Table 4.
13C and 1H NMR chemical shifts, HMBC and ROESY correlations of carbohydrate moiety of chitonoidoside B (3).
| Atom | δC mult. a b,c | δH mult. (J in Hz) d | HMBC | ROESY |
|---|---|---|---|---|
| Xyl1 (1→C-3) | ||||
| 1 | 104.8 CH | 4.67 d (7.6) | C: 3 | H-3; H-3, 5 Xyl1 |
| 2 | 82.5 CH | 3.96 t (8.2) | C: 1 Qui2; 1 Xyl1 | H-1 Qui2 |
| 3 | 75.2 CH | 4.17 t (8.2) | C: 2, 4 Xyl1 | |
| 4 | 77.5 CH | 4.24 m | H-1 Glc5 | |
| 5 | 63.5 CH2 | 4.40 dd (6.0; 12.5) | C: 3 Xyl1 | |
| 3.65 dd (9.2; 12.5) | H-1 Xyl1 | |||
| Qui2 (1→2Xyl1) | ||||
| 1 | 104.7 CH | 5.02 d (8.7) | C: 2 Xyl1 | H-2 Xyl1; H-3, 5 Qui2 |
| 2 | 75.7 CH | 3.87 t (9.0) | C: 3 Qui2 | H-4 Qui2 |
| 3 | 74.9 CH | 3.94 t (9.0) | ||
| 4 | 85.6 CH | 3.50 t (9.0) | C: 3 Qui2, 1 Xyl3 | H-1 Xyl3; H-2 Qui2 |
| 5 | 71.4 CH | 3.66 dd (6.2; 9.0) | H-1 Qui2 | |
| 6 | 17.8 CH3 | 1.63 d (6.2) | C: 4, 5 Qui2 | H-4 Qui2 |
| Xyl3 (1→4Qui2) | ||||
| 1 | 104.4 CH | 4.77 d (7.7) | C: 4 Qui2 | H-4 Qui2; H-3, 5 Xyl3 |
| 2 | 73.2 CH | 3.85 t (7.7) | C: 1, 3 Xyl3 | |
| 3 | 87.0 CH | 4.06 t (8.6) | C: 2 Xyl3; 1 MeGlc4 | H-1 MeGlc4; H-1 Xyl3 |
| 4 | 68.7 CH | 3.91 t (8.6) | ||
| 5 | 65.7 CH2 | 4.12 dd (5.7; 11.5) | C: 3, 4 Xyl3 | |
| 6 | 3.60 t (11.5) | H-1 Xyl3 | ||
| MeGlc4 (1→3Xyl3) | 104.5 CH | 5.12 d (7.7) | C: 3 Xyl3 | H-3 Xyl3; H-3, 5 MeGlc4 |
| 1 | 74.3 CH | 3.80 t (7.7) | C: 1 MeGlc4 | |
| 2 | 86.4 CH | 3.64 t (9.7) | C: 2, 4 MeGlc4, OMe | H-1, 5 MeGlc4 |
| 3 | 69.9 CH | 3.96 t (9.7) | C: 3 MeGlc4 | H-2, 6 MeGlc4 |
| 4 | 75.5 CH | 4.04 m | H-1, 3 MeGlc4 | |
| 5 | 67.1 CH2 | 4.98 d (11.6) | ||
| 6 | 4.72 dd (5.8; 11.6) | C: 5 MeGlc4 | ||
| 60.5 CH3 | 3.76 s | C: 3 MeGlc4 | ||
| Glc5 (1→4Xyl1) | ||||
| 1 | 102.2 CH | 4.93 d (7.9) | C: 4 Xyl1 | H-4 Xyl1; H-3, 5 Glc5 |
| 2 | 73.3 CH | 3.92 t (7.9) | C: 1, 3 Glc5 | |
| 3 | 86.8 CH | 4.09 t (7.9) | C: 4 Glc5; 1 MeXyl6 | H-1 MeXyl6; H-1,5 Glc5 |
| 4 | 69.2 CH | 3.86 t (7.9) | C: 3, 5 Glc5 | H-6 Glc5 |
| 5 | 77.3 CH | 3.86 t (7.9) | H-1, 3 Glc5 | |
| 6 | 61.7 CH2 | 4.32 brd (11.4) | ||
| 4.05 dd (4.8; 11.4) | ||||
| MeXyl6 (1→3Glc5) | ||||
| 1 | 105.3 CH | 5.09 d (7.3) | C: 3 Glc5 | H-3 Glc5; H-3, 5 MeXyl6 |
| 2 | 74.2 CH | 3.80 t (8.4) | C: 1 MeXyl6 | |
| 3 | 86.7 CH | 3.58 t (8.4) | C: 2, 4 MeXyl6; OMe | H-1 MeXyl6; OMe |
| 4 | 69.6 CH | 3.97 m | ||
| 5 | 66.4 CH2 | 4.14 dd (5.5; 11.7) | C: 1, 3, 4 MeXyl6 | |
| 3.60 t (11.0) | H-1 MeXyl6 | |||
| OMe | 60.5 CH3 | 3.79 s | C: 3 MeXyl6 | H-3 MeXyl6 |
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.