Table 1.
1 H and 13 C NMR data of 1, 2, and 3 (CD3OD)
| Position | 1 | 2 | 3 | Position | 1 | 2 | 3 | ||||||
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
| 1 H | 13 C | 1 H | 13 C | 1 H | 13 C | 1 H | 13 C | 1 H | 13 C | 1 H | 13 C | ||
| 1 | 1.12 m, 1.73 m |
39.3 CH2 | 1.12 m, 1.71 m |
39.3 CH2 | 1.12 m, 1.71 m |
39.3 CH2 | 2′- β- Gal | ||||||
| 2 | 1.92 m 1.77 m |
25.7 CH2 | 1.95 m, 1.77 m |
25.7 CH2 | 1.95 m, 1.77 m |
25.7 CH2 | 1′′ | 4.97 d (7.2) | 102.7 CH | 4.97 d (7.2) | 102.8 CH | 4.97 d (7.2) | 102.8 CH |
| 3 | 3.87 m | 86.3 CH | 3.86 m | 86.2 CH | 3,86 m | 86.2 CH | 2′′ | 3.47 m | 73.4 CH | 3.46 m | 73.4 CH | 3.46 m | 73.4 CH |
| 4 | / | 56.2 C | / | 56.2 C | / | 56.2 C | 3′′ | 3.49 m | 75.1 CH | 3.49 m | 75.1 CH | 3.49 m | 75.1 CH |
| 5 | 1.35 m | 48.8 CH | 1.33 m | 49.0 CH | 1.33 m | 48.9 CH | 4′′ | 3.80 m | 71.0 CH | 3.80 m | 71.0 CH | 3.80 m | 71.0 CH |
| 6 | 0.95 m, 1.54 m |
21.2 CH2 | 0.95 m, 1.54 m |
21.1 CH2 | 0.95 m, 1.54 m |
21.1 CH2 | 5′′ | 3.62 m | 76.6 CH | 3.62 m | 76.6 CH | 3.62 m | 76.6 CH |
| 7 | 1.26 m, 1.63 m |
32.5 CH2 | 1.25 m, 1.54 m |
33.1 CH2 | 1.28 m, 1.56 m |
33.1 CH2 | 6′′ | 3.71 m 3.78 m |
62.5 CH2 | 3.71 m 3.78 m |
62.5 CH2 | 3.71 m 3.78 m |
62.5 CH2 |
| 8 | / | 42.6 C | / | 41.4 C | / | 41.4 C | 3′- β- Xyl | ||||||
| 9 | 1.79 m | 48.0 CH | 1.76 m | 48.0 CH | 1.79 m | 47.9 CH | 1′′′ | 4.92 d (7.1) | 102.0 CH | 4.92 d (7.1) | 102.0 CH | 4.92 d (7.1) | 102.0 CH |
| 10 | / | 37.0 C | / | 37.0 C | / | 37.0 C | 2′′′ | 3.39 m | 85.1 CH | 3.39 m | 85.1 CH | 3.39 m | 85.1 CH |
| 11 | 1.96 m, 1.80 m |
24.6 CH2 | 1.95 m, 1.76 m |
24.5 CH2 | 1.93 m, 1.78 m |
25.4 CH2 | 3′′′ | 3.58 m | 77.5 CH | 3.58 m | 77.5 CH | 3.58 m | 77.5 CH |
| 12 | 5.35 t (3.5) | 124.2 CH | 5.37 t (3.7) | 124.9 CH | 5.39 t (3.6) | 125.0 CH | 4′′′ | 3.56 m | 71.0 CH | 3.57 m | 71.0 CH | 3.57 m | 70.9 CH |
| 13 | / | 144.1 C | / | 142.7 C | / | 142.8 C | 5′′′ | 3.23 m (ax) 3.90 dd (11.4, 5.4) (eq) |
66.7 CH2 | 3.23 m (ax) 3.90 dd (11.4, 5.4) (eq) |
66.7 CH2 | 3.23 m (ax) 3.90 dd (11.4, 5.4) (eq) |
66.7 CH2 |
| 14 | / | 41.8 C | / | 42.5 C | / | 42.6 C | 2′′′- β- Xyl | ||||||
| 15 | 1.31 m, 1.73 m |
35.2 CH2 | 1.42 m, 1.99 m |
32.3 CH2 | 1.50 m, 1.99 m |
32.3 CH2 | 1′′′′ | 4.51 d (7.6) | 107.5 CH | 4.51 d (7.6) | 107.5 CH | 4.50 d (7.6) | 107.5 CH |
| 16 | 4.11 brs | 70.9 CH | 5.63 brs | 71.7 CH | 5.64 brs | 72.4 CH | 2′′′′ | 3.27 m | 76.2 CH | 3.27 m | 76.2 CH | 3.27 m | 76.2 CH |
| 17 | / | 45.3 C | / | 44.7 C | / | 44.9 C | 3′′′′ | 3.31 m | 77.8 CH | 3.32 m | 77.8 CH | 3.32 m | 77.9 CH |
| 18 | 2.52 brd (12.0) |
41.3 CH | 2.22 brd (12.0) |
42.6 CH | 2.26 brd (12.0) |
42.6 CH | 4′′′′ | 3.51 m | 71.0 CH | 3.51 m | 71.0 CH | 3.51 m | 71.0 CH |
| 19 | 1.06 m, 2.49 m |
47.9 CH2 | 1.12 m, 2.24 dd |
48.0 CH2 | 1.21 m 2.40 t (13.5) |
48.1 CH2 | 5′′′′ | 3.20 m (ax) 3.96 dd (11.4, 5.4) (eq) |
67.3 CH2 | 3.20 m 3.96 dd (11.4, 5.4) (eq) |
67.3 CH2 | 3.20 m 3.96 dd (11.4, 5.4) (eq) |
67.3 CH |
| 20 | / | 33.2 C | / | 32.1 C | / | 31.8 C | Acyl | ||||||
| 21 | 1.56 m, 2.27 m |
42.1 CH2 | 1.39 m, 1.67 m |
44.7 CH2 | 1.46 m 1.76 m |
44.6 CH2 | 1′′′′′ | / | 168.8 C | / | 168.8 C | / | 167.9 C |
| 22 | 5.44 dd (12.1, 5.6) | 73.8 CH | 4.06 dd (12.1, 5.6) | 73.8 CH | 4.08 dd (12.1, 5.6) | 73.8 CH | 2′′′′′ | / | 130.0 C | / | 129.3 C | 6.35 d (16.0) | 117.2 CH |
| 23 | 9.44 s | 210.6 CH | 9.43 s | 210.5 CH | 9.41 s | 210.4 CH | 3′′′′′ | 6.07 qq (7.3, 1.5) |
138.1 CH | 6.08 qq (7.3, 1.5) |
139.0 CH | 7.75 d (16.0) | 145.8 CH |
| 24 | 1.16 s | 10.8 CH3 | 1.16 s | 10.8 CH3 | 1.15 s | 10.8 CH3 | 4′′′′′ | 1.98 dq (7.3, 1.5) |
15.9 CH3 | 1.96 dq (7.3, 1.5) |
15.9 CH2 | / | 128.2 C |
| 25 | 1.03 s | 16.4 CH3 | 1.03 s | 16.4 CH3 | 1.03 s | 16.4 CH3 | 5′′′′′ | 1.90 m | 20.9 CH3 | 1.99 m | 21.3 CH3 | 7.54 d (8.8) | 130.8 CH |
| 26 | 0.95 s | 17.3 CH3 | 0.98 s | 17.2 CH3 | 0.99 s | 17.2 CH3 | 6′′′′′ | 6.98 d (8.8) | 115.6 CH | ||||
| 27 | 1.50 s | 27.7 CH3 | 1.36 s | 27.5 CH3 | 1.38 s | 27.7 CH3 | 7′′′′′ | / | 163.3 C | ||||
| 28 | 3.05 d (10.9) 3.25 m |
64.8 CH2 | 3.30 m, 3.62 m |
70.1 CH2 | 3.23 m, 3.64 m |
69.9 CH2 | 8′′′′′ | 6.98 d (8.8) | 115.6 CH | ||||
| 29 | 0.91 s | 33.6 CH3 | 0.94 s | 33.4 CH3 | 1.02 s | 34.0 CH3 | 9′′′′′ | 7.54 d (8.8) | 130.8 CH | ||||
| 30 | 1.05 s | 25.2 CH3 | 0.99 s | 25.3 CH3 | 1.04 s | 25.5 CH3 | −OMe | 3.84 s | 55.9 CH3 | ||||
| 3-β-GlcA | |||||||||||||
| 1′ | 4.45 d (7.5) | 104.8 CH | 4.45 d (7.5) | 104.8 CH | 4.45 d (7.5) | 104.8 CH | |||||||
| 2′ | 3.76 m | 77.8 CH | 3.76 m | 77.9 CH | 3.76 m | 77.8 CH | |||||||
| 3′ | 3.74 m | 83.6 CH | 3.74 m | 83.6 CH | 3.74 m | 83.6 CH | |||||||
| 4′ | 3.58 m | 70.9 CH | 3.58 m | 70.9 CH | 3.58 m | 70.9 CH | |||||||
| 5′ | 3.84 d (8.2) | 76.5 CH | 3.84 d (8.2) | 76.5 CH | 3.84 d (8.2) | 76.5 CH | |||||||
| 6′ | / | 170.3 C | / | 170.3 C | / | 170.3 C | |||||||
| 7′ | 4.22 q (7.1) | 62.5 CH2 | 4.22 q (7.1) | 62.5 CH2 | 4.22 q (7.1) | 62.5 CH2 | |||||||
| 8′ | 1.28 t (7.1) | 14.4 CH3 | 1.28 t (7.1) | 14.4 CH3 | 1.28 t (7.1) | 14.4 CH3 | |||||||
aAssignments based on analysis of 2D NMR spectra
bData (δ) measured at 500 MHz and 125 MHz; s singlet, br s broad singlet, d doublet, dd doublet of doublets, ddd doublet of doublets of doublets, dt doublet of triplets, m multiplet. J values are in Hz and are omitted if the signals overlapped as multiplets. The overlapped signals were assigned from HSQC and HMBC spectra without designating multiplicity
cData (δ) measured at 125 MHz; CH3, CH2, CH, and C multiplicities were determined by HSQC experiments
δ in ppm, J in Hz