New Furanocembranoids from Briareum violaceum
Abstract
:1. Introduction
2. Results and Discussion
3. Experimental Section
3.1. General Experimental Procedures
3.2. Animal Material
3.3. Extraction and Isolation
3.4. Molecular Mechanics Calculations
3.5. In Vitro Anti-Inflammatory Assay
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Conflicts of Interest
References
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Position | δH (J in Hz) | δC, type | COSY | HMBC |
---|---|---|---|---|
1 | 154.3, C | |||
2 | 109.5, C | |||
3α/β | 2.78 d (14.0); 3.04 d (14.0) | 44.8, CH2 | C-1, C-2, C-4, C-5, C-18 | |
4 | 127.1, C | |||
5 | 5.30 dd (8.0, 5.6) | 135.1, CH | H2-6 | C-3, C-18 |
6 | 1.93–1.99 m | 26.3, CH2 | H-5, H2-7 | C-4, C-5, C-7, C-8 |
7α/β | 1.80 m; 1.26 m | 34.9, CH2 | H2-6, H-8 | C-5, C-6, C-8, C-9, C-19 |
8 | 0.68 m | 41.4, CH | H2-7, H-9, H3-19 | C-9 |
9 | 3.68 ddd (9.6, 9.6, 6.0) | 85.2, CH | H-8, H2-10 | C-7 |
10α/β | 1.51 m; 1.98 m | 30.3, CH2 | H-9, H2-11 | C-11, C-12 |
11α/β | 1.56 m; 2.38 dd (12.0, 6.4) | 36.9, CH2 | H2-10 | C-9, C-10, C-12, C-13, C-20 |
12 | 84.1, C | |||
13 | 3.60 d (10.0) | 70.7, CH | OH-13 | C-1, C-11, C-12, C-20 |
14 | 5.06 s | 63.9, CH | - | C-1, C-2, C-12, C-15 |
15 | 127.2, C | |||
16 | 2.11 s | 9.2, CH3 | C-1, C-15, C-17 | |
17 | 172.1, C | |||
18 | 1.44 s | 15.3, CH3 | C-3, C-4, C-5 | |
19 | 0.78 d (6.4) | 17.3, CH3 | H-8 | C-7, C-8, C-9 |
20 | 1.30 s | 20.9, CH3 | C-11, C-12, C-13 | |
OMe-2 | 3.39 s | 51.0, CH3 | C-2 | |
OH-13 | 3.14 d (10.0) | H-13 | C-13, C-14 | |
OH-14 | 3.34 s | - | C-1, C-13, C-14 |
Position | δH (J in Hz) | δC, type | COSY | HMBC |
---|---|---|---|---|
1 | 157.9, C | |||
2 | 107.8, C | |||
3α/β | 2.67 d (14.4); 3.15 d (14.4) | 42.2, CH2 | C-1, C-2, C-4, C-5, C-18 | |
4 | 146.4, C | |||
5 | 4.57 dd (7.2, 6.0) | 69.1, CH | H2-6 | C-4, C-6, C-18 |
6/6′ | 1.81m; 1.93 m | 32.2, CH2 | H-5, H2-7 | - |
7/7′ | 1.33 m; 1.89 ddd (14.4, 4.8, 4.4) | 30.6, CH2 | H2-6, H-8 | C-5 |
8 | 1.53 m | 37.4, CH | H2-7, H-9, H3-19 | - |
9 | 3.65 ddd (8.4, 8.4, 6.0) | 85.4, CH | H-8, H2-10 | - |
10/10′ | 1.52 m; 2.10 m | 31.5, CH2 | H-9, H2-11 | - |
11/11′ | 1.65 m; 2.16 m | 37.2, CH2 | H2-10 | C-9, C-10, C-12, C-13, C-20 |
12 | 84.4, C | |||
13 | 3.50 d (5.6) | 75.2, CH | OH-13 | - |
14 | 5.18 br s | 67.7, CH | OH-14 | - |
15 | 130.0, C | |||
16 | 2.11 s | 10.1, CH3 | C-1, C-15, C-17 | |
17 | 171.1, C | |||
18a/b | 5.13 s; 5.30 s | 115.6, CH2 | C-3, C-4, C-5 | |
19 | 0.85 d (6.4) | 16.7, CH3 | H-8 | C-7, C-8, C-9 |
20 | 1.29 s | 21.8, CH3 | C-11, C-12, C-13 | |
OMe-2 | 3.26 s | 50.7, CH3 | C-2 | |
OH-13 | 2.42 br d (5.6) | H-13 | - | |
OH-14 | 2.29 br d (4.4) | H-14 | - |
Position | δH (J in Hz) | δC, type | COSY | HMBC |
---|---|---|---|---|
1 | 159.8, C | |||
2 | 107.7, C | |||
3α/β | 1.76 d (14.4); 3.56 d (14.4) | 39.6, CH2 | C-1, C-2, C-4, C-5, C-18 | |
4 | 131.0, C | |||
5 | 5.29 d (8.4) | 133.5, CH | H-6 | C-3, C-18 |
6 | 4.86 ddd (12.0, 8.4, 3.2) | 68.7, CH | H-5, H2-7 | - |
7/7′ | 1.34 m; 1.80 m | 44.9, CH2 | H-6, H-8 | C-5, C-6, C-8, C-9, C-19 |
8 | 1.21 m | 35.3, CH | H2-7, H-9, H3-19 | - |
9 | 3.65 ddd (10.0, 10.0, 4.4) | 87.3, CH | H-8, H2-10 | - |
10/10′ | 1.38 m; 2.05 m | 32.8, CH2 | H-9, H2-11 | C-9, C-11, C-12 |
11/11′ | 1.61 m; 2.22 dd (13.2, 8.0) | 35.5, CH2 | H2-10 | C-9, C-12, C-13, C-20 |
12 | 85.1, C | |||
13 | 3.40 d (8.4) | 76.7, CH | OH-13 | C-1, C-12, C-20 |
14 | 4.75 d (5.2) | 63.5, CH | OH-14 | C-1, C-2, C-12, C-13, C-15 |
15 | 128.5, C | |||
16 | 2.08 s | 9.6, CH3 | C-1, C-15, C-17 | |
17 | 171.9, C | |||
18 | 1.83 s | 24.0, CH3 | C-3, C-4, C-5 | |
19 | 0.84 d (6.8) | 20.1, CH3 | H-8 | C-7, C-8, C-9 |
20 | 1.28 s | 21.1, CH3 | C-11, C-12, C-13 | |
OMe-2 | 3.20 s | 51.1, CH3 | C-2 | |
OH-13 | 3.05 d (8.4) | H-13 | C-13, C-14 | |
OH-14 | 2.70 d (5.2) | H-14 | C-13, C-14 |
iNOS | |
---|---|
Expression (% of LPS) | |
LPS | 100.0 ± 7.0 |
1 | 109.0 ± 19.2 |
2 | 67.7 ± 2.4 |
3 | 79.5 ± 9.4 |
4 | 61.9 ± 7.3 |
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Huang, P.-C.; Lin, W.-S.; Peng, B.-R.; Chang, Y.-C.; Fang, L.-S.; Li, G.-Q.; Hwang, T.-L.; Wen, Z.-H.; Sung, P.-J. New Furanocembranoids from Briareum violaceum. Mar. Drugs 2019, 17, 214. https://doi.org/10.3390/md17040214
Huang P-C, Lin W-S, Peng B-R, Chang Y-C, Fang L-S, Li G-Q, Hwang T-L, Wen Z-H, Sung P-J. New Furanocembranoids from Briareum violaceum. Marine Drugs. 2019; 17(4):214. https://doi.org/10.3390/md17040214
Chicago/Turabian StyleHuang, Pin-Chang, Wen-Sou Lin, Bo-Rong Peng, Yu-Chia Chang, Lee-Shing Fang, Guo-Qiang Li, Tsong-Long Hwang, Zhi-Hong Wen, and Ping-Jyun Sung. 2019. "New Furanocembranoids from Briareum violaceum" Marine Drugs 17, no. 4: 214. https://doi.org/10.3390/md17040214
APA StyleHuang, P. -C., Lin, W. -S., Peng, B. -R., Chang, Y. -C., Fang, L. -S., Li, G. -Q., Hwang, T. -L., Wen, Z. -H., & Sung, P. -J. (2019). New Furanocembranoids from Briareum violaceum. Marine Drugs, 17(4), 214. https://doi.org/10.3390/md17040214