Table 2.
1D- and 2D NMR spectroscopic data of compounds (1-3) in CDCl3.
| Position | Isosakuranetin (2) | Odoratenin (1) | Subscandenin (3) | |||||
|---|---|---|---|---|---|---|---|---|
| δ H (J in Hz) | δ c | δ H (J in Hz) | δ c | HMBC | δ H (J in Hz) | δ c | HMBC | |
| 2 | 5.36 (dd; J=13.2, 3.2 Hz, 1H) | 79.10 | 5.32 (dd; J=12.8, 3.2 Hz, 1H) | 79.06 | - | 5.34 (dd; J=13.2, 3.2 Hz, 1H) | 79.13 | - |
| 3a | 2.78 (dd; J=17.8, 3.2 Hz, 1H) | 43.20 | 2.78 (dd; J=17.0, 3.2 Hz, 1H) | 43.30 | C-4 | 2.77 (dd; J=17.2, 3.2 Hz, 1H) | 43.29 | C-4 |
| 3b | 3.09 (dd; J=17.0, 13.2 Hz, 1H) | 3.07 (dd; J=17.2, 12.8 Hz, 1H) | C-2, 4 | 3.07 (dd; J=17.2, 12.8 Hz, 1H) | C-2, 4 | |||
| 4 | - | 196.18 | - | 196.07 | - | 196.96 | - | |
| 5 | 12.04 (s; 1H) | 164.43 | 12.01 (s; 1H) | 162.93 | C-6, 7, 8, 10 | 12.19 (s; 1H) | 158.78 | - |
| 6 | 5.97 (d; J=2.4 Hz, 1H) | 96.76 | 6.06 (d; J=2.8 Hz, 1H) | 95.19 | C-4, 7, 9, 10 | 6.10 (s; 1H) | 94.66 | C-5, 8, 9, 10 |
| 7 | 5.76 (br s; 1H) | 164.59 | - | 164.19 | 6.46 (br s; 1H) | 154.43 | - | |
| 7-OMe | - | - | 3.82 (s; 3H) | 55.79 | C-9 | - | - | - |
| 8 | 5.99 (d; J=2.4 Hz, 1H) | 95.54 | 6.04 (d; J=2.4 Hz, 1H) | 94.33 | C-6, 9, 10 | - | 128.38 | - |
| 8-OMe | - | - | - | - | - | 3.94 (s; 3H) | 61.09 | C-4, 8 |
| 9 | - | 163.36 | - | 168.05 | - | - | 157.50 | - |
| 10 | - | 103.20 | - | 103.20 | - | - | 103.19 | - |
| 1' | - | 130.36 | - | 147.06 | - | - | 130.36 | - |
| 2' | 7.37 (d; J=8.8 Hz, 1H) | 114.33 | 7.04 (d; J=2,0 Hz, 1H) | 112.73 | C-2, 1', 4' | 6.95 (d; J=10 Hz, 1H) | 127.81 | C-1', 3', 4', 5' |
| 3' | 6.95 (d; J=8.4 Hz, 1H) | 127.85 | 5.69 (s; 1H) | 145.99 | - | 7.37 (d; J=9,2 Hz, 1H) | 114.30 | C-1', 2', 4', 6' |
| 4' | - | 160.14 | 6.91 (d, J=1.6 Hz, 1H) | 118.26 | C-1' | - | 160.13 | - |
| 4'-OMe | 3.83 (s; 3H) | 55.48 | - | - | - | 3.82 (s; 3H) | 55.46 | C-4' |
| 5' | 6.95 (d; J=8.4 Hz, 1H) | 127.85 | 6.88 (d; J=8.4 Hz, 1H) | 110.72 | C-2, 2', 3', 6' | 7.37 (d; J=9.2 Hz, 1H) | 114.30 | C-1', 2', 4', 6' |
| 6' | 7.37 (d; J=8.8 Hz, 1H) | 114.33 | - | 131.59 | - | 6.95 (d; J=10 Hz, 1H) | 127.81 | C-1', 3', 4', 5' |
| 6'-OMe | - | - | 3.92 (s; 3H) | 56.14 | C-1' | - | - | - |