Carapanosins A–C from Seeds of Andiroba (Carapa guianensis, Meliaceae) and Their Effects on LPS-Activated NO Production
Abstract
:1. Introduction
2. Results and Discussion
3. Experimental
3.1. General Experimental Procedures
3.2. Isolation of Compounds 1–3
3.3. Cell Cultures
3.4. Determination of RAW264.7 Cell Proliferation
4. Conclusions
Acknowledgments
Author Contributions
Conflicts of Interest
References
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Position | 1 | 2 | ||||
---|---|---|---|---|---|---|
1H a (J, Hz) | 13C b | 1H a (J, Hz) | 13C b | HMBC | ||
1 | 84.5 (s) | 84.1 (s) | ||||
2 | 78.4 (s) | 83.4 (s) | ||||
3 | 4.57 s | 83.8 (d) | 5.19 s | 85.3 (d) | 4, 5 | |
4 | 43.9 (s) | 44.5 (d) | ||||
5 | 2.94 d (10.9) | 44.2 (d) | 2.47 brd | 44.7 (d) | 4, 9, 10, 29 | |
6 | A | 4.09 dd (12.1, 10.9) | 71.4 (d) | 6.31 brd | 71.2 (d) | 4, 5, 10 |
B | ||||||
7 | 173.6 (s) | 169.2 (s) | ||||
8 | 83.0 (s) | 83.5 (s) | ||||
9 | 85.2 (s) | 86.1 (s) | ||||
10 | 48.7 (s) | 48.8 (s) | ||||
11 | α | 2.02 dd (14.7, 13.5) | 31.9 (t) | 2.00 t (14.1) | 32.4 (t) | 9, 10, 12, 13 |
β | 3.21 dd (14.7, 4.2) | 2.35 dd (14.1, 4.1) | 2, 8, 9, 12 | |||
12 | α | 68.8 (d) | 68.5 (d) | 17, 18 | ||
β | 4.99 dd (13.5, 4.2) | 4.94 dd (14.1, 4.1) | ||||
13 | 42.1 (s) | 42.9 (s) | ||||
14 | 162.7 (s) | 152.6 (s) | ||||
15 | 6.06 s | 122.1 (d) | 6.62 s | 124.2 (d) | 8, 14, 16, | |
16 | 159.6 (s) | 163.4 (s) | ||||
17 | 5.29 s | 78.7 (d) | 5.91 s | 78.9 (d) | 12, 13, 14, 18, 20, 22, 23 | |
18 | 1.47 s | 14.8 (q) | 1.59 s | 14.4 (q) | 12, 13, 14, 17 | |
19 | 1.34 s | 14.8 (q) | 1.31 s | 16.4 (q) | 1, 5, 9, 10 | |
20 | 121.7 (s) | 121.0 (s | ||||
21 | 7.55 brs | 141.7 (d) | 7.45 brs | 142.1 (d) | 20, 22, 23 | |
22 | 6.54 dd (1.7, 0.6) | 110.2 (d) | 6.56 dd (2.0, 1.2) | 110.2 (d) | 21, 23 | |
23 | 7.42 t (1.7) | 143.2 (d) | 7.40 t (1.2) | 143.0 (d) | 20, 21, 22 | |
28 | 0.89 s | 15.7 (q) | 0.92 s | 15.3 (q) | 3, 4, 5, 29 | |
29 | pro-S | 1.75 d (10.8) | 39.9 (t) | 1.75 d (11.1) | 40.8 (t) | 1, 2, 3, 8 |
pro-R | 2.05 d (10.8) | 2.23 d (11.1) | ||||
30 | 5.71 s | 68.9 (d) | 5.35 s | 74.1 (d) | 1, 2, 8, 9 | |
31 | 119.7 (s) | 119.6 (s) | ||||
32 | 1.68 s | 21.0 (q) | 1.69 s | 16.4 (q) | 31 | |
1′ | 171.1 (s) | 169.0 (s) | ||||
2′ | 2.05 s | 20.8 (q) | 2.08 s | 21.7 (q) | 1′ | |
1′′ | 3.78 s | 52.5 (q) | 171.7 (s) | 7 | ||
2′′ | 2.20 s | 20.9 (q) | 7 | |||
1′′′′ | 172.3 (s) | 3.74 | 53.3 (q) | |||
2′′′′ | 1.58 s | 20.1 (q) | 1′′′ | |||
1′′′′ | 174.0 (s) | 170.4 (s) | ||||
2′′′′ | A | 2.31 dq (10.5, 7.4) | 27.8 (t) | 1.55 s | 19.8 (q) | 1′′′′, 3′′′′ |
B | 2.42 m | |||||
3′′′′ | 1.10 t (7.4) | 8.9 (q) | 1′′′′, 2′′′′ | |||
1′′′′′ | 173.9 (s) | |||||
2′′′′′ | 2.43 dq (10.6, 7.3) | 28.1 (t) | 1′′′′′, 3′′′′′ | |||
2.50 m | ||||||
3′′′′′ | 1.16 t (7.3) | 8.9 (q) | 1′′′′′, 2′′′′′ | |||
1-OH | ||||||
2-OH | 3.65 s |
Position | 3 | Position | 3 | |||
---|---|---|---|---|---|---|
1H a (J, Hz) | 13C b | 1H a (J, Hz) | 13C b | |||
1 | 7.06 d (10.3) | 156.4 (d) | 14 | 170.3 (s) | ||
2 | 5.87 d (10.3) | 125.8 (d) | 15 | 5.64 s | 111.0 (d) | |
3 | 203.8 (s) | 16 | 163.4 (s) | |||
4 | 43.7 (s) | 17 | 104.0 (s) | |||
5 | 2.16 dd (12.6, 4.1) | 45.5 (d) | 18 | 1.16 s | 23.3 (q) | |
6 | α | 1.97 m | 23.0 (t) | 19 | 1.25 s | 18.8 (q) |
β | 1.99 m | 20 | 125.0 (s) | |||
7 | 5.25 t (2.9) | 73.2 (d) | 21 | 7.58 brs | 142.9 (d) | |
8 | 44.4 (s) | 22 | 6.48 dd (1.8, 0.9) | 125.0 (d) | ||
9 | 2.20 dd (11.4, 8.5) | 37.2 (d) | 23 | 7.43 t (1.8) | 141.6 (d) | |
10 | 40.4 (s) | 28 | 1.08 s | 26.8 (q) | ||
11 | α | 2.00 m | 15.1 (t) | 29 | 1.09 s | 21.1 (q) |
β | 1.86 ddd (14.1, 11.4, 1.7) | 30 | 1.36 s | 24.1 (q) | ||
12 | α | 2.30 dt (14.1, 9,9) | 23.2 (t) | 1′ | 169.6 (s) | |
β | 1.60 m | 2′ | 1.98 s | 20.7 (q) | ||
13 | 42.0 (s) |
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Higuchi, K.; Miyake, T.; Ohmori, S.; Tani, Y.; Minoura, K.; Kikuchi, T.; Yamada, T.; Tanaka, R. Carapanosins A–C from Seeds of Andiroba (Carapa guianensis, Meliaceae) and Their Effects on LPS-Activated NO Production. Molecules 2017, 22, 502. https://doi.org/10.3390/molecules22030502
Higuchi K, Miyake T, Ohmori S, Tani Y, Minoura K, Kikuchi T, Yamada T, Tanaka R. Carapanosins A–C from Seeds of Andiroba (Carapa guianensis, Meliaceae) and Their Effects on LPS-Activated NO Production. Molecules. 2017; 22(3):502. https://doi.org/10.3390/molecules22030502
Chicago/Turabian StyleHiguchi, Keiichiro, Teppei Miyake, Shoko Ohmori, Yoshimi Tani, Katsuhiko Minoura, Takashi Kikuchi, Takeshi Yamada, and Reiko Tanaka. 2017. "Carapanosins A–C from Seeds of Andiroba (Carapa guianensis, Meliaceae) and Their Effects on LPS-Activated NO Production" Molecules 22, no. 3: 502. https://doi.org/10.3390/molecules22030502