2-(2-Phenylethyl)-4H-chromen-4-one Derivatives from the Resinous Wood of Aquilaria sinensis with Anti-Inflammatory Effects in LPS-Induced Macrophages
Abstract
:1. Introduction
2. Results and Discussion
2.1. Isolation and Structural Elucidation
2.2. Structure Identification of the Known Isolates
2.3. Biological Studies
3. Experimental Section
3.1. General Procedures
3.2. Plant Material
3.3. Extraction and Isolation
3.4. Biological Assay
3.4.1. Cells and Culture Medium
3.4.2. Luciferase Reporter Assay
3.4.3. Cytotoxicity Assay
3.4.4. Determination of Nitric Oxide (NO) Production
3.4.5. Statistical Analysis
4. Conclusions
Supplementary Materials
Acknowledgments
Author Contributions
Conflicts of Interest
References
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Sample Availability: Samples of the compounds are available from the authors. |
Compounds a | Relative Luciferase Activity |
---|---|
Mean ± SD c | |
1 | 0.89 ± 0.05 |
2 | 0.93 ± 0.06 |
3 | 0.74 ± 0.03 * |
4 | 0.92 ± 0.01 |
5 | 0.55 ± 0.09 * |
6 | 0.75 ± 0.05 * |
7 | 0.72 ± 0.16 * |
8 | 0.98 ± 0.07 |
9 | 1.26 ± 0.40 |
10 | 0.54 ± 0.03 * |
11 | 0.31 ± 0.05 * |
12 | 0.38 ± 0.14 * |
13 | 1.09 ± 0.21 |
LPS-treated vehicle control b | 1.03 ± 0.02 |
Andrographolide d | 0.35 ± 0.17 * |
Position | 1 a | 2 a | 3 a | 4 b |
---|---|---|---|---|
3 | 6.07 s | 6.16 s | 6.02 s | 6.06 s |
5 | 8.08 d (8.5) | 8.02 d (9.0) | – | – |
6 | 6.95 dd (8.5, 2.0) | 7.09 dd (9.0, 2.5) | – | – |
7 | – | – | 7.28 d (9.0) | 7.30 d (9.3) |
8 | 6.83 d (2.0) | 6.84 d (2.5) | 6.86 d (9.0) | 7.14 d (9.3) |
2′ | 7.06 d (8.5) | 7.13 d (8.5) | 6.78 d (2.0) | 7.20 d (7.8) |
3′ | 6.76 d (8.5) | 6.83 d (8.5) | – | 7.30 t (7.8) |
4′ | – | – | – | 7.22 t (7.8) |
5′ | 6.76 d (8.5) | 6.83 d (8.5) | 6.76 d (8.0) | 7.30 t (7.8) |
6′ | 7.06 d (8.5) | 7.13 d (8.5) | 6.64 dd (8.0, 2.0) | 7.20 d (7.8) |
7′ | 2.98 t (8.0) | 3.05 t (8.0) | 2.96 t (7.0) | 3.04 t (7.8) |
8′ | 2.86 t (8.0) | 2.96 t (8.0) | 2.88 t (7.0) | 2.88 t (7.8) |
OH-5 | – | – | 12.50 s | – |
OH-6 | – | – | 5.43 s | – |
OH-3′ | – | – | 5.58 s | – |
OMe-5 | – | – | – | 3.98 s |
OMe-7 | 3.91 s | – | – | – |
OMe-4′ | – | 3.79 | 3.87 s | – |
Position | 1 a | 2 a | 3 a | 4 b |
---|---|---|---|---|
2 | 168.5 | 168.1 | 170.4 | 167.0 |
3 | 109.8 | 110.3 | 108.2 | 110.5 |
4 | 177.9 | 177.1 | 183.2 | 177.5 |
5 | 127.2 | 125.2 | 145.3 | 143.5 |
6 | 116.5 | 113.8 | 140.2 | 146.1 |
7 | 164.1 | 156.1 | 121.6 | 120.7 |
8 | 100.1 | 103.9 | 110.7 | 114.1 |
9 | 158.1 | 156.6 | 144.0 | 151.4 |
10 | 115.4 | 118.4 | 111.0 | 117.9 |
1′ | 131.5 | 131.5 | 129.5 | 139.8 |
2′ | 129.4 | 129.2 | 115.9 | 128.3 |
3′ | 115.6 | 114.1 | 144.6 | 128.7 |
4′ | 154.5 | 158.3 | 145.9 | 126.6 |
5′ | 115.6 | 114.1 | 112.0 | 128.7 |
6′ | 129.4 | 129.2 | 123.9 | 128.3 |
7′ | 32.0 | 31.9 | 30.3 | 32.9 |
8′ | 36.3 | 36.1 | 34.7 | 35.6 |
OMe-5 | – | – | – | 62.8 |
OMe-7 | 56.1 | – | – | – |
OMe-4′ | – | 55.3 | 56.3 | – |
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Wang, S.-L.; Tsai, Y.-C.; Fu, S.-L.; Cheng, M.-J.; Chung, M.-I.; Chen, J.-J. 2-(2-Phenylethyl)-4H-chromen-4-one Derivatives from the Resinous Wood of Aquilaria sinensis with Anti-Inflammatory Effects in LPS-Induced Macrophages. Molecules 2018, 23, 289. https://doi.org/10.3390/molecules23020289
Wang S-L, Tsai Y-C, Fu S-L, Cheng M-J, Chung M-I, Chen J-J. 2-(2-Phenylethyl)-4H-chromen-4-one Derivatives from the Resinous Wood of Aquilaria sinensis with Anti-Inflammatory Effects in LPS-Induced Macrophages. Molecules. 2018; 23(2):289. https://doi.org/10.3390/molecules23020289
Chicago/Turabian StyleWang, Sin-Ling, Yun-Chen Tsai, Shu-Ling Fu, Ming-Jen Cheng, Mei-Ing Chung, and Jih-Jung Chen. 2018. "2-(2-Phenylethyl)-4H-chromen-4-one Derivatives from the Resinous Wood of Aquilaria sinensis with Anti-Inflammatory Effects in LPS-Induced Macrophages" Molecules 23, no. 2: 289. https://doi.org/10.3390/molecules23020289