Anti-Inflammatory Cembrane-Type Diterpenoids and Prostaglandins from Soft Coral Lobophytum sarcophytoides
Abstract
1. Introduction
2. Results and Discussion
3. Materials and Methods
3.1. General Experimental Procedures
3.2. Biological Material
3.3. Extraction, Isolation and Characterization
3.3.1. Lobophytin A (1)
3.3.2. Lobophytin B (3)
3.3.3. (5E)-PGB2 (10)
3.3.4. (5E)-13,14-dihydro-PGB2 (11)
3.3.5. 13,14-dihydro-PGB2 (12)
3.3.6. 13,14-dihydro-PGB2-Me (13)
3.4. Preparation of (S)-MTPA Ester and (R)-MTPA Ester
3.4.1. (S)-MTPA Ester (15a) and (R)-MTPA Ester (15b)
3.4.2. (S)-MTPA Ester (10a) and (R)-MTPA Ester (10b)
3.5. Calculation of ECD Spectra
3.6. Cytotoxic Assay
3.7. Anti-Inflammation Bioassays
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Acknowledgments
Conflicts of Interest
References
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No. | 1 | 3 | ||
---|---|---|---|---|
δC | δH, Mult. | δC | δH, Mult. | |
1 | 162.8, C | 161.4, C | ||
2 | 79.8, CH | 5.64, dd (10.0, 1.7) | 79.2, CH | 5.42, d (10.2) |
3 | 122.9, CH | 4.99, dt (10.0, 1.0) | 120.1, CH | 4.90, d (10.2) |
4 | 143.5, C | 143.7, C | ||
5 | 36.7, CH2 | 2.19, m 2.56, ddd (13.1, 9.9, 3.3) | 41.7, CH2 | 2.73, dd (13.8, 7.2) 2.81, dd (13.8, 7.2) |
6 | 32.9, CH2 | 1.40, m 2.00, m | 125.2, CH | 5.83, dt (15.6, 7.2) |
7 | 70.1, CH | 3.83, dd (10.7, 6.3) | 140.2, CH | 5.68, d (15.6) |
8 | 155.1, C | 72.6, C | ||
9 | 31.3, CH2 | 2.13, m 2.37, (13.7, 7.9, 2.8) | 39.6, CH2 | 1.81, m |
10 | 31.7, CH2 | 1.41, m | 24.1, CH2 | 1.64, m 1.77, m |
11 | 62.1, CH | 2.69, dd (10.3, 2.6) | 62.0, CH | 2.76, m |
12 | 61.1, C | 60.1, C | ||
13 | 35.0, CH2 | 1.56, m 1.91, m | 35.7, CH2 | 1.27, m 1.9, m |
14 | 22.4, CH2 | 2.27, m | 23.7, CH2 | 2.20, m 2.38, m |
15 | 123.7, C | 123.8, C | ||
16 | 174.5, C | 174.7, C | ||
17 | 8.8, CH3 | 1.79, s | 9.1, CH3 | 1.85, s |
18 | 16.0, CH3 | 1.91, s | 17.4, CH3 | 1.83, s |
19 | 110.5, CH2 | 4.92, d (0.9) 5.19, t (1.6) | 28.5, CH3 | 1.41, s |
20 | 17.9, CH3 | 1.21, s | 16.7, CH3 | 1.29, s |
No. | 10 a | 11 a | 12 a | 13 b | ||||
---|---|---|---|---|---|---|---|---|
δC, Type | δH, Mult (J in Hz) | δC, Type | δH, Mult (J in Hz) | δC, Type | δH, Mult (J in Hz) | δC, Type | δH, Mult (J in Hz) | |
1 | 177.6, C | 178.0, C | 174.1, C | 177.8, C | ||||
2 | 34.7, CH2 | 2.19, t (6.9) | 34.6, CH2 | 2.22, t (7.4) | 33.8, CH2 | 2.33, t (7.5) | 34.6, CH2 | 2.30, t (7.4) |
3 | 26.0, CH2 | 1.59, m | 25.9, CH2 | 1.61, m | 25.6, CH2 | 1.66, m | 26.1, CH2 | 1.66, m |
4 | 32.9, CH2 | 1.97, m | 32.9, CH2 | 1.99, m | 27.2, CH2 | 2.20, q (7.2) | 27.7, CH2 | 2.20, q (7.1) |
5 | 131.8, CH | 5.37, m | 131.5, CH | 5.39, m | 129.8, CH | 5.32, m | 130.6, CH | 5.34, m |
6 | 128.3, CH | 5.37, m | 128.4, CH | 5.39, m | 128.2, CH | 5.32, m | 128.0, CH | 5.30, m |
7 | 26.7, CH2 | 2.95, m | 26.8, CH2 | 2.89, m | 21.9, CH2 | 2.92, m | 22.1, CH2 | 2.94, d (6.6) |
8 | 139.3, C | 139.3, C | 139.1, C | 139.9, C | ||||
9 | 211.9, C | 212.4, C | 208.3, C | 212.3, C | ||||
10 | 34.7, CH2 | 2.40, m | 35.2, CH2 | 2.36, m | 34.5, CH2 | 2.25, m | 35.2, CH2 | 2.35, m |
11 | 26.7, CH2 | 2.71, m | 30.4, CH2 | 2.59, m | 29.6, CH2 | 2.55, m | 30.3, CH2 | 2.58, m |
12 | 167.5, C | 178.8, C | 174.6, C | 178.2, C | ||||
13 | 124.3, CH | 6.86, d (15.7) | 28.7, CH2 | 2.53, m | 28.3, CH2 | 2.55, m | 28.8, CH2 | 2.55, m |
2.61, m | 2.62, m | 2.61, m | ||||||
14 | 143.7, CH | 6.37, dd (15.7, 5.8) | 35.9, CH2 | 1.58, m | 36.0, CH2 | 1.59, m | 35.9, CH2 | 1.59, m |
1.67, m | 1.69, m | 1.67, m | ||||||
15 | 72.8, CH | 4.23, q (5.8) | 72.2, CH | 3.53 | 71.2, CH | 3.57 | 72.2, CH | 3.53, m |
16 | 38.1, CH2 | 1.54, m | 38.4, CH2 | 1.45, m | 38.4, CH2 | 1.45, m | 38.4, CH2 | 1.45, m |
17 | 26.2, CH2 | 1.32, m | 26.5, CH2 | 1.32, m | 26.2, CH2 | 1.34, m | 26.5, CH2 | 1.32, m |
1.41, m | 1.45, m | 1.46, m | 1.45, m | |||||
18 | 32.9, CH2 | 1.31, m | 33.1, CH2 | 1.31, m | 32.7, CH2 | 1.30, m | 33.1, CH2 | 1.31, m |
19 | 23.7, CH2 | 1.31, m | 23.7, CH2 | 1.32, m | 23.4, CH2 | 1.31, m | 23.7, CH2 | 1.32, m |
20 | 14.4, CH3 | 0.88, t (6.7) | 14.3, CH3 | 0.90, t (6.9) | 14.3, CH3 | 0.88 t (6.7) | 14.4, CH3 | 0.90, t (6.7) |
OCH3 | 51.5, CH3 | 3.62, s |
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Shen, H.; Liu, X.; Jiang, M.; Luo, G.; Wu, Z.; Chen, B.; Li, J.; Liu, L.; Chen, S. Anti-Inflammatory Cembrane-Type Diterpenoids and Prostaglandins from Soft Coral Lobophytum sarcophytoides. Mar. Drugs 2019, 17, 481. https://doi.org/10.3390/md17080481
Shen H, Liu X, Jiang M, Luo G, Wu Z, Chen B, Li J, Liu L, Chen S. Anti-Inflammatory Cembrane-Type Diterpenoids and Prostaglandins from Soft Coral Lobophytum sarcophytoides. Marine Drugs. 2019; 17(8):481. https://doi.org/10.3390/md17080481
Chicago/Turabian StyleShen, Hongjie, Xiaowan Liu, Minghua Jiang, Guangyuan Luo, Zhenger Wu, Bin Chen, Jing Li, Lan Liu, and Senhua Chen. 2019. "Anti-Inflammatory Cembrane-Type Diterpenoids and Prostaglandins from Soft Coral Lobophytum sarcophytoides" Marine Drugs 17, no. 8: 481. https://doi.org/10.3390/md17080481
APA StyleShen, H., Liu, X., Jiang, M., Luo, G., Wu, Z., Chen, B., Li, J., Liu, L., & Chen, S. (2019). Anti-Inflammatory Cembrane-Type Diterpenoids and Prostaglandins from Soft Coral Lobophytum sarcophytoides. Marine Drugs, 17(8), 481. https://doi.org/10.3390/md17080481