Table 1.
NMR spectral data for metabolites 1 – 4 a.
| # | 1 (δH) | 1 (δC) | 2 (δH) | 2 (δC) | 3 (δH) | 3 (δC) | 4 (δH) | 4 (δC) |
|---|---|---|---|---|---|---|---|---|
| 1 | α,1.40 (m) β,1.91 (m) |
39.4 | α, 1.90 (ddd, 4.4, 7.6, 13.2) β, 1.38 (m) |
39.5 | α,1.39 (m) β,1.91 (m) |
39.5 | α, 0.90(m) β, 1.63 (m) |
38.7 |
| 2 | α, 2.40 (ddd, 4.7, 7.8, 15.7) β, 2.47 (ddd, 7.5, 9.6, 15.7) |
34.0 | α, 2.40 (m), β, 2.47 (ddd, 7.3, 9.7, 15.9) |
34.1 | α, 2.42 (ddd, 4.4, 7.9, 15.8) β, 2.46 (ddd, 7.5, 9.8, 15.8) |
34.1 | α, 1.58 (m) β, 1.63 (m) |
27.4 |
| 3 | 218.5 | 217.8 | 218.0 | 3.18 (dd, 4.4, 10.6) | 79.0 | |||
| 4 | 47.3 | 47.3 | 47.3 | 38.9 | ||||
| 5 | 1.33 (m) | 54.7 | 1.32 (m) | 54.8 | 1.34 (m) | 54.7 | 0.67 (dd, 2.72, 9.20) | 55.2 |
| 6 | α,1.44 (m) β,1.56 (m) |
19.6 | 2H, 1.41-1.53 (m) | 19.6 | 2Η ,1.48 (m) | 19.7 | α, 1.38 (m) β, 1.52 (m) |
18.3 |
| 7 | 2H, 1.44 (m) | 33.4 | 2H, 1.45 (m) | 33.6 | 2Η , 1.44 (m) | 33.5 | 2H, 1.37 (m) | 34.3 |
| 8 | 40.6 | 40.8 | 40.9 | 40.8 | ||||
| 9 | 1.38 (m) | 49.2 | 1.38 (m) | 49.3 | 1.40 (m) | 49.3 | 1.28 (m) | 50.0 |
| 10 | 36.7 | 36.8 | 36.8 | 37.1 | ||||
| 11 | α, 1.55 (m) β, 1.40 (m) |
21.3 | α, 1.06 (m) β, 1.52 (m) |
21.2 | α, 1.51 (m) β, 1.35 (m) |
21.3 | α, 1.47 (m) β, 128 (m) |
20.7 |
| 12 | α, 1.38 (m) β, 1.56 (m) |
27.4 | α, 1.35 (m) β, 1.65 (m) |
26.5 | α, 1.34 (m) β, 1.55 (m) |
27.6 | α, 1.65 (m) β, 1.38 (m) |
26.5 |
| 13 | 1.74 (m) | 37.8 | 1.79 (ddd, 4.1, 11.7, 11.7) | 37.8 | 1.70 (m) | 37.0 | 1.77 (ddd 4.4, 11.6 , 11.6) | 37.7 |
| 14 | 42.9 | 43.1 | 42.9 | 42.8 | ||||
| 15 | α, 1.05 (m) β, 1.69 (m) |
27.1 | α, 1.03 (m) β, 1.69 (m) |
27.2 | α, 1.07 (m) β, 1.72 (m) |
26.8 | α, 1.03 (m) β, 1.70 (m) |
27.2 |
| 16 | 2H, 1.47 (m) | 35.1 | a, 1.46 (m) b, 1.53 (m) |
35.2 | α, 1.19 (m) β, 1.92 (m) |
29.1 | α, 1.48 (m) β, 1.59 (m) |
35.3 |
| 17 | 43.0 | 42.9 | 47.8 | 43.0 | ||||
| 18 | 1.43 (m) | 48.9 | 1.26 (m) | 47.0 | 1.64 (m) | 49.3 | 1.24 (m) | 47.1 |
| 19 | 1.89 (m) | 42.6 | 2.35 (m) | 37.3 | 1.91 (m) | 42.7 | 2.35 (m) | 37.4 |
| 20 | 2.60 (m) | 48.9 | 2.63 (dq, 2.9, 6.8) | 49.7 | 2.57 (m) | 49.0 | 2.64 (dq, 3.1, 6.8) | 49.7 |
| 21 | α, 1.51 (m) β, 1.88 (m) |
25.0 | α, 1.15 (m) β, 1.68 (m) |
23.6 | α, 1.55 (m) β, 1.92 (m) |
24.9 | α, 1.15 (m) β, 1.68 (m) |
23.6 |
| 22 | α, 1.36 (m) β, 1.47 (m) |
39.9 | α, 1.39 (m) β, 1.45 (m) |
40.4 | α, 0.98(m) β,1.92 (m) |
33.7 | α, 1.08 (m) β, 1.38 (m) |
40.4 |
| 23 | 1.06 (s) | 26.6 | 1.06 (s) | 26.6 | 1.06 (s) | 26.7 | 0.96 (s) | 28.0 |
| 24 | 1.01 (s) | 21.0 | 1.01 (s) | 21.1 | 1.01 (s) | 21.1 | 0.75 (s) | 15.4 |
| 25 | 0.91 (s) | 15.7 | 0.93 (s) | 15.9 | 0.91 (s) | 16.0 | 0.82 (s) | 16.0 |
| 26 | 1.06 (s) | 15.7 | 1.07 (s) | 15.8 | 1.06 (s) | 15.8 | 1.03 (s) | 15.9 |
| 27 | 0.92 (s) | 14.2 | 0.93 (s) | 14.3 | 0.94 (s) | 14.5 | 0.92 (s) | 14.3 |
| 28 | 0.75 (s) | 17.5 | 0.78 (s) | 17.9 | α, 3.26 (d, 10.9) β, 3.76 (d, 10.9) |
60.1 | 0.78 (s) | 17.9 |
| 29 | 1.07 (d, 7.2) | 14.4 | 1.01 (d, 6.8) | 7.4 | 1.09 (d, 7.20) | 14.5 | 1.01 (d, 6.8) | 7.4 |
| 30 | 9.84 (d, 2.0) | 207.1 | 9.60 (s) | 205.1 | 9.83 (d, 2.0) | 206.7 | 9.60 (s) | 205.1 |
a 1H (400 MHz) and 13C (50.3 MHz) NMR spectra were recorded in CDCl3 with TMS as internal standard, δ (ppm), (J) in Hz