Table 2.
1H NMR and 13C NMR shifts of compounds 1–4 (in CDCl3, δ in ppm, and J in Hz).
| Position | Turcicanol A (1) | Turcicanol A Acetate (2) | Turcicanol B (3) | Turcica Ketone (4) | ||||
|---|---|---|---|---|---|---|---|---|
| 1H-NMR | 13C-NMR | 1H-NMR | 13C-NMR | 1H-NMR | 13C-NMR | 1H-NMR | 13C-NMR | |
| 2 | - | 161.5 | - | 161.5 | - | 161.4 | - | 161.4 |
| 3 | 6.25; d; 9.4; 1H | 113.0 | 6.24; d; 9.5; 1H | 113.1 | 6.25; d; 9.4; 1H | 113.1 | 6.25; d; 9.4; 1H | 113.2 |
| 4 | 7.64; d; 9.4; 1H | 143.5 | 7.64; d; 9.5; 1H | 143.6 | 7.64; d; 9.4; 1H | 143.6 | 7.64; d; 9.4; 1H | 143.5 |
| 5 | 7.36; d; 8.9; 1H | 128.8 | 7.37; d; 8.5; 1H | 128.8 | 7.37; d; 7.5; 1H | 128.7 | 7.37; d; 9.2; 1H | 129.0 |
| 6 | 6.87; dd; 2.3; 8.9; 1H | 113.4 | 6.89; dd; 2.2; 8.5; 1H | 113.2 | 6.87; dd; 2.3; 7.5; 1H | 113.3 | 6.85; dd; 2.4; 9.2; 1H | 113.2 |
| 7 | - | 162.9 | - | 162.5 | - | 162.5 | - | 162.3 |
| 8 | 6.87; d; 2.3; 1H | 101.4 | 6.87; d; 2.2; 1H | 101.6 | 6.86; d; 2.3; 1H | 101.5 | 6.86; d; 2.4; 1H | 101.5 |
| 9 | - | 156.2 | - | 156.0 | - | 156.0 | - | 156.0 |
| 10 | - | 112.5 | - | 112.5 | - | 112.6 | - | 112.7 |
| 1′α | 1.80; td; 3.7; 13.4; 1H | 29.4 | 1.45; dd; 3.1; 9.6; 1H | 30.0 | 1.70; m; 1H ** | 34.5 | 1.91; dd; 6.3; 8.5; 2H | 34.7 |
| 1′β | 1.43; dt; 3.7; 13.4; 1H | 1.67; m; 1H * | 1.49; td; 2.4; 13.1; 1H | |||||
| 2′α | 1.96; tt; 3.3; 14.3; 1H | 25.7 | 1.90; tddd; 1.7; 5.3; 14.1; 1H | 23.3 | 1.70; m; 2H ** | 27.8 | 2.51; m; 2H * | 34.2 |
| 2′β | 1.62; dq; 3.3; 15.3; 1H | 1.64; m; 1H * | ||||||
| 3′ | 3.46; t; 2.8; 1H | 75.8 | 4.69; t; 2.4; 1H | 77.7 | 3.29; dd; 4.5; 11.7; 1H | 78.9 | - | 217.0 |
| 4′ | - | 37.7 | - | 36.9 | - | 38.9 | - | 47.2 |
| 5′ | 1.68; m; 1H * | 44.8 | 1.7; dd; 1.7; 10.7; 1H | 45.9 | 1.24; dd; 2; 12.3; 1H | 50.7 | 1.83; dd; 2.4; 12.4; 1H | 50.8 |
| 6′α | 1.54; qd; 6.5; 12.6; 1H | 18.5 | 1.53; m; 1H * | 18.4 | 1.54; m; 1H * | 18.7 | 1.61; ddd; 6.5; 11.1; 12.7; 1H | 19.9 |
| 6′β | 1.64; m; 1H * | 1.66; m; 1H * | 1.75; dd; 6.8; 13.5; 1H | 1.67; ddt; 2.4; 6.5; 8.6; 1H | ||||
| 7′α | 2.16; dtd; 6.8; 18.2; 2H | 33.8 | 2.16; td; 6.4; 18.5; 1H | 33.6 | 2.17; d; 6.8; 2H | 34.0 | 2.21; m; 2H * | 33.6 |
| 7′β | 2.20; d; 7.6; 1H | |||||||
| 8′ | - | 135.8 | - | 136.0 | - | 136.2 | - | 136.7 |
| 9′ | - | 135.3 | 2.93; t; 5.1; 1H | 135.2 | - | 135.1 | - | 133.7 |
| 10′ | - | 37.8 | - | 37.8 | - | 37.9 | - | 37.67 |
| 11′a | 4.40; d; 9.9; 1H | 64.6 | 4.56; d; 9.9; 1H | 64.7 | 4.38; d; 9.9; 1H | 64.8 | 4.41; d; 10.1; 1H | 64.7 |
| 11′b | 4.55; d; 9.9; 1H | 4.40; d; 9.9; 1H | 4.54; d; 9.9; 1H | 4.55; d; 10.1; 1H | ||||
| 12′ | 1.68; s; 3H | 19.6 | 1.71; s; 3H | 19.7 | 1.69; s; 3H | 19.5 | 1.72; s; 3H | 19.7 |
| 13′ | 0.88; s; 3H | 22.1 | 0.90; s; 3H | 27.7 | 0.83; s; 3H | 15.7 | 1.08; s; 3H | 21.1 |
| 14′ | 1.00; s; 3H | 28.2 | 0.94; s; 3H | 21.7 | 1.04; s; 3H | 28.2 | 1.13; s; 3H | 27.0 |
| 15′ | 1.04; s; 3H | 20.8 | 1.05; s; 3H | 20.7 | 1.03; s; 3H | 20.9 | 1.11; s; 3H | 20.6 |
| CH3–(OAc) | - | - | 2.07; s; 3H | 21.5 | - | - | - | - |
| C=O (OAc) | - | - | - | 171.1 | - | - | - | - |
| Position | 11′-Dehydrokaratavicinol (5) | Galbanaldehyde (6) | Turcicasulphide (7) | |||||
| 1 H-NMR | 13 C-NMR | 1 H-NMR | 13 C-NMR | 1 H-NMR | 13 C-NMR | |||
| 1 | - | - | - | - | 0.97; t; 7.4; 3H | 11.7 | ||
| 2a | - | 161.5 | - | 161.2 | 1.51; m; 1H * | 28.2 | ||
| 2b | 1.68; td; 6.5; 13.2; 1H | |||||||
| 3 | 6.25; d; 9.5; 1H | 113.0 | 6.24; d; 9.4; 1H | 113.0 | 2.79; h; 6.7; 1H | 48.1 | ||
| 4 | 7.64; d; 9.5; 1H | 143.7 | 7.63; d; 9.4; 1H | 143.2 | 1.28; d; 6.9; 3H | 20.2 | ||
| 5 | 7.35; d; 8.6; 1H | 128.8 | 7.34; d; 8.6; 1H | 128.7 | 6.31; dt; 1.3; 14.8; 1H | 133.1 | ||
| 6 | 6.85; dd; 2.4; 8.6; 1H | 113.4 | 6.81; dd; 2.4; 8.6; 1H | 113.3 | 5.96; dt; 6.5; 14.8; 1H | 122.5 | ||
| 7 | - | 162.2 | - | 162.8 | 4.6; dd; 1.3; 6.5; 2H | 64.4 | ||
| 8 | 6.82; d; 2.4 | 101.6 | 6.75; d; 2.4; 1H | 101.2 | - | 171.3 | ||
| 9 | - | 155.8 | - | 156.0 | 3.63; s; 2H | 41.5 | ||
| 10 | - | 112.5 | - | 112.4 | - | - | ||
| 1′ | 4.60; d; 6.5; 2H | 65.4 | 1.84; m; 2H** | 19.6 | - | 134.0 | ||
| 2′ | 5.46; td; 1.2; 6.5; 1H | 118.6 | 2.29; t; 7.6; 2H | 42.3 | 7.29; m; 1H * | 129.4 | ||
| 3′ | - | 142.2 | 9.74; t; 1.5; 1H | 203.5 | 7.32; m; 1H ** | 128.3 | ||
| 4′ | 2.1; dd; 4.6; 11.6; 2H | 39.6 | - | 126.5 | 7.28; m; 1H * | 127.3 | ||
| 5′ | 2.15; q; 6.7; 2H | 26.2 | - | 129.7 | 7.32; m; 1H ** | 128.7 | ||
| 6′α | 5.14; t; 6.7; 1H | 124.1 | 1.86; m; 1H ** | 24.6 | 7.29; m; 1H * | 129.4 | ||
| 6′β | 2.5; dt; 3.1; 14.3; 1H | |||||||
| 7′α | - | 135.4 | 1.2; dd; 4.6; 13.5; 1H | 32.0 | - | - | ||
| 7′β | 1.6; m; 1H * | |||||||
| 8′a | 1.99; ddd; 6.4; 9.1; 14.4; 1H | 35.8 | 1.9; m; 1H ** | 34.8 | - | - | ||
| 8′b | 2.03; ddd; 6.22; 9.1; 15.1; 1H | - | - | |||||
| 9′ | 1.63; m; 2H * | 33.1 | - | 40.8 | - | - | ||
| 10′ | 4.03; dd; 5.4; 7.5; 1H | 75.6 | 2.92; dd; 4.2; 12; 1H | 42.7 | - | - | ||
| 11′a | - | 147.7 | 3.7; d; 8.2; 1H | 71.8 | - | - | ||
| 11′b | 3.87; d; 8.2; 1H | |||||||
| 12′a | 4.83; brs; 1H | 111.2 | 0.91; d; 6.7; 3H | 16.1 | - | - | ||
| 12′b | 4.93; brs; 1H | |||||||
| 13′ | 1.72; s; 3H | 17.8 | 1.43; s; 3H | 20.4 | - | - | ||
| 14′ | 1.61; s; 3H | 16.1 | 1.61; s; 3H | 20.4 | - | - | ||
| 15′ | 1.75; s; 3H | 16.9 | 1.16; s; 3H | 22.6 | ||||
*, ** Partially overlapped signals.