Table 1.
400 MHz 1H NMR Data of 1, 2, 4–7, 10 and 11 in DMSO-d6 (δH, J in Hz) a.
| Position | 1 b | 2 b | 4 | 5 | 6 | 7 | 10 | 11 |
|---|---|---|---|---|---|---|---|---|
| 1 | 5.55 dd (8.0, 6.4) | 5.55 dd (8.2, 6.4) | 5.56 dd (8.2, 6.3) | 5.55 dd (8.1, 6.4) | 5.55 dd (8.1, 6.2) | 5.55 dd (8.1, 6.3) | 5.53 dd (8.4, 6.4) | 5.53 dd (8.3, 6.4) |
| 2α | 2.07 m | 2.07 m | 2.07 m | 2.07 m | 2.07 m | 2.08 m | 2.07 m | 2.07 m |
| β | 2.34 ddd (13.0, 11.4, 6.4) | 2.34 ddd (13.2, 11.2, 6.4) | 2.34 ddd (13.0, 11.5, 6.3) | 2.34 ddd (13.2, 11.2, 6.4) | 2.34 m | 2.34 ddd (12.7, 11.3, 6.3) | 2.33 ddd (13.1, 11.3, 6.3) | 2.33 ddd (13.0, 11.2, 6.3) |
| 3 | 3.12 m | 3.12 m | 3.12 m | 3.12 m | 3.12 m | 3.13 m | 3.11 m | 3.11 m |
| 4α | 2.63 br d (13.1) | 2.63 br d (12.8) | 2.63 br d (13.2) | 2.63 br d (13.1) | 2.63 br d (13.0) | 2.64 br d (13.1) | 2.62 br d (13.0) | 2.62 br d (12.9) |
| β | 1.53 m | 1.52 m | 1.53 m | 1.52 m | 1.52 m | 1.53 m | 1.51 m | 1.51 m |
| 5 | 2.69 m | 2.69 m | 2.68 m | 2.68 m | 2.68 m | 2.68 m | 2.67 m | 2.67 m |
| 7 | 5.43 s | 5.43 s | 5.42 s | 5.42 s | 5.42 s | 5.42 s | 5.37 s | 5.38 s |
| 9 | 2.86 dd (12.0, 5.5) | 2.86 dd (11.3, 5.6) | 2.85 dd (11.7, 5.4) | 2.84 dd (11.8, 5.6) | 2.85 dd (12.0, 5.4) | 2.85 dd (11.4, 5.7) | 2.79 dd (12.2, 5.4) | 2.79 dd (12.1, 5.5) |
| 11α | 1.54 m | 1.52 m | 1.54 m | 1.55 m | 1.54 m | 1.56 m | 1.50 m | 1.49 m |
| β | 1.75 m | 1.74 m | 1.80 m | 1.76 m | 1.80 m | 1.79 m | 1.75 m | 1.75 m |
| 12α | 1.41 td (12.7, 4.1) | 1.40 td (12.8, 4.3) | 1.50 m | 1.43 td (13.7, 4.6) | 1.47 m | 1.43 m | 1.42 m | 1.42 m |
| β | 1.63 m | 1.69 m | 1.74 m | 1.73 m | 1.74 m | 1.74 m | 2.12 m | 2.13 m |
| 14 | 2.26 br t (8.9) | 2.25 br t (8.6) | 2.26 br t (9.0) | 2.22 br t (8.8) | 2.25 br t (8.6) | 2.22 br t (9.0) | 2.10 m | 2.10 m |
| 15α | 1.62 m | 1.61 m | 1.56 m | 1.57 m | 1.56 m | 1.57 m | 1.38 m | 1.38 m |
| β | 1.62 m | 1.61 m | 1.52 m | 1.52 m | 1.49 m | 1.53 m | 1.46 m | 1.47 m |
| 16α | 1.66 m | 1.69 m | 1.83 m | 1.82 m | 1.83 m | 1.82 m | 1.56 m | 1.58 m |
| β | 1.84 m | 1.85 m | 1.65 m | 1.68 m | 1.67 m | 1.68 m | 1.66 m | 1.66 m |
| 17 | 2.89 br t (9.8) | 2.86 t (9.5) | 2.24 br t (9.5) | 2.27 br t (9.7) | 2.23 br t (9.1) | 2.27 br t (9.6) | 1.66 m | 1.66 m |
| 18α | 2.48 br s | 2.48 br s | 2.48 br s | 2.48 br s | 2.48 br s | 2.48 br s | 2.47 br s | 2.47 br s |
| β | 2.48 br s | 2.48 br s | 2.48 br s | 2.48 br s | 2.48 br s | 2.48 br s | 2.47 br s | 2.47 br s |
| 19 | 0.64 s | 0.63 s | 0.50 s | 0.53 s | 0.49 s | 0.53 s | 0.70 s | 0.70 s |
| 21 | 1.70 s | 1.70 d (1.1) | 1.68 s | 1.65 s | 1.65 s | 1.64 s | 1.20 s | 1.20 s |
| 22 | 5.33 d (9.2) | 5.33 dd (9.3, 1.1) | 5.17 d (8.7) | 5.15 d (8.8) | 5.22 d (8.2) | 5.22 d (8.4) | 5.62 dd (15.6, 0.9) | 5.64 dd (15.6, 1.1) |
| 23 | 3.99 ddd (9.2, 6.0, 4.6) | 4.11 ddd (9.3, 4.9, 4.1) | 3.96 ddd (8.7, 6.6, 4.3) | 3.95 ddd (8.8, 6.6, 4.3) | 4.09 ddd (8.2, 4.7, 4.0) | 4.06 ddd (8.4, 4.7, 3.9) | 5.49 dd (15.6, 5.9) | 5.49 dd (15.6, 5.3) |
| 24 | 3.41 m | 3.47 m | 3.41 m | 3.40 m | 3.49 m | 3.50 m | 4.09 m | 4.09 m |
| 25 | 1.00 d (6.3) | 1.01 d (6.3) | 0.95 d (6.3) | 0.96 d (6.3) | 0.96 d (6.3) | 0.98 d (6.3) | 1.08 d (6.4) | 1.08 d (6.4) |
| 3-OH | 4.62 d (4.3) | 4.62 d (4.3) | 4.59 d (4.4) | 4.63 d (4.3) | 4.62 d (4.3) | 4.60 d (4.2) | 4.61 d (4.3) | 4.61 d (4.3) |
| 20-OH | - | - | - | - | - | - | 4.23 s | 4.22 s |
| 23-OH | 4.30 d (4.6) | 4.28 d (4.9) | 4.46 d (4.3) | 4.48 d (4.3) | 4.40 d (4.7) | 4.35 d (4.7) | - | - |
| 24-OH | 4.31 d (4.7) | 4.31 d (4.9) | 4.33 d (4.1) | 4.39 d (4.1) | 4.29 d (5.0) | 4.27 d (4.6) | 4.57 d (4.4) | 4.57 d (4.6) |
a Chemical shifts were recorded in δH values using the solvent DMSO-d6 signal δH 2.50 as reference; b Signals of two new compounds 1 and 2 were assigned on the basis of DEPT, 1H-1H COSY, HMQC, HMBC, NOESY, and 1D difference NOE experiments, respectively.