Table 2. 13C and 1H NMR Data (J in Hz) of the Aglycone Moieties of Compounds 2–5 (Pyridine-d5)a.
| agameroside
E (2) |
macroacanthoside
A (3) |
macroacanthoside
B (4) |
macroacanthoside
C (5) |
|||||
|---|---|---|---|---|---|---|---|---|
| δC | δH | δC | δH | δC | δH | δC | δH | |
| 1ax | 36.7 | 0.69 ddd (13.4, 13.4, 3.8) | 35.0 | 1.18b | 45.1 | 1.11b | 43.6 | 1.58b |
| 1eq | 1.29 m | 1.49 ddd (13.3, 3.7, 3.7) | 2.04 dd (12.8, 4.9) | 2.24 dd (12.7, 4.9) | ||||
| 2ax | 29.7 | 1.53b | 29.6 | 1.64b | 70.2 | 3.92b | 69.8 | 4.03b |
| 2eq | 1.98 brd (12.9) | 2.10 brd (12.4) | ||||||
| 3 | 77.1 | 3.85 m | 76.7 | 3.84 m | 83.9 | 3.84 m | 83.5 | 3.84 dddd (11.4, 9, 2, 5.0, 5.0) |
| 4ax | 34.7 | 1.31 m | 34.6 | 1.36b | 33.9 | 1.46 ddd (12.1, 12.1, 12.1) | 33.8 | 1.51b |
| 4eq | 1.77 brd (13.6) | 1.83 brd (13.5) | 1.85 ddd (13.1, 3.8, 3.0) | 1.93 ddd (13.1, 4.3, 3.3) | ||||
| 5 | 44.5 | 0.82b | 42.5 | 1.05 dddd (12.6, 12.6, 3.0, 3.0) | 44.4 | 0.94b | 42.5 | 1.16b |
| 6ax | 28.7 | 1.10 m (2H) | 27.9 | 1.26b | 27.9 | 1.05 m | 27.3 | 1.19b (2H) |
| 6eq | 1.14 m | 1.12 m | ||||||
| 7ax | 31.8 | 0.74 dddd (11.7, 11.7, 11.7, 5.2) | 32.7 | 0.89 m | 31.6 | 0.72 m | 32.6 | 0.89 m |
| 7eq | 1.52b | 1.71b | 1.50b | 1.74b | ||||
| 8 | 34.4 | 1.72 dddd (11.0, 11.0, 11.0, 3.7) | 36.9 | 2.38 m | 33.8 | 1.71b | 36.2 | 2.36 m |
| 9 | 55.5 | 0.87b | 171.4 | 55.4 | 0.97b | 170.6 | ||
| 10 | 36.3 | 39.6 | 37.3 | 40.6 | ||||
| 11ax | 38.1 | 2.35 dd (13.8, 13.8) | 120.0 | 5.77 d (1.9) | 38.1 | 2.40 dd (12.4, 11.9) | 120.3 | 5.96 d (1.3) |
| 11eq | 2.21 dd (14.3, 4.9) | 2.34 dd (14.3, 5.3) | ||||||
| 12 | 212.8 | 204.4 | 212.6 | 204.3 | ||||
| 13 | 55.4 | 51.4 | 55.4 | 51.4 | ||||
| 14 | 55.9 | 1.34b | 52.7 | 1.69b | 55.7 | 1.33b | 52.7 | 1.68b |
| 15a | 31.5 | 1.57 m | 31.9 | 1.64b | 31.5 | 1.56b | 31.9 | 1.63b |
| 15b | 2.08 ddd (12.5, 6.8, 6.8) | 2.17 ddd (11.9, 5.1, 5.1) | 2.08 ddd (12.4, 7.0, 5.5) | 2.17 m | ||||
| 16 | 79.8 | 4.46b | 80.3 | 4.51b | 79.8 | 4.46b | 80.3 | 4.50b |
| 17 | 54.4 | 2.74 dd (8.7, 6.7) | 54.6 | 2.62 dd (8.8, 7.1) | 54.3 | 2.73 dd (8.7, 6.7) | 54.6 | 2.61 dd (8.7, 7.2) |
| 18 | 16.2 | 1.06 s | 15.3 | 0.99 s | 16.2 | 1.05 s | 15.3 | 0.98 s |
| 19 | 11.8 | 0.65 s | 18.4 | 0.81 s | 13.0 | 0.73 s | 19.5 | 0.90 s |
| 20 | 42.7 | 1.90 dq. (6.9, 6.9) | 43.0 | 1.99 dq (6.9, 6.9) | 42.7 | 1.89 dq. (6.9, 6.9) | 43.0 | 1.98 dq (7.2, 7.2) |
| 21 | 14.0 | 1.34 d (6.9) | 13.9 | 1.39 d (6.9) | 14.0 | 1.33 d (6.9) | 13.9 | 1.38 d (6.9) |
| 22 | 109.4 | 109.5 | 109.4 | 109.5 | ||||
| 23ax | 31.9 | 1.60b | 31.8 | 1.63b | 31.9 | 1.60b | 31.8 | 1.62b |
| 23eq | 1.67b | 1.71b | 1.66b | 1.71b | ||||
| 24 | 29.3 | 1.53 (2H)b | 29.3 | 1.54 (2H)b | 29.3 | 1.53 (2H)b | 29.3 | 1.55 (2H)b |
| 25 | 30.6 | 1.55b | 30.6 | 1.57b | 30.6 | 1.55b | 30.6 | 1.56b |
| 26ax | 67.0 | 3.46 dd (10.7, 10.7) | 67.0 | 3.48 dd (10.7, 10.7) | 67.0 | 3.46 dd (10.7, 10.7) | 67.1 | 3.47 dd (10.6, 10.6) |
| 26eq | 3.57 dd (11.1, 3.8) | 3.57 dd (10.7, 4.0) | 3.57 dd (11.1, 3.9) | 3.58 dd (10.8, 3.6) | ||||
| 27 | 17.4 | 0.66 d (5.9) | 17.4 | 0.67 d (5.7) | 17.4 | 0.66 d (5.8) | 17.4 | 0.67 d (5.3) |
a
The assignments were confirmed by 1H–1H-COSY, 2D-TOCSY, HSQC, HSQC-TOCSY, and HMBC experiments.
b
Overlapped with other signals.