Table 7.
13C and 1H NMR chemical shifts and HMBC and ROESY correlations of the carbohydrate moiety of kuriloside E (5).
| Atom | δC mult. a,b,c | δH mult. (J in Hz) d | HMBC | ROESY |
|---|---|---|---|---|
| Xyl1 (1→C-3) | ||||
| 1 | 105.1 CH | 4.71 d (7.4) | C: 3 | H-3; H-3, 5 Xyl1 |
| 2 | 82.7 CH b | 4.02t (9.7) | C: 1 Xyl1 | H-1 Glc2 |
| 3 | 75.6 CH | 4.16 t (9.7) | C: 4 Xyl1 | H-1, 5 Xyl1 |
| 4 | 80.8 CH b | 4.09 m | H-1 Glc4 | |
| 5 | 63.7 CH2 | 4.29 dd (5.9; 12.6) | C: 3 Xyl1 | |
| 3.60 dd (9.7; 12.2) | H-1, 3 Xyl1 | |||
| Glc2 (1→2Xyl1) | ||||
| 1 | 105.4CH | 5.10 d (7.7) | C: 2 Xyl1 | H-2 Xyl1; H-3, 5 Glc2 |
| 2 | 76.1 CH | 4.00 t (8.6) | ||
| 3 | 75.2 CH | 4.30 t (8.6) | H-1, 5 Glc2 | |
| 4 | 81.0 CH b | 4.30 t (8.6) | C: 1 Glc3 | H-1 Glc3 |
| 5 | 76.5 CH | 3.85 m | H-1, 3 Glc2 | |
| 6 | 61.5 CH2 | 4.55 brd (12.2) | ||
| 4.34 dd (3.2; 12.2) | ||||
| Glc3 (1→4Glc2) | ||||
| 1 | 104.8 CH | 5.11 d (7.0) | C: 4 Glc2 | H-4 Glc2; H-3, 5 Glc3 |
| 2 | 74.6 CH | 4.04 t (8.9) | C: 1, 3 Glc3 | |
| 3 | 77.9 CH | 4.18 t (8.9) | C: 2, 4Glc3 | H-1 MeGlc5; H-1, 5 Glc3 |
| 4 | 71.3 CH | 4.12 t (8.9) | C: 5, 6 Glc3 | |
| 5 | 78.3CH | 4.00 m | H-1, 3 Glc3 | |
| 6 | 62.1 CH2 | 4.48 d (12.2) | ||
| 4.22 dd (7.0; 12.2) | ||||
| Glc4 (1→4Xyl1) | ||||
| 1 | 104.0 CH | 4.90 d (7.8) | C: 4 Xyl1 | H-4 Xyl1; H-3 Glc4 |
| 2 | 73.3 CH | 3.94 t (8.6) | C: 1, 3 Glc4 | |
| 3 | 87.0 CH b | 4.18 t (8.6) | C: 1 MeGlc5; C: 2, 4 Glc4 | H-1 Glc4 |
| 4 | 69.8 CH | 3.88 t (8.6) | H-6 Glc4 | |
| 5 | 75.7 CH | 4.20 m | ||
| 6 | 67.5 CH2 c | 5.23 d (10.9) | ||
| 4.72 t (10.1) | H-4 Glc4 | |||
| MeGlc5 (1→3Glc4) | ||||
| 1 | 105.4 CH | 5.27 d (7.8) | C: 3 Glc4 | H-3 Glc4; H-3, 5 MeGlc5 |
| 2 | 74.9 CH | 3.96 t (8.6) | C: 1, 3 MeGlc5 | H-4 MeGlc5 |
| 3 | 87.8 CH | 3.69 t (8.6) | C: 2, 4 MeGlc5; OMe | H-1, 5 MeGlc5; OMe |
| 4 | 70.3 CH | 4.15 t (8.6) | C: 3, 5, 6MeGlc5 | |
| 5 | 78.2 CH | 3.94 m | H-1, 3 MeGlc5 | |
| 6 | 61.9 CH2 | 4.45 brd (9.4) | ||
| 4.27 dd (5.5; 11.7) | C: 5 MeGlc5 | |||
| OMe | 60.5 CH3 | 3.86 s | C: 3 MeGlc5 | H-3 MeGlc5 |
a Recorded at 176.04 MHz in C5D5N/D2O (4/1). b Bold = interglycosidic positions. c Italic = sulfate position. d Recorded at 700.13 MHz in C5D5N/D2O (4/1). Multiplicity by 1D TOCSY.