Table 1.
13C (100 MHz, CDCl3) and 1H-NMR (400 MHz, CDCl3) data of 15-copaenol, 15-copaenyl acetate, and 15-copaenal.
| Hydrogen and carbon number a | 13C chemical shift (ppm) | 1H chemical shift (ppm) | ||||
|---|---|---|---|---|---|---|
| 15-Copaenol (6) c | 15-Copaenyl acetate (6AC) | 15-Copaenal (6OX) | 15-Copaenol (6) c | 15-Copaenyl acetate (6AC) | 15-Copaenal (6OX) | |
| 1 b | 44.8 | 44.7 | 44.3 | 1.59 m (1) | 1.61–1.57 m (1) | 1.58 s (1) |
| 2 | 50.7 | 50.9 | 45.0 | 1.72 d, J = 1 (1) | 1.77–1.70 m (1) | 2.46 d, J = 6 (1) |
| 3 | 147.6 | 142.8 | 151.3 | – | – | – |
| 4 | 118.3 | 121.7 | 148.3 | 5.48 m (1) | 5.58–5.14 m (1) | 6.73–6.68 m (1) |
| 5 | 30.3 | 30.4 | 32.2 | 2.26 bs (2) | 2.26 bs (2) | 2.55 d, J = 3 (2) |
| 6 | 37.6 | 37.5 | 37.6 | 2.12 m (1) | 2.14–2.10 m (1) | 2.23–2.18 m (1) |
| 7 | 39.7 | 39.8 | 39.3 | – | – | – |
| 8 | 36.4 | 36.4 | 35.9 | 1.73/1.63 m (1) | 1.77–1.70/1.63–1.61 m (1) | 1.77–1.71 m (2) |
| 9 | 22.1 | 22.0 | 22.1 | 1.53/1.59 m (1) | 1.61–1.57/1.54–1.50 m (1) | 1.70–1.60/1.56–1.44 m (1) |
| 10 b | 44.9 | 44.9 | 44.3 | 1.69 m (1) | 1.70–1.68 m (1) | 1.70–1.60 m (1) |
| 11 | 32.5 | 32.5 | 32.5 | 1.51 m (1) | 1.54–1.50 m (1) | 1.56–1.44 m (1) |
| 12 b | 20.0 | 19.8 | 19.8 | 0.82 d, J = 7 (3) | 0.83 d, J = 7 (3) | 0.81 d, J = 7 (3) |
| 13 b | 20.0 | 20.0 | 20.1 | 0.84 d, J = 7 (3) | 0.84 d, J = 7 (3) | 0.84 d, J = 7 (3) |
| 14 | 20.4 | 20.3 | 20.3 | 0.78 s (3) | 0.77 s (3) | 0.70 s (3) |
| 15 | 66.4 | 67.4 | 191.9 | 3.98 d, J = 1 (2) | 4.44 dd, J = 7;1 (2) | 9.43 s (1) |
| 1’ | - | 171.4 | - | - | - | - |
| 2’ | - | 21.4 | - | - | 2.05 s (3) | - |
s, singlet; bs, broad singlet; d, doublet; dd, doublet of doublets; m, multiplet; (No), Integration; J (Hz). a Hydrogen assignment was performed using COSY, HSQC-ed, and HMBC data; carbon assignment was performed using DEPT 135 and HSQC-ed data. b Assignment could be exchanged. c Indicates data of 15-copaenol extracted from Espinoza et al. (2018).