Table 1.
1H NMR spectroscopic data for derrisisoflavones H–K (1–4) and 6-hydroxyisosativan (5)
| No. | 1 a | 2 b | 3 a | 4 a | 5 a |
|---|---|---|---|---|---|
| 2 | 8.17 (s) | 8.51 (s) | 7.97 (s) | 8.00 (s) | 4.17 (ddd, 10.2, 3.3, 1.9, Heq) |
| 3.90 (t, 10.2, Hax) | |||||
| 3 | 3.43 (dddd, 10.7, 10.2, 5.3, 3.3, Hax) | ||||
| 4 | 2.91 (dd, 15.9, 10.7, Hax) | ||||
| 2.73 (ddd, 15.9, 5.3, 1.9, Heq) | |||||
| 5 | 6.51 (s) | ||||
| 8 | 6.37 (s) | 6.36 (s) | 6.37 (s) | ||
| 2′ | 7.05 (br. s) | 7.05 (d, 1.6) | 7.19 (d, 2.0) | 7.25 (d, 2.3) | |
| 3′ | 6.38 (d, 2.5) | ||||
| 5′ | 6.82 (d, 8.0) | 6.81 (d, 8.0) | 6.79 (d, 8.2) | 6.82 (d, 8.2) | 6.36 (dd, 8.4, 2.5) |
| 6′ | 6.87 (br. d, 8.0) | 6.85 (dd, 8.0, 1.6) | 7.15 (dd, 8.2, 2.0) | 7.21 (dd, 8.2, 2.3) | 6.95 (d, 8.4) |
| 1″ | 6.86 (s) | 3.48 (d, 7.3) | 2.92 (t, 7.3) | 3.30 (overlapped) | |
| 2″ | 5.29 (t, 7.3) | 3.68 (t, 7.3) | 5.22 (t, 7.2) | ||
| 4″ | 1.60 (s) | 1.62 (s) | 1.65 (s) | ||
| 5″ | 1.60 (s) | 1.79 (s) | 1.77 (s) | ||
| 1′′′ | 3.64 (d, 6.8) | 7.07 (s) | 3.32 (d, 7.3) | 2.87 (t, 7.0) | |
| 2′′′ | 5.30 (t, 6.8) | 5.33 (t, 7.3) | 3.78 (t, 7.0) | ||
| 4′′′ | 1.67 (s) | 1.56 (s) | 1.72 (s) | ||
| 5′′′ | 1.85 (s) | 1.56 (s) | 1.72 (s) | ||
| 5-OH | 13.21 (s) | ||||
| 3′-OH | 9.14 (br. s) | ||||
| 4′-OH | 9.14 (br. s) | ||||
| 7-OCH3 | 3.78 (s) | ||||
| 4′-OCH3 | 3.71 (s) | ||||
| 3″-OCH3 | 3.11 (s) | ||||
| 3′′′-OCH3 | 3.00 (s) |
aMeasured in CD3OD (δ H 3.30 ppm)
bMeasured in DMSO-d 6 (δ H 2.50 ppm)