New Isomalabaricane-Derived Metabolites from a Stelletta sp. Marine Sponge
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. Compound Characteristics
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Acknowledgments
Conflicts of Interest
Sample Availability
References
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No. 1 | 1 | 2 | ||
---|---|---|---|---|
δH mult (J in Hz) | δC | δH mult (J in Hz) | δC | |
1α | 1.57, td (13.0, 3.9) | 33.1 | 1.57, m | 32.9 |
1β | 1.38, m | 1.36, m | ||
2α | 1.82, m | 25.1 | 1.81, m | 25.1 |
2β | 1.71, m | 1.68, m | ||
3α | 4.54, dd (11.7, 5.2) | 80.8 | 4.53, dd (11.6, 5.2) | 80.7 |
4 | 38.2 | 38.2 | ||
5α | 1.73, m | 46.5 | 1.75, m | 46.4 |
6α | 1.70, m | 18.2 | 1.68, m | 18.2 |
6β | 1.48, m | 1.48, m | ||
7α | 1.99, m | 37.7 | 2.06, m | 38.5 |
7β | 2.00, m | 1.93, m | ||
8 | 44.2 | 43.8 | ||
9β | 1.75, m | 50.3 | 1.77, m | 50.3 |
10 | 35.4 | 35.4 | ||
11α | 2.13, m | 36.4 | 2.15, m | 36.4 |
11β | 2.13, m | 2.15, m | ||
12 | 206.6 | 206.9 | ||
13 | 146.8 | 146.0 | ||
14 | 147.9 | 147.5 | ||
15 | 4.75, m | 45.0 2 | 3.22, dt (9.2, 6.0) | 48.0 |
16α | 2.27, m | 37.9 | 2.52, m | 38.4 |
16β | 3.02, ddt (19.4, 9.3, 2.5) | 2,89, ddt (19.4, 9.2, 2.7) | ||
17 | 6.80, br s | 144.6 | 6.78, dd (4.3, 2.5) | 143.6 |
18 | 1.79, s | 16.2 2 | 2.06, s | 15.7 |
19 | 1.02, s | 22.4 | 1.01, s | 22.4 |
20 | 195.6 | 195.1 | ||
21 | 2.29, s | 26.9 | 2.30, s | 27.0 |
22 | 146.6 | 146.7 | ||
23 | 3.86, br t (8.3) | 47.5 | 3.95, m | 48.0 |
24 | 6.57, br d (10.2) | 145.9 | 6.59, dd (10.6, 1.5) | 144.6 |
25 | 126.3 | 127.3 | ||
26 | 171.0 | 170.7 | ||
27 | 1.88, br s | 12.6 | 1.86, d (1.3) | 12.5 |
28 | 0.91, s | 29.0 | 0.90, s | 29.0 |
29 | 0.89, s | 16.9 | 0.88, s | 17.0 |
30 | 1.29, s | 24.1 | 1.23, s | 26.4 |
OAc | 2.06, s | 171.021.2 | 2.05, s | 170.921.2 |
No. 1 | 3 | 4 | 5 | 6 | ||||
---|---|---|---|---|---|---|---|---|
δH mult (J in Hz) | δC | δH mult (J in Hz) | δC | δH mult (J in Hz) | δC | δH mult (J in Hz) | δC | |
1α | 1.76, m | 35.9 | 1.33, m | 34.3 | 1.78, m | 35.5 | 1.79, m | 35.6 |
1β | 1.57, ddd (13.3, 6.3, 3.7) | 1.28, m | 1.57, ddd (13.5, 6.0, 4.0) | 1.60, m | ||||
2α | 2.33, m | 34.8 | 1.72, m | 23.3 | 2.31, m | 34,8 | 2.32, dt (15.4, 4.5) | 34.8 |
2β | 2.70, ddd (15.6, 12.3, 6.4) | 1.68, m | 2.65, ddd (15.4, 12.6, 6.1) | 2.66, ddd (15.4, 12.6, 6.1) | ||||
3 | 216.5 | α: 4.44, dd (11.2, 5.1) | 80.3 | 216.1 | 216.0 | |||
4 | 47.7 | 37.6 | 47.5 | 47.5 | ||||
5α | 1.33, dd (12.4, 2.7) | 47.5 | 1.01, dd (11.9; 2.7) | 46.2 | 1.40, dd (12.6; 3.0) | 46.7 | 1.39, dd (12.7; 3.0) | 46.8 |
6α | 1.47, dq (13.6, 3.2) | 21.1 | 1.65, m | 17.9 | 1.46, m | 20.4 | 1.47, m | 20.5 |
6β | 1.83, qd (13.2, 3.4) | 1.47, m | 1.79, m | 1.78, m | ||||
7α | 1.25, td (13.2, 3.7) | 36.5 | 1.51, m | 30.0 | 1.11, m | 31.2 | 1.08, m | 31.5 |
7β | 1.74, m | 1.59, m | 2.20, br d (15.1) | 2.23, br d (14.2) | ||||
8 | 34.1 | 52.5 | 44.5 | 44.5 | ||||
9β | 2.22, t (5.1) | 51.2 | 2.31 br d (8.0) | 49.4 | 2.78 br t (5.0) | 48.3 | 2.74 br t (4.6) | 48.3 |
10 | 38.5 | 38.6 | 38.5 | 38.4 | ||||
11a | 2.40, dd (18.1, 5.8) | 31.1 | 2.58, dd (18.9, 7.9) | 34.1 | 2.41, dd (17.7, 5.3) | 31.1 | 2.48, dd (18.1, 5.4) | 30.5 |
11b | 2.33, dd (17.7, 4.8) | 1.70, br d (18.9) | 2.30, m | 2.38, dd (18.1, 4.8) | ||||
12 | 178.8 | 175.2 2 | 173.7 | 177.6 3 | ||||
13 | 88.1 | 213.0 | 183.8 | 178.0 3 | ||||
14 | 77.8 | 2.12, s | 24.7 | |||||
15–17 | ||||||||
18 | 1.80, s | 3.7 | ||||||
19 | 1.62, s | 23.3 | 1.27, s | 24.6 | 1.24, s | 20.8 | 1.14, s | 20.7 |
20–27 | ||||||||
28 | 1.08, s | 25.9 | 0.89, s | 27.9 | 1.07, s | 25.7 | 1.07, s | 25.7 |
29 | 1.06, s | 21.6 | 0.87, s | 16.2 | 1.00, s | 21.5 | 0.99, s | 21.5 |
30 | 1.25, s | 30.8 | 1.31,s | 24.6 | 1.17, s | 27.8 | 1.12, s | 27.7 |
OAc | 2.05, s | 170.9 21.2 | ||||||
OEt | 4.15, q (7.1), 2H, 1.26, t (7.1), 3H | 60.8 14.1 | 4.23, dq (10.9, 7.1), H 4.13, dq (10.9, 7.1), H 1.31, t (7.1), 3H | 60.6 14.0 |
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Kolesnikova, S.A.; Lyakhova, E.G.; Kozhushnaya, A.B.; Kalinovsky, A.I.; Berdyshev, D.V.; Popov, R.S.; Stonik, V.A. New Isomalabaricane-Derived Metabolites from a Stelletta sp. Marine Sponge. Molecules 2021, 26, 678. https://doi.org/10.3390/molecules26030678
Kolesnikova SA, Lyakhova EG, Kozhushnaya AB, Kalinovsky AI, Berdyshev DV, Popov RS, Stonik VA. New Isomalabaricane-Derived Metabolites from a Stelletta sp. Marine Sponge. Molecules. 2021; 26(3):678. https://doi.org/10.3390/molecules26030678
Chicago/Turabian StyleKolesnikova, Sophia A., Ekaterina G. Lyakhova, Anastasia B. Kozhushnaya, Anatoly I. Kalinovsky, Dmitrii V. Berdyshev, Roman S. Popov, and Valentin A. Stonik. 2021. "New Isomalabaricane-Derived Metabolites from a Stelletta sp. Marine Sponge" Molecules 26, no. 3: 678. https://doi.org/10.3390/molecules26030678