Table 1.
13C and 1H NMR chemical shifts and HMBC and ROESY correlations of the carbohydrate moiety of kurilosides A1 (1), A2 (2) and A (7).
| Atom. | δC mult. a,b,c | δH mult. d (J in Hz) | HMBC | ROESY |
|---|---|---|---|---|
| Xyl1 (1→C-3) | ||||
| 1 | 105.0 CH | 4.69 d (7.2) | C-3; C: 5 Xyl1 | H-3; H-3, 5 Xyl1 |
| 2 | 83.2 CH b | 3.95 t (8.8) | C: 3 Xyl1 | H-1 Qui2 |
| 3 | 75.7 CH | 4.13 t (9.0) | C: 2, 4 Xyl1 | |
| 4 | 79.8 CH b | 4.07m | H-1 Glc4 | |
| 5 | 63.8 CH2 | 4.29 dd (5.3; 11.3) | C: 1, 3 Xyl1 | |
| 3.58 t (11.3) | C: 1 Xyl1 | H-1 Xyl1 | ||
| Qui2 (1→2Xyl1) | ||||
| 1 | 105.3CH | 5.02 d (7.6) | C: 2 Xyl1 | H-2 Xyl1; H-3, 5 Qui2 |
| 2 | 76.1 CH | 3.98 t (8.3) | C: 1, 3 Qui2 | |
| 3 | 75.3 CH | 4.13 t (8.3) | ||
| 4 | 86.8 CH b | 3.57 t (8.3) | C: 1 Glc3; C: 3, 5 Qui2 | H-1 Glc3 |
| 5 | 71.7 CH | 3.76 dd (6.2; 8.3) | H-1 Qui2 | |
| 6 | 17.9 CH3 | 1.70 d (6.2) | C: 4, 5 Qui2 | |
| Glc3 (1→4Qui2) | ||||
| 1 | 105.3 CH | 4.92 d (8.0) | C: 4 Qui2 | H-4 Qui2; H-3,5 Glc3 |
| 2 | 74.7 CH | 4.00 t (8.5) | C: 1, 3 Glc3 | |
| 3 | 78.2 CH | 4.21 t (9.1) | C: 2, 4Glc3 | H-1 Glc3 |
| 4 | 71.4 CH | 4.11 t (8.5) | C: 5, 6 Glc3 | |
| 5 | 78.4CH | 4.05 m | H-1 Glc3 | |
| 6 | 62.3 CH2 | 4.55 brd (10.7) | ||
| 4.23 dd (6.4; 11.7) | ||||
| Glc4 (1→4Xyl1) | ||||
| 1 | 103.7CH | 4.87 d (8.0) | C: 4Xyl1 | H-4 Xyl1; H-3, 5 Glc4 |
| 2 | 73.2 CH | 3.89 t (8.9) | C: 1, 3 Glc4 | |
| 3 | 86.9 CH b | 4.16 t (8.9) | C: 2, 4 Glc4, C: 1 MeGlc5 | H-1 MeGlc5; H-1 Glc4 |
| 4 | 69.6 CH | 3.90 t (8.9) | C: 3, 5, 6 Glc4 | |
| 5 | 75.7 CH | 4.13 m | H-1 Glc4 | |
| 6 | 67.3 CH2 c | 5.18 d (9.8) | ||
| 4.75 dd (6,3; 11.6) | C: 5 Glc4 | |||
| MeGlc5 (1→3Glc4) | ||||
| 1 | 105.3 CH | 5.25 d (8.7) | C: 3 Glc4 | H-3 Glc4; H-3, 5 MeGlc5 |
| 2 | 74.9 CH | 3.95 t (8.7) | C: 1, 3 MeGlc5 | |
| 3 | 87.8 CH | 3.68 t (8.7) | C: 2, 4 MeGlc5, OMe | H-1 MeGlc5 |
| 4 | 70.3 CH | 4.13 t (8.7) | C: 3, 5, 6 MeGlc5 | |
| 5 | 78.1 CH | 3.93 m | H-1, 3 MeGlc5 | |
| 6 | 61.9 CH2 | 4.44 d (12.0) | C: 4 MeGlc5 | |
| 4.26 dd (5.5; 12.0) | ||||
| OMe | 60.5 CH3 | 3.85 s | C: 3 MeGlc5 |
a Recorded at 176.03 MHz in C5D5N/D2O (4/1). b Bold = interglycosidic positions. c Italic = sulphate position. d Recorded at 700.00 MHz in C5D5N/D2O (4/1). Multiplicity by 1D TOCSY.