Table 7.
13C and 1H NMR chemical shifts, HMBC and ROESY correlations of carbohydrate moiety of chitonoidoside E (6).
| 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 (6.9) | C: 3 | H-3; H-3, 5 Xyl1 |
| 2 | 82.1 CH | 3.97 t (6.9) | C: 1 Qui2; 3 Xyl1 | H-1 Qui2 |
| 3 | 75.2 CH | 4.17 m | C: 4 Xyl1 | H-1, 5 Xyl1 |
| 4 | 77.8 CH | 4.17 m | H-1 Glc5; H-2 Xyl1 | |
| 5 | 63.5 CH2 | 4.38 dd (5.5; 11.5) | C: 3 Xyl1 | |
| 3.64 m | H-1 Xyl1 | |||
| Qui2 (1→2Xyl1) | ||||
| 1 | 104.5 CH | 5.05 d (7.8) | C: 2 Xyl1 | H-2 Xyl1; H-3, 5 Qui2 |
| 2 | 75.7 CH | 3.86 t (9.1) | C: 1, 3 Qui2 | H-4 Qui2 |
| 3 | 74.8 CH | 3.97 t (9.1) | C: 2 Qui2 | H-1 Qui2 |
| 4 | 85.6 CH | 3.49 t (9.1) | C: 1 Xyl3; 3, 5 Qui2 | H-1 Xyl3; H-2 Qui2 |
| 5 | 71.4 CH | 3.68 dd (5.8; 9.1) | H-1 Qui2 | |
| 6 | 17.8 CH3 | 1.62 d (5.8) | C: 4, 5 Qui2 | H-4 Qui2 |
| Xyl3 (1→4Qui2) | ||||
| 1 | 104.4 CH | 4.75 d (7.6) | C: 4 Qui2 | H-4 Qui2; H-3, 5 Xyl3 |
| 2 | 73.2 CH | 3.84 t (8.4) | C: 1 Xyl3 | |
| 3 | 87.0 CH | 4.04 t (8.4) | C: 1 MeGlc4; 2, 4 Xyl3 | H-1 MeGlc4 |
| 4 | 68.8 CH | 3.91 m | ||
| 5 | 65.7 CH2 | 4.12 dd (5.9; 11.0) | C: 4 Xyl3 | |
| 6 | 3.59 t (11.0) | C: 1, 3 Xyl3 | H-1 Xyl3 | |
| MeGlc4 (1→3Xyl3) | 104.6 CH | 5.12 d (7.6) | C: 3 Xyl3 | H-3 Xyl3; H-3, 5 MeGlc4 |
| 1 | 74.2 CH | 3.80 t (8.4) | C: 1 MeGlc4 | |
| 2 | 86.4 CH | 3.64 t (8.4) | C: 2, 4 MeGlc4, OMe | H-1, 5 MeGlc4 |
| 3 | 69.9 CH | 3.95 t (8.4) | C: 6 MeGlc4 | |
| 4 | 75.3 CH | 4.03 m | H-1, 3 MeGlc4 | |
| 5 | 67.1 CH2 | 4.96 d (11.0) | C: 5 MeGlc4 | |
| 6 | 4.71 dd (5.9; 11.8) | C: 5 MeGlc4 | ||
| 60.5 CH3 | 3.76 s | C: 3 MeGlc4 | ||
| Glc5 (1→4Xyl1) | ||||
| 1 | 102.2 CH | 4.90 d (7.6) | C: 4 Xyl1 | H-4 Xyl1; H-3, 5 Glc5 |
| 2 | 73.2 CH | 3.84 t (9.3) | C: 1, 3 Glc5 | |
| 3 | 86.0 CH | 4.06 t (9.3) | C: 1 MeXyl6; 2 Glc5 | H-1 MeXyl6; H-1 Glc5 |
| 4 | 68.9 CH | 3.88 t (9.3) | H-6 Glc5 | |
| 5 | 75.5 CH | 4.02 m | H-1 Glc5 | |
| 6 | 67.1 CH2 | 4.95 d (10.1) | C: 4, 5 Glc5 | |
| 4.70 dd (5.9; 11.8) | ||||
| MeXyl6 (1→3Glc5) | ||||
| 1 | 105.2 CH | 5.07 d (7.6) | C: 3 Glc5 | H-3 Glc5; H-3, 5 MeXyl6 |
| 2 | 74.3 CH | 3.79 t (8.4) | C: 1 MeXyl6 | |
| 3 | 86.8 CH | 3.57 t (8.4) | C: 2, 4 MeXyl6; OMe | H-1 MeXyl6; OMe |
| 4 | 69.7 CH | 3.97 m | C: 3, 5 MeXyl6 | |
| 5 | 66.4 CH2 | 4.14 dd (5.1; 11.8) | C: 1, 3, 4 MeXyl6 | |
| 3.60 t (11.0) | C: 1 MeXyl6 | 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.