Table 2.
1H-NMR data for sesquiterpenoids drimenol, polygodial (1), isotadeonal (2), drimenal (3) and winterdial (4). Data were acquired in a 600 MHz spectrometer, in CDCl3. Chemical shifts (δ) are reported in ppm. Coupling constants (J) are reported in Hz. Hydrogen positions correspond to the labels provided in Figure 1.
| Position | Compound | ||||
|---|---|---|---|---|---|
| Drimenol | 1 | 2 | 3 | 4 | |
| 1 | 1.06, td, J = 13.1, 3.7 | 1.39, td, J = 13.2, 2.5 | 1.77, m | 1.28, td, J = 13.3, 4.3 | |
| 1.95, ov | 1.84, dq, J = 13.2, 2.5 | 1.47, ov | 1.67, m | - | |
| 2 | 1.45, ov | 1.52, 2H, m | 1.62, dt, J = 16.0, 2.8 | 1.55, m | 1.74, m |
| 1.56, qt, J = 13.6, 3.1 | 1.47, ov | 1.43, ov | 1.83, m | ||
| 3 | 1.42, ov | 1.49, m | 1.17, m | 1.43, ov | 2.52, m |
| 1.18, ov | 1.24, m | 1.47, ov | 1.22, dd, J = 13.5, 3.5 | 2.93, dt, J = 20.4, 2.9 | |
| 4 | - | - | - | - | - |
| 5 | 1.17, ov | 1.26, m | 1.55, dd, J = 6.8, 4.9 | 1.16, dd, J = 12.1, 4.7 | - |
| 6 | 1.98, ov | 2.51, ddddd, J = 20.3, 5.5, 4.5, 2.1, 0.8 | 2.55, dt, J = 20.6, 4.6 | 2.07, d, J = 17.7 | 1.27, m |
| 1.86, ov | 2.32, dddd, J = 20.4, 12.1, 3.9, 2.4 | 2.20, ddt, J = 20.6, 11.8, 2.2 | 1.96, m | 2.02, ov | |
| 7 | 5.54, m | 7.14, dt, J = 5.0, 2.2 | 7.08, dd, J= 2.6, 2.3 | 5.68, m | 7.01, dd, J = 5.4, 2.7 |
| 8 | - | - | - | - | - |
| 9 | 1.84, ov | 2.83, ddd, J = 6.1, 4.1, 2.1 | 3.25, t, J = 1.91 | 2.59, s | 3.74, s |
| 10 | - | - | - | - | - |
| 11 | 3.85, dd, J = 11.3, 3.4 | 9.53, d, J = 4.4 | |||
| 3.73, dd, J = 11.3, 5.0 | 9.84, d, J = 2.6 | 9.68, d, J = 5.6 | 9.87, d, J = 3.3 | ||
| 12 | 1.78, s | 9.46, s | 9.40, s | 1.63, s | 9.36, s |
| 13 | 0.86, s | 0.92, s | 0.95, s | 1.06, s | 1.17, s |
| 14 | 0.88, s | 0.96, s | 0.92, s | 0.93, s | 1.06, s |
| 15 | 0.85, s | 0.95, s | 0.90, s | 0.89, s | 1.23, s |
| 2’ | 6.29, d, J = 16.2 | ||||
| 3’ | 7.55, ov | ||||
| 5’ | 7.55, ov | ||||
| 6’ | 6.89, d, J = 8.7 | ||||