Table 1.
1H NMR, 13 C NMR and 2D NMR Correlations Data of luteolin 5-methyl ether (1) and cirsilineol (2)
| Position | 1 H NMR | 13 C NMR** | TCOSY | HMBC | COSY | NOESY | ||||||
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| δ H mult. (J in Hz) | (H→C) | (H→H) | ||||||||||
| Com. 1 | Com. 2 | Com. 1 | Com. 2 | Com. 1 | Com. 2 | Com. 1 | Com. 2 | Com. 1 | Com. 2 | Com. 1 | Com. 2 | |
| 1 | - | - | - | - | - | - | - | - | - | - | - | - |
| 2 | - | - | 165.5 | - | - | - | - | - | - | - | - | - |
| 3 | 6.46, d (2) | 6.67, s | 105.8 | - | - | - | 2, 4 | 1’, 2, 4, 10 | - | - | - | 6’ |
| 4 | - | - | 183.4 | 184.9 | - | - | - | - | - | - | - | - |
| 5 | - | - | 159.5 | - | - | - | - | - | - | - | - | - |
| 6 | 6.20, d (2) | - | 100.0 | 133.7 | 8 | - | - | - | - | - | - | - |
| 7 | - | - | 166.1 | 154.4 | - | - | - | - | - | - | - | - |
| 8 | 6.62,s | 6.58, s | 95.1 | 95 | 6 | - | 7, 9, 10, 6 | 10, 6, 9, 7, 4 | - | - | - | - |
| 9 | - | - | 158.3 | 159.4 | - | - | - | - | - | - | - | - |
| 10 | - | - | 103.7 | 105.7 | - | - | - | - | - | - | - | - |
| 1’ | - | - | 124.1 | 124.4 | - | - | - | - | - | - | - | - |
| 2’ | 7.48, d (2) | 7.49, d (2) | 110.3 | 111.6 | 5’ | 6’, 5’ | 3’, 4’, 2, 6’ | 6’, 3’, 4’, 2 | - | 6’ | 3 | 6’ |
| 3’ | - | - | 149.7 | 151.6 | - | - | - | - | - | - | - | - |
| 4’ | - | - | 152.8 | 153.8 | - | - | - | - | - | - | - | - |
| 5’ | 6.94, d (8.5) | 7.11, d (8) | 117.3 | 113.7 | 6’, 2’ | 2’ | 3’, 4’, 1’ | 6’, 3’, 4’ | 6’ | 6’ | - | 6’ |
| 6’ | 7.52, dd (8.5,2) | 7.63, dd (8, 2) | 122.4 | 121.2 | 5’ | 2’ | 4’ | 2’, 4’ | 5’ | 5’, 2’ | 3, 5’ | 5’, 2’ |
| (in 5) OCH 3 | 3.95, s | - | 56.3 | - | - | - | 5 | - | - | - | - | - |
| (in 6) OCH3 | - | 3.92, s | - | 56.1 | - | - | - | 7 | - | - | - | - |
| (in 7) OCH3 | - | 3.91, s | - | 56.3 | - | - | - | 6 | - | - | - | - |
| (in 3’) OCH3 | 3.87 s | - | 61.2 | - | - | - | 2 | - | - | - | - |
* All 1H assignments are based on 2D NMR (COSY, HSQC and HMBC) experiments.
**13C assignments are based on HSQC and HMBC.