Table 3.
NMR spectroscopic data (methanol-d4, 500 MHz) for the sugar and phenolic acid units of compounds 4–10.
| 4 | 5 | 6 | 7 | 8 | 9 | 10 | |||||||||
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
| δH (J in Hz) | δC | δH (J in Hz) | δC | δH (J in Hz) | δC | δH (J in Hz) | δC | δH (J in Hz) | δC | δH (J in Hz) | δC | δH (J in Hz) | δC | ||
| 7-O-β-GlcA | 7-O-β-GlcA | 7-O-β-GlcA | 7-O-β-GlcA | 7-O-β-GlcA | 7-O-β-GlcA | 7-O-β-GlcA | |||||||||
| 1 | 5.12 d (7.6) | 101.2 | 5.17 d (7.3) | 101.3 | 5.19 d (7.2) | 101.2 | 5.15 d (6.8) | 101.2 | 5.14 d (7.4) | 101.4 | 5.14 d (7.2) | 101.2 | 5.13 d (7.4) | 101.3 | |
| 2 | 3.53 dd (9.0, 7.4) | 74.5 | 3.57 t (7.5) | 74.4 | 3.58 dd (9.1, 7.3) | 74.5 | 3.57 dd (9.3, 6.8) | 74.4 | 3.57 dd (9.2, 7.2) | 74.4 | 3.55 t (9.3) | 74.4 | 3.55 dd (9.2, 7.1) | 74.4 | |
| 3 | 3.59 t (9.1) | 77.5 | 3.61 t (9.0) | 77.1 | 3.62 t (9.0) | 77.2 | 3.61 t (9.1) | 77.1 | 3.62 t (9.0) | 77.1 | 3.58 t (9.1) | 77.1 | 3.59 t (8.6) | 77.1 | |
| 4 | 3.56 t (9.2) | 73.4 | 3.66 t (9.3) | 72.9 | 3.67 t (9.2) | 73.0 | 3.66 t (8.0) | 72.9 | 3.67 t (9.5) | 72.9 | 3.65 t (9.5) | 72.9 | 3.64 t (9.1) | 72.9 | |
| 5 | 3.94 d (8.9) | 76.3 | 4.13 d (9.5) | 76.5 | 4.13 d (9.4) | 76.5 | 4.14 d (9.5) | 76.5 | 4.13 d (9.5) | 76.5 | 4.12 d (9.6) | 76.4 | 4.12 d (9.5) | 76.5 | |
| 6 | ND | 172.3 | 172.6 | 172.3 | 172.3 | 172.3 | 172.3 | ||||||||
| 3-O-β-Gal | 3-O-β-Gal | 3-O-β-Gal | 3-O-β-Gal | 3-O-β-Gal | 3-O-β-Gal | 3-O-β-Gal | |||||||||
| 1 | 5.10 d (8.1) | 101.3 | 5.20 br d (7.6) | 101.3 | 5.06 br d (7.4) | 101.4 | 5.19 br d (7.2) | 101.4 | 5.11 br d (7.4) | 101.3 | 5.01 br d (7.5) | 101.4 | 4.94 br d (7.4) | 101.5 | |
| 2 | 3.98 dd (9.6, 7.6) | 83.5 | 4.01 dd (9.6, 7.5) | 83.3 | 4.00 dd (9.5, 7.5) | 83.4 | 4.03 dd (9.6, 7.5) | 83.2 | 4.01 dd (9.6, 7.6) | 83.5 | 3.98 dd (9.5, 7.6) | 83.3 | 3.96 dd (9.5, 7.6) | 83.5 | |
| 3 | 3.66 dd (9.7, 3.4) | 74.7 | 3.71 dd (9.6, 3.3) | 74.7 | 3.68 dd (10.2, 3.8) | 74.8 | 3.70 dd (9.3, 3.3) | 74.7 | 3.69 dd (9.0, 3.6) | 74.8 | 3.65 dd (9.7, 2.8) | 74.8 | 3.63 dd (9.5, 3.8) | 74.8 | |
| 4 | 3.79 d (3.5) | 70.1 | 3.83 d (3.3) | 70.1 | 3.81 d (3.5) | 70.1 | 3.84 d (3.2) | 70.1 | 3.82 d (3.7) | 70.1 | 3.78 d (3.3) | 70.1 | 3.77 d (3.3) | 70.1 | |
| 5 | 3.34 a | 76.9 | 3.40 t (5.6) | 76.9 | 3.37 t (6.1) | 76.9 | 3.41 t (5.9) | 76.9 | 3.38 t (6.0) | 76.9 | 3.37 t (6.1) | 76.9 | 3.32 t (6.1) | 76.9 | |
| 6 | 3.55 a | 61.7 | 3.59 dd (11.2, 5.7) | 61.8 | 3.59 dd (11.2, 5.8) | 61.8 | 3.60 dd (11.3, 5.7) | 61.8 | 3.59 dd (11.0, 4.2) | 61.8 | 3.57 dd (11.3, 5.8) | 61.8 | 3.55 dd (11.2, 5.8) | 61.8 | |
| 3.48 a | 3.52 dd (11.0, 6.2) | 3.50 dd (11.3, 6.4) | 3.53 dd (11.3, 6.3) | 3.50 dd (11.0, 5.0) | 3.48 dd (11.2, 6.4) | 3.45 dd (11.5, 6.2) | |||||||||
| 2Gal-O-β-Glc | 2Gal-O-β-Glc | 2Gal-O-β-Glc | 2Gal-O-β-Glc | 2Gal-O-β-Glc | 2Gal-O-β-Glc | 2Gal-O-β-Glc | |||||||||
| 1' | 4.70 d (7.6) | 106.8 | 4.75 d (7.5) | 106.6 | 4.72 d (7.6) | 106.7 | 4.77 d (7.4) | 106.5 | 4.76 d (7.6) | 106.7 | 4.70 d (7.7) | 106.6 | 4.69 d (7.7) | 106.8 | |
| 2' | 3.42 dd (9.4, 7.6) | 76.3 | 3.46 dd (9.4, 7.4) | 76.2 | 3.43 dd (9.3, 7.9) | 76.3 | 3.48 dd (9.3, 7.6) | 76.1 | 3.47 t (8.6) | 76.3 | 3.41 dd (9.0, 8.0) | 76.2 | 3.41 dd (9.2, 7.8) | 76.3 | |
| 3' | 3.48 dd (9.3, 8.6) | 77.8 | 3.51 t (9.2) | 77.8 | 3.52 t (9.2) | 77.8 | 3.53 t (9.2) | 77.8 | 3.54 t (8.7) | 77.8 | 3.49 t (9.1) | 77.8 | 3.50 t (9.1) | 77.8 | |
| 4' | 3.33 dd (9.7, 8.5) | 72.4 | 3.39 t (8.8) | 72.1 | 3.39, t (9.2) | 72.2 | 3.40 dd (9.7, 8.4) | 72.0 | 3.40 t (8.7) | 72.2 | 3.39 t (9.4) | 72.1 | 3.37 dd (9.5, 8.7) | 72.3 | |
| 5' | 3.74 ddd(9.8, 6.3, 3.6) | 75.6 | 3.75 ddd(9.7, 6.5, 3.0) | 75.7 | 3.70 ddd(9.7, 6.6, 2.9) | 75.6 | 3.74 ddd(9.8, 6.1, 3.5) | 75.7 | 3.79 ddd(9.5, 7.6, 2.3) | 75.6 | 3.68 ddd(9.5, 5.6, 3.8) | 75.6 | 3.70 ddd(9.7, 7.2, 2.5) | 75.5 | |
| 6' | 4.41 m (2H) | 64.8 | 4.43 m (2H) | 64.8 | 4.45 dd (11.9, 6.7)) | 64.9 | 4.44 m (2H) | 64.8 | 4.49 dd (11.8, 7.1) | 64.8 | 4.42 m (2H) | 64.9 | 4.47 dd (11.8, 7.2) | 64.9 | |
| 4.42 dd (11.9, 3.0) | 4.44 dd (11.7, 2.4) | 4.41 dd (11.7, 2.3) | |||||||||||||
| 6Glc-O-triOHCin | 6Glc-O-Caf | 6Glc-O-Caf | 6Glc-O-Cou | 6Glc-O-Fer | 6Glc-O-Cou | 6Glc-O-Fer | |||||||||
| 1 | 126.3 | 127.4 | 127.3 | 126.8 | 127.3 | 126.7 | 127.2 | ||||||||
| 2 | 6.23 s | 108.5 | 6.75 d (1.9) | 114.9 | 6.71 d (1.9) | 114.8 | 7.12 d (8.1) | 130.8 | 6.76 d (1.8) | 110.8 | 7.06 d(8.6) | 130.7 | 6.71 d (1.6) | 110.7 | |
| 3 | 147.1 | 146.4 | 146.4 | 6.67 d (8.1) | 116.7 | 148.9 | 6.62 d (8.6) | 116.7 | 148.9 | ||||||
| 4 | 137.7 | 149.2 | 149.2 | 160.8 | 150.1 | 160.8 | 150.1 | ||||||||
| 5 | 147.1 | 6.62 d (8.3) | 116.4 | 6.60 d (8.0) | 116.4 | 6.67 d (8.1) | 116.7 | 6.65 d (8.1) | 116.3 | 6.62 d (8.6) | 130.7 | 6.60 d (8.1) | 116.3 | ||
| 6 | 6.23 s | 108.5 | 6.59 dd (8.2, 1.9) | 122.7 | 6.56 dd (8.0, 1.9) | 122.6 | 7.12 d (8.1) | 130.8 | 6.70 dd (8.2, 1.8) | 124.1 | 7.06 d (8.6) | 116.7 | 6.65 dd (8.2, 1.7) | 123.8 | |
| 7 | 7.13 d (15.8) | 147.2 | 7.28 d (15.9) | 146.8 | 7.25 d (15.9) | 146.8 | 7.35 d (15.9) | 146.4 | 7.31 d (15.9) | 146.7 | 7.30 d (15.9) | 146.4 | 7.27 d (15.9) | 146.6 | |
| 8 | 5.85 d (15.8) | 114.5 | 5.95 d (15.9) | 114.5 | 5.93 d (15.8) | 114.5 | 6.02 d (15.9) | 114.6 | 6.02 d (15.9) | 114.8 | 5.98 d (15.9) | 114.6 | 5.98 d (15.9) | 114.8 | |
| 9 | 167.5 | 168.9 | 168.9 | 168.9 | 168.9 | 168.9 | 168.8 | ||||||||
| OCH3 | 3.79 s | 56.2 | 3.75 s | 56.2 | |||||||||||
a: overlapping signals.