Table 2 1H (500 MHz, MeOD) and 13C (150 MHz, MeOD) data of HOP1, HOP2 and HOP3
From: Cycloartanes from Oxyanthus pallidus and derivatives with analgesic activities
Positions | HOP1 | HOP2 | HOP3 | |||
|---|---|---|---|---|---|---|
δC | δH (mult, J(Hz) | δC | δH (mult, J(Hz) | δC | δH (mult, J (Hz) | |
1 | 30.4 | 1.40 (1H, m, Hβ), 1.60 (1H, m, Hα) | 29.1 | 1.62 (1H, m, Hβ), 1.72 (1H, m, Hα) | 29.1 | 1.62 (1H, m, Hβ), 1.72 (1H, m, Hα) |
2 | 29.1 | 1.62 (1H, m, Hα), 1.73 (1H, m, Hβ) | 27.0 | 1.43 (1H, m, Hα), 1.62 (1H, m, Hβ) | 27.0 | 1.43 (1H, m, Hα), 1.62 (1H, m, Hβ) |
3 | 77.8 | 3.22 (dd, 4.4, 11.1) | 77.8 | 3.23 (dd, 4.2, 10.9) | 77.8 | 3.23 (dd, 4.2, 10.9) |
4 | 39.8 | / | 39.8 | / | 39.8 | / |
5 | 44.3 | 1.42 (dd, 3.9, 13.3) | 44.2 | 1.45 (dd, 3.9, 13.1) | 44.2 | 1.45 (dd, 3.9, 13.1) |
6 | 28.1 | 1.08 (1H, m, Hα), 2.13 (1H, m, Hβ) | 28.1 | 1.10 (1H, m, Hα), 2.13 (1H, m, Hβ) | 28.1 | 1.10 (1H, m, Hα), 2.13 (1H, m, Hβ) |
7 | 80.0 | 3.63 (ddd (4,0, 7.63, 12.6) | 80.0 | 3.63 (ddd (4,0, 7.1, 12.7) | 80.0 | 3.63 (ddd (4,0, 7.1, 12.7) |
8 | 50.2 | 2.09 (1H, d, 7.63) | 50.0 | 2.11 (1H, d, 6.0) | 50.0 | 2.11 (1H, d, 6.0) |
9 | 20.1 | / | 20.2 | / | 20.2 | / |
10 | 26.4 | / | 26.4 | / | 26.4 | / |
11 | 26.5 | 1.33 (1H, m, Hα), 1.90 (1H, m, Hβ) | 30.3 | 1.42 (1H, m, Hα), 1.62 (1H, m, Hβ) | 30.3 | 1.42 (1H, m, Hα), 1.62 (1H, m, Hβ) |
12 | 32.3 | 1.60 (1H, m, Hα), 1.68 (1H, m, Hβ) | 32.4 | 1.60 (1H, m, Hα), 1.69 (1H, m, Hβ) | 32.4 | 1.60 (1H, m, Hα), 1.69 (1H, m, Hβ) |
13 | 46.4 | / | 46.4 | / | 46.4 | / |
14 | 45.3 | / | 45.3 | / | 45.3 | / |
15 | 46.6 | 1.64 (1H, dd, 5.0, 7.5, Hβ), 2.33 (1H, dd, 5.0 7.5, Hα) | 46.4 | 1.63 (1H, dd, 5.2, 7.6, Hβ), 2.31 (1H, dd, 5.2, 7.6, Hα) | 46.4 | 1.63 (1H, dd, 5.2, 7.6, Hβ), 2.31 (1H, dd, 5.2, 7.6, Hα) |
16 | 71.9 | 4.46 (1H, ddd, 5.0, 7.6, 7.8) | 72.3 | 4.43 (1H, ddd, 5.2, 7.6, 7.9) | 72.3 | 4.43 (1H, ddd, 5.2, 7.6, 7.9) |
17 | 56.0 | 1.62 (1H, dd, 7.7, 12.2) | 56.0 | 1.64 (1H, dd, 7.9, 12.4) | 56.0 | 1.64 (1H, dd, 7.9, 12.4) |
18 | 16.2 | 1.18 (3H, s) | 16.1 | 1.20 (3H, s) | 16.1 | 1.20 (3H, s) |
19 | 24.9 | 0.20 (1H, d, 4.5, Hα) 0.85 (1H, d, 4.5, Hβ) | 24.7 | 0.18 (1H, d, 4.6, Hα), 0.87 (1H, d, 4.6, Hβ) | 24.7 | 0.18 (1H, d, 4.6, Hα), 0.87 (1H, d, 4.6, Hβ) |
20 | 29.7 | 1.72 (1H, m) | 28.5 | 1.95 (1H, m) | 28.5 | 1.91 (1H, m) |
21 | 17.0 | 0.97 (1H, d, 7.6) | 17.2 | 0.97 (1H, d, 7.6) | 17.2 | 0.97 (1H, d, 7.6) |
22 | 32.9 | 2.78 (1H, m, Hα), 2.86 (1H, m, Hβ) | 32.4 | 1.22 (1H, m, Hα), 1.81 (1H, m, Hβ) | 32.4 | 1.82 (1H, m, Hα), 1.01 (1H, m, Hβ) |
23 | 29.5 | 1.21 (1H, m, Hα), 1.97 (1H, m, Hβ) | 30.3 | 1.42 (1H, m, Hα), 1.62 (1H, m, Hβ) | 31.3 | 2.12 (1H, m, Hα), 1.12 (1H, m, Hβ) |
24 | 218.1 | / | 77.0 | 3.36 (1H, dd, 5.1, 12.0) | 79.5 | 3.46 (1H, dd, 5.1, 12.0) |
25 | 76.5 | / | 71.9 | / | 71.9 | / |
26 | 25.4 | 1.32 (3H, s) | 25.4 | 1.32 (3H, s) | 25.4 | 1.32 (3H, s) |
27 | 24.8 | 1.00 (3H, s) | 24.0 | 1.18 (3H, s) | 24.5 | 1.18 (3H, s) |
28 | 24.9 | 1.00 (3H, s) | 24.9 | 1.00 (3H, s) | 24.9 | 1.00 (3H, s) |
29 | 12.2 | 0.82 (3H, s) | 12.8 | 0.82 (3H, s) | 12.8 | 0.82 (3H, s) |
30 | 18.5 | 0.96 (3H, s) | 18.5 | 0.94 (3H, s) | 18.5 | 0.94 (3H, s) |
1’ | 102.6 | 4.36 (1H, d, 7.8) | 102.6 | 4.35 (1H, d, 7.7) | 102.5 | 4.35 (1H, d, 7.7) |
2’ | 73.9 | 3.18 (1H, dd, 7.8, 8.8) | 73.9 | 3.18 (1H, dd, 7.7, 8.7) | 73.9 | 3.18 (1H, dd, 7.7, 8.7) |
3’ | 76.9 | 3.37 (1H, dd, 8.5, 8.8) | 76.9 | 3.40 (1H, dd, 8.7, 9.0) | 76.9 | 3.40 (1H, dd, 8.7, 9.0) |
4’ | 70.2 | 3.28 (1H, dd, 8.5, 9.0) | 70.2 | 3.27 (1H, dd, 9.0, 9.2) | 70.2 | 3.27 (1H, dd, 9.0, 9.2) |
5’ | 73.7 | 3.48 (1H, m) | 73.7 | 3.48 (1H, m) | 73.7 | 3.48 (1H, m) |
6’ | 63.9 | 4.11 (1H, dd, 2.1, 11.9), 4.48 (1H, dd, 2.1, 11.9) | 63.9 | 4.11 (1H, dd, 2.0, 12.0), 4.48 (1H, dd, 2.0, 12) | 63.9 | 4.11 (1H, dd, 2.0, 12.0), 4.48 (1H, dd, 2.0, 12) |