Table 5.
13C and 1H NMR chemical shifts, HMBC, and ROESY correlations of carbohydrate moiety of chitonoidoside C (4).
| Atom | δC mult. a,b,c | δH mult. (J in Hz) d | HMBC | ROESY |
|---|---|---|---|---|
| Xyl1 (1→C-3) | ||||
| 1 | 104.8 CH | 4.68 d (6.6) | C: 3 | H-3; H-3, 5 Xyl1 |
| 2 | 82.1 CH | 3.98 t (6.6) | C: 1 Qui2; 1, 3 Xyl1 | H-1 Qui2 |
| 3 | 75.1 CH | 4.17 t (7.4) | C: 4 Xyl1 | H-1, 5 Xyl1 |
| 4 | 77.9 CH | 4.18 t (7.4) | H-1 Glc3 | |
| 5 | 63.5 CH2 | 4.39 dd (4.5; 11.6) | C: 3 Xyl1 | |
| 3.64 m | H-1 Xyl1 | |||
| Qui2 (1→2Xyl1) | ||||
| 1 | 104.9 CH | 5.06 d (7.5) | C: 2 Xyl1 | H-2 Xyl1; H-3, 5 Qui2 |
| 2 | 76.3 CH | 3.89 t (8.6) | C: 1, 3 Qui2 | H-4 Qui2 |
| 3 | 76.8 CH | 4.07 t (8.6) | C: 4 Qui2 | H-1, 5 Qui2 |
| 4 | 76.2 CH | 3.59 t (8.6) | C: 3 Qui2 | H-2 Qui2 |
| 5 | 72.8 CH | 3.70 dd (6.3; 8.7) | H-1 Qui2 | |
| 6 | 18.2 CH3 | 1.53 d (6.3) | C: 4, 5 Qui2 | H-4 Qui2 |
| Glc3 (1→4Xyl1) | ||||
| 1 | 102.2 CH | 4.90 d (8.2) | C: 4 Xyl1 | H-4 Xyl1; H-3 Glc3 |
| 2 | 73.3 CH | 3.82 t (8.2) | C: 1, 3 Glc3 | |
| 3 | 85.8 CH | 4.06 t (8.2) | C: 2, 4 Glc3; 1 MeXyl4 | H-1 MeXyl4 |
| 4 | 68.8 CH | 3.86 t (8.9) | C: 3 Glc3 | |
| 5 | 75.3 CH | 4.02 m | H-1 Glc3 | |
| 6 | 67.2 CH2 | 4.96 d (11.6) | ||
| 4.70 dd (5.6; 11.6) | ||||
| MeXyl4 (1→3Glc3) | ||||
| 1 | 104.8 CH | 5.08 d (7.5) | C: 3 Glc3 | H-3 Glc3; H-3, 5 MeXyl4 |
| 2 | 73.7 CH | 3.82 t (7.5) | C: 1 MeXyl4 | |
| 3 | 84.1 CH | 3.65 t (8.8) | C: 2, 4 MeXyl4, OMe | |
| 4 | 75.5 CH | 4.93 m | C: 3 MeXyl4 | |
| 5 | 64.5 CH2 | 4.88 dd (5.2; 11.7) | C: 3, 4 MeXyl4 | |
| 3.74 t (10.2) | H-4 MeXyl4 | |||
| OMe | 60.1 CH3 | 3.81 s | C: 3 MeXyl4 |
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.