Table 1.
1H NMR (400 MHz) and 13C NMR (100 MHz) data of 4-benzyloxylonchocarpin (1) and muracatane A (2).
| 1 | 2 | ||||
|---|---|---|---|---|---|
| No | δH (nH, Multiplicity, J in Hz) | δC | No | δH (nH, Multiplicity, J in Hz) | δC |
| 1′ | - | 109.4 | 1 | - | 158.7 |
| 2′ | - | 160.9 | 2 | - | 138.4 |
| 3′ | - | 114.1 | 3 | 7.60 (1H, d, J = 8.0 Hz) | 136.4 |
| 4′ | - | 159.6 | 4 | 8.00 (1H, d, J = 8.0 Hz) | 123.2 |
| 5′ | 6.37 (1H, d, J = 9.0 Hz) | 108.1 | 4a | - | 137.0 |
| 6′ | 7.72 (1H, d, J = 9.0 Hz) | 130.5 | 5 | - | 159.8 |
| α | 7.45 (1H, d, J = 16 Hz, 1H) | 127.8 | 6 | 7.30 (1H, dd, J = 8.0, 2.0 Hz) | 117.1 |
| β | 7.86 (1H, d, J = 16.0 Hz, 1H) | 144.0 | 7 | 7.70 (1H, t, J = 8.0 Hz) | 135.0 |
| keto | - | 191.9 | 8 | 7.90 (1H, dd, J = 8.0, 2.0 Hz) | 119.6 |
| OH-2′ | 13.77 | 8a | - | 137.0 | |
| 1 | - | 128.0 | 9 | - | 182.7 |
| 2,6 | 7.60 (2H, BB′) | 130.3 | 9a | - | 124.8 |
| 3,5 | 7.00 (2H, AA′) | 115.3 | 10 | - | 182.1 |
| 4 | - | 160.9 | 10a | - | 120.9 |
| 1′′ | 6.76 (1H, d, J = 10 Hz) | 115.9 | 1′ | 3.34 (1H, d, J = 8.0 Hz) | 30.1 |
| 2′′ | 5.59 (1H, d, J = 10 Hz) | 127.4 | 2′ | 3.90 (1H, t, J = 8.0 Hz) | 51.3 |
| 3′′ | - | 77.7 | CO2Me | 3.70 (6H, s) | 52.6 |
| 4′′,5′′ | 1.47 (6H, s) | 28.3 | CO2Me | - | 169.0 |
| 1′′′ | - | 136.3 | 1-OMe | 3.97 (3H, s) | 62.0 |
| 2′′′–6′′′ | 7.46 (2H, m) | 127.4 | 5-OMe | 4.04 (3H, s) | 56.3 |
| 3′′′,5′′′ | 7.40 (2H, m) | 128.6 | |||
| 4′′′ | 7.32 (1H, m) | 127.8 | |||
| CH2Bn | 5.12 (2H, s) | 70.1 |