Table 4. 1H NMR (500 MHz, coupling constant J in Hz in parentheses, CD3OD) data of iridoids 7-11 .
Chemical shift dH in ppm | |||||
Position | 7 | 8 | 9 | 10 | 11 |
1 | 5.61 d (2.6) | 5.38 s | 5.89 s | 5.85 s | 5.95 s |
2 | - | - | - | - | - |
3 | 7.44 d (0.9) | 7.46 s | 7.54 s | 7.59 s | 7.48 d (1.3) |
4 | - | - | - | - | - |
5 | 3.04 dd (10.1, 2.9) | - | - | - | 3.11 dd (9.0, 1.4) |
6 | 4.08 m | 4.18 d (4.5) | 3.78 d (9.7) | 4.32 t (4.47) | 4.37 m |
7a | 1.86 dd (13.2, 6.0) | 3.66 d (4.5) | 4.08 d (9.7) | 1.52 m | 2.05 dd (14.9, 5.3) |
7b | 2.06 dd (13.2, 6.4) | - | - | 1.83 m | 2.24 d (15.0) |
8 | - | - | - | 2.54-2.70* | - |
9 | 2.65 dd (10.2, 2.5) | 2.51 s | 2.56 s | 2.54-2.70* | 3.03 dd (9.0, 2.1) |
10 | 1.30 s | 1.39 s | 1.16 s | 0.98 d (6.9) | 1.55 s |
11 | - | - | - | - | - |
11-OMe | 3.77 s | 3.73 s | 3.78 s | 3.76 s | 3.75 s |
Me-COO | - | - | - | - | 2.05 s |
1’ | 3.67 (d (7.8) | 4.61 d (8.0) | 4.64 d (7.8) | 4.61 d (7.7) | 4.67d (7.8) |
2’ | 3.20 t (8.3) | 3.20 t (8.5) | 3.23 t (8.8) | 3.22 dd (8.9, 7.9) | 3.21 t (8.4) |
3’ | 3.36-3.44* | 3.35-3.38* | 3.36-3.47* | .3.36-3.46* | 3.36-3.45* |
4’ | 3.25-3.34* | 3.22-3.31* | 3.27-3.35* | 3.22-3.35* | 3.25-3.35* |
5’ | 3.33-3.40* | 3.31-3.36* | 3.32-3.39* | 3.33-3.39* | 3.33-3.40* |
6’a | 3.68 dd (12.0, 5.7) | 3.66-3.71* | 3.70 dd (11.9, 5.5) | 3.69 dd (12.0, 5.8) | 3.64-3.75* |
6’b | 3.94 dd (11.9, 1.6) | 3.90 d (12.0) | 3.94 dd (11.9, 1.6) | 3.95 dd (11.9, 1.8) | 3.90-3.96* |