Six New Tetraprenylated Alkaloids from the South China Sea Gorgonian Echinogorgia pseudossapo
Abstract
:1. Introduction
2. Results and Discussion
2.1. Structural Elucidation of New Compounds
No. | 1 a | 2 a | 3 a | 4 b | 5 b | 6 b |
---|---|---|---|---|---|---|
1 | 7.23, brs | 7.22, brs | ||||
2 | 8.26, br s | 8.57, br s | 8.62, br s | 8.23, s | 8.23, s | 8.23, s |
8 | 7.69, s | 7.73, s | 7.73, s | 7.59, s | 7.59, s | 7.57, s |
10 | 3.86, s | 3.94, s | 3.95, s | 3.13, s | 3.13, s | 3.13, s |
11 | 2.84, s | 2.84, s | 2.84, d (4.7) | |||
1′ | 5.07, d (7.3) | 5.09, d (7.2) | 5.08, d (7.4) | 4.90, d (7.0) | 4.90, d (7.0) | 4.89, d (7.1) |
2′ | 5.45, t (7.0) | 5.47, t (6.9) | 5.47, t (6.9) | 5.40, t (7.1) | 5.41, t (7.0) | 5.39, t (7.0) |
4′ | 2.08, m | 2.11, m | 2.11, m | 2.07, m | 2.08, m | 2.09, m |
5′ | 2.09, m | 2.11, m | 2.12, m | 2.12, m | 2.13, m | 2.13, m |
6′ | 5.05, m | 5.08, m | 5.07, m | 5.14, t (6.2) | 5.14, t (6.1) | 5.14, t (6.3) |
8′ | 1.98, m | 1.99, m | 1.97, m | 2.01, m | 2.01, m | 2.02, m |
9′ | 2.04, m | 2.07, m | 1.55, m | 2.12, m | 2.12, m | 1.56, m |
10′ | 5.19, t (6.4) | 5.32, t (6.6) | 2.06, m | 5.26, t (6.8) | 5.30, t (6.3) | 2.55, br t, (7.9) |
12′ | 2.99, s | 3.09, s | 6.00, br s | 3.01, s | 3.12, s | 6.08, br s |
14′ | 6.07, br s | 6.06, br s | 6.04, br s | 6.17, br s | 6.15, br s | 6.10, br s |
16′ | 1.84, s | 1.87, s | 1.87, d (0.9) | 1.86, d (1.1) | 1.87, d (1.1) | 1.86, d (1.0) |
17′ | 2.10, s | 2.13, s | 2.13, d (1.0) | 2.09, d (1.1) | 2.09, d (1.0) | 2.12, d (1.0) |
18′ | 1.58, s | 1.69, s | 2.15, d (1.2) | 1.61, s | 1.66, d (1.2) | 1.87, d (1.3) |
19′ | 1.56, s | 1.58, s | 1.58, s | 1.59, s | 1.60, s | 1.62, s |
20′ | 1.77, s | 1.79, s | 1.80, s | 1.79, s | 1.79, s | 1.79, s |
No. | 1 a | 2 a | 3 a | 4 b | 5 b | 6 b |
---|---|---|---|---|---|---|
2 | 147.7 | 148.1 | 148.1 | 163.3 | 163.3 | 163.3 |
4 | 147.3 | 147.2 | 147.2 | 141.8 | 141.8 | 141.8 |
5 | 115.0 | 115.2 | 115.2 | 118.2 | 118.2 | 118.2 |
6 | 162.0 | 160.4 | 160.3 | 160.9 | 160.9 | 161.0 |
8 | 140.3 | 140.7 | 140.8 | 137.6 | 137.6 | 137.6 |
10 | 35.0 | 35.5 | 35.5 | 31.9 | 31.9 | 31.9 |
11 | 26.1 | 26.1 | 26.3 | |||
1′ | 44.5 | 44.6 | 44.7 | 45.2 | 45.2 | 45.2 |
2′ | 117.6 | 117.3 | 117.4 | 120.5 | 120.5 | 120.4 |
3′ | 143.4 | 143.7 | 143.7 | 142.0 | 142.0 | 142.0 |
4′ | 39.4 | 39.5 | 39.4 | 40.1 | 40.2 | 40.2 |
5′ | 26.1 | 26.1 | 26.1 | 27.0 | 26.9 | 26.9 |
6′ | 123.5 | 123.6 | 123.9 | 124.8 | 124.8 | 124.8 |
7′ | 135.5 | 135.5 | 135.4 | 135.8 | 135.8 | 136.0 |
8′ | 39.3 | 39.5 | 39.1 | 40.1 | 40.3 | 40.6 |
9′ | 26.7 | 26.9 | 25.8 | 27.4 | 27.7 | 27.2 |
10′ | 129.0 | 128.2 | 40.8 | 129.4 | 128.7 | 33.8 |
11′ | 129.6 | 129.2 | 157.8 | 130.7 | 130.2 | 158.6 |
12′ | 55.3 | 47.9 | 125.7 | 55.8 | 48.3 | 126.9 |
13′ | 199.3 | 198.6 | 191.7 | 198.8 | 198.1 | 191.0 |
14′ | 122.9 | 123.0 | 126.3 | 123.7 | 124.0 | 127.0 |
15′ | 155.5 | 155.8 | 154.2 | 155.0 | 155.3 | 154.2 |
16′ | 27.7 | 27.7 | 27.7 | 27.5 | 27.5 | 27.6 |
17′ | 20.6 | 20.7 | 20.5 | 20.5 | 20.5 | 20.4 |
18′ | 16.4 | 24.1 | 19.1 | 16.5 | 24.4 | 25.5 |
19′ | 16.0 | 16.0 | 15.9 | 16.1 | 16.1 | 16.0 |
20′ | 16.5 | 16.6 | 16.6 | 16.5 | 16.5 | 16.5 |
2.2. In Vitro Inhibitory Activity Screening against PDEs
Compound | Inhibition (%) of Compounds at 50 µM | Inhibition (%) of Compounds at 5 µM | |||||
---|---|---|---|---|---|---|---|
PDE4D | PDE5A | PDE9A | PDE4D | PDE5A | PDE9A | ||
1 | 85 | 53 | 18 | 17 | 11 | <10 | |
2 | 72 | 32 | 15 | <10 | <10 | <10 | |
3 | 81 | 35 | 27 | 17 | <10 | 10 | |
4 | 79 | 38 | <10 | 18 | <10 | <10 | |
5 | 75 | 36 | 11 | 14 | <10 | <10 | |
6 | 85 | 38 | 15 | 18 | <10 | <10 |
3. Experimental Section
3.1. General Experimental Procedures
3.2. Animal Material
3.3. Extraction and Isolation
4. Conclusions
Supplementary Files
Acknowledgments
Conflicts of Interest
References
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Sun, Z.-H.; Cai, Y.-H.; Fan, C.-Q.; Tang, G.-H.; Luo, H.-B.; Yin, S. Six New Tetraprenylated Alkaloids from the South China Sea Gorgonian Echinogorgia pseudossapo. Mar. Drugs 2014, 12, 672-681. https://doi.org/10.3390/md12020672
Sun Z-H, Cai Y-H, Fan C-Q, Tang G-H, Luo H-B, Yin S. Six New Tetraprenylated Alkaloids from the South China Sea Gorgonian Echinogorgia pseudossapo. Marine Drugs. 2014; 12(2):672-681. https://doi.org/10.3390/md12020672
Chicago/Turabian StyleSun, Zhang-Hua, Ying-Hong Cai, Cheng-Qi Fan, Gui-Hua Tang, Hai-Bin Luo, and Sheng Yin. 2014. "Six New Tetraprenylated Alkaloids from the South China Sea Gorgonian Echinogorgia pseudossapo" Marine Drugs 12, no. 2: 672-681. https://doi.org/10.3390/md12020672
APA StyleSun, Z. -H., Cai, Y. -H., Fan, C. -Q., Tang, G. -H., Luo, H. -B., & Yin, S. (2014). Six New Tetraprenylated Alkaloids from the South China Sea Gorgonian Echinogorgia pseudossapo. Marine Drugs, 12(2), 672-681. https://doi.org/10.3390/md12020672