Table 1.
1H and 13C NMR Data a for 1, 2 and 6 in D2O b.
| No. | 1 c | 2 c | 6 | |||
|---|---|---|---|---|---|---|
| δC, Type | δH (J in Hz) | δC, Type | δH (J in Hz) | δC, Type | δH (J in Hz) | |
| A1α | 94.8, CH | 5.23, d (3.5) | 94.8, CH | 5.23, d (3.5) | 94.8, CH | 5.23, d (3.5) |
| A2α | 74.2, CH | 3.57, m | 74.2, CH | 3.57, m | 74.1, CH | 3.57, m |
| A3α | 76.1, CH | 3.98, m | 76.0, CH | 3.98, m | 76.0, CH | 3.98, m |
| A4α | 79.6, CH | 3.66, m | 79.6, CH | 3.66, m | 79.6, CH | 3.66, m |
| A5α | 72.8, CH | 3.94, m | 72.8, CH | 3.94, m | 72.8, CH | 3.94, m |
| A6α | 63.3, CH2 | 3.84, m | 63.3, CH2 | 3.84, m | 63.3, CH2 | 3.84, m |
| A1β | 98.6, CH | 4.66, d (8.0) | 98.7, CH | 4.66, d (8.0) | 98.6, CH | 4.66, d (8.0) |
| A2β | 76.9, CH | 3.28, dd (9.5, 8.0) | 76.7, CH | 3.28, dd (9.5, 8.0) | 76.8, CH | 3.28, dd (9.5, 8.0) |
| A3β | 79.1, CH | 3.78, m | 79.1, CH | 3.77, m | 79.0, CH | 3.77, m |
| A4β | 79.7, CH | 3.66, m | 79.7, CH | 3.66, m | 79.7, CH | 3.66, m |
| A5β | 77.4, CH | 3.60, m | 77.4, CH | 3.60, m | 77.4, CH | 3.60, m |
| A6β | 63.3, CH2 | 3.91, m | 63.4, CH2 | 3.91, m | 63.3, CH2 | 3.91, m |
| B1 | 102.5, CH | 5.41, d (3.5) | 102.5, CH | 5.41, d (3.5) | 102.5, CH | 5.41, d (3.5) |
| B2 | 74.4, CH | 3.63, m | 74.4, CH | 3.63, m | 74.4, CH | 3.63, m |
| B3 | 76.2, CH | 3.96, m | 76.2, CH | 3.96, m | 76.2, CH | 3.96, m |
| B4 | 79.9, CH | 3.67, m | 79.9, CH | 3.67, m | 79.9, CH | 3.67, m |
| B5 | 74.0, CH | 3.85, m | 74.0, CH | 3.85, m | 74.0, CH | 3.85, m |
| B6 | 63.4, CH2 | 3.84, m | 63.4, CH2 | 3.84, m | 63.4, CH2 | 3.84, m |
| C1 | 102.5, CH | 5.41, d (3.5) | 102.5, CH | 5.41, d (3.5) | 102.5, CH | 5.41, d (3.5) |
| C2 | 74.4, CH | 3.63, m | 74.4, CH | 3.63, m | 74.4, CH | 3.63, m |
| C3 | 76.2, CH | 3.96, m | 76.2, CH | 3.96, m | 76.2, CH | 3.96, m |
| C4 | 79.9, CH | 3.67, m | 79.9, CH | 3.67, m | 79.9, CH | 3.67, m |
| C5 | 74.0, CH | 3.85, m | 74.0, CH | 3.85, m | 74.0, CH | 3.85, m |
| C6 | 63.4, CH2 | 3.84, m | 63.5, CH2 | 3.84, m | 63.4, CH2 | 3.84, m |
| D1 | 102.5, CH | 5.41, d (3.5) | 102.5, CH | 5.40, d (3.5) | 102.5, CH | 5.41, d (3.5) |
| D2 | 74.4, CH | 3.66, m | 74.4, CH | 3.66, m | 74.4, CH | 3.66, m |
| D3 | 76.2, CH | 3.95, m | 76.2, CH | 3.96, m | 76.2, CH | 3.96, m |
| D4 | 80.7, CH | 3.66, m | 80.8, CH | 3.66, m | 79.8, CH | 3.66, m |
| D5 | 71.7, CH | 4.06, m | 71.8, CH | 4.07, m | 74.0, CH | 3.85, m |
| D6a | 66.5, CH2 | 4.43, dd (12.5, 2.0) | 66.5, CH2 | 4.50, dd (12.5, 2.0) | 63.5, CH2 | 3.84, m |
| D6b | 4.24, m | 4.26, m | ||||
| E1 | 103.4, CH | 5.30, d (3.5) | 103.4, CH | 5.29, d (3.5) | 102.7, CH | 5.33, d (3.5) |
| E2 | 74.1, CH | 3.59, m | 74.1, CH | 3.60, m | 74.1, CH | 3.60, m |
| E3 | 75.8, CH | 3.63, m | 75.8, CH | 3.63, m | 75.8, CH | 3.63, m |
| E4 | 67.1, CH | 2.46, t (9.0) | 67.1, CH | 2.47, t (9.0) | 67.0, CH | 2.47, t (9.0) |
| E5 | 72.6, CH | 3.74, m | 72.6, CH | 3.76, m | 72.5, CH | 3.74, m |
| E6 | 20.2, CH3 | 1.31, d (6.0) | 20.2, CH3 | 1.32, d (6.0) | 20.2, CH3 | 1.32, d (6.0) |
| F1 | 57.8, CH | 3.53, m | 57.9, CH | 3.53, m | 57.9, CH | 3.53, m |
| F2 | 72.5, CH | 3.80, m | 72.5, CH | 3.80, m | 72.4, CH | 3.80, m |
| F3 | 73.6, CH | 4.16, m | 73.7, CH | 4.16, m | 73.5, CH | 4.16, m |
| F4 | 79.1, CH | 4.24, d (6.4) | 79.1, CH | 4.23, d (6.4) | 78.9, CH | 4.23, d (6.4) |
| F5 | 139.4, C | 139.3, C | 139.3, C | |||
| F6a | 64.9, CH2 | 4.22, m | 64.9, CH2 | 4.22, m | 64.9, CH2 | 4.22, m |
| F6b | 4.14, m | 4.14, m | 4.14, m | |||
| F7 | 129.2, CH | 5.98, d (4.5) | 129.2, CH | 5.98, d (4.5) | 129.1, CH | 5.98, d (4.5) |
| G1 | 100.4, CH | 5.38, d (4.0) | 100.4, CH | 5.38, d (4.0) | 100.4, CH | 5.38, d (4.0) |
| G2 | 74.3, CH | 3.63, m | 74.3, CH | 3.63, m | 74.4, CH | 3.63, m |
| G3 | 76.4, CH | 3.92, m | 76.4, CH | 3.92, m | 76.3, CH | 3.92, m |
| G4 | 79.9, CH | 3.61, m | 79.9, CH | 3.61, m | 79.9, CH | 3.61, m |
| G5 | 74.0, CH | 3.90, m | 74.0, CH | 3.90, m | 74.0, CH | 3.90, m |
| G6 | 63.5, CH2 | 3.86, m | 63.6, CH2 | 3.86, m | 63.5, CH2 | 3.86, m |
| H1 | 102.8, CH | 5.33, d (3.5) | 102.8, CH | 5.34, d (3.5) | 102.7, CH | 5.33, d (3.5) |
| H2 | 74.2, CH | 3.58, m | 74.2, CH | 3.59, m | 74.1, CH | 3.58, m |
| H3 | 75.4, CH | 3.61, m | 75.4, CH | 3.63, m | 75.4, CH | 3.61, m |
| H4 | 67.8, CH | 2.48, t (9.0) | 67.8, CH | 2.49, t (9.0) | 67.8, CH | 2.48, t (9.0) |
| H5 | 72.5, CH | 3.76, m | 72.5, CH | 3.78, m | 72.3, CH | 3.76, m |
| H6 | 20.2, CH3 | 1.35, d (6.0) | 20.2, CH3 | 1.36, d (6.0) | 20.2, CH3 | 1.35, d (6.0) |
| I1 | 58.8, CH | 3.54, m | 58.9, CH | 3.54, m | 58.8, CH | 3.54, m |
| I2 | 75.5, CH | 3.67, m | 75.5, CH | 3.67, m | 75.5, CH | 3.67, m |
| I3 | 75.6, CH | 3.77, m | 75.6, CH | 3.77, m | 75.6, CH | 3.77, m |
| I4 | 73.8, CH | 4.05, d (6.4) | 73.8, CH | 4.05, d (6.4) | 73.7, CH | 4.05, d (6.4) |
| I5 | 141.8, C | 141.8, C | 141.8, C | |||
| I6a | 64.5, CH2 | 4.23, m | 64.5, CH2 | 4.24, m | 64.4, CH2 | 4.23, m |
| I6b | 4.12, m | 4.12, m | 4.12, m | |||
| I7 | 126.6, CH | 5.90, dd (5.0, 1.0) | 126.7, CH | 5.91, dd (5.0, 1.0) | 126.6, CH | 5.91, dd (5.0, 1.0) |
| D6-O-acetyl | 177.0, C | - | - | - | - | |
| 23.1, CH3 | 2.17 (3H, s) | - | - | - | - | |
| D6-O-2-hydroxybutyryl | - | - | 176.6, C | - | - | |
| - | - | 45.9, CH2 | 2.67, dd (15.0, 4.5) 2.59, dd (15.0, 8.0) |
- | - | |
| - | - | 67.3, CH | 4.27, m | - | - | |
| - | - | 24.8, CH3 | 1.26, d (6.5) | - | - | |
a 1H NMR data recorded at 500 MHz and 13C NMR data recorded at 125 MHz, 298 K, 18.0 mg/mL for 1 and 2.8 mg/mL for 2; b Unstable in D2O; c Every spin system in rings A–I was acquired by 1D-selective TOCSY experiments with the same NMR parameters. Meanwhile, although the coupling constants and concentration were identical in rings E and H, the intensity of the spin systems in both rings were different; one (ring H) was strong while the other (ring E) was relatively weak. This phenomenon maybe greatly related to their locations in the molecules.