Table 2 1H NMR spectroscopic data of compounds 1–7 (400 MHz).
From: Neuroprotective metabolites via fungal biotransformation of a novel sapogenin, cyclocephagenol
Position | 1a | 2a | 3a | 4a | 5a | 6a | 7a |
|---|---|---|---|---|---|---|---|
δH (J in Hz) | δH (J in Hz) | δH (J in Hz) | δH (J in Hz) | δH (J in Hz) | δH (J in Hz) | δH (J in Hz) | |
1 | 1.20 m, 1.61 m | 1.37 m, 1.65 m | 1.40 m, 1.94 m | 1.27 m, 1.58 m | 1.29 m, 1.95 dt (14.7, 8.5) | 1.32 m, 1.64 td (12.5, 4.5) | 1.27 m, 1.63 m |
2 | 1.92 m, 2.00 m | 1.94 m, 2.03 m | 2.48 m, 2.60 m | 1.88 m, 2.00 m | 2.45 m, 2.62 m | 1.94 m (2H) | 1.98 m (2H) |
3 | 3.64 dd (8.6, 2.7) | 3.66 dd (11.5, 4.5) | 3.60 td (7.9, 1.7) | 3.63 dt (10.7, 5.1) | 3.64 m | ||
4 | |||||||
5 | 1.70 m | 1.74 d (9.0) | 2.11 d (9.2) | 1.69 d (9.2) | 2.13 m | 1.72 m | 1.70 m |
6 | 3.78 t (8.7) | 3.89 dp (11.7, 3.9, 3.3) | 3.72 m | 3.80 q (7.7) | 3.68 m | 3.76 tdd (9.5, 5.8, 3.0) | 3.75 ddd (12.3, 8.9, 3.4) |
7 | 1.62 m, 1.79 m | 1.67 m, 1.93 m | 1.55 m, 1.77 m | 1.54 m, 1.74 m | 1.54 d (13.3), 1.66 dt (12.0, 3.6) | 1.79 td (8.0, 3.5) (2H) | 1.66 m (2H) |
8 | 1.94 m | 2.25 m | 2.05 dd (11.5, 4.8) | 1.96 d (5.7) | 1.85 m | 1.86 m | 1.76 m |
9 | |||||||
10 | |||||||
11 | 1.14 m, 1.97 m | 1.72 m, 2.43 dd (15.2, 8.1) | 1.46 dd (15.5, 4.3), 2.49 m | 1.58 m, 2.49 dd (15.5, 8.6) | 1.38 m, 2.56 dd (15.6, 9.0) | 1.89 m, 2.37 dd (14.9, 5.8) | 1.85 td (8.3, 6.9, 3.5), 2.33 m |
12 | 1.72 m, 1.87 m | 4.24 t (7.2) | 4.18 dd (6.7, 2.5) | 4.16 dd (8.8, 4.3) | 4.14 dd (9.1, 2.7) | 4.27 ddd (9.1, 5.9, 2.6) | 4.19 dt (9.5, 4.8) |
13 | |||||||
14 | |||||||
15 | 1.79 m, 2.11 m | 1.98 m, 2.20 m | 1.93 m, 2.11 m | 2.10 d (17.6), 2.36 d (17.7) | 2.11 d (17.6), 2.38 d (17.9) | 1.86 m, 2.15 dd (12.6, 7.9) | 2.09 d (17.4), 2.28 d (17.8) |
16 | 4.90 dtd (8.0, 5.7, 3.1) | 4.87 tt (8.1, 4.4) | 4.82 tt (8.3, 4.6) | 4.88 tt (8.0, 5.0) | |||
17 | 2.10 d (5.9) | 2.60 d (7.6) | 2.49 m | 3.06 s | 3.02 s | 2.93 d (8.0) | 3.56 s |
18 | 1.70 s | 1.84 s | 1.80 s | 1.47 s | 1.49 s | 1.71 s | 1.37 s |
19 | 0.30 d (3.1), 0.58 d (4.1) | 0.36 d (4.3), 0.71 d (4.4) | 0.45 d (4.3), 0.76 d (4.4) | 0.44 d (4.3), 0.67 d (4.4) | 0.54 d (3.7), 0.76 d (4.1) | 0.48 d (4.2), 0.59 d (4.2) | 0.53 d (4.5), 0.58 d (4.2) |
20 | |||||||
21 | 1.57 s | 2.04 s | 2.00 s | 1.44 s | 1.44 s | 1.94 s | 1.52 s |
22 | 1.24 m, 3.09 td (11.2, 4.3) | 2.30 m, 2.66 m | 2.22 d (16.4), 2.62 m | 2.64 dd (12.8, 5.1), 2.27 dd (14.2, 3.2) | 2.27 d (13.3), 2.62 m | 2.08 dd (13.3, 3.5), 2.75 td (13.4, 4.1) | 2.33 m (2H) |
23 | 1.88 m, 2.18 m | 1.95 m, 2.32 m | 1.89 m, 2.30 d (13.9) | 1.82 m, 2.20 d (14.1) | 1.84 m, 2.20 dd (13.9, 3.0) | 1.89 m, 2.28 dt (13.8, 3.4) | 1.81 m, 2.15 m |
24 | 3.67 brs | 3.74 brs | 3.69 m | 3.64 brs | 3.66 brs | 3.69 brs | 3.64 brs |
25 | |||||||
26 | 1.45 s | 1.41 s | 1.36 s | 1.57 s | 1.58 s | 1.52 s | 1.47 s |
27 | 1.29 s | 1.62 s | 1.56 s | 1.30 s | 1.31 s | 1.35 s | 1.30 s |
28 | 1.88 s | 1.86 s | 1.72 s | 1.84 s | 1.74 s | 1.91 s | 1.92 s |
29 | 1.34 s | 1.34 s | 1.38 s | 1.31 s | 1.41 s | 1.37 s | 1.37 s |
30 | 0.97 s | 1.04 s | 0.87 s | 1.00 s | 0.92 s | 1.26 s | 1.32 s |