Table 3.
1H NMR Data for Withanolides 4–7 and 16–19 (400 or 500 MHz)
| Pos. | 4a | 5a | 6a | 7b | 16a | 17a | 18b,c | 19b |
|---|---|---|---|---|---|---|---|---|
| 2 | Hβ 2.86 dd (8.3, 16.4) | Hβ 2.86 dd (6.5, 17.5) | 5.93 d (6.4) | Hβ 3.65 dd (8.1, 18.0) | 6.18 d (10.0) | Hβ 2.99 dd (6.3, 15.0) | Hβ 3.62 dd (10.0, 17.1) | Hβ 3.62 dd (9.7, 17.6) |
| Hα 2.56 dd (2.6, 16.4) | Hα 2.56 dd (2.2, 17.5) | Hα 3.22 dd (6.2, 18.0) | Hα 2.56 dd (2.2, 15.0) | Hα 3.02 dd (5.5, 17.1) | Hα 3.30 dd (2.0, 17.6) | |||
| 3 | 3.70 ddd (8.3, 3.4, 2.6) | 3.75 ddd (6.5, 4.0, 2.2) | 7.57 d (6.4) | 5.61 brt (8.1) | 6.91 dd (10.0, 5.9) | 3.68 ddd (6.3, 3.2, 2.2) | 4.67 br | 5.62 ddd (9.7, 6.5, 2.0) |
| 4 | 3.42 d (3.4) | 3.56 d (4.0) | --- | 4.54 br | 3.74 d (5.9) | 3.46 d (3.2) | 4.05 br | 4.51 br |
| 6 | 3.22 brs | 3.15 brs | 5.76 t (3.5) | 3.37 brs | 3.21 s | 3.19 s | 3.30 br | 3.62 br |
| 7 | 2.25 m | 2.31 dd (5.2, 14.8) | 2.37 ddd (3.5, 8.8, 15.0) | 2.35 m | 2.12 ddd (2.2, 3.7, 14.6) | 2.14 ddd (2.2, 3.7, 14.6) | 2.22 ddd (1.7, 4.3, 15.0) | 2.07 m |
| 1.42 m | 1.34 m | 1.70 m | 2.11 m | 1.30 m | 1.31 m | 1.40 ddd (2.0, 10.2, 15.0) | 1.23 m | |
| 8 | 1.41 m | 1.70 dq (4.5, 10.8) | 1.75 m | 1.50 m | 1.39 m | 1.39 m | 1.50 m | 1.41 m |
| 9 | 1.14 m | 1.28 m | 1.17 m | 1.16 m | 1.14 m | 1.16 m | 1.17 m | 1.04 m |
| 11 | 1.27 m, 1.18 m | 3.88 m | 2.24 m, 1.58 m | 1.57 m, 1.34 m | 1.27 m, 1.18 m | 1.35 m | 1.52 m | 1.44 m |
| 12 | 1.90 m, 1.02 m | 2.15 dd (13.9, 2.4), 1.38 m | 1.99 m, 1.18 m | 1.76 m, 1.02 m | 1.88 m, 1.08 m | 1.88 m, 1.08 m | 1.85 m, 1.05 m | 1.80 m, 1.05 m |
| 14 | 0.95 m | 0.94 m | 1.03 m | 0.91 m | 0.95 m | 0.94 m | 0.93 m | 0.92 m |
| 15 | 1.64 m, 1.13 m | 1.66 m, 1.21 m | 1.61 m, 1.19 m | 1.52 m, 0.90 m | 1.64 m, 1.13 m | 1.61 m, 1.12 m | 1.54 m, 0.96 m | 1.54 m, 0.92 m |
| 16 | 1.66 m, 1.35 m | 1.64 m, 1.38 m | 1.64 m, 1.35 m | 1.57 m, 1.13 m | 1.66 m, 1.35 m | 1.64 m, 1.31 m | 1.54 m, 1.15 m | 1.57 m, 1.15 m |
| 17 | 1.07 m | 1.04 m | 1.10 m | 1.13 m | 1.07 m | 1.05 m | 1.07 m | 1.14 m |
| 18 | 0.62 s | 0.85 s | 0.75 s | 0.47 s | 0.67 s | 0.64 s | 0.55 s | 0.52 s |
| 19 | 4.38 d, 3.61 d (10.2) | 1.49 s | 1.15 s | 4.80 d, 4.01 d (9.4) | 1.38 s | 1.28 s | 1.76 s | 1.69 s |
| 20 | 1.96 m | 1.99 m | 1.99 m | 1.86 m | 1.97 m | 1.97 m | 1.90 m | 1.90 m |
| 21 | 0.95 d (6.7) | 1.00 d (6.7) | 1.01 d (6.6) | 0.95 d (6.6) | 0.97 d (6.6) | 0.96 d (6.6) | 0.97 d (6.6) | 0.97 d (6.6) |
| 22 | 4.39 dt (13.2, 3.5) | 4.39 dt (13.2, 3.5) | 4.42 dt (13.3, 3.4) | 4.38 dt (13.2, 3.3) | 4.39 dt (13.2, 3.5) | 4.39 dt (13.2, 3.5) | 4.39 dt (13.2, 3.3) | 4.40 dt (13.2, 3.3) |
| 23 | 2.46 dd (13.2, 17.0) | 2.47 dd (13.7, 17.8) | 2.48 dd (13.6, 17.6) | 2.35 dd (13.9, 18.0) | 2.47 dd (13.6, 17.4) | 2.47 dd (13.6, 17.4) | 2.35 dd (13.4, 17.7) | 2.36 dd (13.7, 17.8) |
| 1.93 dd (3.5, 17.0) | 1.94 dd (3.2, 17.8) | 1.98 dd (3.2, 17.6) | 2.07 m | 1.94 dd (3.2, 17.4) | 1.94 dd (3.2, 17.4) | 2.01 dd (3.3, 17.7) | 2.07 m | |
| 27 | 4.36 d, 4.32 d (12.5) | 4.37 d, 4.31 d (12.6) | 4.37 d, 4.32 d (12.5) | 4.85 d, 4.75 d (11.7) | 4.36 d, 4.31 d (12.6) | 4.36 d, 4.31 d (12.6) | 4.80 d, 4.78 d (11.8) | 4.85 d, 4.75 d (11.7) |
| 28 | 2.02 s | 2.01 s | 2.01 s | 2.09 s | 2.01 s | 2.01 s | 2.10 s | 2.09 s |
| 3-OMe | 3.35 s | 3.34 s | 3.32 s |
a
In CDCl3.
b
In C5D5N.
c
OH-4 signal 7.75 s, OH-3 signal 6.91 brs, OH-27 signal 6.61 brs.