Table 1 NMR data of the new compounds (1–3) isolated from Tirpitzia sinensis (δ in ppm, 1H NMR 600 MHz; 13C NMR 151 MHz)
Position | Compound 1 (in CD3OD) | Compound 2 (in CD3OD) | Compound 3 (in DMSO) | |||
|---|---|---|---|---|---|---|
13C NMR | 1H NMR | 13C NMR | 1H NMR | 13C NMR | 1H NMR | |
1 | 134.8 | – | 132.9 | – | ||
2 | 110.7 | 6.94 (1H, s, overlapped) | 166.2 | – | 152.7 | – |
3 | 149.3 | – | 104.1 | 6.65 (1H, s) | 104.5 | 6.61 (1H, s) |
4 | 147.7 | – | 184.4 | – | 138.2 | – |
5 | 116.3 | 6.76 (1H, d, 8.1) | 164.9 | – | 104.5 | 6.61 (1H, s) |
6 | 119.9 | 6.83 (1H, dd, 8.1, 1.3) | 110.5 | – | 152.7 | – |
7 | 89.3 | 5.53 (1H, d, 6.2) | 166.2 | – | 62.9 | 4.40 (2H, d,4.2) |
8 | 55.5 | 3.52 (1H, dt, 12.6, 5.3) | 95.6 | 6.53 (1H, s) | 56.2 | 3.37 (3H, s) |
9 | 65.0 | 3.78 (1H, m); 3.83 (1H, m) | 158.7 | – | 56.2 | 3.73 (3H, s) |
10 | 56.6 | 3.81 (3H, s) | 105.4 | – | 56.2 | 3.73 (3H, s) |
11 | 108.5 | 5.32 (1H, d, 1.1) | ||||
12 | 74.0 | 3.51 (1H, d, 9.2) | ||||
13 | 76.6 | 3.79 (1H, d, 3.4) | ||||
14 | 79.3 | 5.19 (1H, m) | ||||
1′ | 136.9 | – | 123.6 | – | 100.7 | 4.93 (1H, d, 7.3) |
2′ | 112.7 | 6.93 (1H, s, overlapped) | 110.5 | 7.48 (1H, d, 8.1) | 77.1 | 3.46 (1H, m) |
3′ | 145.4 | – | 149.5 | – | 70.1 | 3.46 (1H, m) |
4′ | 149.1 | – | 152.3 | – | 64.6 | 3.19 (1H, dq, 10.8, 3.9) |
5′ | 129.9 | – | 116.7 | 6.94 (1H, d, 8.3) | 76.8 | 3.57 (1H, ddd, 11.7, 4.6, 2.3) |
6′ | 117.0 | 6.92 (1H, s) | 121.5 | 7.51 (1H, dd, 8.4, 1.4) | 61.0 | 3.86 (1H, d, 9.3); 3.02 m |
7′ | 75.6 | 4.62 (1H, d, 6.2) | 56.3 | 3.96 (3H, s) | ||
8′ | 76.1 | 3.83 (1H, m) | ||||
9′ | 78.1 | 3.52 (1H, dt, 12.6, 6.2); 3.92 (1H, d, 2.5) | ||||
10′ | 56.9 | 3.88 (3H, s) | ||||
1′′ | 111.1 | 4.88 (1H, d, 2.6) | 73.5 | 4.95 (1H, d, 11.3) | ||
2′′ | 70.7 | 3.46 (1H, dd, 10.4, 4.2) | 72.1 | 3.58 (1H, m) | ||
3′′ | 80.6 | – | 82.5 | 3.42 (1H, m) | ||
4′′ | 75.1 | 3.71 (1H, d, 3.6); 3.95 (1H, d, 5.5) | 81.1 | 3.46 (1H, m) | ||
5′′ | 65.5 | 3.58 (2H, d, 2.9) | 101.9 | 3.73 (1H, m) | ||
6′′ | 69.8 | 3.89 (1H, d, 1.7); 3.87 (1H, m) | ||||
1′′′ | 102.4 | 5.23 (1H, s) | ||||
2′′′ | 72.1 | 3.87 (1H, m) | ||||
3′′′ | 72.5 | 3.12 (1H, t, 9.3) | ||||
4′′′ | 69.5 | 2.57 (1H, dd, 9.3, 6.2) | ||||
5′′′ | 71.8 | 3.41 (1H, m) | ||||
6′′′ | 17.2 | 0.75 (1H, d, overlapped) | ||||