Table 1.
13C- (125 MHz) and 1H-NMR (500 MHz) spectral data for KSR1* (D2O).
| C/H | δC | δH (m, J Hz) | C/H | δC | δH (m, J Hz) |
|---|---|---|---|---|---|
| Aglycone | |||||
| 2 | 163.84 | 8a | 105.58 | ||
| 3 | 102.89 | 6.79 (s) | 1′ | 123.01 | |
| 4 | 182.12 | 2′ | 112.86 | 7.44 (d, 2.3) | |
| 4a | 148.78 | 3′ | 146.78 | ||
| 5 | 146.78 | 4′ | 151.10 | ||
| 6 | 130.75 | 5′ | 112.01 | 7.12 (d, 8.7) | |
| 7 | 150.87 | 6′ | 118.60 | 7.55 (dd, 8.7, 2.3) | |
| 8 | 93.70 | 6.98 (s) | OCH3 | 55.71 | 3.88 (s) |
| 3′-cyclopent-1-ene | |||||
| 1a′ | 158.20 | 5a′ | 26.30 | ||
| 2a′ | 132.70 | 5.02 (d, 7.2 ) | 3a′-CO | 168.3 | |
| 3a′ | 74.20 | 5.12 (ddd,12.8, 4.9, 5) | CO-CH3 | 18.7 | 2.06 (s) |
| 4aα′ | 29.60 | 1.94 (m, dd, 12.8) | 5a′-αCH3 | 16.5 | 1.12 (s) |
| 4aβ′ | 29.60 | 1.66 (m, dd) | 5a′-βCH3 | 16.5 | 1.12 (s) |
| 7-O-glucopyranosyl | |||||
| 1′′ | 97.27 | 5.49 (d, 7.3) | 5′′ | 76.85 | 3.25 (t, 9.8) |
| 2′′ | 76.53 | 3.81 (d, 9.4) | 6′′ | 60.89 | 3.44 (dd, 12.0, 6.0) |
| 3′′ | 86.63 | 3.73 (t, 9.4) | OCOCH3 | 20.38 | 1.94 (s) |
| 4′′ | 68.14 | 3.44† | OCOCH3 | 170.04 | |
| 2′′-O-rhamnopyranosyl | |||||
| 1′′′ | 101.03 | 5.21 (d, 1.5) | 4′′′ | 71.97 | 3.18 (t, 9.8) |
| 2′′′ | 70.20 | 3.85† | 5′′′ | 68.89 | 3.64 (dd, 9.5, 6.1) |
| 3′′′ | 70.20 | 3.37 (m) | 6′′′ | 17.78 | 1.04 (d, 6.1) |
| 3′′-O-glucopyranosyl | |||||
| 1′′′′ | 103.01 | 4.42 (d, 7.6) | 4′′′′ | 69.93 | 3.13 (t, 9.8) |
| 2′′′′ | 73.33 | 3.13 (t, 9.8) | 5′′′′ | 72.91 | 3.85† |
| 3′′′′ | 76.53 | 3.22 (t, 9.2) | 6′′′′ | 62.89 | 4.10 (dd, 11.9, 6.7), 4.32 (brd, 9.8) |
* The 13C- and 1H- assignments were based on 2D NMR experiments (DQF-COSY, HMQC and HMBC); †Signal patterns are unclear due to overlapping; s = singlet, d = doublet, dd = doublet of doublets, t = triplet, m = multiplet, brd = broad doublet, ddd = triplet of doublets.