Table 3. 13C and 1H NMR Data (J in Hz) of the Sugar Portions of Compounds 2–5 (Pyridine-d5)a.
| agameroside
E (2) |
macroacanthoside
A (3) |
macroacanthoside
B (4) |
macroacanthoside
C (5) |
|||||||||
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| δC | δH (C–H) | δH (O–H) | δC | δH (C–H) | δH (O–H) | δC | δH (C–H) | δH (O–H) | δC | δH (C–H) | δH (O–H) | |
| β-d-Gal | β-d-Gal | β-d-Gal | β-d-Gal | |||||||||
| 1 | 102.5 | 4.83 d (7.7) | 102.6 | 4.83 d (7.6) | 103.2 | 4.88 d (7.9) | 103.2 | 4.89 d (7.6) | ||||
| 2 | 73.2 | 4.40 dd (8.8, 7.8) | 6.95 | 73.2 | 4.41 dd (8.6, 8.6) | 6.97 | 72.5 | 4.50 dd (9.0, 7.9) | 72.7 | 4.50 dd (8.6, 8.0) | ||
| 3 | 75.6 | 4.10b | 5.07 | 75.6 | 4.10b | 5.08 | 75.6 | 4.12b | 5.30 | 75.6 | 4.13 dd (9.6, 3.0) | 5.32 |
| 4 | 79.8 | 4.57 brd (3.9) | 79.8 | 4.58 brd (3.6) | 79.0 | 4.58 brd (3.4) | 79.0 | 4.58 brd (3.3) | ||||
| 5 | 75.5 | 3.99b | 75.5 | 3.99b | 75.9 | 4.02b | 75.9 | 4.02b | ||||
| 6 | 60.8 | 4.20 dd (11.2, 5.8) | 6.03 | 60.8 | 4.21b | 6.04 | 60.8 | 4.18b | 6.03 | 60.8 | 4.18 dd (12.5. 4.6) | 6.06 |
| 4.65b | 4.64b | 4.57 brd (8.2) | 4.57b | |||||||||
| β-d-Glc | β-d-Glc | β-d-Glc | β-d-Glc | |||||||||
| 1 | 104.9 | 5.16 d (8.0) | 104.8 | 5.16 d (7.9) | 104.3 | 5.22 d (7.9) | 104.3 | 5.22 d (7.9) | ||||
| 2 | 81.1 | 4.30 dd (8.4, 8.9) | 81.0 | 4.31 dd (8.4, 8.8) | 80.8 | 4.26 dd (8.5, 7.9) | 80.8 | 4.27 dd (8.4, 8.9) | ||||
| 3 | 87.2 | 4.07 dd (8.8, 8.7) | 87.2 | 4.08 dd (8.8, 8.8) | 87.3 | 4.05 dd (8.6, 8.8) | 87.3 | 4.05b | ||||
| 4 | 70.4 | 3.80 dd (8.9, 8.9) | 5.36 | 70.4 | 3.79 dd (9.4, 9.4) | 5.36 | 70.4 | 3.80 dd (7.9, 7.8) | 5.34 | 70.3 | 3.81b | 5.35 |
| 5 | 77.7 | 3.84b | 77.7 | 3.82b | 77.7 | 3.81 m | 77.7 | 3.80b | ||||
| 6 | 63.0 | 4.04 brd (8.2) | 6.74 | 63.0 | 4.04b | 6.74 | 63.0 | 4.04b | 6.65 | 62.9 | 4.05b | 6.65 |
| 4.50b | 4.49b | 4.48b | 4.46b | |||||||||
| β-d-Glc′ | β-d-Glc′ | β-d-Glc′ | β-d-Glc′ | |||||||||
| 1 | 104.4 | 5.48 d (8.1) | 104.4 | 5.49 d (8.0) | 104.3 | 5.49 d (8.1) | 104.3 | 5.49 d (8.1) | ||||
| 2 | 76.6 | 3.99 dd (9.0, 9.0) | 6.71 | 76.6 | 3.98 dd (8.8, 8.8) | 6.72 | 76.5 | 3.95 dd (8.4, 8.4) | 6.77 | 76.5 | 3.94 dd (8.7, 8.1) | 6.77 |
| 3 | 83.2 | 4.21 dd (9.1, 9.1) | 83.2 | 4.22 dd (9.1, 9.3) | 83.5 | 4.21 dd (9.1, 9.1) | 83.7 | 4.22 dd (9.2, 8.6) | ||||
| 4 | 69.2 | 4.11 dd (8.8, 8.8) | 6.86 | 69.2 | 4.10b | 6.87 | 69.5 | 3.96 dd (9.3, 9.3) | 6.86 | 69.5 | 3.97b | 6.87 |
| 5 | 78.5 | 3.76 ddd (9.7, 3.8, 1.6) | 78.5 | 3.77 ddd (9.5, 4.3, 2.4) | 78.1 | 3.72 ddd (9.7, 5.0, 2.4) | 78.1 | 3.71 ddd (9.3, 4.7, 2.2) | ||||
| 6 | 62.3 | 4.33b | 5.90 | 62.3 | 4.35 | 5.92 | 62.5 | 4.36 dd (11.7, 3.4) | 5.62 | 62.5 | 4.35 ddb | |
| 4.50 da (11.7) | 4.50 | 4.47b | 4.47b | |||||||||
| β-d-Xyl | β-d-Xyl | β-d-Xyl | β-d-Xyl | |||||||||
| 1 | 105.0 | 5.11 d (7.7) | 105.0 | 5.12 d (7.7) | 105.0 | 5.12 d (7.7) | 105.0 | 5.12 d (7.7) | ||||
| 2 | 75.3 | 3.94 dd (8.8, 8.8) | 8.38 | 75.3 | 3.93 dd (9.0, 9.0) | 8.38 | 75.4 | 3.93 dd (8.3, 8.3) | 8.30 | 75.4 | 3.93 dd (8.3, 8.3) | 8.31 |
| 3 | 78.6 | 3.99 dd (9.0, 9.0) | 78.6 | 3.99 dd (8.8, 8.8) | 78.6 | 3.98 dd (8.9, 8.9) | 78.6 | 3.98 dd (8.9, 8.9) | 7.68 | |||
| 4 | 70.7 | 4.10b | 70.7 | 4.08b | 70.7 | 4.09 dddb | 70.7 | 4.09b | ||||
| 5 | 67.3 | 3.63 dd (10.8; 10.8) | 67.3 | 3.63 dd (10.8; 10.8) | 67.3 | 3.61 dd (10.9; 10.9) | 67.3 | 3.61 dd (10.9; 10.9) | ||||
| 4.21 dd (11.1; 5.1) | 4.20 dd (11.2; 5.5) | 4.19 dd (11.2; 5.3) | 4.19 dd (11.2; 5.5) | |||||||||
| α-l-Rha | α-l-Rha | α-l-Rha | α-l-Rha | |||||||||
| 1 | 102.8 | 6.10 s | 102.8 | 6.10 d (1.6) | 102.8 | 6.10 d (1.5) | 102.8 | 6.10 s | ||||
| 2 | 72.4 | 4.66 d (3.4) | 72.4 | 4.66 brs | 6.58 | 72.5 | 4.66 dd (3.5, 1.6) | 72.5 | 4.66 brs | 6.62 | ||
| 3 | 72.7 | 4.47 brd (10.9) | 72.7 | 4.46 dd (9.3, 2.9) | 6.26 | 72.7 | 4.46 dd (9.3, 3.7) | 72.7 | 4.46b | |||
| 4 | 74.2 | 4.27 dd (9.6, 9.6) | 74.2 | 4.28 dd (9.6, 9.6) | 74.2 | 4.29 dd (9.6, 9.6) | 74.2 | 4.28b | 6.76 | |||
| 5 | 69.8 | 4.91 dq (6.2, 9.7) | 69.8 | 4.92 dq (6.3, 9.3) | 69.8 | 4.90 dq (6.5, 11.0) | 69.8 | 4.89b | ||||
| 6 | 18.7 | 1.62 d (6.2) | 18.7 | 1.62 d (6.3) | 18.7 | 1.61 d (6.2) | 18.7 | 1.61 d (6.2) | ||||
a
The assignments were confirmed by 1H–1H-COSY, 2D-TOCSY, HSQC, HSQC-TOCSY, and HMBC experiments.
b
Overlapped with other signals.