Table 3.
1H and 13C-NMR (400 MHz) data for isolated proanthocyanidin compounds (2, 4, and 5) in CDCl3 (δ in ppm).
| 2 | 4 | 5 | |||||
|---|---|---|---|---|---|---|---|
| 13C | 1H | 13C | 1H | 13C | 1H | ||
| C | 2 | 114.0 | 113.7 | 112.0 | |||
| 3 | 67.1 | 5.24 (d, 3.4) | 35.3 | 2.35, 2.49 (d, 4.12) | 77.7 | 7.13 (d, 3.5) | |
| 4 | 56.2 | 3.9 (d, 3.4) | 67.5 | 3.90 (t) | 36.5 | 2.65 (d, 3.5) | |
| A | 5 | 167.7 | 161.3 | 154.0 | |||
| 6 | 130.1 | 5.23 (brs) | 79.7 | 4.08 (brs) | 127.0 | 5.25 (brs) | |
| 7 | 167.7 | 152.1 | 154.1 | ||||
| 8 | 130.1 | 5.23 (brs) | 78.8 | 6.72 (brs) | 130.2 | 5.32 (brs) | |
| 9 | 158.9 | 157.2 | 160.1 | ||||
| 10 | 105.0 | 102.3 | 100.4 | ||||
| B | 1′ | 130.8 | 127.3 | 132.4 | |||
| 2′ | 130.0 | 7.61 (s) | 138.2 | 6.60 (d, 8.5) | 129.2 | 7.64 (s) | |
| 3′ | 144.2 | 114.9 | 6.42 (d, 8.5) | 140.2 | |||
| 4′ | 129.7 | 153.4 | 130.8 | ||||
| 5′ | 144.0 | 114.9 | 6.42 (d, 8.5) | 147.3 | |||
| 6′ | 130.0 | 7.61 (s) | 127.5 | 6.60 (d, 8.5) | 129.2 | 7.62 (s) | |
| F | 2′ | 71.2 | 4.37 (d, 7.3) | 150.2 | 67.5 | 4.25 (d, 7.4) | |
| 3′ | 114.2 | 4.91–4.93 (m) | 135.3 | 60.2 | 4.17–4.15 (m) | ||
| 4′ | 56.1 | 3.82 (d, 2.5) | 179.1 | 34.2 | 2.21, 2.41 (d, 5.2, 14.3) | ||
| D | 5′ | 105.0 | 162.1 | 151.9 | |||
| 6′ | 115.0 | 5.00 (s) | 79.5 | 7.75 (s) | 130.5 | 5.25 (s) | |
| 7′ | 158.1 | 161.2 | 149.8 | ||||
| 8′ | 103.4 | 107.2 | 128.0 | ||||
| 9′ | 157.0 | 151.2 | 152.5 | ||||
| 10′ | 105.4 | 105.2 | 103.2 | ||||
| E | 1′ | 130.8 | 123.1 | 130.1 | |||
| 2′ | 130.6 | 7.62 (brs) | 130.5 | 6.63 (d, 8.2) | 130.6 | 7.4 (brs) | |
| 3′ | 144.0 | 115.8 | 6.65 (d, 8.4) | 142.3 | |||
| 4′ | 129.7 | 155.2 | 144.5 | ||||
| 5′ | 144.0 | 114.7 | 6.41 (d, 8.4) | 112.3 | 6.7 (d, 8.1) | ||
| 6′ | 130.0 | 7.62 (brs) | 138.2 | 7.67 (d, 8.2) | 130.1 | 7.3 (d, 8.1) | |
| I | 2″ | 71.2 | 4.37 (d, 9.4) | ||||
| 3″ | 68.1 | 4.15–4.17 (m) | |||||
| 4″ | 37.9 | 2.25, 1.80 (d, 8.5, 16.3) | |||||
| G | 5″ | 167.7 | |||||
| 6″ | 130.1 | 5.24 (s) | |||||
| 7″ | 167.7 | ||||||
| 8″ | 105.0 | ||||||
| 9″ | 157.0 | ||||||
| 10″ | 103.5 | ||||||
| H | 1 | 128.8 | |||||
| 2 | 131.2 | 7.43 (brs) | |||||
| 3 | 144.0 | ||||||
| 4 | 129.7 | ||||||
| 5 | 144.0 | ||||||
| 6 | 131.1 | 6.20 (brs) | |||||