Briarenols Q–T: Briaranes from A Cultured Octocoral Briareum stechei (Kükenthal, 1908)
Abstract
1. Introduction
2. Results and Discussion
3. Materials and Methods
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 | 1 | 2 | 3 | 4 |
---|---|---|---|---|
1 | 44.3, C a | 41.1, C | 43.9, C | 44.1, C |
2 | 72.1, CH | 76.0, CH | 78.1, CH | 79.5, CH |
3 | 41.8, CH2 | 60.2, CH | 34.5, CH2 | 31.6, CH2 |
4 | 94.0, C | 57.4, CH | 74.2, CH | 28.9, CH2 |
5 | 138.4, C | 133.6, C | n. o. c | 147.2, C |
6 | 128.0, CH | 60.9, CH | 62.3, CH | 118.1, CH |
7 | 70.1, CH | 76.3, CH | 77.2, CH | 77.7, CH |
8 | 80.8, C | 84.2, C | 85.0, C | 82.2, C |
9 | 77.2, CH | 68.4, CH | 74.2, CH | 71.3, CH |
10 | 40.7, CH | 39.2, CH | 38.8, CH | 38.3, CH |
11 | 131.1, C | 44.7, CH | 47.3, CH | 48.5, CH |
12 | 122.0, CH | 201.6, C | 202.4, C | 202.6, C |
13 | 28.4, CH2 | 124.4, CH | 124.5, CH | 124.1, CH |
14 | 71.8, CH | 152.5, CH | 155.1, CH | 154.6, CH |
15 | 13.4, CH3 | 14.6, CH3 | 18.1, CH3 | 15.4, CH3 |
16 | 164.6, C | 120.3, CH2 | 122.8, CH2 | 28.4, CH3 |
17 | 48.0, CH | 45.5, CH | 45.4, CH | 42.6, CH |
18 | 8.7, CH3 | 6.2, CH3 | 7.7, CH3 | 6.8, CH3 |
19 | 174.9, C | 173.7, C | 175.6, C | 175.5, C |
20 | 24.2, CH3 | 15.6, CH3 | 15.3, CH3 | 15.0, CH3 |
OAc-2 | 169.2, C b 21.3, CH3 | 169.6, C 20.9, CH3 | 169.8, C 21.0, CH3 | 168.9, C 21.7, CH3 |
OAc-4 | 169.1, C 21.0, CH3 | |||
OAc-9 | 169.7, C 21.0, CH3 | 169.3, C 21.8, CH3 | 170.2, C 21.1, CH3 | |
OAc-14 | 173.2, C b 21.3, CH3 | |||
OCH3-16 | 52.4, CH3 |
Position | 1 | 2 | 3 | 4 |
---|---|---|---|---|
2 | 5.11 d (7.2) | 4.75 d (9.0) | 4.63 dd (3.6, 3.0) | 4.44 dd (6.6, 1.2) |
3α | 2.46 d (16.8) | 1.86 ddd (15.6, 3.6, 3.6) | 1.70 m | |
β | 3.40 dd (16.8, 7.2) | 3.48 dd (9.0, 4.2) | 3.00 ddd (15.6, 12.0, 3.0) | 2.75 m |
4α | 5.81 dd (12.0, 3.6) | 2.06 ddd (14.4, 14.4, 4.8) | ||
β | 3.67 d (4.2) | 2.54 m | ||
6 | 6.84 d (4.8) | 5.39 m | 5.29 br s | 5.44 br d (10.2) |
7 | 4.44 d (4.8) | 5.08 d (3.6) | 5.41 d (3.0) | 5.23 d (10.2) |
9 | 6.05 s | 5.57 d (8.4) | 3.90 dd (6.0, 6.0) | 5.30 d (4.8) |
10 | 3.10 br s | 2.51 dd (8.4, 4.2) | 2.67 br s | 2.69 dd (4.8, 4.2) |
11 | 2.87 qd (7.2, 4.2) | 2.45 m | 2.50 qd (7.2, 4.2) | |
12 | 5.56 br s | |||
13α/β | 2.02 m; 2.38 br d (18.0) | 5.88 dd (10.2, 0.6) | 5.89 d (10.2) | 5.85 d (10.2) |
14 | 5.18 d (4.2) | 6.37 d (10.2) | 6.47 d (10.2) | 6.39 d (10.2) |
15 | 1.04 s | 1.28 s | 1.46 s | 1.23 s |
16a/b | 5.79 d (3.0); 6.06 d (3.0) | 5.72 s; 5.89 s | 1.99 d (1.2) | |
17 | 2.79 q (7.2) | 2.50 q (7.2) | 3.05 q (7.8) | 2.44 q (7.2) |
18 | 1.46 d (7.2) | 1.25 d (7.2) | 1.19 d (7.8) | 1.21 d (7.2) |
20 | 1.96 br s | 1.30 d (7.2) | 1.25 d (7.2) | 1.32 d (7.2) |
OH-4 | 6.11 s | |||
OH-8 | 3.52 s | 3.42 s | n. o. b | |
OAc-2 | 2.04 s a | 2.23 s | 2.09 s a | 2.24 s |
OAc-4 | 2.17 s a | |||
OAc-9 | 2.03 s | 2.27 s | 2.13 s | |
OAc-14 | 2.11 s a | |||
OCH3-16 | 3.81 s |
Compound | iNOS | COX-2 |
---|---|---|
Expression (% of LPS) at 10 μM | ||
Control | 1.28 ± 0.29 | 0.76 ± 0.13 |
LPS | 100.00 ± 1.87 | 100.00 ± 3.26 |
1 | 98.27 ± 5.13 | 94.00 ± 3.47 |
2 | 84.53 ± 4.66 * | 112.96 ± 4.54 |
3 | 78.50 ± 3.45 * | 97.66 ± 4.60 |
4 | 79.95 ± 2.94 * | 104.66 ± 7.86 |
Dexamethasone | 24.56 ± 1.85 * | 6.56 ± 1.18 * |
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Zhang, Y.-L.; Chiang, C.-C.; Lee, Y.-T.; Wen, Z.-H.; Wu, Y.-C.; Wu, Y.-J.; Hwang, T.-L.; Wu, T.-Y.; Chang, C.-Y.; Sung, P.-J. Briarenols Q–T: Briaranes from A Cultured Octocoral Briareum stechei (Kükenthal, 1908). Mar. Drugs 2020, 18, 383. https://doi.org/10.3390/md18080383
Zhang Y-L, Chiang C-C, Lee Y-T, Wen Z-H, Wu Y-C, Wu Y-J, Hwang T-L, Wu T-Y, Chang C-Y, Sung P-J. Briarenols Q–T: Briaranes from A Cultured Octocoral Briareum stechei (Kükenthal, 1908). Marine Drugs. 2020; 18(8):383. https://doi.org/10.3390/md18080383
Chicago/Turabian StyleZhang, Yi-Lin, Chih-Chao Chiang, Yi-Ting Lee, Zhi-Hong Wen, Yang-Chang Wu, Yu-Jen Wu, Tsong-Long Hwang, Tung-Ying Wu, Chia-Yuan Chang, and Ping-Jyun Sung. 2020. "Briarenols Q–T: Briaranes from A Cultured Octocoral Briareum stechei (Kükenthal, 1908)" Marine Drugs 18, no. 8: 383. https://doi.org/10.3390/md18080383
APA StyleZhang, Y.-L., Chiang, C.-C., Lee, Y.-T., Wen, Z.-H., Wu, Y.-C., Wu, Y.-J., Hwang, T.-L., Wu, T.-Y., Chang, C.-Y., & Sung, P.-J. (2020). Briarenols Q–T: Briaranes from A Cultured Octocoral Briareum stechei (Kükenthal, 1908). Marine Drugs, 18(8), 383. https://doi.org/10.3390/md18080383