Poecillastrosides, Steroidal Saponins from the Mediterranean Deep-Sea Sponge Poecillastra compressa (Bowerbank, 1866)
Abstract
:1. Introduction
2. Results and Discussion
3. Material and Methods
3.1. General Experimental Procedures
3.2. Biological Material
3.3. Extraction and Isolation
3.4. Determination of the Absolute Configuration of the Pyranoses
3.5. Evaluation of the Biological Activities
4. Conclusions
Supplementary Materials
Acknowledgments
Author Contributions
Conflicts of Interest
References
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No. | 1 | 2 | 3 | 4 | ||||
---|---|---|---|---|---|---|---|---|
δH, mult. (J in Hz) | δC | δH, mult. (J in Hz) | δC | δH, mult. (J in Hz) | δC | δH, mult. (J in Hz) | δC | |
1 | 1.70, m | 38.1 | 1.69, m | 38.1 | 1.69, m | 38.1 | 1.69, m | 38.2 |
0.98, m | 0.98, m | 0.98, m | 0.98, m | |||||
2 | 1.90, m | 30.5 | 1.90, m | 30.5 | 1.90, m | 30.5 | 1.92, m | 30.5 |
1.50, m | 1.50, m | 1.50, m | 1.48, m | |||||
3 | 3.72, m | 80.2 | 3.72, m | 80.2 | 3.72, m | 80.2 | 3.72, m | 80.3 |
4 | 1.71, m | 35.5 | 1.71, m | 35.6 | 1.71, m | 35.5 | 1.70, m | 35.6 |
1.34, m | 1.34, m | 1.34, m | 1.32, m | |||||
5 | 1.12, m | 46.2 | 1.12, m | 46.2 | 1.12, m | 46.2 | 1.12, m | 46.1 |
6 | 1.34, m | 29.9 | 1.34, m | 29.9 | 1.34, m | 29.8 | 1.32, m | 29.9 |
1.32, m | 1.31, m | 1.31, m | 1.29, m | |||||
7 | 1.73, m | 33.3 | 1.74, m | 33.3 | 1.75, m | 33.3 | 1.74, m | 33.1 |
0.94, m | 0.94, m | 0.95, m | 0.92, m | |||||
8 | 1.67, m | 36.1 | 1.67, m | 36.1 | 1.67, m | 36.1 | 1.38, m | 38.5 |
9 | 0.75, m | 56.2 | 0.74, m | 56.2 | 0.74, m | 56.2 | 0.72, m | 55.9 |
10 | 36.8 | 36.9 | 36.8 | 36.8 | ||||
11 | 1.51, m | 22.8 | 1.52, m | 22.8 | 1.52, m | 22.8 | 1.63, m | 24.4 |
1.31, m | 1.32, m | 1.32, m | 1.34, m | |||||
12 | 2.01, m | 38.9 | 2.01, m | 38.8 | 2.01, m | 38.8 | 2.64, m | 38.2 |
1.11, m | 1.10, m | 1.10, m | 1.09, m | |||||
13 | 48.1 | 48.1 | 48.1 | 55.8 | ||||
14 | 1.10, m | 55.1 | 1.10, m | 55.1 | 1.10, m | 55.1 | 1.39, m | 58.4 |
15 | 2.17, m | 38.5 | 2.16, m | 38.6 | 2.16, m | 38.6 | 1.81, m | 26.5 |
1.34, m | 1.33, m | 1.33, m | 1.19, m | |||||
16 | 4.26, td (7.7, 3.7) | 72.8 | 4.26, td (7.9, 3.7) | 72.8 | 4.26, td (7.9, 3.7) | 72.8 | 1.80, m | 24.4 |
0.89, m | ||||||||
17 | 1.19, m | 62.3 | 1.19, m | 62.3 | 1.19, m | 62.3 | 1.48, m | 57.4 |
18 | 3.95, d (11.6) | 62.6 | 3.95, d (11.6) | 62.6 | 3.95, d (11.6) | 62.4 | 180.1 | |
3.59, d (11.6) | 3.60, d (11.6) | 3.60, d (11.6) | ||||||
19 | 0.88, s | 12.8 | 0.88, s | 12.8 | 0.88, s | 12.9 | 0.76, s | 12.8 |
20 | 1.94, m | 31.6 | 1.93, m | 32.2 | 1.93, m | 32.0 | 1.49, m | 38.8 |
21 | 1.02, d (6.8) | 19.0 | 1.07, d (6.7) | 19.1 | 1.02, d (6.7) | 19.1 | 1.09, d (6.3) | 19.1 |
22 | 1.87, m | 35.5 | 1.73, m | 35.5 | 1.83, m | 36.8 | 1.45, m | 36.0 |
1.21, m | 1.18, m | 1.18, m | 1.14, m | |||||
23 | 2.15, m | 32.4 | 2.13, m | 26.8 | 2.04, m | 29.1 | 2.07, m | 29.9 |
1.98, m | 1.94, m | 1.83, m | 1.90, m | |||||
24 | 158.0 | 148.2 | 146.9 | 147.9 | ||||
241 | 4.71, br s 4.70, br s | 106.7 | 5.19, q (6.7) | 116.6 | 5.17, q (6.7) | 117.7 | 5.18, q (6.7) | 116.8 |
242 | 1.59, d (6.3) | 13.4 | 1.58, d (6.3) | 12.8 | 1.56, d (6.7) | 13.4 | ||
25 | 2.29, h (6.5) | 34.8 | 2.24, m | 36.0 | 2.85, m | 29.8 | 2.19, m | 35.6 |
26 | 1.03, d (6.8) | 22.5 | 0.99, d (6.8) | 22.7 | 0.99, d (6.8) | 21.4 | 0.98, d (6.8) | 22.7 |
27 | 1.03, d (6.8) | 22.3 | 0.99, d (6.8) | 22.6 | 0.99, d (6.8) | 21.4 | 0.98, d (6.8) | 22.6 |
1′ | 4.49, d (7.6) | 101.8 | 4.49, d (7.6) | 101.8 | 4.49, d (7.6) | 101.8 | 4.48, d (7.5) | 101.8 |
2′ | 3.70, m | 80.8 | 3.69, t (10.2) | 80.8 | 3.69, t (10.2) | 80.8 | 3.70, t (10.2) | 80.8 |
3′ | 3.65, dd (9.6, 3.3) | 74.8 | 3.65, dd (9.6, 3.3) | 74.8 | 3.65, dd (9.6, 3.3) | 74.8 | 3.64, dd (9.5, 3.3) | 74.8 |
4′ | 3.84, d (3.2) | 70.0 | 3.84, d (3.2) | 70.0 | 3.84, d (3.2) | 70.0 | 3.84, d (3.1) | 70.0 |
5′ | 3.50, t (6.1) | 76.4 | 3.50, t (6.1) | 76.4 | 3.50, t (6.1) | 76.4 | 3.49, t (6.2) | 76.4 |
6′ | 3.73, m | 62.7 | 3.73, m | 62.7 | 3.73, m | 62.7 | 3.73, m | 62.7 |
3.71, m | 3.71, m | 3.71, m | 3.71, m | |||||
1″ | 4.56, d (7.9) | 105.2 | 4.56, d (7.9) | 105.2 | 4.56, d (7.9) | 105.2 | 4.56, d (7.9) | 105.2 |
2″ | 3.25, dd (9.1, 7.9) | 75.8 | 3.25, dd (9.1, 7.9) | 75.8 | 3.25, dd (9.1, 7.9) | 75.8 | 3.25, dd (9.0, 7.8) | 75.8 |
3″ | 3.37, t (8.8) | 77.7 | 3.37, t (8.8) | 77.7 | 3.37, t (8.8) | 77.7 | 3.37, t (8.9) | 77.7 |
4″ | 3.33, t (9.3) | 71.4 | 3.33, t (9.3) | 71.4 | 3.33, t (9.3) | 71.4 | 3.33, t (9.4) | 71.4 |
5″ | 3.29, m | 78.4 | 3.29, m | 78.4 | 3.29, m | 78.4 | 3.28, m | 78.4 |
6″ | 3.84, dd (11.2, 2.3) | 62.4 | 3.84, dd (11.1, 2.3) | 62.4 | 3.84, dd (11.1, 2.3) | 62.4 | 3.84, dd (13.5, 2.8) | 62.4 |
3.71, m | 3.71, m | 3.71, m | 3.71, m |
No. | 5 | 6 | 7 | |||
---|---|---|---|---|---|---|
δH, mult. (J in Hz) | δC | δH, mult. (J in Hz) | δC | δH, mult. (J in Hz) | δC | |
1 | 1.70, m | 38.0 | 1.72, m | 38.2 | 1.72, m | 38.2 |
0.97, m | 0.97, m | 0.98, m | ||||
2 | 1.85, m | 30.4 | 1.86, m | 30.7 | 1.87, m | 30.8 |
1.44, m | 1.46, m | 1.46, m | ||||
3 | 3.62, m | 79.9 | 3.63, m | 80.0 | 3.62, m | 80.0 |
4 | 1.58, m | 35.8 | 1.58, m | 35.9 | 1.58, m | 36.0 |
1.17, m | 1.17, m | 1.19, m | ||||
5 | 1.12, m | 46.0 | 1.09, m | 46.1 | 1.10, m | 46.1 |
6 | 1.32, m | 30.3 | 1.32, m | 29.9 | 1.31, m | 30.4 |
1.29, m | 1.29, m | 1.27, m | ||||
7 | 1.76, m | 33.1 | 1.68, m | 33.5 | 1.67, m | 33.5 |
0.94, m | 0.87, m | 0.87, m | ||||
8 | 1.53, m | 38.8 | 1.43, m | 37.1 | 1.43, m | 37.0 |
9 | 0.73, m | 55.9 | 0.68, m | 56.0 | 0.68, m | 56.0 |
10 | 36.7 | 36.8 | 36.8 | |||
11 | 1.63, m | 24.4 | 1.53, m | 22.3 | 1.53, m | 22.3 |
1.31, m | 1.36, m | 1.34, m | ||||
12 | 2.63, m | 38.4 | 2.44, d (12.8) | 35.9 | 2.44, dt (12.7, 3.4) | 35.9 |
1.10, m | 0.94, m | 0.94, m | ||||
13 | 55.6 | 47.9 | 47.9 | |||
14 | 1.38, m | 58.4 | 1.11, m | 57.6 | 1.12, m | 57.6 |
15 | 1.75, m | 30.8 | 1.70, m | 29.9 | 1.71, m | 29.9 |
1.30, m | 1.30, m | 1.29, m | ||||
16 | 1.78, m | 25.8 | 1.54, m | 25.0 | 1.54, m | 24.9 |
1.53, m | 0.98, m | 0.98, m | ||||
17 | 1.46, m | 57.3 | 1.15, m | 58.2 | 1.16, m | 58.1 |
18 | 180.1 | 3.65, d (11.5) | 60.2 | 3.65, d (11.1) | 60.4 | |
3.45, d (11.6) | 3.45, d (11.7) | |||||
19 | 0.73, s | 12.7 | 0.83, s | 12.7 | 0.83, s | 12.7 |
20 | 1.92, m | 42.4 | 2.26, m | 41.7 | 2.26, m | 41.7 |
21 | 1.07, d (6.3) | 21.2 | 1.07, d (5.9) | 22.1 | 1.07, d (6.4) | 22.1 |
22 | 5.21, dd (15.1, 8.5) | 134.6 | 5.22, dd (14.8, 9.0) | 136.0 | 5.22, dd (15.2, 8.9) | 136.0 |
23 | 4.90, m | 132.4 | 4.94, dd (14.8, 8.1) | 131.6 | 4.94, dd (15.2, 8.3) | 131.6 |
24 | 0.96, m | 23.4 | 0.93, m | 23.4 | 0.93, m | 23.4 |
25 | 0.62, m | 15.5 | 0.62, m | 15.5 | 0.62, m | 15.5 |
26 | 0.44, td (9.0, 4.5) | 15.2 | 0.45, m | 15.2 | 0.45, m | 15.2 |
0.36, dt (9.0, 4.5) | 0.36, m | 0.35, m | ||||
27 | 1.03, d (5.9) | 18.8 | 1.03, d (5.8) | 18.9 | 1.03, d (5.9) | 18.9 |
1′ | 4.56, d (8.0) | 101.1 | 4.55, d (7.9) | 101.2 | 4.56, d (8.0) | 101.2 |
2′ | 5.11, dd (8.4, 8.1) | 72.5 | 5.12, dd (9.0, 7.7) | 72.6 | 5.11, dd (10.1, 8.0) | 72.4 |
2′-Ac | 2.06, s | 21.2 | 2.06, s | 21.2 | 2.06, s | 21.2 |
172.2 | 171.2 | 172.2 | ||||
3′ | 3.76, dd (10.2, 3.3) | 82.4 | 3.80, dd (10.0, 2.8) | 82.2 | 3.76, dd (10.1, 3.2) | 82.4 |
4′ | 4.07, d (3.2) | 70.2 | 4.11, d (3.1) | 70.2 | 4.07, d (3.4) | 70.2 |
5′ | 3.55, t (6.1) | 76.4 | 3.56, t (6.2) | 76.4 | 3.55, t (6.4) | 76.4 |
6′ | 3.74, m | 62.3 | 3.74, m | 62.2 | 3.74, m | 62.1 |
3.73, m | 3.72, m | 3.72, m | ||||
1″ | 4.39, d (7.6) | 106.0 | 4.38, d (7.9) | 106.0 | 4.38, d (8.0) | 106.0 |
2″ | 3.21, t (8.3) | 74.6 | 3.19, t (8.3) | 74.8 | 3.21, t (8.3) | 74.7 |
3″ | 3.32, t (10.1) | 77.7 | 3.35, m | 77.9 | 3.33, m | 77.9 |
4″ | 3.28, t (9.6) | 71.6 | 3.28, m | 71.3 | 3.29, m | 71.5 |
5″ | 3.46, m | 75.3 | 3.64, m | 80.0 | 3.46, m | 75.3 |
6″ | 4.38, d (11.9) | 64.7 | 3.84, m | 62.5 | 4.38, dd (11.9, 2.7) | 64.7 |
4.20, dd (11.9, 6.1) | 3.67, m | 4.20, dd (11.9, 6.2) | ||||
6″-Ac | 2.06, s | 20.8 | 2.06, s | 20.8 | ||
172.8 | 172.8 |
© 2017 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
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Calabro, K.; Kalahroodi, E.L.; Rodrigues, D.; Díaz, C.; Cruz, M.d.l.; Cautain, B.; Laville, R.; Reyes, F.; Pérez, T.; Soussi, B.; et al. Poecillastrosides, Steroidal Saponins from the Mediterranean Deep-Sea Sponge Poecillastra compressa (Bowerbank, 1866). Mar. Drugs 2017, 15, 199. https://doi.org/10.3390/md15070199
Calabro K, Kalahroodi EL, Rodrigues D, Díaz C, Cruz Mdl, Cautain B, Laville R, Reyes F, Pérez T, Soussi B, et al. Poecillastrosides, Steroidal Saponins from the Mediterranean Deep-Sea Sponge Poecillastra compressa (Bowerbank, 1866). Marine Drugs. 2017; 15(7):199. https://doi.org/10.3390/md15070199
Chicago/Turabian StyleCalabro, Kevin, Elaheh Lotfi Kalahroodi, Daniel Rodrigues, Caridad Díaz, Mercedes de la Cruz, Bastien Cautain, Rémi Laville, Fernando Reyes, Thierry Pérez, Bassam Soussi, and et al. 2017. "Poecillastrosides, Steroidal Saponins from the Mediterranean Deep-Sea Sponge Poecillastra compressa (Bowerbank, 1866)" Marine Drugs 15, no. 7: 199. https://doi.org/10.3390/md15070199
APA StyleCalabro, K., Kalahroodi, E. L., Rodrigues, D., Díaz, C., Cruz, M. d. l., Cautain, B., Laville, R., Reyes, F., Pérez, T., Soussi, B., & Thomas, O. P. (2017). Poecillastrosides, Steroidal Saponins from the Mediterranean Deep-Sea Sponge Poecillastra compressa (Bowerbank, 1866). Marine Drugs, 15(7), 199. https://doi.org/10.3390/md15070199