Table 3.
NMR data (600 MHz, DMSO-d6) of aplysinin A (2), hexadellin B (10), and diacetylhexadellin B (20).
| position | 2 | 10 | 20a | ||||
| δC | δH | δC | δH | δC | |||
| 1 | 73.5, CH | 3.93, d (8.2) | 74.0 | 3.92, d (7.3) | 73.1 | ||
| 2 | 113.1, C | – | 113.5 | – | 122.1b | ||
| 3 | 147.1, C | – | 147.6 | – | 149.7 | ||
| 4 | 120.9, C | – | 121.4 | – | 107.8b | ||
| 5 | 131.1, CH | 6.56, s | 131.6 | 6.58, d (0.8) | 130.2 | ||
| 6 | 90.3, C | – | 90.7 | – | 89.9 | ||
| 7 | 39.7, CH2 | 3.17, d (18.4); | 39.6 | 3.19, d (18.1); | 39.9 | ||
| 3.61, d (18.4) | 3.60, d (18.1) | ||||||
| 8 | 154.3, C | – | 154.9 | – | 153.5 | ||
| 9 | 159.0, C | – | 159.4 | – | 158.6 | ||
| 10 | 46.3, CH2 | 3.33, 2H, overlapped | 40.4 | 3.38, m | 40.4 | ||
| 11 | 69.3, CH | 4.67, t (6.1) | 33.6 | 2.77, t (7.1) | 34.4 | ||
| 12 | 142.5, C | – | 139.5 | – | 137.2 | ||
| 13,17 | 130.4, 2CH | 7.57, 2H, s | 133.5 | 7.54, s | 132.8 | ||
| 14,16 | 117.3, 2C | – | 117.7 | – | 118.2 | ||
| 15 | 151.4, C | – | 150.9 | – | 151.5 | ||
| 18 | 71.3, CH2 | 3.96, 2H, t (6.2) | 70.8 | 4.00, t (6.1) | 72.1 | ||
| 19 | 29.8, CH2 | 1.91, 2H, q (6.9) | 28.2 | 2.08, m | 29.4 | ||
| 20 | 35.7, CH2 | 3.25, 2H, q (6.7) | 37.0 | 3.08, br s | 37.7 | ||
| 21 | 169.1, C | – | – | – | 170.0 | ||
| 22 | 22.6, CH3 | 1.80, 3H, s | – | – | 23.6 | ||
| 3-OMe | 59.6, CH3 | 3.65, 3H, s | 60.1 | 3.65, s | 60.3 | ||
| 9-NH | – | 8.39, t (5.9) | – | 8.59, t (5.9) | – | ||
| 1-OH | – | 6.36, d (8.2) | – | 6.37, d (7.8) | – | ||
| 11-OH | – | 5.72, d (4.4) | – | – | – | ||
| 20-NH | – | 7.86, t (5.3) | – | – | – | ||
aThe 13C NMR data were obtained in CDCl3 [23]. bAssignments should be reversed.