Table 1.
1H-NMR data for the downfield region of DB[a,l]P-trans-11,12-diol and the isolated glucuronides.
| peak 1 | peak 2 | peak 3 | ||
|---|---|---|---|---|
| proton | DB[a,l]P-diol | (+)-DB [a,l]P-11 -Gluc | (+)-DB [a,l]P-12-Gluc | (−)-DB [a,l]P-11 -Gluc |
| 1 | 8.50 (d, J=8.4 Hz) | 8.50 (d, J=8.4 Hz) | 8.54 (d J=7.8 Hz) | 8.52 (d, J=8.1 Hz) |
| 2 | 7.70 (m) | 7.70 (m) | 7.76 (m) | 7.73 (m) |
| 3 | 7.76 (m) | 7.77 (m) | 7.80 (m) | 7.80 (m) |
| 4 | 8.94 (d, J=7.5 Hz) | 8.95(d) | 8.97 (d, J=7.9 | 8.97 d, J=8.1 Hz) |
| 5 | 8.98 (d, J=7.7Hz) | 8.99 (d, J= 8.4 Hz) | 9.01 (d, J=7.9 | 9.02 d 8.1 |
| 6 | 8.02 (t, J=7.7 Hz) | 8.03 (t, J=8.1 Hz) | 8.06 (t, J=8.0 Hz) | 8.05 (m) |
| 7 | 8.24 (d, J= 7.5 Hz) | 8.25 (d, J= 6.6 Hz) | 8.28 (d, J=7.60 Hz) | 8.27 (d, J= 9.0 Hz) |
| 8 | 8.13 (d, J= 9.3 Hz) | 8.05–8.12 (m) | 8.20 (d, J=8.80 Hz) | 8.14 (d, J=9.0 Hz) |
| 9 | 8.09 (d, J= 9.1 Hz) | 8.05–8.12 (m) | 8.12 (d, J=8.80 Hz) | 8.06 (m) |
| 10 | 8.41 (s) | 8.95 (s) | 8.49 (s) | 8.80 (s) |
| 11 | 4.71 (m) | 4.98 (m) | 4.99 (m) | 4.96 (m) |
| 12 | 4.59 (m) | 4.91 (m) | 4.78 (m) | 4.81 (m) |
| 13 | 6.28 (dd, J= 10.3, 2.1 Hz) | 6.32 (dd, J= 10.6, 2.2 Hz) | 6.62 (dd, J=10.4, 2.4 Hz) | 6.26 (dd, J=10.4, 2.4Hz) |
| 14 | 7.26 (dd, J= 10.6, 2.1 Hz) | 7.24 (dd, J= 10.6, 2.1 Hz) | 7.30 (dd, J=10.4, 2.4 Hz) | 7.30 (dd, J= 10.1, 2.4 Hz) |
| 11-OH | 5.84 (d, J= 5.6 Hz) | |||
| 12-OH | 5.43 (d, J= 4.8 Hz) | |||
| 1’ | 4.71 (d, J=6.8 Hz) | 4.58 (m) | 4.60 (d, J=7.1 Hz) | |