Cytotoxic and Antiviral Triterpenoids from the Mangrove Plant Sonneratia paracaseolaris
Abstract
:1. Introduction
2. Results and Discussion
2.1. Structure Elucidation
2.2. Biological Evaluations
3. Materials and Methods
3.1. General Experimental Procedures
3.2. Plant Material
3.3. Extraction and Isolation
3.4. Cytotoxicity Assay
3.5. Anti-H1N1 Virus Assay
4. Conclusions
Supplementary Materials
Acknowledgments
Author Contributions
Conflicts of Interest
References
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Sample Availability: Samples of the compounds are not available from the authors. |
Compounds | 1 b,c | 2 b | 3 b | 4 b | ||||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|
No. | δH | δC | δH | δC | δH | δC | δH | δC | ||||
1 | 3.14 m (W1/2 22.1) | 77.9 | d | 3.30 dd (10.8, 4.7) | 77.2 | d | 3.27 d | 77.2 | d | 1.87 m 0.84m | 47.7 | d |
2 | 1.47 m | 38.5 | t | 1.68 m | 34.0 | t | 1.68 m | 33.8 | t | 3.67 m (W1/2 26.6 ) | 64.9 | t |
3 | 2.96 m (W1/2 22.8) | 74.0 | d | 4.47 dd (11.9, 4.7) | 76.7 | d | 4.40 dd (12.5, 4.5) | 76.9 | d | 4.48 d (10.0 ) | 83.4 | d |
4 | 38.0 | s | 37.6 | s | 37.4 | s | 39.1 | s | ||||
5 | 0.46 d (11.0) | 52.6 | d | 0.68 m | 52.2 | d | 0.65 m | 52.2 | d | 0.86 m | 54.5 | d |
6 | 1.38 m | 17.6 | t | 1.43 m | 17.4 | t | 1.43 m | 17.4 | t | 1.28 m | 17.8 | t |
7 | 1.28 m | 33.9 | t | 1.28 m | 33.8 | t | 1.28 m | 33.8 | t | 1.40 m 1.29 m | 33.6 | t |
8 | 41.0 | t | 41.0 | t | 41.0 | t | 40.5 | t | ||||
9 | 1.36 m | 51.0 | d | 1.44 m | 50.7 | d | 1.43 m | 50.7 | d | 1.32 m | 49.6 | d |
10 | 42.9 | s | 42.8 | s | 42.8 | s | 37.7 | s | ||||
11 | 1.13 m 2.35 m | 23.1 | t | 1.15 m 2.35 m | 23.0 | t | 1.11 m 2.32 m | 23.0 | t | 1.29 m 2.34 m | 20.5 | t |
12 | 0.87 m 1.48 m | 25.1 | d | 0.90 m 1.49 m | 25.0 | d | 0.97 m 1.49 m | 25.1 | d | 0.93 m 1.60 m | 24.7 | d |
13 | 1.59 m | 36.5 | d | 1.59 m | 36.5 | d | 1.60 m | 36.5 | d | 1.60 m | 36.7 | d |
14 | 42.3 | s | 42.3 | s | 42.3 | s | 42.3 | s | ||||
15 | 1.57 m | 26.7 | t | 1.61 m | 26.8 | t | 1.61 m | 26.7 | t | 1.62 m | 26.6 | t |
16 | 1.01 m 1.88 m | 29.1 | t | 1.04 m 1.88 m | 29.1 | t | 1.02 m 1.88 m | 29.1 | t | 1.01 m 1.88 m | 29.0 | t |
17 | 47.3 | s | 47.3 | s | 47.3 | s | 47.3 | s | ||||
18 | 1.45 m | 48.2 | d | 1.44 m | 48.2 | d | 1.46 m | 48.2 | d | 1.46 m | 48.1 | d |
19 | 2.36 m | 47.3 | d | 2.36 m | 47.3 | d | 2.36 m | 47.3 | d | 2.35 m | 47.4 | d |
20 | 150.4 | s | 150.4 | s | 150.4 | s | 150.3 | s | ||||
21 | 1.22 m 1.83 m | 29.3 | t | 1.22 m 1.83 m | 29.3 | t | 1.24 m 1.84 m | 29.2 | t | 1.24 m 1.84 m | 29.3 | t |
22 | 0.87 m 1.85 m | 33.8 | t | 0.86 m 1.85 m | 33.7 | t | 0.83 m1.85 m | 33.7 | t | 0.84 m 1.85 m | 33.8 | t |
23 | 0.83 s | 28.0 | q | 0.77 s | 27.6 | q | 0.76 s | 27.5 | q | 0.78 s | 28.3 | q |
24 | 0.61 s | 15.4 | q | 0.84 s | 16.0 | q | 0.71 s | 16.0 | q | 0.83 s | 17.6 | q |
25 | 0.76 s | 12.2 | q | 0.84 s | 12.2 | q | 0.81 s | 12.1 | q | 0.87 s | 17.0 | q |
26 | 0.98 s | 16.0 | q | 1.00 s | 16.2 | q | 0.99 s | 16.1 | q | 0.99 s | 15.7 | q |
27 | 0.93 s | 14.5 | q | 0.96 s | 14.5 | q | 0.95 s | 14.5 | q | 0.96 s | 14.4 | q |
28 | 3.07 d (10.8) | 58.0 | t | 3.07 d (10.7) | 58.0 | t | 3.07 d (10.8) | 57.9 | t | 3.07 d (10.8) | 57.9 | t |
3.51 d (10.8) | 3.51 d (10.7) | 3.51 d (10.8) | 3.51 d (10.8) | |||||||||
29 | 4.53 s 4.66 s | 109.6 | t | 4.54 s 4.67 s | 109.5 | t | 4.54 s 4.67 s | 109.6 | t | 4.55 s 4.68 s | 109.6 | t |
30 | 1.63 s | 18.7 | q | 1.64 s | 18.7 | q | 1.64 s | 18.7 | q | 1.65 s | 18.8 | q |
1′ | 160.0 | s | 159.6 | s | 159.9 | s | ||||||
2′,6′ | 7.53 d (8.6) | 130.3 | d | 7.60 d (8.6) | 132.4 | d | 7.49 d (8.6) | 130.1 | d | |||
3′,5′ | 6.77 d (8.6) | 115.8 | d | 6.72 d (8.6) | 115.0 | d | 6.74 d (8.6) | 116.0 | d | |||
4′ | 124.9 | s | 125.1 | s | 124.3 | s | ||||||
7′ | 7.51 d (16.0) | 144.5 | d | 6.82 d (13.0) | 143.1 | d | 7.51 d (16.2) | 144.2 | d | |||
8′ | 6.33 d (16.0) | 114.4 | d | 5.73 d (13.0) | 115.0 | d | 6.32 d (16.2) | 114.4 | d | |||
9′ | 166.2 | s | 165.8 | s | 166.7 | s |
Compound | 11 b | ||
---|---|---|---|
No. | δH | δC | |
1 | 1.88 m 0.95 m | 47.6 | t |
2 | 3.69 m (W1/2 22.9) | 64.8 | d |
3 | 4.51 d (9.9) | 83.6 | d |
4 | 39.8 | s | |
5 | 0.93 m | 54.4 | d |
6 | 1.47 m 1.88 m | 17.9 | t |
7 | 1.54 m | 32.5 | t |
8 | 41.7 | t | |
9 | 1.56 m | 46.8 | d |
10 | 37.5 | s | |
11 | 1.89 m | 23.9 | t |
12 | 5.15 br s | 125.1 | d |
13 | 138.4 | s | |
14 | 41.7 | s | |
15 | 1.80 m | 27.5 | t |
16 | 1.53 m | 23.0 | t |
17 | 30.3 | s | |
18 | 2.12 d (11.0) | 52.4 | d |
19 | 1.32 m | 38.5 | d |
20 | 1.56 m | 38.5 | d |
21 | 1.91 m | 36.4 | t |
22 | 1.80 m | 39.6 | t |
23 | 0.80 s | 28.5 | q |
24 | 0.85 s | 17.1 | q |
25 | 0.97 s | 17.1 | q |
26 | 0.76 s | 16.4 | q |
27 | 1.07 s | 23.2 | q |
28 | 0.92 s | 21.1 | q |
29 | 0.83 d (6.1) | 23.2 | q |
30 | 181.4 | s | |
1′ | 125.1 | s | |
2′,6′ | 7.55 d (8.8) | 130.2 | d |
3′,5′ | 6.79 d (8.8) | 115.8 | d |
4′ | 159.8 | s | |
7′ | 7.52 d (16.4) | 144.1 | d |
8′ | 6.38 d (16.4) | 115.0 | d |
9′ | 166.7 | s |
Compounds | P388 a | HeLa b | A549 b | K562 a |
---|---|---|---|---|
1 | >50 | >50 | >50 | >50 |
2 | 27.25 | >50 | >50 | >50 |
3 | 22.39 | 33.20 | 14.43 | >50 |
4 | 10.56 | 19.13 | 1.89 | >50 |
5 | >50 | >50 | >50 | >50 |
6 | 44.40 | 42.46 | >50 | >50 |
7 | 41.97 | >50 | >50 | >50 |
8 | 34.38 | >50 | 27.49 | >50 |
9 | 22.36 | 27.15 | 15.43 | >50 |
10 | 39.03 | >50 | 37.32 | >50 |
11 | >50 | 30.41 | >50 | >50 |
12 | 39.77 | >50 | 18 | >50 |
13 | >50 | >50 | 23.90 | >50 |
14 | 11.04 | 13.10 | >50 | >50 |
15 | 23.04 | 24.90 | >50 | 16.28 |
16 | >50 | >50 | >50 | >50 |
17 | >50 | >50 | >50 | >50 |
ADM (Adriamycin) c | 0.3 | 0.6 | 0.2 | 0.2 |
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Share and Cite
Gong, K.-K.; Li, P.-L.; Qiao, D.; Zhang, X.-W.; Chu, M.-J.; Qin, G.-F.; Tang, X.-L.; Li, G.-Q. Cytotoxic and Antiviral Triterpenoids from the Mangrove Plant Sonneratia paracaseolaris. Molecules 2017, 22, 1319. https://doi.org/10.3390/molecules22081319
Gong K-K, Li P-L, Qiao D, Zhang X-W, Chu M-J, Qin G-F, Tang X-L, Li G-Q. Cytotoxic and Antiviral Triterpenoids from the Mangrove Plant Sonneratia paracaseolaris. Molecules. 2017; 22(8):1319. https://doi.org/10.3390/molecules22081319
Chicago/Turabian StyleGong, Kai-Kai, Ping-Lin Li, Dan Qiao, Xing-Wang Zhang, Mei-Jun Chu, Guo-Fei Qin, Xu-Li Tang, and Guo-Qiang Li. 2017. "Cytotoxic and Antiviral Triterpenoids from the Mangrove Plant Sonneratia paracaseolaris" Molecules 22, no. 8: 1319. https://doi.org/10.3390/molecules22081319