Table 4.
13C and 1H NMR chemical shifts, HMBC and ROESY correlations of carbohydrate moiety of chitonoidoside G (3).
| Atom | δC Mult. a–c | δH Mult. (J in Hz) d | HMBC | ROESY |
|---|---|---|---|---|
| Xyl1 (1→C-3) | ||||
| 1 | 104.8 CH | 4.66 d (6.9) | C: 3 | H-3; H-3, 5 Xyl1 |
| 2 | 82.1 CH | 3.97 t (8.8) | C: 1 Qui2; 1, 3 Xyl1 | H-1 Qui2 |
| 3 | 75.1 CH | 4.16 t (8.8) | C: 4 Xyl1 | |
| 4 | 77.8 CH | 4.16 m | ||
| 5 | 63.5 CH2 | 4.37 dd (4.1; 11.8) | ||
| 3.62 m | H-1 Xyl1 | |||
| Qui2 (1→2Xyl1) | ||||
| 1 | 104.5 CH | 5.04 d (7.3) | C: 2 Xyl1 | H-2 Xyl1; H-3, 5 Qui2 |
| 2 | 75.7 CH | 3.87 t (9.0) | C: 1, 3 Qui2 | H-4 Qui2 |
| 3 | 74.8 CH | 3.98 t (9.0) | C: 2, 4 Qui2 | H-5 Qui2 |
| 4 | 85.6 CH | 3.49 t (9.0) | C: 1 Xyl3; 3, 5 Qui2 | H-1 Xyl3; H-2 Qui2 |
| 5 | 71.4 CH | 3.68 dd (6.2; 9.0) | H-1 Qui2 | |
| 6 | 17.8 CH3 | 1.62 d (6.2) | C: 4, 5 Qui2 | H-4, 5 Qui2 |
| Xyl3 (1→4Qui2) | ||||
| 1 | 104.4 CH | 4.75 d (7.7) | C: 4 Qui2 | H-4 Qui2; H-3, 5 Xyl3 |
| 2 | 73.2 CH | 3.84 t (8.3) | C: 1, 3 Xyl3 | |
| 3 | 87.0 CH | 4.04 t (8.3) | C: 1 MeGlc4; 2, 4 Xyl3 | H-1 MeGlc4; H-1 Xyl3 |
| 4 | 68.8 CH | 3.89 m | C: 5 Xyl3 | |
| 5 | 65.7 CH2 | 4.12 dd (5.3; 11.2) | ||
| 3.59 d (11.2) | C: 1 Xyl3 | H-1 Xyl3 | ||
| MeGlc4 (1→3Xyl3) | ||||
| 1 | 104.6 CH | 5.12 d (7.9) | C: 3 Xyl3 | H-3 Xyl3; H-3, 5 MeGlc4 |
| 2 | 74.3 CH | 3.80 t (8.5) | C: 1 MeGlc4 | |
| 3 | 86.4 CH | 3.64 t (8.5) | C: 4 MeGlc4, OMe | H-1 MeGlc4; OMe |
| 4 | 69.9 CH | 3.96 t (8.5) | C: 3, 5, 6 MeGlc4 | H-2, 6 MeGlc4 |
| 5 | 75.5 CH | 4.03 m | H-1, 3 MeGlc4 | |
| 6 | 67.1 CH2 | 4.97 d (10.7) | ||
| 4.71 dd (5.6; 11.3) | C: 5 MeGlc4 | |||
| OMe | 60.5 CH3 | 3.76 s | C: 3 MeGlc4 | |
| Glc5 (1→4Xyl1) | ||||
| 1 | 102.2 CH | 4.88 d (7.9) | C: 4 Xyl1 | H-4 Xyl1; H-3, 5 Glc5 |
| 2 | 73.2 CH | 3.84 t (9.0) | C: 1, 3 Glc5 | |
| 3 | 86.0 CH | 4.16 t (9.0) | C: 1 MeGlc6; 2 Glc5 | H-1 MeGlc6; H-1 Glc5 |
| 4 | 69.0 CH | 3.89 t (9.0) | C: 3 Glc5 | |
| 5 | 75.5 CH | 4.02 m | H-1 Glc5 | |
| 6 | 67.1 CH2 | 4.93 d (10.7) | ||
| 4.68 dd (6.2; 11.3) | ||||
| MeGlc6 (1→3Glc5) | ||||
| 1 | 104.4 CH | 5.18 d (7.5) | C: 3 Glc5 | H-3 Glc5; H-3, 5 MeGlc6 |
| 2 | 74.5 CH | 3.84 t (8.8) | C: 1 MeGlc6 | |
| 3 | 86.8 CH | 3.66 t (8.8) | C: 2, 4 MeGlc6, OMe | H-1 MeGlc6 |
| 4 | 70.3 CH | 3.89 m | C: 5 MeGlc6 | H-6 MeGlc6 |
| 5 | 77.5 CH | 3.89 m | H-1 MeGlc6 | |
| 6 | 61.7 CH2 | 4.34 dd (2.2; 11.7) | ||
| 4.05 dd (5.1; 11.7) | C: 4 MeGlc6 | |||
| OMe | 60.6 CH3 | 3.80 s | C: 3 MeGlc6 |
a Recorded at 125.67 MHz in C5D5N/D2O (4/1). b Bold = interglycosidic positions. c Italic = sulfate position. d Recorded at 500.12 MHz in C5D5N/D2O (4/1). Multiplicity by 1D TOCSY. The original spectra of 1 are provided in Figures S17–S23.