Neosuberitenone, a New Sesterterpenoid Carbon Skeleton; New Suberitenones; and Bioactivity against Respiratory Syncytial Virus, from the Antarctic Sponge Suberites sp.
Abstract
1. Introduction
2. Results and Discussion
3. Materials and Methods
3.1. General Experimental Procedures
3.2. Biological Material, Extraction and Isolation
3.3. X-ray Crystallography
3.4. RSV Antiviral Assay
3.5. Cytotoxicity Assay
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Data Availability Statement
Acknowledgments
Conflicts of Interest
Correction Statement
References
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Position | 1 a,c | 2 b,c | 3 b,d | 4 b,d | 5 b,d | 6 b,d | 8 a,d |
---|---|---|---|---|---|---|---|
1 | 67.5, CH | 65.9, CH | 66.0, CH | 64.7, CH | 66.6, CH | 71.0, CH | 63.6, CH |
2 | 42.9, CH2 | 145.5, CH | 145.8, CH | 145.5, CH | 88.6, CH | 79.9, CH | 141.7, CH |
3 | 48.7, C | 136.9, C | 136.9, C | 136.8, C | 44.6, CH | 48.1, CH | 137.6, C |
4 | 214.3, C | 201.6, C | 202.6, C | 202.2, C | 214.6, C | 212.8, C | 200.0 C |
5 | 41.9, CH2 | 35.3, CH2 | 38.5, CH2 | 37.7, CH2 | 37.4, CH2 | 46.7, CH2 | 37.3, CH2 |
6 | 44.1, CH | 47.9, CH | 45.4, CH | 38.8, CH | 48.3, CH | 45.5, CH | 45.5, CH |
7 | 134.3, C | 63.4, C | 137.2, C | 135.7, C | 75.1, C | 132.0, C | 148.8, C |
8 | 40.8, CH | 26.7, CH2 | 128.9, CH | 147.2, CH | 38.7, CH2 | 70.8, CH | 34.2, CH2 |
9 | 21.5, CH2 | 16.9, CH2 | 24.1, CH2 | 24.6, CH2 | 18.0, CH2 | 26.0, CH2 | 22.5, CH2 |
10 | 55.1, CH | 49.2, CH | 46.8, CH | 54.7, CH | 59.7, CH | 55.1, CH | 57.5, CH |
11 | 35.7, C | 34.8, C | 38.0, C | 45.7, C | 35.5, C | 37.1, C | 144.4, C |
12 | 45.5, CH2 | 42.5, CH2 | 39.8, CH2 | 39.4, CH2 | 48.1, CH2 | 44.3, CH2 | 47.8, CH2 |
13 | 70.8, CH | 72.0, CH | 72.3, CH | 71.3, CH | 72.3, CH | 72.1, CH | 69.5, CH |
14 | 57.1, CH | 57.5, CH | 57.2, CH | 56.5, CH | 57.7, CH | 57.7, CH | 57.6, CH |
15 | 38.2, C | 38.0, C | 38.0, C | 39.0, C | 38.3, C | 38.0, C | 41.2, C |
16 | 41.7, CH2 | 43.1, CH2 | 43.5, CH2 | 42.6, CH2 | 43.0, CH2 | 42.6, CH2 | 42.2, CH2 |
17 | 18.4, CH2 | 19.6, CH2 | 19.6, CH2 | 19.4, CH2 | 19.7, CH2 | 19.5, CH2 | 19.7, CH2 |
18 | 44.2, CH | 45.2, CH2 | 45.1, CH2 | 44.9, CH2 | 45.4, CH2 | 45.3, CH2 | 44.0, CH2 |
19 | 34.0, C | 35.0, C | 34.8, C | 34.8, C | 35.0, C | 35.0, C | 34.6, C |
20 | 33.2, CH3 | 33.4, CH3 | 33.8, CH3 | 33.5, CH3 | 33.3, CH3 | 33.1, CH3 | 33.8, CH3 |
21 | 16.4, CH3 | 15.7, CH3 | 15.6, CH3 | 15.6, CH3 | 10.4, CH3 | 11.6, CH3 | 15.8, CH3 |
22 | 140.0, CH | 70.1, CH | 75.3, CH | 205.5, C | 55.3, CH2 | 140.9, CH | 112.4, CH2 |
23 | 19.6, CH3 | 19.7, CH3 | 20.8, CH3 | 19.6, CH3 | 23.4, CH3 | 23.7, CH3 | 110.4, CH2 |
24 | 16.1, CH3 | 17.9, CH3 | 17.6, CH3 | 18.1, CH3 | 17.9, CH3 | 18.1, CH3 | 17.3, CH3 |
25 | 23.2, CH3 | 23.6, CH3 | 23.8, CH3 | 23.7, CH3 | 23.7, CH3 | 23.5, CH3 | 23.8, CH3 |
26 | 170.6, C | 172.3, C | 172.4, C | 172.0, C | 172.3, C | 172.1, C | |
27 | 22.0, CH3 | 21.8, CH3 | 21.9, CH3 | 21.8, CH3 | 21.8, CH3 | 21.8, CH3 | |
28 | 59.1, CH3 |
Position | 1 a,c | 2 b,c | 3 b,d | 4 b,c | 5 b,c | 6 b,c | 8 a,d |
---|---|---|---|---|---|---|---|
1 | 4.18, dd (8.7, 3.5) | 4.40, t (4.4) | 4.30, dd (5.6, 3.3) | 4.14, br t (4.2) | 4.46, br t (3.3) | 4.17 br t (2.7) | 4.31, br t |
2a | 2.13, o/l | 6.76, dq (5.4, 1.3) | 6.85, dq (5.5, 1.4) | 6.80, dq (5.6, 1.5) | 3.52, t (3.6) | 4.03, br s | 6.78, br d (4.4) |
2b | 1.64, o/l | 3.03, m | 2.64, m | ||||
5a | 2.25, d (18.6) | 2.73, dd (16.6, 12.4) | 2.83, dd (15.9, 12.8) | 2.82, dd (16.2, 13.4) | 2.65, t (13.7) | 2.83, dd (16.2, 5.2) | 2.84, m |
5b | 2.10, o/l | 2.37, dd (16.6, 4.1) | 2.31, (16.1, 2.8) | 2.18, dd (16.2, 3.6) | 2.23, dd (13.8, 4.7) | 2.30, dd (16.2, 2.5) | 2.36, o/l |
6 | 2.69, o/l | 1.90, o/l | 2.90, m | 3.39, m | 1.81, o/l | 2.68, m | 2.75, m |
8a | 2.68, o/l | 2.35, o/l | 5.67, t (3.2) | 6.78, m | 1.91, o/l | 3.79, dd (9.4, 6.6) | 2.35, o/l |
8b | 1.71, o/l | 1.21, o/l | 1.86 o/l | ||||
9a | 1.75, m | 1.43, o/l | 2.12, o/l | 2.52, m | 1.66, td (12.8, 3.4) | 1.90, o/l | 1.76, o/l |
9b | 1.26, o/l | 1.57, m | 1.67, td (12.4, 9.5) | 1.52, o/l | |||
10 | 1.02, o/l | 1.28, m | 1.60, dd (11.3, 5.9) | 1.71, o/l | 0.99, dd (12.3, 2.5) | 1.13, o/l | 1.68, m |
12a | 2.09, o/l | 1.87, o/l | 2.16, o/l | 2.13, dd (15.5, 2.7) | 1.88, o/l | 1.88, o/l | 2.34, o/l |
12b | 1.44, dd (15.1, 3.7) | 1.65, dd (14.6, 3.6) | 1.53, dd (15.0, 2.7) | 1.69, o/l | 1.32, m | 1.41, dd (14.6, 3.7) | |
13 | 5.51, br q (2.5) | 5.55, br q (2.5) | 5.61, dt (4.4, 2.4) | 5.61, q (3.2) | 5.48, br q (3.2) | 5.49, q (3.1) | 4.38, br t |
14 | 1.04, o/l | 1.07, br d (2.0) | 1.13, d (2.1) | 1.13, m | 1.14, br s | 1.12, o/l | 1.08, o/l |
16a | 1.55, br d (13) | 1.69, m | 1.72, o/l | 1.76, o/l | 1.77, o/l | 1.74, o/l | 1.78, o/l |
16b | 0.82, td (13.1, 3.1) | 0.87, m | 0.99, o/l | 0.98, m | 0.92, o/l | 0.85, td (13.1, 3.9) | 1.07, o/l |
17a | 1.66, o/l | 1.74, o/l | 1.73, o/l | 1.77, o/l | 1.77, o/l | 1.78, o/l | 1.64, m |
17b | 1.41, o/l | 1.45, o/l | 1.46, m | 1.49, m | 1.47, m | 1.49, m | 1.50, m |
18a | 1.35, br d (13.1) | 1.36, m | 1.39, m | 1.40, m | 1.37, o/l | 1.36, m | 1.39, m |
18b | 1.14, o/l | 1.22, m | 1.24, td (13.1, 3.9) | 1.24, m | 1.23, o/l | 1.23, o/l | 1.19, m |
20 | 0.92, s | 0.92, s | 0.96, s | 0.95, s | 0.91, s | 0.91, s | 1.01, s |
21 | 1.01, s | 1.76, s | 1.78, s | 1.79, s | 1.02, d (6.8) | 1.19, d (6.8) | 1.84, s |
22a | 5.60, d (3.1) | 2.63, br s | 3.15, s | 1.81, o/l | 5.24, s | 5.16, s | |
22b | 1.15/ o/l | 4.92, s | |||||
23a | 1.18, s | 1.27, s | 0.99, s | 1.27, s | 1.37, s | 1.26, s | 5.03, s |
23b | 4.77, s | ||||||
24 | 1.28, s | 1.21, s | 1.34, s | 1.42, s | 1.23, s | 1.24, s | 1.00, s |
25 | 1.01, s | 1.02, s | 1.04, s | 1.04, s | 1.04, s | 1.03, s | 1.22, s |
27 | 2.06, s | 2.05, s | 2.04, s | 2.04, s | 2.03, s | 2.04, s | |
28 | 3.35, s |
Compound | IC50 (µM) | CC50 (mM) | Selectivity Index |
---|---|---|---|
2 | 20.5 ± 0.7 | 87.3 ± 38.1 | 4.3 |
3 | 9.8 ± 1.4 | 36.0 ± 5.3 | 3.7 |
4 | 11.0 ± 1.3 | 40.7 ± 8.3 | 3.7 |
5 | 10.9 ± 1.8 | 51.1 ± 17.5 | 4.7 |
10 | 7.8 ± 0.2 | 33.3 ± 1.3 | 4.3 |
11 | 3.2 ± 0.4 | 67.6 ± 16.3 | 21.1 |
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Bracegirdle, J.; Olsen, S.S.H.; Teng, M.N.; Tran, K.C.; Amsler, C.D.; McClintock, J.B.; Baker, B.J. Neosuberitenone, a New Sesterterpenoid Carbon Skeleton; New Suberitenones; and Bioactivity against Respiratory Syncytial Virus, from the Antarctic Sponge Suberites sp. Mar. Drugs 2023, 21, 107. https://doi.org/10.3390/md21020107
Bracegirdle J, Olsen SSH, Teng MN, Tran KC, Amsler CD, McClintock JB, Baker BJ. Neosuberitenone, a New Sesterterpenoid Carbon Skeleton; New Suberitenones; and Bioactivity against Respiratory Syncytial Virus, from the Antarctic Sponge Suberites sp. Marine Drugs. 2023; 21(2):107. https://doi.org/10.3390/md21020107
Chicago/Turabian StyleBracegirdle, Joe, Stine S. H. Olsen, Michael N. Teng, Kim C. Tran, Charles D. Amsler, James B. McClintock, and Bill J. Baker. 2023. "Neosuberitenone, a New Sesterterpenoid Carbon Skeleton; New Suberitenones; and Bioactivity against Respiratory Syncytial Virus, from the Antarctic Sponge Suberites sp." Marine Drugs 21, no. 2: 107. https://doi.org/10.3390/md21020107
APA StyleBracegirdle, J., Olsen, S. S. H., Teng, M. N., Tran, K. C., Amsler, C. D., McClintock, J. B., & Baker, B. J. (2023). Neosuberitenone, a New Sesterterpenoid Carbon Skeleton; New Suberitenones; and Bioactivity against Respiratory Syncytial Virus, from the Antarctic Sponge Suberites sp. Marine Drugs, 21(2), 107. https://doi.org/10.3390/md21020107