 4.23 d | 4.37 m | 4.33 c | |
5 | 4.44 e | 4.29 d | 4.28 d | 4.22 d | 4.30 m | 4.08 m | |
6 | 4.29 d | 4.43 e | 4.39 e; 4.45 e | 4.27 d; 4.39 e | 4.38 m; 4.47 m | 4.39 m; 4.50 m |
Position | 1 a | 2 b | 3 b | 4 b | 5 b | 6 b | 7 b |
---|---|---|---|---|---|---|---|
1 | 38.6 | 38.5 | 39.1 | 39.1 | 38.3 | 39.1 | 38.8 |
2 | 27.9 | 26.6 | 26.8 | 26.8 | 26.6 | 27.1 | 26.5 |
3 | 89.9 | 89.8 | 89.9 | 89.9 | 89.9 | 89.0 | 89.7 |
4 | 40.1 | 40.1 | 40.0 | 40.0 | 39.9 | 39.9 | 39.6 |
5 | 55.7 | 55.7 | 56.2 | 56.2 | 55.5 | 56.4 | 55.8 |
6 | 18.6 | 18.5 | 18.8 | 18.8 | 18.6 | 18.9 | 18.6 |
7 | 32.8 | 32.6 | 32.8 | 33.4 | 32.8 | 33.7 | 33.4 |
8 | 41.1 | 41.1 | 40.1 | 40.2 | 43.4 | 40.1 | 40.5 |
9 | 54.8 | 54.8 | 48.3 | 48.3 | 134.6 | 48.4 | 47.6 |
10 | 37.0 | 36.9 | 37.2 | 37.3 | 36.7 | 37.4 | 36.9 |
11 | 127.7 | 128.4 | 24.1 | 24.1 | 128.6 | 24.2 | 24.0 |
12 | 130.8 | 130.4 | 123.1 | 123.1 | 125.8 | 127.9 | 128.4 |
13 | 142.5 | 143.9 | 144.4 | 144.6 | 138.6 | 137.7 | 139.3 |
14 | 41.8 | 41.7 | 42.4 | 42.4 | 41.6 | 43.1 | 42.0 |
15 | 26.8 | 26.7 | 28.5 | 28.6 | 25.4 | 28.7 | 29.2 |
16 | 27.0 | 27.9 | 23.7 | 23.7 | 33.4 | 26.6 | 26.0 |
17 | 48.0 | 48.0 | 47.3 | 47.7 | 51.8 | 49.6 | 48.6 |
18 | 129.6 | 127.0 | 42.0 | 41.5 | 55.4 | 47.5 | 54.4 |
19 | 212 | 212.3 | 46.5 | 41.2 | 45.0 | 37.6 | 72.6 |
20 | 47.8 | 47.6 | 31.0 | 36.7 | 39.7 | 153.6 | 42.1 |
21 | 28.5 | 28.0 | 34.2 | 29.1 | 33.6 | 28.2 | 26.6 |
22 | 39.3 | 38.9 | 33.4 | 32.3 | 40.2 | 31.9 | 37.7 |
23 | 28.4 | 28.4 | 28.6 | 28.6 | 28.1 | 28.5 | 28.3 |
24 | 16.5 | 16.4 | 17.0 | 17.0 | 16.2 | 17.3 | 16.9 |
25 | 18.3 | 18.3 | 15.8 | 15.8 | 18.4 | 16.1 | 15.6 |
26 | 17.1 | 16.9 | 17.7 | 17.8 | 16.9 | 17.6 | 17.3 |
27 | 20.4 | 20.2 | 26.3 | 26.3 | 19.3 | 26.0 | 24.6 |
28 | 178.9 | 175.1 | 176.8 | 176.8 | 176.5 | 176.5 | 177.3 |
29 | 28.2 | 28.3 | 33.4 | 74.0 | 21.1 | 21.1 | 27.0 |
30 | 16.6 | 16.5 | 23.9 | 20.0 | 20.5 | 113.1 | 16.7 |
3-O- | Xyl | Xyl | Xyl | Xyl | Xyl | Xyl | 2-sulfo-Xyl |
1 | 106.2 | 106.2 | 106.1 | 106.1 | 106.1 | 108 | 104.8 |
2 | 79.3 | 79.7 | 79.7 | 79.7 | 79.0 | 75.9 | 80.2 |
3 | 78.1 | 78.2 | 78.2 | 78.2 | 78.0 | 79.0 | 77.2 |
4 | 71.6 | 71.6 | 71.6 | 71.6 | 71.4 | 71.6 | 70.7 |
5 | 67.0 | 66.9 | 66.9 | 67.0 | 66.8 | 67.4 | 65.9 |
Intermediate | Glc | Glc | Glc | Glc | Glc | ||
1 | 102.6 | 102.5 | 102.5 | 102.5 | 102.2 | ||
2 | 79.7 | 79.6 | 79.6 | 79.6 | 79.5 | ||
3 | 79.4 | 79.3 | 79.4 | 79.4 | 79.1 | ||
4 | 72.7 | 72.9 | 72.9 | 73.0 | 72.4 | ||
5 | 78.9 | 79.0 | 79.2 | 79.3 | 78.7 | ||
6 | 63.6 | 63.6 | 63.6 | 63.6 | 63.4 | ||
Terminal | Rha | Rha | Rha | Rha | Rha | ||
1 | 102.3 | 102.4 | 102.3 | 102.3 | 102.1 | ||
2 | 72.9 | 72.7 | 72.7 | 72.7 | 72.6 | ||
3 | 73.0 | 72.9 | 72.9 | 72.9 | 72.7 | ||
4 | 74.6 | 74.6 | 74.6 | 74.4 | 74.3 | ||
5 | 69.8 | 69.8 | 69.7 | 69.8 | 69.5 | ||
6 | 19.2 | 19.2 | 19.2 | 19.3 | 19.0 | ||
28-O- | Glc | Glc | Glc | Glc | Glc | Glc | |
1 | 95.6 | 96.0 | 96.0 | 96.2 | 96.3 | 95.8 | |
2 | 74.5 | 74.4 | 74.7 | 74.3 | 74.4 | 73.9 | |
3 | 78.9 | 79.1 | 79.2 | 79.4 | 79.7 | 78.7 | |
4 | 71.5 | 71.3 | 71.4 | 71.3 | 71.4 | 71.2 | |
5 | 78.9 | 78.8 | 78.8 | 78.8 | 79.2 | 79.1 | |
6 | 62.6 | 62.4 | 62.5 | 62.3 | 62.5 | 62.3 |
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Qiao, X.; Ji, M.; Yao, Y.; Ma, L.; Wu, J.; Liao, G.; Zhou, H.; Liu, Z.; Wu, P. Pubescenosides E–K, Seven New Triterpenoid Saponins from the Roots of Ilex pubescens and Their Anti-Inflammatory Activity. Molecules 2018, 23, 1426. https://doi.org/10.3390/molecules23061426
Qiao X, Ji M, Yao Y, Ma L, Wu J, Liao G, Zhou H, Liu Z, Wu P. Pubescenosides E–K, Seven New Triterpenoid Saponins from the Roots of Ilex pubescens and Their Anti-Inflammatory Activity. Molecules. 2018; 23(6):1426. https://doi.org/10.3390/molecules23061426
Chicago/Turabian StyleQiao, Xiaoxu, Mengying Ji, Yunda Yao, Leilei Ma, Jinjun Wu, Guochao Liao, Hua Zhou, Zhongqiu Liu, and Peng Wu. 2018. "Pubescenosides E–K, Seven New Triterpenoid Saponins from the Roots of Ilex pubescens and Their Anti-Inflammatory Activity" Molecules 23, no. 6: 1426. https://doi.org/10.3390/molecules23061426