Table 1. 1H and 13C NMR Data for Aglycones of Compounds 1, 2, and 5a.
1 |
2 |
5 |
|||||
---|---|---|---|---|---|---|---|
position | δH | δC | δH | δC | position | δH | δC |
1a | 1.77b | 39.9 | 1.71b | 39.0 | 2 | 174.0 | |
1b | 1.07, m | 1.08b | 3 | 5.91, s | 126.6 | ||
2a | 1.92b | 27.0 | 2.05, m | 26.5 | 4 | 140.0 | |
2b | 1.76b | 1.74b | 5 | 7.91, d (16.0) | 133.8 | ||
3 | 3.18, dd (11.5, 4.3) | 89.6 | 3.19, dd (12.0, 4.0) | 89.5 | 6 | 6.25, d (16.0) | 126.7 |
4 | 39.1 | 39.0 | 7 | 80.5 | |||
5 | 0.83, br d (11.7) | 57.3 | 0.84, br d (11.5) | 57.2 | 8 | 51.0 | |
6a | 1.64b | 19.0 | 1.59b | 19.0 | 9a | 2.09, dd (14.0, 7.5) | 39.1 |
6b | 9b | 1.93, dd (14.0, 11.0) | |||||
7a | 1.66b | 34.3 | 1.68b | 34.2 | 10 | 4.01, m | 72.8 |
7b | 1.41, m | 1.41, m | 11a | 2.45, dd (14.4, 6.5) | 39.0 | ||
8 | 43.0 | 40.0 | 11b | 1.99, dd (14.4, 10.0) | |||
9 | 1.61b | 52.2 | 1.71b | 48.5 | 12 | 87.5 | |
10 | 36.9 | 36.0 | 13 | 2.04, s | 20.1 | ||
11a | 1.61b | 23.5 | 2.00b | 24.1 | 14 | 178.0 | |
11b | 1.98b | 15 | 1.12, s | 14.0 | |||
12a | 2.67, br dd (16.0, 12.0) | 134.0 | 5.26, t (3.0) | 129.4 | 16 | 1.40, s | 18.2 |
12b | 1.99, m | Glc-1 | 4.37, d (7.8) | 103.0 | |||
13 | 153.3 | 133.0 | 2 | 3.16, br t (9.0) | 74.6 | ||
14 | 45.0 | 41.8 | 3 | 3.26, t (9.5) | 77.4 | ||
15a | 1.92b | 27.0 | 1.99b | 28.0 | 4 | 3.30, t (9.5) | 71.3 |
15b | 1.76b | 1.82, m | 5 | 3.38, m | 77.7 | ||
16a | 2.15, ddd (14.3, 6.5, 3.8) | 34.3 | 1.89b | 27.0 | 6a | 3.86, dd (12.0, 3.0) | 62.2 |
16b | 1.93b | 1.62b | 6b | 3.68, dd (12.0, 5.0) | |||
17 | 53.1 | 50.0 | |||||
18 | 134.0 | 3.79, s | 56.8 | ||||
19 | 211.0 | 216.5 | |||||
20 | 45.5 | 44.0 | |||||
21a | 1.85, ddd (17.0, 14.3, 3.8) | 36.6 | 1.93b | 35.2 | |||
21b | 1.65b | 1.77b | |||||
22a | 2.30, ddd (14.3, 6.6, 3.3) | 32.0 | 2.26, ddd (15.0, 11.0, 4.0) | 31.0 | |||
22b | 1.63b | 1.80b | |||||
23 | 1.06, s | 28.0 | 1.07, s | 28.1 | |||
24 | 0.87, s | 17.0 | 0.89, s | 17.0 | |||
25 | 0.99, s | 17.0 | 1.00, s | 16.0 | |||
26 | 0.94, s | 14.0 | 0.85, s | 17.5 | |||
27 | 1.27, s | 21.0 | 0.97, s | 23.0 | |||
28 | 174.2 | 175.0 | |||||
29 | 1.09, s | 26.5 | 1.22, s | 27.0 | |||
30 | 1.10, s | 25.5 | 1.11, s | 25.6 |
Spectra were recorded in methanol-d4 at 600 MHz (1H) and 150 MHz (13C). J values are in parentheses and reported in Hz; chemical shifts are given in ppm; assignments were confirmed by 1D-TOCSY, COSY, HSQC, and HMBC experiments.
Overlapped signal.