Frajunolides L–O, Four New 8-Hydroxybriarane Diterpenoids from the Gorgonian Junceella fragilis
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. Human Neutrophils Superoxide Generation and Elastase Release
4. Conclusion
Supplementary Data
Supporting Information
marinedrugs-09-01477-s001.pdfAcknowledgements
- Samples Availability: Not available.
References
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1 b | 2 b | 3 c | 4 c | |||||
---|---|---|---|---|---|---|---|---|
Position | δH (J in Hz) a | δH, mult. d | δH (J in Hz) | δH, mult. | δH (J in Hz) | δH, mult. | δH (J in Hz) | δH, mult. |
1 | 47.0, C | 45.7, C | 48.9, C | 48.3, C | ||||
2 | 4.94, t (3.3) | 74.2, CH | 5.01, m | 75.0, CH | 6.68, d (8.5) | 73.2, CH | 6.62, d (8.0) | 74.8, CH |
3 | 2.16, m | 30.8, CH2 | 2.54, m | 33.3, CH2 | 3.58, dd (16.0, 10.5) | 37.3, CH2 | 2.88, m | 29.3, CH2 |
1.72, m | 1.61, m | 2.03, dd (16.0, 8.5) | 1.70, m | |||||
4 | 2.58, m | 29.0, CH2 | 1.95, m | 29.7, CH2 | 5.90, d (10.5) | 77.6, CH | 2.52, m | 33.4, CH2 |
2.08, m | ||||||||
5 | 145.2, C | 146.1, C | 144.0, C | 144.9, C | ||||
6 | 5.58, d (9.6) | 120.0, CH | 5.41, d (9.2) | 117.7, CH | 5.42, d (3.5) | 54.2, CH | 5.21, d (3.2) | 56.2, CH |
7 | 5.28, d (9.6) | 78.0, CH | 5.32, d (9.2) | 79.1, CH | 4.94, d (3.5) | 85.3, CH | 4.92, m | 84.9, CH |
8 | 82.6, C | 82.5, C | 82.7, C | 82.1, C | ||||
9 | 5.62, d (5.1) | 72.6, CH | 5.74, s | 71.4, CH | 6.30, s | 72.6, CH | 6.28, s | 79.3, CH |
10 | 3.57, d (5.1) | 40.6, CH | 3.07, s | 39.9, CH | 3.62, s | 42.4, CH | 3.82, s | 44.6, CH |
11 | 146.3, C | 134.2, C | 58.2, C | 147.0, C | ||||
12 | 5.32, m | 71.5, CH | 5.85 br, s | 127.6, CH | 2.27, m | 31.6, CH2 | 2.63, t (12.4) | 38.6, CH2 |
1.28, m | 2.49, m | |||||||
13 | 2.20, m | 33.5, CH2 | 2.28, m | 28.1, CH2 | 1.94, m | 25.5, CH2 | 5.27, ddd (3.2, 5.2, 12.0) | 70.1, CH |
1.95, m | 2.11, m | |||||||
14 | 4.77 br, s | 73.6, CH | 4.75 br, s | 73.7, CH | 5.25, s | 75.2, CH | 5.66, s | 73.8, CH |
15 | 1.15, s | 15.4, CH3 | 0.99, s | 16.2, CH3 | 1.31, s | 15.2, CH3 | 1.27, s | 14.4, CH3 |
16 | 2.03, s | 27.0, CH3 | 1.99, s | 29.0, CH3 | 5.83, s | 125.5, CH2 | 4.92, s | 118.3, CH2 |
5.42, s | 5.49, s | |||||||
17 | 2.54, q (6.9) | 43.2, CH | 2.45, q (7.2) | 44.7, CH | 3.44, q (7.0) | 51.8, CH | 3.41, q (7.6) | 51.4, CH |
18 | 175.9, C | 174.7, C | 176.4, C | 175.8, C | ||||
19 | 1.15, d (6.9) | 6.7, CH3 | 1.17, d (6.8) | 8.7, CH3 | 1.41, d (7.0) | 7.3, CH3 | 1.26, d (7.6) | 6.7, CH3 |
20 | 5.34, s | 118.3, CH2 | 4.67, d (12.0) | 68.7, CH2 | 2.84, d (4.0) | 52.6, CH2 | 4.92, s | 113.1, C |
5.30, s | 5.02, d (12.0) | 2.59 br, s | 5.19, s | |||||
OAc | 2.21, s | 170.4, C | 2.16, s | 169.9, C | 2.30, s | 172.5, C | 2.28, s | 171.8, C |
2.13, s | 170.4, C | 2.07, s | 169.7, C | 2.30, s | 171.1, C | 2.09, s | 170.9, C | |
1.98, s | 170.3, C | 2.01, s | 169.3, C | 2.11, s | 171.1, C | 2.07, s | 170.8, C | |
1.94, s | 168.9, C | 1.92, s | 168.4, C | 1.99, s | 170.3, C | 1.99, s | 170.3, C | |
21.7, CH3 | 23.1, CH3 | 22.2, CH3 | 21.9, CH3 | |||||
21.2, CH3 | 22.9, CH3 | 21.9, CH3 | 21.1, CH3 | |||||
21.2, CH3 | 22.8, CH3 | 21.8, CH3 | 21.0, CH3 | |||||
21.1, CH3 | 22.7, CH3 | 21.5, CH3 | 20.9, CH3 | |||||
8-OH | 8.05 br, s |
Compounds | Superoxide anion Inh % a | Elastase release Inh % a |
---|---|---|
1 | 18.7 ± 2.6 ** | 16.2 ± 0.7 *** |
2 | 2.0 ± 2.3 | 13.3 ± 3.1 * |
3 | 0.6 ± 1.5 | 22.3 ± 7.7 |
4 | 8.3 ± 3.6 | 17.2 ± 6.7 * |
Genistein | 65.0 ± 5.7 | 51.6 ± 5.9 |
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Liaw, C.-C.; Kuo, Y.-H.; Lin, Y.-S.; Hwang, T.-L.; Shen, Y.-C. Frajunolides L–O, Four New 8-Hydroxybriarane Diterpenoids from the Gorgonian Junceella fragilis. Mar. Drugs 2011, 9, 1477-1486. https://doi.org/10.3390/md9091477
Liaw C-C, Kuo Y-H, Lin Y-S, Hwang T-L, Shen Y-C. Frajunolides L–O, Four New 8-Hydroxybriarane Diterpenoids from the Gorgonian Junceella fragilis. Marine Drugs. 2011; 9(9):1477-1486. https://doi.org/10.3390/md9091477
Chicago/Turabian StyleLiaw, Chia-Ching, Yao-Haur Kuo, Yun-Sheng Lin, Tsong-Long Hwang, and Ya-Ching Shen. 2011. "Frajunolides L–O, Four New 8-Hydroxybriarane Diterpenoids from the Gorgonian Junceella fragilis" Marine Drugs 9, no. 9: 1477-1486. https://doi.org/10.3390/md9091477