Table 1. 1H and 13C NMR data of the aglycone moiety of saponins 1–6 in pyridine-d5.
Position | 1 | 2 | 3 | 4 | 5 | 6 | ||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|
δC | δH J (Hz) | δC | δH J (Hz) | δC | δH J (Hz) | δC | δH J (Hz) | δC | δH J (Hz) | δC | δH J (Hz) | |
1 | 37.5 | 0.94 m, 1.64 m | 37.5 | 0.92 m, 1.64 m | 37.0 | 0.85 m, 1.40 m | 37.5 | 0.93 m, 1.65 m | 37.5 | 0.93 m, 1.66 o | 36.5 | 0.94 o, 1.65 o |
2 | 30.1 | 1.67 m, 2.06 m | 30.1 | 1.67 m, 2.07 m | 29.8 | 1.63 m, 2.03 m | 30.1 | 1.69 m, 2.08 m | 30.1 | 1,65 o, 2.04 o | 29.8 | 1.70 o, 2.10 m |
3 | 78.2 | 3.86 m | 78.2 | 3.88 m | 77.7 | 3.87 m | 78.1 | 3.88 m | 78.2 | 3.84 m | 77.1 | 3.90 m |
4 | 39.3 | 2.39 m, 2.63 br d (12.6) | 39.3 | 2.41 o, 2.64 m | 39.0 | 2.37 m, 2.66 dd (3.0, 13.2) | 39.3 | 2.37 m, 2.64 dd (3.0, 13.2) | 39.2 | 2.39 br t (12.0), 2.64 dd (3.0, 12.0) | 39.0 | 2.44 t (12.0), 2.73 br d (12.0) |
5 | 141.1 | – | 141.2 | – | 141.0 | – | 141.2 | – | 141.1 | – | 165.3 | – |
6 | 121.6 | 5.28 br s | 121.6 | 5.30 br s | 121.2 | 5.27 br s | 121.4 | 5.28 br s | 121.8 | 5.28 br s | 126.1 | 5.72 s |
7 | 32.0 | 1.46 m, 1.84 m | 32.1 | 1.50 m, 1.85 m | 31.3 | 1.48 m, 1.87 m | 31.9 | 1.48 m, 1.82 m | 32.2 | 1.44 m, 1.87 m | 201.0 | – |
8 | 31.2 | 1.48 m | 31.6 | 1.49 m | 30.4 | 1.81 m | 31.0 | 1.47 m | 30.9 | 1.54 m | 45.1 | 2.38 t (12.0) |
9 | 50.4 | 0.83 m | 50.5 | 0.90 m | 53.1 | 1.31 m | 50.4 | 0.87 m | 50.1 | 1.28 m | 50.0 | 1.36 m |
10 | 37.0 | – | 37.0 | – | 37.7 | – | 37.0 | – | 37.2 | – | 39.0 | – |
11 | 20.8 | 1.37 m, 1.40 m | 21.0 | 1.47 o | 37.0 | 2.23 dd (5.4, 13.2),2.57 t (13.2) | 20.6 | 1.40 o | 31.5 | 1.67 m, 1.85 m | 21.1 | 1.40 o |
12 | 39.7 | 1.11 dt (4.8, 12.6), 1.63 o* | 40.1 | 1.34 dt (4.8, 13.2), 2.65 m | 211.9 | – | 38.2 | 1.07 m, 2.14 m | 79.1 | 3.57 m | 38.7 | 1.03 m, 1.69 o |
13 | 42.5 | – | 43.0 | – | 56.8 | – | 42.3 | – | 46.6 | – | 41.6 | – |
14 | 54.7 | 0.76 m | 54.3 | 0.89 m | 54.0 | 1.18 m | 54.1 | 0.75 m | 55.4 | 1.11 m | 50.0 | 1.48 dt (6.0, 12.0) |
15 | 37.5 | 1.52 dt (4.2, 12.6), 2.22 m | 36.0 | 1.16 m, 2.41 m | 34.7 | 1.52 o, 2.47 m | 35.5 | 1.25 m, 2.40 m | 32.2 | 1.60 m, 2.06 o | 34.5 | 1.73 dt (6.0, 13.2), 3.27 dt (6.0, 13.2) |
16 | 72.9 | 4.83 o | 75.4 | 5.33 dt (4.2 7.8) | 73.4 | 5.62 dt (4.2, 7.8) | 74.7 | 5.64 dt (4.2 7.8) | 81.2 | 5.02 o | 81.3 | 5.04 m |
17 | 59.9 | 1.86 d (7.2) | 62.4 | 1.58 m | 59.0 | 3.27 d (7.8) | 66.6 | 2.46 d (7.2) | 63.7 | 2.30 dd (6.6, 8.4) | 62.9 | 1.86 dd (6.6, 7.8) |
18 | 15.8 | 1.38 s | 13.3 | 1.18 s | 13.9 | 1.52 s | 13.8 | 1.19 s | 11.3 | 1.14 s | 16.6 | 0.88 s |
19 | 19.4 | 0.87 s | 19.5 | 0.89 s | 18.9 | 0.90 s | 19.4 | 0.87 s | 19.4 | 0.90 s | 17.1 | 0.95 s |
20 | 82.5 | – | 65.2 | 4.45 m | 204.4 | – | 205.5 | – | 41.8 | 2.45 m | 40.7 | 2.21 q (6.6) |
21 | 28.6 | 1.72 s | 24.2 | 1.43 d (6.6) | 30.7 | 2.26 s | 30.5 | 2.12 s | 15.7 | 1.59 d (6.6) | 16.6 | 1.31 d (6.6) |
22 | 215.8 | – | 173.1 | – | 173.3 | – | 173.3 | – | 110.9 | – | 110.7 | – |
23 | 36.0 | 3.14 m | 32.5 | 2.41 o, 2.46 dd (6.6, 9.0) | 32.2 | 2.37 m, 2.42 m | 32.2 | 2.36 m, 2.42 m | 37.3 | 1.99 m, 2.11 m | 37.3 | 1.96 m, 2.04 m |
24 | 27.7 | 1.60 m, 2.13 m | 29.2 | 1.58 m, 1.99 m | 29.0 | 1.57 m, 1.94 m | 29.0 | 1.57 m, 1.94 m | 28.4 | 1.67 m, 2.04 o | 28.4 | 1.66 m, 2.05 o |
25 | 33.7 | 1.97 m | 33.6 | 1.92 m | 33.5 | 1.86 m | 33.5 | 1.86 m | 34.5 | 1.92 m | 34.7 | 1.91 m |
26 | 75.6 | 3.50 dd (6.6, 9.0), 4.07 o | 74.8 | 3.46 dd (6.6, 9.6), 3.99 o | 74.7 | 3.44 dd (6.0, 9.6), 3.95 o | 74.8 | 3.44 dd (6.6, 9.6), 3.95 o | 75.5 | 3.45 dd (7.2, 9.0), 4.07 o | 75.4 | 3.45 dd (7.2, 9.6), 4.07 o |
27 | 17.2 | 1.00 d (7.2) | 16.9 | 0.96 d (6.6) | 16.9 | 0.91 d (6.6) | 16.9 | 0.91 d (6.6) | 17.5 | 1.01 d (7.2) | 17.5 | 1.01 d (6.6) |
* o = overlapped