Benzophenone and Benzoylphloroglucinol Derivatives from Hypericum sampsonii with Anti-Inflammatory Mechanism of Otogirinin A
Abstract
:1. Introduction
2. Results and Discussion
2.1. Effect of Different Fractions of MeOH Extract and Isolation of Compounds
2.2. Structure Identification of the Known Isolates
2.3. Biological Studies
2.3.1. Reduction of LPS-Triggered Nitric Oxide (NO) Production in RAW264.7 Cells by Compounds 8 and 9
2.3.2. Effect of Otogirinin A (9) on Proinflammatory Mediators in LPS-Stimulated RAW264.7 Cells
2.3.3. Effect of Otogirinin A (9) on M2 Polarization of Macrophages in LPS-Stimulated RAW264.7 Cells
2.3.4. Effect of Otogirinin A (9) on MAPK Phosphorylation Pathway in LPS-Stimulated RAW264.7 Cells
2.3.5. Effect of Otogirinin A (9) on IκBα Phosphorylation in LPS-Stimulated RAW264.7 Cells
3. Experimental Section
3.1. General Procedures
3.2. Plant Material
3.3. Extraction and Isolation
3.4. Biologic Assay
3.4.1. Chemicals and Antibodies
3.4.2. Cells and Culture Medium
3.4.3. Determination of NO Production
3.4.4. MTT Assay
3.4.5. Enzyme-Linked Immunosorbent Assay
3.4.6. Western Blotting
3.4.7. Statistical Analysis
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Conflicts of Interest
References
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Sample Availability: Samples of the compounds are available from the authors. |
Compounds | IC50 (μM) b or (Inh%) c |
---|---|
4-Geranyloxy-2-hydroxy-6-isoprenyloxybenzophenone (1) | (6.23 ± 3.71) |
Hypericumone A (2) | 40.32 ± 2.05 ** |
Hypericumone B (3) | (14.12 ± 2.19) |
1-Hydroxy-7-methoxyxanthone (4) d | elicit NO generation |
2-Methoxyxanthone (5) d | elicit NO generation |
2,4,6-Trihydroxybenzophenone-4-O-geranyl ether (6) | (23.41 ± 2.56) * |
Sampsonin B (7) | (10.48 ± 3.52) |
Sampsonione J (8) | 35.25 ± 2.46 ** |
Otogirinin A (9) | 32.87 ± 1.60 ** |
Andrographolide e | 19.36 ± 1.72 *** |
Position | 1 a | 2 b | 3 b |
---|---|---|---|
1 | |||
2 | 7.99 br d (7.5) | ||
3 | 6.16 d (2.5) | 7.45 br t (7.5) | |
4 | 7.55 br t (7.5) | ||
5 | 5.93 d (2.5) | 7.45 br t (7.5) | |
6 | 2.08 dd (13.8, 4.1) 2.32 dd (13.8, 2.0) | 7.99 br d (7.5) | |
7 | 1.80 m | ||
8 | 4.35 s | ||
9 | 7.48 d (7.5) | ||
10 | 7.35 br t (7.5) | 2.88 m | |
11 | 7.43 br t (7.5) | 1.14 m 2.20 m | |
12 | 7.35 br t (7.5) | 7.56 br d (8.4) | 2.64 m |
13 | 7.48 d (7.5) | 7.33 br dd (8.4, 7.4) | |
14 | 7.45 br t (7.4) | 1.98 m 2.32 m | |
15 | 7.33 br dd (8.4, 7.4) | 5.05 br t (7.6) | |
16 | 7.56 br d (8.4) | ||
17 | 1.36 s | 1.95 m | |
18 | 1.44 s | 2.02 m | |
19 | 1.93 m | 5.07 br t (6.8) | |
20 | 2.80 br t (10.0) | ||
21 | 1.66 s | ||
22 | 1.85 s | 1.58 s | |
23 | 5.01 br s 5.25 br s | 1.59 s | |
24 | 1.67 m 2.15 m | ||
25 | 5.21 br t (7.4) | ||
26 | |||
27 | 1.73 s | ||
28 | 1.60 s | ||
29 | 2.58 m | 0.91 s | |
30 | 5.40 br t (7.5) | 0.99 s | |
31 | |||
32 | 1.69 s | ||
33 | 2.11 m | ||
34 | 2.14 m | ||
35 | 5.10 br t (6.7) | ||
36 | |||
37 | 1.62 s | ||
38 | 1.68 s | ||
1ʹ | 4.58 d (6.5) | ||
2ʹ | 5.48 br t (6.5) | ||
3ʹ | |||
4ʹ | 2.11 br t (6.5) | ||
5ʹ | 2.14 m | ||
6ʹ | 5.10 br t (6.5) | ||
7ʹ | |||
8ʹ | 1.69 s | ||
9ʹ | 1.76 s | ||
10ʹ | 1.62 s | ||
1ʹʹ | 4.18 d (6.0) | ||
2ʹʹ | 4.62 br t (6.0) | ||
3ʹʹ | |||
4ʹʹ | 1.57 s | ||
5ʹʹ | 1.50 s | ||
2-OH | 12.37 s | ||
3-OH | 3.38 s |
Position | 1 a | 2 a | 3 a |
---|---|---|---|
1 | 105.7 | 80.6 | 138.5 |
2 | 166.1 | 211.6 | 128.7 |
3 | 94.1 | 82.6 | 128.6 |
4 | 165.8 | 133.2 | |
5 | 92.5 | 58.6 | 128.6 |
6 | 161.4 | 36.1 | 128.7 |
7 | 199.6 | 42.0 | 196.7 |
8 | 142.3 | 50.8 | 72.1 |
9 | 127.4 | 212.3 | 208.4 |
10 | 127.5 | 193.3 | 47.6 |
11 | 130.2 | 134.5 | 34.5 |
12 | 127.5 | 129.1 | 40.3 |
13 | 127.4 | 128.1 | 43.3 |
14 | 132.8 | 27.4 | |
15 | 128.1 | 121.6 | |
16 | 129.1 | 136.7 | |
17 | 21.7 | 39.8 | |
18 | 24.5 | 26.8 | |
19 | 26.0 | 124.3 | |
20 | 41.6 | 131.3 | |
21 | 142.5 | 25.7 | |
22 | 21.7 | 16.2 | |
23 | 118.5 | 17.7 | |
24 | 28.1 | ||
25 | 123.6 | ||
26 | 132.4 | ||
27 | 25.8 | ||
28 | 17.8 | ||
29 | 26.3 | 22.1 | |
30 | 118.5 | 26.1 | |
31 | 139.0 | ||
32 | 16.2 | ||
33 | 40.2 | ||
34 | 26.4 | ||
35 | 124.1 | ||
36 | 131.7 | ||
37 | 17.7 | ||
38 | 25.8 | ||
1ʹ | 65.2 | ||
2ʹ | 118.4 | ||
3ʹ | 142.3 | ||
4ʹ | 39.5 | ||
5ʹ | 26.3 | ||
6ʹ | 123.6 | ||
7ʹ | 131.9 | ||
8ʹ | 25.7 | ||
9ʹ | 16.7 | ||
10ʹ | 17.7 | ||
1ʹʹ | 65.1 | ||
2ʹʹ | 118.4 | ||
3ʹʹ | 137.0. | ||
4ʹʹ | 25.5 | ||
5ʹʹ | 18.0 |
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Huang, C.-Y.; Chang, T.-C.; Wu, Y.-J.; Chen, Y.; Chen, J.-J. Benzophenone and Benzoylphloroglucinol Derivatives from Hypericum sampsonii with Anti-Inflammatory Mechanism of Otogirinin A. Molecules 2020, 25, 4463. https://doi.org/10.3390/molecules25194463
Huang C-Y, Chang T-C, Wu Y-J, Chen Y, Chen J-J. Benzophenone and Benzoylphloroglucinol Derivatives from Hypericum sampsonii with Anti-Inflammatory Mechanism of Otogirinin A. Molecules. 2020; 25(19):4463. https://doi.org/10.3390/molecules25194463
Chicago/Turabian StyleHuang, Chun-Yi, Tzu-Cheng Chang, Yu-Jing Wu, Yun Chen, and Jih-Jung Chen. 2020. "Benzophenone and Benzoylphloroglucinol Derivatives from Hypericum sampsonii with Anti-Inflammatory Mechanism of Otogirinin A" Molecules 25, no. 19: 4463. https://doi.org/10.3390/molecules25194463