Three New Malyngamides from the Marine Cyanobacterium Moorea producens
Abstract
:1. Introduction
2. Results
2.1. 6,8-Di-O-Acetylmalyngamide 2 (1) and 6-O-Acetylmalyngamide 2 (2)
2.2. N-Demethyl-isomalyngamide I (3)
2.3. Biological Activities
3. Experimental Section
3.1. General Experimental Procedures
3.2. Collection, Extraction, and Isolation
3.3. Identification of the Marine Cyanobacterium
3.4. Preparation of MTPA Esters of 2
3.5. Preparation of Acetylated Compound 2
3.6. Base Hydrolysis of Compounds 2 and 3
3.7. Preparation of MTPA Ester of Compound 3
3.8. Culture of L6 Myoblasts
3.9. Determination of Glucose Uptake
3.10. Western Blotting
4. Conclusions
Supplementary Materials
Acknowledgments
Author Contributions
Conflicts of Interest
References
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Position | 1 | 2 | ||||
---|---|---|---|---|---|---|
δC a | δH, Mult (J in Hz) b | HMBC | δC a | δH, Mult (J in Hz) b | HMBC | |
1a | 41.6 | 3.95, ddd (16.5, 5.8, 1.8) | 2, 3, 4, 1’ | 41.7 | 3.95, ddd (16.3, 5.6, 1.6) | 2, 3, 4, 1’ |
1b | 4.23, dd (16.5, 6.7) | 2, 3, 4, 1’ | 4.24, dd (16.3, 6.8) | 2, 3, 4, 1’ | ||
2 | 136.3 | - | - | 136.5 | - | - |
3 | 121.6 | 6.29, d (1.8) | 1, 2, 4 | 121.4 | 6.27, d (1.6) | 1, 2, 4 |
4 | 56.1 | 4.27, s | 1, 2, 3, 5, 9, 10 | 55.1 | 4.36, s | 1, 2, 3, 5, 9, 10 |
5 | 201.9 | - | - | 203.3 | - | - |
6 | 72.4 | 5.41, dd (12.9, 6.7) | 5, 7, 6-OAc | 72.7 | 5.60, dd (12.9, 6.8) | 5, 7, 6-OAc |
7a | 31.3 | 2.32, m | 5, 6, 8, 9 | 34.1 | 2.26, m | 5, 6, 9 |
7b | 2.60, ddd (13.3, 12.9, 2.6) | 6 | 2.54, dt (12.9, 2.3) | 5, 6 | ||
8 | 74.8 | 5.11, dd (2.6, 2.6) | 4, 6, 9, 10, 8-OAc | 73.8 | 3.90, dd (6.1, 3.0) | 4, 6, 9, 10 |
9 | 78.9 | - | - | 80.4 | - | - |
10 | 23.5 | 1.26, s | 4, 5, 8, 9 | 23.9 | 1.34, s | 4, 8, 9 |
NH | - | 6.68, dd (6.7, 5.8) | 1, 1’ | - | 6.84, dd (6.8, 5.6) | 1, 1’ |
1’ | 173.8 | - | - | 173.8 | - | - |
2’ | 36.2 | 2.27, m | 1’, 3’ | 36.2 | 2.27, m | 1’, 3’, 4’ |
3’ | 28.7 | 2.28, m | 4’ | 28.7 | 2.32, m | 1’, 2’, 4’, 5’ |
4’ | 130.7 | 5.45, m | 3’, 6’ | 130.7 | 5.45, m | 2’, 3’, 5’ |
5’ | 128.3 | 5.47, m | 4’, 7’ | 128.1 | 5.47, m | 3’, 4’, 7’ |
6’ | 36.3 | 2.18, m | 4’, 5’, 7’, 8’ | 36.3 | 2.19, m | 4’, 5’, 7’, 8’ |
7’ | 80.7 | 3.17, m | 5’, 8’, 9’, 15’ | 80.8 | 3.17, m | 5’, 8’, 9’, 15’ |
8’ | 33.3 | 1.42, m | 6’, 7’, 9’, 10’ | 33.4 | 1.43, m | 7’, 9’, 10’ |
9’ | 25.5 | 1.27, m e | - | 25.5 | 1.26, m f | - |
10’ | 29.9 | 1.27, m e | - | 29.9 | 1.26, m f | - |
11’ | 29.4 | 1.27, m e | - | 29.4 | 1.26, m f | - |
12’ | 32.0 c | 1.27, m e | - | 31.9 d | 1.26, m f | - |
13’ | 22.8 c | 1.27, m e | - | 22.8 d | 1.26, m f | - |
14’ | 14.2 | 0.87, t (6.7) | 12’, 13’ | 14.2 | 0.87, t (6.8) | 12’, 13’ |
15’ | 56.5 | 3.31, s | 7’ | 56.5 | 3.31, s | 7’ |
6-OAc | 170.3 | - | - | 170.4 | - | - |
20.8 | 2.16, s | 6-OAc | 20.9 | 2.15, s | 6-OAc | |
8-OAc/OH | 169.9 | - | - | - | 3.00, d (3.9) | 7, 8, 9 |
21.3 | 2.19, s | 8-OAc | - | - | - | |
9-OH | - | 5.69, s | 8, 9, 10 | - | 5.33, s | 8, 9, 10 |
Position | δC a | δH, mult (J in Hz) b | HMBC |
---|---|---|---|
1 | 37.3 | 4.08, d (6.1) | 2, 3, 4, 1’ |
2 | 135.1 | - | - |
3 | 120.9 | 6.29, s | 1, 2, 4 |
4 | 61.4 | - | - |
5 | 204.2 | - | - |
6 | 51.0 | 2.41, m | 5, 7, 8, 10 |
7 | 68.7 | 3.81, m | 6, 8, 9, 10 |
8a | 31.7 | 2.08, ddd (14.9, 8.5, 2.0) | 6, 7, 9 |
8b | 2.61, ddd (14.9, 4.7, 2.6) | 4, 6, 7 | |
9 | 62.1 | 3.26, dd (2.6, 2.0) | 4, 7, 8 |
10 | 12.4 | 1.24, d (7.0) | 5, 6, 7 |
NH | - | 6.03, t (6.1) | 1, 1’ |
1’ | 173.0 | - | - |
2’ | 36.4 | 2.21, m | 1’, 3’, 4’ |
3’ | 28.6 | 2.30, m | 2’, 4’, 5’ |
4’ | 130.7 | 5.45, m | 3’, 5’ 6’ |
5’ | 128.0 | 5.47, m | 3’, 4’, 6’, 7’ |
6’ | 36.4 | 2.18, m | 7’, 8’ |
7’ | 80.8 | 3.16, m | 5’, 8’, 9’, 15’ |
8’ | 33.5 | 1.42, m | 7’, 9’, 10’ |
9’ | 25.5 | 1.27, m d | - |
10’ | 29.9 | 1.27, m d | - |
11’ | 29.4 | 1.27, m d | - |
12’ | 32.0 c | 1.27, m d | - |
13’ | 22.8 c | 1.27, m d | - |
14’ | 14.2 | 0.88, t (6.8) | 12’, 13’ |
15’ | 56.6 | 3.31, s | 7’ |
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Sueyoshi, K.; Yamano, A.; Ozaki, K.; Sumimoto, S.; Iwasaki, A.; Suenaga, K.; Teruya, T. Three New Malyngamides from the Marine Cyanobacterium Moorea producens. Mar. Drugs 2017, 15, 367. https://doi.org/10.3390/md15120367
Sueyoshi K, Yamano A, Ozaki K, Sumimoto S, Iwasaki A, Suenaga K, Teruya T. Three New Malyngamides from the Marine Cyanobacterium Moorea producens. Marine Drugs. 2017; 15(12):367. https://doi.org/10.3390/md15120367
Chicago/Turabian StyleSueyoshi, Kosuke, Aki Yamano, Kaori Ozaki, Shimpei Sumimoto, Arihiro Iwasaki, Kiyotake Suenaga, and Toshiaki Teruya. 2017. "Three New Malyngamides from the Marine Cyanobacterium Moorea producens" Marine Drugs 15, no. 12: 367. https://doi.org/10.3390/md15120367