Table 4.
400 MHz 1H-NMR data of 1–12 in CD3OD a.
| Position | δH | |||||
| 1 | 2 | 3 | 4 | 5 | 6 | |
| glucose | ||||||
| 1 | 5.69 (d, J = 6.3 Hz) | 5.79 (d, J = 8.3 Hz) | 5.90 (d, J = 8.6 Hz) | 5.79 (d, J = 8.2 Hz) | 6.06 (d, J = 8.3 Hz) | 6.60 (d, J = 3.5 Hz) |
| 2 | 3.56–3.49 (m) | 3.66 (dd, J = 9.5, 8.3 Hz) | 5.19 (t, J = 8.6 Hz) | 3.79–3.68 (m) | 5.42 (dd, J = 9.7, 8.3 Hz) | 5.29 (dd, J = 10.1, 3.5 Hz) |
| 3 | 3.56–3.49 (m) | 3.85 (t, J = 9.5 Hz) | 3.82–3.70 (m) | 5.25 (t, J = 9.4 Hz) | 5.54 (t, J = 9.7 Hz) | 5.86 (t, J = 10.1 Hz) |
| 4 | 3.56–3.49 (m) | 5.23 (t, J = 9.5 Hz) | 3.58–3.52 (m) | 3.79–3.68 (m) | 3.88 (t, J = 9.7 Hz) | 4.01–3.91 (m) |
| 5 | 3.76–3.67 (m, 1H) | 4.07 (ddd, J = 9.5, 4.6, 2.0 Hz) | 3.58–3.52 (m) | 3.61–3.53 (m) | 3.70 (ddd, J = 9.7, 4.6, 2.2 Hz) | 4.01–3.91 (m) |
| 6 | 4.55 (br d, J = 12.0 Hz) | 4.45 (dd, J = 12.4, 2.0 Hz) | 3.90 (br d, J = 11.9 Hz) | 3.88 (br d, J = 12.1 Hz) | 3.93 (dd, J = 12.3, 2.2 Hz) | 3.90–3.78 (2H, m) |
| 4.40 (dd, J = 12.0, 4.5 Hz) | 4.22 (dd, J = 12.4, 4.7 Hz) | 3.82–3.70 (m) | 3.79–3.68 (m) | 3.81 (dd, J = 12.3, 4.6 Hz) | ||
| galloyl | ||||||
| 2,6 | 7.13 (2H, s) | 7.15 (2H, s) | 7.04 (2H, s) | 7.15 (2H, s) | 7.03 (2H, s) | 7.17 (2H, s) |
| 7.08 (2H, s) | 7.11 (2H, s) | 7.01 (2H, s) | 7.12 (2H, s) | 7.02 (2H, s | 7.06 (2H, s) | |
| 7.07 (2H, s) | 6.92 (2H, s) | 6.91 (2H, s) | ||||
| Position | δH | |||||
| 7 | 8 | 9 | 10 | 11 | 12 | |
| glucose | ||||||
| 1 | 5.05–4.98 (m) | 4.77 (d, J = 3.6 Hz) | 4.77 (d, J = 3.7 Hz) | 4.86 (d, J = 3.7 Hz) | 5.15 (d, J = 3.6 Hz) | 4.73 (d, J = 8.0 Hz) |
| 2 | 5.05–4.98 (m) | 3.58 (dd, J = 9.5, 3.6 Hz) | 3.71 (dd, J = 9.9, 3.7 Hz) | 3.88 (dd, J = 9.9, 3.7 Hz) | 4.99 (dd, J = 10.2, 3.6 Hz) | 5.08 (dd, J = 9.8, 8.0 Hz) |
| 3 | 5.66 (t, J = 8.3 Hz) | 3.93 (t, J = 9.5 Hz) | 5.38 (t, J = 9.9 Hz) | 5.64 (t, J = 9.7 Hz) | 5.68 (dd, J = 10.2, 8.6 Hz) | 5.39 (dd, J = 9.8, 9.6 Hz) |
| 4 | 3.82–3.70 (m) | 5.10 (t, J = 9.5 Hz) | 3.66 (t, J = 9.9 Hz) | 5.35 (t, J = 9.7 Hz) | 3.91–3.70 (m) | 3.74 (t, J = 9.6 Hz) |
| 5 | 3.82–3.70 (m) | 4.11–4.05 (m) | 3.95 (ddd, J = 9.9, 5.8, 2.0 Hz) | 4.27–4.20 (m) | 3.91–3.70 (m) | 3.51 (ddd, J = 9.6, 5.3, 2.2 Hz) |
| 6 | 3.89 (br d, J = 11.6 Hz) | 4.38 (br d, J = 11.8 Hz) | 4.55 (dd, J = 11.9, 2.0 Hz) | 4.43 (br d, J = 10.3 Hz) | 3.91–3.70 (2H, m) | 3.77 (dd, J = 12.1, 5.3 Hz) |
| 3.82–3.70 (m) | 4.19 (dd, J = 11.8, 5.8 Hz) | 4.41 (dd, J = 11.9, 5.8 Hz) | 4.30–4.24 (m) | 3.98–3.89 (m) | ||
| galloyl | ||||||
| 2,6 | 7.03 (2H, s) | 7.09 (2H, s) | 7.13 (2H, s) | 7.08 (2H, s) | 7.03 (2H, s) | 7.00 (2H, s) |
| 6.98 (2H, s) | 7.07 (2H, s) | 7.09 (2H, s) | 6.99 (2H, s) | 6.98 (2H, s) | 6.96 (2H, s) | |
| 6.95 (2H, s) | ||||||
| OCH3 | 3.44 (3H, s) | 3.46 (3H, s) | 3.48 (3H, s) | 3.52 (3H, s) | — | — |
| OCH2CH3 | — | — | — | — | 3.91–3.70 (1H, m) | 3.98–3.89 (1H, m) |
| 3.52 (1H, dq, J = 10.3, 7.1 Hz) | 3.61 (1H, dq, J = 9.7, 7.1 Hz) | |||||
| OCH2CH3 | — | — | — | — | 1.23 (3H, t, J = 7.1 Hz) | 1.12 (3H, t, J = 7.1 Hz) |
Notes: a Chemical shifts were recorded in δC values using the solvent signal (CD3OD: δH 3.31) as reference. Signal assignments were based on the results of 1H-1H COSY and HMQC experiments.