TABLE 1.
1H and 13C NMR assignments of germacrene C (1) and valerena-1,10-diene (2)
Compound 1 was purified from root tissue, whereas compound 2 was purified from yeast cultures overexpressing the VoTPS1 gene.
| Position | Germacrene C (1)a |
Valerena 1,10 diene (2)b |
||
|---|---|---|---|---|
| δC (125 MHz) | δH (500 MHz) | δC (125 MHz) | δH (500 MHz) | |
| 1 | 123.6 | 6.28 (d, J = 9.2; 1H) | 136.2 | |
| 2 | 131.5 | 5.26 (d, J = 9.3; 1H) | 33.8 | 3.39 (dd, J = 9.7; 5.4; 1H) |
| 3a | 127.9 | 24.8 | 1.50 1.60 (m, overlap, 1H) | |
| 3b | 1.70 1.86 (m, overlap, 1H) | |||
| 4a | 41.4 | 2.22 (dt, J = 12.1, 3.3; 1H) | 28.9 | 1.30 1.40 (m, overlap, 1H) |
| 4b | 1.78 (td, J = 12.3, 5.2; 1H) | 1.70 1.80 (m, overlap, 1H) | ||
| 5a | 29.1 | 2.14 2.18 (m, overlap, 1H) | 33.8 | 1.93 (m, 1H) |
| 5b | 2.05 (ddd, J = 24.3, 12.4, 3.9; 1H) | |||
| 6 | 126.6 | 4.96 (br dd, J = 11.4, 4.6; 1H) | 47.6 | 2.91 (br s, 1H) |
| 7a | 142.3 | 26.8 | 1.30 1.40 (m, overlap, 1H) | |
| 7b | 1.30 1.40 (m, overlap, 1H) | |||
| 8a | 41.6 | 2.55 2.62 (m, 1H) | 37.7 | 2.16 2.25 (m, overlap, 1H) |
| 8b | 1.95 (td, J = 12.8, 4.8; 1H) | 2.16 2.25 (m, overlap, 1H) | ||
| 9a | 33.2 | 2.38 2.50 (m, overlap, 1H) | 128.6 | |
| 9b | 2.12 2.13 (m, overlap, 1H) | |||
| 10 | 145.3 | 126.4 | 5.46 (dd, J = 9.2; 1H) | |
| 11 | 38.4 | 2.38 2.50 (m, overlap, 1H) | 129.9 | |
| 12 | 23.6 | 1.14 (d, J = 3.5; 3H) | 26.3 | 1.68 (s, 3H) |
| 13 | 23.3 | 1.12 (d, J = 3.6; 3H) | 17.9 | 1.66 (s, 3H) |
| 14 | 17.8 | 1.61 (s, 3H) | 13.6 | 1.62 (s, 3H) |
| 15 | 21.8 | 1.20 (s, 3H) | 12.3 | 0.75 (d, J = 7; 3H) |
a Recorded on Bruker 500 MHz spectrometer in hexane d14, J in Hz.
b Recorded on a Varian J NMR 500 MHz spectrometer in CDCl3, J in Hz.