Table 9.
13C and 1H NMR chemical shifts and HMBC and ROESY correlations of the carbohydrate moiety of kuriloside F (6).
| Atom | δC mult. a,b,c | δH mult. (J in Hz) d | HMBC | ROESY |
|---|---|---|---|---|
| Xyl1 (1→C-3) | ||||
| 1 | 104.7 CH | 4.70 d (7.2) | C: 3 | H-3; H-3, 5 Xyl1 |
| 2 | 83.2 CH b | 3.96 m | C: 1 Xyl1 | H-1 Qui2 |
| 3 | 75.7 CH | 4.13 t (8.8) | C: 2 Xyl1 | |
| 4 | 79.8 CH b | 4.07 m | H-1 Glc5 | |
| 5 | 63.8 CH2 | 4.29 dd (5.3; 11.4) | C: 3 Xyl1 | |
| 3.58 dd (9.7; 11.4) | H-1 Xyl1 | |||
| Qui2 (1→2Xyl1) | ||||
| 1 | 105.0CH | 5.02 d (7.3) | C: 2 Xyl1 | H-2 Xyl1; H-5 Qui2 |
| 2 | 76.0 CH | 3.97 t (9.4) | C: 1 Qui2 | |
| 3 | 75.3 CH | 4.10 m | ||
| 4 | 86.9 CH b | 3.56 t (9.4) | C: 1 Glc3; C: 3, 5 Qui2 | H-1 Glc3 |
| 5 | 71.6 CH | 3.76 m | H-1 Qui2 | |
| 6 | 17.8 CH3 | 1.70 d (5.9) | C: 4, 5 Qui2 | |
| Glc3 (1→4Qui2) | ||||
| 1 | 104.7 CH | 4.90 d (7.4) | C: 4 Qui2 | H-4 Qui2; H-3, 5 Glc3 |
| 2 | 73.5 CH | 4.01 t (8.3) | C: 1, 3 Glc3 | |
| 3 | 87.8 CH | 4.20 t (8.3) | C: 4Glc3 | H-1 MeGlc4; H-1, 5 Glc3 |
| 4 | 69.6 CH | 4.00 m | ||
| 5 | 77.9CH | 4.00 t (8.3) | H-1, 3 Glc3 | |
| 6 | 61.9 CH2 | 4.45 m | ||
| 4.14 dd (5.5; 12.0) | ||||
| MeGlc4 (1→3Glc3) | ||||
| 1 | 105.5 CH | 5.26 d (8.1) | C: 3 Glc3 | H-3 Glc3; H-3, 5MeGlc4 |
| 2 | 74.9 CH | 3.99 t (8.1) | C: 1, 3 MeGlc4 | |
| 3 | 87.8 CH | 3.70 t (8.1) | C: 2, 4 MeGlc4; OMe | H-1 MeGlc4; OMe |
| 4 | 70.5 CH | 4.13 t (8.5) | C: 3, 5, 6 MeGlc4 | |
| 5 | 78.2 CH | 3.95 m | H-1 MeGlc4 | |
| 6 | 62.1 CH2 | 4.46 dd (4.1; 12.2) | C: 4 MeGlc4 | |
| 4.26 dd (6.1; 11.2) | C: 5 MeGlc4 | |||
| OMe | 60.5 CH3 | 3.85 s | C: 3 MeGlc4 | H-3 MeGlc4 |
| Glc5 (1→4Xyl1) | ||||
| 1 | 103.7 CH | 4.86 d (8.1) | C: 4 Xyl1 | H-4 Xyl1; H-3 Glc5 |
| 2 | 73.2 CH | 3.86 t (8.1) | C: 1 Glc5 | |
| 3 | 86.9 CH | 4.15 t (9.1) | C: 1 MeGlc6; C: 2, 4 Glc5 | H-1 MeGlc6 |
| 4 | 69.6 CH | 3.91 m | C: 3 Glc5 | |
| 5 | 75.7 CH | 4.13 m | H-1 Glc5 | |
| 6 | 67.2 CH2 c | 5.19 d (11.2) | ||
| 4.77 dd (5.1; 11.2) | ||||
| MeGlc6 (1→3Glc5) | ||||
| 1 | 105.3 CH | 5.25 d (8.6) | C: 3 Glc5 | H-3 Glc5; H-3, 5 MeGlc6 |
| 2 | 74.8 CH | 3.96 t (8.6) | C: 1, 3 MeGlc6 | |
| 3 | 87.9 CH | 3.68 t (8.6) | C: 2, 4 MeGlc6; OMe | H-1, 5 MeGlc6; OMe |
| 4 | 70.3 CH | 4.14 t (8.6) | C: 3, 5, 6MeGlc6 | |
| 5 | 78.2 CH | 3.93 m | H-1, 3 MeGlc6 | |
| 6 | 61.9 CH2 | 4.44 brd (11.8) | C: 4 MeGlc6 | |
| 4.27 dd (5.5; 11.8) | C: 5 MeGlc6 | |||
| OMe | 60.6 CH3 | 3.86 s | C: 3 MeGlc6 | H-3 MeGlc6 |
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.